California to Oregon Road Trip: A Full Guide

In May 2013 we drove 1,840 miles from San Diego, California to Portland, Oregon. Just two states but we covered such a significant part of the west coast which included over five national parks, three breweries, three factory tours, a visit to one of the best restaurants in the world, and countless other amazing things along the way. As you can see we avoided Los Angeles and the coast, which was done on purpose to diversify our California experience. Check out our route:

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I organized each post about our trip by location/region. Here are all of the links:

Sort of related/may be helpful if you’re interested:

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California to Oregon Road Trip | Day 10: Portland, OR

Get ready for the final day, Day 10, of our California to Oregon road trip recap!

In May 2013 we drove 1,840 miles from San Diego, California to Portland, Oregon. Just two states but we covered such a significant part of the west coast which included over five national parks, three breweries, three factory tours, a visit to one of the best restaurants in the world, and countless other amazing things along the way. As you can see we avoided Los Angeles and the coast, which was done on purpose to diversify our California experience. Check out our route:

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The final day of our trip was bittersweet – we were finally in Portland, our favorite city, but our trip was coming to an end. We were also exhausted from the entire road trip and were feeling ready to go home. Still, we made our last day in Portland count!

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We started bright and early with biscuits of course. Pine State Biscuits are legendary in Portland and did not disappoint. I could totally eat these everyday.

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After breakfast John had a straight razor shave and haircut scheduled at Rooks. I took the opportunity to drive around PDX, blast Paramore, and just be present in that moment.

At 11am we met up with the daily Secrets of Portlandia tour that met right outside the courthouse.

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It was your standard downtown walking tour but was made extra awesome by the tour guide, Erik. Before coming to Portland he did walking tours in Spain. He was super funny, knowledgeable, and full of fun facts about Portland.

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One such fun fact was about the Benson Bubblers all over Portland. Simon Benson was a wealthy business man and philanthropist, as well as a teetotaler who wanted to discourage his workers from drinking alcohol in the middle of the day. In 1912, Benson gave the city $10,000 for the installation of twenty bronze drinking fountains. Today there are still 40 working Benson Bubblers in Portland. The more you know!

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The tour took us past the Portland State University campus, through South Block Parks, and over to The Portland Building. (Which you should totally recognize if you’ve ever seen the opening credits of Portlandia.)

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We went through Lownsdale Square known for its several large old elm and gingko trees.

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Another hilarious only-in-Portland thing we saw? Mill Ends Park, a tiny, 2 foot, official city park dedicated as “the only leprechaun colony west of Ireland.” Click that link to read more, it’s totally worth it.

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The tour took about 2 hours and ended, of course, at the original Voodoo Doughnut location. We didn’t get any donuts here though, we were waiting for later.

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We were, however, in the mood for lunch! We headed to one of the many food truck pods in Portland. I hit up the Portland Soup Company and John went elsewhere for a gyro.

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I got up to the window and could not make up my mind. Everything looked amazing! I ended up getting a cup of the tomato soup and a half of the smoked pork butt sandwich. The soup was rich and creamy, with gorgeous buttery croutons on top. The sandwich was on super fresh bread and had the best cole slaw on top. I could eat that everyday.

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After lunch it became a little overcast and rainy so we headed to the Oregon Museum of Science and Industry.

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The museum was definitely geared more towards kids but it was still a fun place to spend an hour at, out of the rain. We found a really sweet spot up on the second floor with couches and a great view of the Willamette River.

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As the skies cleared we drove up to the International Rose Test Garden.

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I have wanted to come here for the last three years but the weather/timing never worked out. I’m so glad we made it on this trip though, it was beautiful!

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Portland has so many of these unique urban respites where you can be among nature without ever leaving the city. Just another reason why I love Portland so much.

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The view of downtown from the Rose Garden is pretty incredible.

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Afterward we headed back down to the Pearl District for some shopping and dinner. The shops in the Pearl are awesome, so many adorable boutiques and home decor shops. We grabbed some amazing Thai food and beers at Jinx. Because it was happy hour all of this cost like $20. Wish we had happy hour in Boston!

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Our final stop of the trip was to get donuts at our favorite Voodoo location, Voodoo Doughnut Too in northeast PDX. I know it’s gimmicky and overexposed, on TV all the time, and super touristy but the donuts at Voodoo are legit. Their quality and flavor totally back up the hype. Every time we go I expect the quality to have declined but it actually gets better and better.

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As our final day in Portland, and on our trip, came to a close we were feeling sad but so, so happy. We experienced so many amazing things on our trip and became more familiar with the entire west coast. Plus, we celebrated our two year wedding anniversary which was really special. It was only fitting that as we headed back to the hotel to pack for our return flight home, a huge rainbow crossed the sky. I couldn’t have imagined a more perfect ending to our trip.

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California to Oregon Road Trip | Day 9: Milwaukie and Portland, OR

Get ready for Day 9 of our California to Oregon road trip recap!

In May 2013 we drove 1,840 miles from San Diego, California to Portland, Oregon. Just two states but we covered such a significant part of the west coast which included over five national parks, three breweries, three factory tours, a visit to one of the best restaurants in the world, and countless other amazing things along the way. As you can see we avoided Los Angeles and the coast, which was done on purpose to diversify our California experience. Check out our route:

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As I mentioned in my Day 8 post, the FivePine Lodge in Sisters, OR was my favorite place that we stayed on our trip. When I woke up on Day 9 I knew we had to get on the road but I seriously did not want to leave. We started the morning with a light breakfast.

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Then we walked around the grounds for a little bit.

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The main lodge was spectacular, so inviting and lovely. There was a huge pool out in the back and an adjacent athletic club. Oh, and a full spa too. Annnd a bunch of hiking trails leading into the Deschutes National Forest which abutted the property.

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We didn’t have time for either but the FivePine Lodge also has a movie theater (Sisters Movie House) and brewery (Three Creeks Brewing) on the premises. We were actually the closest cabin to them. Isn’t this place awesome?!

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I never wanted to leave Sisters and have been actively trying to plan a way back as soon as possible.

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Shortly after leaving Sisters we entered the Deschutes National Forest. It was a gorgeous day, perfect for driving through such a stunning area.

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Not far into our drive we spotted the Mt. Washington Viewpoint and pulled over to snap some pictures.

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Because our route took us through the convergence of three National Forests (Deschutes, Mt. Hood, and Willamette) that are extremely mountainous and high in elevation (8,000 ft), we hit snow again. Of course. It wasn’t as bad as the snow in the days prior, thankfully.

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Through the mountain pass, about an hour and a half later, we stopped for some lunch (unexpectedly awesome roadside pizza, win!). Day 9 was our last driving day and we still had a lot of road to cover before getting to Portland.

About 2 hours later we stopped at one of our final must-see stops, Bob’s Red Mill Headquarters in Milwaukie, OR.

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Bob’s Red Mill began in 1978 when Bob Moore bought an old mill in Oregon City. Within a few months of ownership he began providing stone ground flours and cereal for his neighbors and other locals. The headquarters and whole grain store moved to Milwaukie in the 1980s after a fire destroyed the original location.

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In 2010, for his 81st birthday, Bob surprised all of his employees by giving them total ownership of Bob’s Red Mill through an Employee Share Ownership Program. Super cool.

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Bob’s Red Mill Natural Foods is one of the most prominent producers of natural and organic milled grain products in North America, billing itself as the “nation’s leading miller of diverse whole-grain foods.”

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Bob’s Red Mill produces over 400 products: primarily whole grains that are ground with 120 year old millstones, as well as beans, seeds, nuts, dried fruits, spices, and herbs.

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We didn’t buy anything from Bob’s Red Mill because we didn’t really have the room for bulk dried goods in our luggage. Fortunately Bob’s Red Mill products are available in Boston at our local Whole Foods, Stop & Shop, etc. It was awesome to come here though – next time we go to Portland we’re going to go back and take the tour (sadly we missed it on this trip).

A quick 20 minute drive later, we were finally in Portland, Oregon!

After a long morning and afternoon of driving, John and I were ready to get up on our feet so our first stop in Portland was Macleay Park.

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So pretty, right? We walked the trail for about 20 minutes until it started pouring (that’s Portland for ya). Back to the car!

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We spent the rest of the afternoon shopping instead. One shop we visited (and adored) was Wanderlust, a ridiculously cute vintage shop.

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I also fell in love with Artemisia, an amazing DIY terrarium shop. I need one of these in Boston!

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On our last trip to Portland (almost exact a year ago for our first wedding anniversary), we had dinner at Screen Door. I got their famed fried chicken and John got something else. After tasting my chicken John would not stop talking about it. For an entire year! So he requested that we make a return trip so he could get his own. I was happy to oblige and got the exact same thing, they are doing fried chicken right at Screen Door!

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After dinner we headed up to the Northwest/Alphabet District in Portland. Northwest is residential but very green and lush. Alphabet within Northwest is a quaint little downtown with cute shops and amazing restaurants.

For years I had been hearing about the legendary ice cream shop in the Alphabet called Salt & Straw. They do funky artisinal flavors and are a self proclaimed farm-to-cone ice cream shop (only in Portland!). When I told John about the place he scoffed, he said the flavors sounded too wacky. With a line up including flavors like balsamic strawberry with cracked pepper, fermented pear and fudge, and smoked hefeweizen, I guess I couldn’t blame him. Maybe that’s why it took s us 3 years to get here.

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But after looking over the menu and getting to taste a bunch with the help of the incredible staff there, I think John was convinced. Just look at that happy face!

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We ended up getting the ice cream tasting flight because we couldn’t decide on anything. From left to right here, we had the olive oil, snickerdoodle, pear & blue cheese, and almond brittle ice creams. Hands down, the olive oil was my favorite – fruity, creamy, and light, just amazing. I need to figure out to make it at home!

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After a long day of driving in more crazy weather and eating our way through Portland, we were ready for bed. We headed to our hotel, our go-to place to stay while in Portland: the Heathman Hotel.

Stay tuned for Day 10, the final day of our trip!

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California to Oregon Road Trip | Day 8: Medford, Crater Lake, Bend, and Sisters, OR

Get ready for Day 8 of our California to Oregon road trip recap!

In May 2013 we drove 1,840 miles from San Diego, California to Portland, Oregon. Just two states but we covered such a significant part of the west coast which included over five national parks, three breweries, three factory tours, a visit to one of the best restaurants in the world, and countless other amazing things along the way. As you can see we avoided Los Angeles and the coast, which was done on purpose to diversify our California experience. Check out our route:

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We planned to end Day 7 in Medford, Oregon so we could wake up in our first destination of the day and not have to get on the road right away. Up first on the itinerary – a tour of the Harry and David factory, conveniently located in Medford!

Who doesn’t love the Harry and David company? Established in 1934, Harry and David, sons of founder Samuel Rosenberg, created a mail order catalog built up from their father’s Comice pear selling days.

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The tour met up at the Country Village Store and a little Harry and David minibus drove us up to the factory.

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The first stop – the Moose Munch production line! How awesome is Moose Munch? John is addicted to the stuff so I try to always buy him a few bags for his birthday or for the holidays. Can you tell how thrilled he is in this photo?

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We saw the whole process of how Moose Munch is made – first the butter, sugar, and flavorings are mixed in a big drum to make the signature caramel sauce and then plain popcorn is added.

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The caramel and popcorn are mixed together, then any add ins like nuts or candy are added, and then the whole batch is dumped out on to a belt to cool and to later be sent to packaging. So awesome!

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Following the Moose Munch area we got to see the rest of the candy production part of the factory. This included the truffle packing line and the room where they make chocolate covered cherries.

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We also saw where they assemble the sandwich cookies and where the Moose Munch goes for packaging.

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The last stop was the chocolate room where they have a huge enrober that is constantly covering cookies and candy in chocolate!

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We hopped back on the bus to go to the packaging and shipping facility. On the way we got to see the original pear orchards that Samuel Rosenberg purchased in 1910. They are still producing perfect Comice pears that are sold through the company.

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The packaging and shipping facility was enormous. It was fairly quiet during our tour as it was the off-season in May but during peak holiday season (October through January) this place is apparently a zoo. We walked along a catwalk (made with wood from the original Harry and David factory) that overlooked the packaging floor. The packaging area is also where they do all of their custom wrapping and hand bow making.

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We also saw the assembly line areas for the fruit of the month club boxes and gift baskets.

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The whole tour was a little over and hour and it was really informative. I already loved Harry and David’s products but now it will be a little bit more special when we enjoy them because we’ve seen how they are made and where they come from.

At the end of the tour each person was given a special box of treats: truffles and cookies. Yum!

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Of course we hit up the Country Village Store and bought a ton of Moose Munch.

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We grabbed some sandwiches before leaving Medford since we would be taking another drive up in to the mountains and weren’t sure if there would be a lunch place to stop at up there.

Onward! We had about a 2 hour drive ahead of us to get to Crater Lake. An hour or so into the drive we pulled over to check out the Rogue Gorge Viewpoint.

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This area was so quintessentially Oregon: lush, verdant, full of fresh, clean air, and just beautiful.

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Oh, and did I mention it was snowing? This continued our snow adventures from the night before and, little did we know, it was about to get worse.

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We snapped a few pictures and then ran back to the car – it was cold!

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As we drove toward Crater Lake the snow continued to fall, getting heavier as we drove higher in elevation (about 6,000 ft). Still, we continued on.

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When we arrived at the Crater Lake park entrance (about a 30 minute drive from the lake itself) the park ranger told us they expected 4-5 inches of snow that day. In an almost marriage ending rookie movie, I insisted we keep going up to the lake to which John vehemently disagreed. The roads were not plowed or salted so it was a scary drive up there. And with us fighting the whole way (real talk), it was not a high point of the trip.

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Oh, and once we got up there? We obviously couldn’t SEE anything because of the clouds and snow.

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Overall, that experience sucked and I should have known better. But at least we’re laughing about it now.

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Because the road conditions were so crappy we burned up a lot of time driving. When we finally got out of Crater Lake we realized we had 2 hours to drive to Bend, OR for our 4PM tour of the Deschutes Brewery. It was 2PM and we thought we’d miss the tour entirely. That didn’t add to our moods at all but somehow we got to Bend at 3:59PM and miraculously were allowed to hop on the 4PM tour. So thankfully, it all worked out. I’ve mentioned road tripping stress before and, while it isn’t pleasant, and you definitely don’t want to be squabbling with your spouse on vacation, it’s just something you have to deal with. Thankfully we got over it quickly and didn’t let it ruin our day (or trip).

On to the Deschutes Brewery tour!

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Beer making ingredients!

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We each got a hop leaf to tear open and check out/smell. I’m not a hops fan but this was really cool.

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The brewery itself isn’t huge but we toured the brew kettle room, hop room, fermenting area, and the bottling/packaging facility.

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And, of course, the tour ended in the taproom.

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I tried the Twilight Summer Ale (very tasty!) and the Imperial Smoked Porter. The Smoked Porter was incredible, it literally tasted like smoky BBQ!

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After the tour it was time for dinner. We figured ‘when in Rome,’ so we headed to the Deschutes Public House. The public house is about 10 minutes from the brewery and serves all their beers on tap and uses the spent grains to make bread, veggie burgers, and garnishes. There was candied spent barley on top of my salad and it was awesome!

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As we were leaving Bend we spied a food truck that we could not resist for dessert: Glazed and Amused Doughnuts.

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We got the zombie nuts (doughnut holes) and the Smores doughnut. All freshly made to order and super delicious! (Also coma inducing.)

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As the sun set we drove the last leg of our trip that day – 30 minutes to Sisters, OR.

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Our final destination for the night was the FivePine Lodge where we had our own private cabin.

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This was, hands down, my favorite place that we stayed on our trip. I fell in love with FivePine, and Sisters, immediately.

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The room was rustic but luxurious, with a huge tub and big fireplace, and the biggest comfiest bed I have ever laid on. Our trip was awesome up until this point, and I was really excited to continue on to Portland, but I seriously did not want to leave here. Everything was so peaceful and quaint.

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Stay tuned for Day 9 when we finally arrive in Portland!

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California to Oregon Road Trip | Day 7: Fairfield, Sacramento, & Chico, CA

Get ready for Day 7 of our California to Oregon road trip recap!

In May 2013 we drove 1,840 miles from San Diego, California to Portland, Oregon. Just two states but we covered such a significant part of the west coast which included over five national parks, three breweries, three factory tours, a visit to one of the best restaurants in the world, and countless other amazing things along the way. As you can see we avoided Los Angeles and the coast, which was done on purpose to diversify our California experience. Check out our route:

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Sadly our time in San Francisco had come to an end. Early on Day 7 we packed up the car and headed out. It felt so weird to be back on the road at first! We parked the car for 2 days in San Fran and barely touched it.

Instead of crossing the Golden Gate Bridge again we left by way of the Bay Bridge and headed 30 minutes west to Oakland for a quick breakfast. We stopped at Monkey Forest Road for tea and muffins. What a gorgeous place this was! (Too bad they have the stupidest name ever.)

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After breakfast we drove 40 minutes due north to Fairfield, California.

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What’s in Fairfield, you ask? Oh, just the Jelly Belly Factory tour!!!

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We got there early and had no problem getting on one of the first tours of the day. We weren’t allowed to take pictures on the tour but it was pretty standard – you walk around a catwalk that overlooks the factory floor, observing the various stages of jelly bean making below. The majority of the factory information is shared on TV screens via short historical/informational movies, not our guide which was odd to me. The guide basically just led us from TV to TV. Strange but still fun!

At the end of the tour we got a complimentary bag of jelly beans, score!

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The tour drops you off at the gift shop, of course.

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In the gift shop is the sample bar where you can try as many jelly bean flavors as you want. I tried the Dr. Pepper (natch), Candy Corn (yup, Jelly Belly makes candy corn!), and Baby Wipes (part of their Bean Boozled line of wacky flavors).

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The gift shop was vast and I picked up a bag of Belly Flops to send to my nephews. Belly Flops are Jelly Belly’s reject jelly beans that have messed up shapes, sizes, and colors but still taste perfectly fine.

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Our loot!

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Needless to say, John loved the Jelly Belly factory.

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We got back in the car and kept heading north. About 45 minutes later we stopped in Sacramento for lunch at the one and only, In-N-Out Burger.

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John was thrilled, me a little less so since I don’t eat red meat and all they serve is burgers. Thankfully I did some research and found that there is a whole secret In-N-Out menu that you can order from. So I got the grilled cheese (basically everything that’s on a burger, minus the burger). And it was actually really good!

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Super stuffed we hit the road again. Our next destination was Chico, CA, about an hour and a half away, for our 3PM reservation to tour the Sierra Nevada brewery. We arrived at about 1:50PM though and asked if they could squeeze us on to the 2PM tour. Unfortunately they couldn’t and we had a tough choice to make – kill an hour in Chico somehow or get back on the road. The thing about road tripping is that wasting driving time sucks. It’s all about staying on track with time and always moving towards your destination for the day. Anything that delays that is risky and can set back everything. We toiled for about 10 minutes, really torn on this one.

After a quick Yelp search I found something we could do to kill time and convinced John that we should stay in Chico. He agreed and we headed over to the Bird In Hand toy store to check out the National Yo-Yo Museum.

The museum features the largest public display of yo-yo’s and yo-yo memorabilia in the country. This includes “Big-Yo,” the 1982 Guinness Book of Worlds Records world’s largest working wood yo-yo weighing 256 lbs.

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The Museum features displays of yo-yos from the earliest commercial production in the 1920s and 1930s to the current performance designed yo-yo’s that are used by top competitors today.

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The Yo-Yo Museum ended up being an awesome stop. I love this type of roadside Americana. This is exactly what a road trip is all about: discovering a hidden gem that is fun, a little historical, a little bizarre, but totally unique.

Finally it was about 2:45PM so we headed back over to the Sierra Nevada Brewing Company for their brewery tour.

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Our tour guide started us off with Sierra Nevada’s signature Pale Ale as we watched a gorgeous introductory video to the company.

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The tour covered the entire complex and we got to see a ton. From the quality assurance lab, to the hop storage room, to the brew kettle room, to the bottling and packaging facility – the tour was fabulous and our guide was excellent, super knowledgeable, and clearly passionate about Sierra Nevada.

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While we were in the brew kettle room our guide gave us all a sample of wort. Wort is the liquid extracted from the mashing process; what remains after all of the ingredients steep together (water, barley, hops, etc.). Wort contains all of the sugars that will be fermented by the brewing yeast to produce alcohol so it is pre-yeast and pre-carbonation. So basically it just tasted like warm barley tea, if you can imagine that. This was a real treat for John and I – after 30+ brewery tours we have never sampled wort before and in fact, most brewers will tell you its garbage, that it shouldn’t be tasted. But I disagree. This is a critical part of brewing and was a really neat opportunity.

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Another cool thing we saw on the tour was Sierra Nevada’s solar panels. While walking from the main brewery building to the bottling and packaging facility, we passed by all of these on the roof. Sierra Nevada houses one of the largest privately owned solar arrays in the country. They have 10,573 panels that provide the brewery with roughly 20% of their energy needs. They also have hydrogen fuel cells, divert 99% of their waste away from landfills, use biodiesel from their restaurant as fuel, and have a hop field on their estate. Sierra Nevada has a strong commitment to sustainability and you could see that throughout the entire brewery.

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The brewery is huge and the tour took over an hour.

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The walls near the taproom are covered with amazing art and show the original packaging concept pieces.

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On to the taproom for a tasting!

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We tried 8 different kinds of Sierra Nevada beer.

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One of the most memorable was the Brandy Barrel Aged Belgian-Style Trippel. This beer is aged for five months in California brandy barrels which makes it taste more like brandy and less like beer. It was strong!

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My favorites were the Belgian-Style Abbey Saison and the Kellerweis. So tasty!

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We finished up at the brewery around 4:30PM and got back on the road. At 6PM we stopped in Redding, CA for dinner and ended up at Kobe Steak & Seafood, a teppanyaki/hibachi place. It was really fun – onion volcano!

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After dinner we had our longest stretch of driving of the day in front of us – 2.5 hours over the border into Medford, Oregon.

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The drive was gorgeous – taking us through Klamath National Forest, past the Shasta Lake region, and up and over Mount Shasta.

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Little did we realize that with mountains comes snow. I spent about 45 white knuckled minutes driving through almost white out conditions as we drove down the mountain. I could have kissed the ground when we finally got to our hotel for the night. You can’t tell how bad it was from this picture, but it was bad (John took the photo, not me!).

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Stay tuned for Day 8 where we begin the Oregon leg of the road trip (and encounter more snow)!

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California to Oregon Road Trip | Day 6: San Francisco

Get ready for Day 6 of our California to Oregon road trip recap!

In May 2013 we drove 1,840 miles from San Diego, California to Portland, Oregon. Just two states but we covered such a significant part of the west coast which included over five national parks, three breweries, three factory tours, a visit to one of the best restaurants in the world, and countless other amazing things along the way. As you can see we avoided Los Angeles and the coast, which was done on purpose to diversify our California experience. Check out our route:

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Our second full day in San Francisco began bright and early, and again at the Ferry Building.

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This time we went through the front doors which lead into a huge foyer with huge hanging historical placards. The Ferry Building was built in 1898 as a terminal for ferries traveling across the San Francisco Bay. In the 1950′s the building was adapted for office use after usage of the building decreased. In 2002 a full renovation of the building occurred and the marketplace in the first floor was created.

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John and I got breakfast at Cowgirl Creamery (I told you we’d go back).

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We then headed to the TCHO Chocolate Factory right next to the Ferry Building for a tour.

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We couldn’t take photos during the tour or tasting so my pictures are a bit limited.

The tour started with a comprehensive video about the company, where they source their cacao, and how they make chocolate in San Francisco.

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They passed around some cacao pods, beans, and a sample of cocoa butter.

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This is where I had to stash my camera here are a few pictures of the chocolate and interior of TCHO.

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The chocolate at TCHO was incredible: expertly made with care and love, perfect in its depth and robustness, full developed in its unique flavors. I am officially a fan and plan to buy a stash online soon.

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We bought a few small samples on the way out (the dark and fruity for him, the serious milk chocolate for her).

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We took a trek back to the Mission district to get the highest rated burrito on Yelp. Too bad it was utter garbage, worst burrito I’ve ever eaten. John managed to keep a smile on his face though!

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After the sad burritos we hustled over to the Anchor Brewing Company for their brewery tour.

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The tour was awesome – our guide was extremely knowledgeable and passionate about Anchor beer. The building was really amazing too – it definitely has that century-old brewery feel.

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We got to check out the fermentation room which was cool – of the 30+ breweries we’ve been to I’ve never seen a set up for fermentation like this.

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We also checked out the hop room and the storage tanks.

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I love Anchor’s packaging; there is so much amazing detail in their labels.

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After the tour it was back to the tap room for some free samples.

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We sampled the Anchor Steam, Liberty Ale, and California Lager.

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After the brewery tour we took a really long, hot bus ride back to our hotel. We were in need of some relaxing after such a busy day so far so we vegged for a couple hours.

At 6ish we grabbed the car and headed downtown to Tyler Florence’s Wayfare Tavern for dinner.

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In addition to The French Laundry I was also really excited about eating at Wayfare on our trip. I’ve been hearing about it for years and couldn’t wait to go.

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For starters the drinks and popovers were amazing. The iced tea I ordered had lemon granita ice cubes in it. I loved it so much I immediately made my own version when we got home from our trip (I’ll share the recipe soon!). It also made me want to make popovers ASAP too.

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I got the butter lettuce salad to start and it was exquisite: fresh butter lettuce, avocado, and grapefruit with the lightest, most delicate dressing. For dinner I had the chicken paillard – the chicken was cooked perfectly and the turnips and mushrooms paired beautifully with the earthiness of the dish.

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For dessert I had to get the mint chocolate chip ice cream dessert (decked out with local TCHO chocolate). We also received a complimentary tasting of the cinnamon coffee cake which was so yummy.

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Stuffed is not the word to describe how we felt when we left but it didn’t stop us from making one last stop to end our time in San Francisco.

We hit the road and headed over the Golden Gate Bridge one more time.

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The first stop was Fort Baker to check out the bay views of the Golden Gate Bridge.

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I took this panorama too!

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After freezing our butts off down there we drove all the way back up to the Marin Headlands.

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It’s pretty cool because you can see down to Fort Baker from up in the Marin Headlands. The view was unreal.

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The views of the bridge were incredible, I am so glad we made the time to drive up here and check these two places out.

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Stay tuned for Day 7 where we explore northern California and cross into Oregon in the snow!

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California to Oregon Road Trip | Day 5: San Francisco

Get ready for Day 5 of our California to Oregon road trip recap!

In May 2013 we drove 1,840 miles from San Diego, California to Portland, Oregon. Just two states but we covered such a significant part of the west coast which included over five national parks, three breweries, three factory tours, a visit to one of the best restaurants in the world, and countless other amazing things along the way. As you can see we avoided Los Angeles and the coast, which was done on purpose to diversify our California experience. Check out our route:

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Day 5 began our two full day stay in San Francisco. Normally on a road trip we are just passing through in any given place, even in the bigger cities, so having two full days in San Fran was really exciting. It gave us a break from driving and the road, and allowed us to fully explore this awesome city.

Up first – Alcatraz! We reserved tickets for the first tour of the day and took the Alcatraz Cruises ferry to the island. The views of the San Francisco skyline from the boat were awesome.

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And off in the distance, the Golden Gate Bridge with the last bit of morning fog rolling out.

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Alcatraz from the ferry:

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The location of Alcatraz is, of course, strategic for many reasons but it’s so cool that it’s in the bay because the views are amazing.

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There are many buildings on the island (old and new, administrative and residences) but the actual prison is the building at the very top of the island with the lighthouse coming up out of it.

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Welcome to The Rock! Early settlers and explorers referenced the island as The Rock simply because that’s what it was. They didn’t pay much attention to it since it was resource-less and they couldn’t easily quarry the rock there. Over time the nickname took on multiple meanings but originally, it was called a rock because it was a rock.

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Alcatraz has a long and extremely interesting history. In addition to being a famous prison it was also a military fortification, was taken over by American Indians for a time, and is now a nature preserve.

During the military garrison days (1853 to mid-1900′s), Alcatraz served as a defensive base in the bay.

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A model of Military Point Alcatraz, 1866–1868:

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From 1969 to 1971 Alcatraz was taken over by Native American activists who occupied the island to protest federal policies related to American Indians. They demanded reparation for the many treaties broken by the US government and for the lands which were taken from many Native American tribes. As a result, the U.S. government eventually returned unused land to the Taos, Yakama, Navajo and Washoe tribes. The occupation ended on June 11, 1971.

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More recently, Alcatraz has become a nature preserve. It’s a sanctuary for thousands of nesting seabirds and is home to some beautiful flora as well. Gardens on Alcatraz were originally planted by members of the military and have been restored by local nature conservancies.

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How cute are these goslings we saw?!

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In 1972 Alcatraz became a national recreation area and received designation as a National Historic Landmark in 1986.

The thing I found the most amazing about Alcatraz is that despite it’s long and storied past, you can still see the remnants each individual piece of the island’s history to this day. It’s pretty amazing that it has all been preserved and that the history of the island has been told for this long.

But on to the prison! Since the prison itself is at the top of the island you have to walk about a quarter mile uphill to get to it. You pass many of the old administrative military buildings and gorgeous gardens as you go.

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Here’s a pretty good view of the hairpin turn leading from the bottom of the island to the top of the island:

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The US Disciplinary Barracks on Alcatraz were acquired by the US Department of Justice on October 12, 1933 and the island became a federal prison in August 1934.

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There was a self guided tour that took about an hour that led us through the entire prison.

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The solitary confinement area was pretty ominous. The guided tour narration suggested standing inside one of the cells for a few minutes but I couldn’t step foot in there. Too creepy!

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We also toured through the prison library.

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And saw some exhibits about the inmates and life inside the prison.

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While it was in use, some of the most famous criminals held were Al Capone, Robert Franklin Stroud, George “Machine Gun” Kelly, Bumpy Johnson, Mickey Cohen, Arthur R. “Doc” Barker, and James “Whitey” Bulger. (Whitey Bulger is from our neighborhood, have I mentioned that before?)

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Due to increased operating costs and salt water erosion, the Alcatraz prison closed on March 21, 1963. During its 29 years of operation, the penitentiary claimed that no prisoner successfully escaped.

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The tour led us outside at the top of the island and the views of San Francisco from that vantage point were also incredible:

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After the tour we went through the gift shop and bought a bunch of souvenirs. It was kind of cool to see the all the movies made about Alcatraz over the years.

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The ferry ride back to San Francisco was quick and so nice. The weather in San Fran was simply lovely – high 60s, not a cloud in the sky, light breeze. Just perfection.

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We got another set of great skyline views on the ferry ride back as well.

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Back on land, we headed to the Ferry Building.

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I didn’t expect too much in terms of the eateries in the Ferry Building since I assumed they would have that kind of dumbed down mass tourist appeal but I was totally and completely wrong on that. They have so many vendors doing amazing, unique, and very niche things with their food. I was extremely impressed.

John wanted to stop immediately at Boccalone (owned by Chris Cosentino) for a meat cone.

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We then got lunch proper at Prather Ranch Meat Company. My grilled pork loin sandwich was super good.

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After lunch we walked around and checked out all the vendors at the Ferry Building.

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There was so much to see and do in here! Much like Fanueil Hall here in Boston.

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Cowgirl Creamery teased us with all of their yummy looking cheeses but we planned to come back the next day.

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Our final stop in the Ferry Building was Miette, the french inspired patisserie.

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It’s so cute and feminine! I love Miette, I’ve been following them and their cookbook for years.

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We got a little afternoon treat – how could we resist?

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After that super busy morning and early afternoon we headed back to our hotel for some downtime. We thought we’d do some laundry while we recharged but the hotel didn’t have a washer/dryer. Ugh! So we ended up walking a few blocks to the local laundromat and doing a few loads of laundry there. Not the most glamorous activity but totally necessary on a road trip!

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A few hours later we were looking to get back out and explore San Francisco. We headed over to the Mission district and walked around a bit.

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Overall the Mission wasn’t horrible but we thought it was a little shady with a lot of unsavory characters lurking around. Not an area we’d go back to (except we did the next day, kinda by accident). The architecture was really pretty though.

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After that it was dinnertime! We headed to Seven Hills restaurant in the Nob Hill neighborhood. The meal was perfection. I had the turkey meatballs to start and they were, without question, the best meatballs I have ever had. They were served with garlic bread that was so delicious, I could eat like 8 loaves of the stuff. For dinner I had the penne with chicken bolognese which was equally amazing. I don’t eat red meat and was extremely impressed that the offerings at Seven Hills had so much (unbelievably tasty) white meat options. Usually I have to pass on meatballs and bolognese but I got to have both! For dessert we had the cookies and cream sundae which was just over the top good, of course.

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Totally stuffed, we walked back to the hotel to crash for the night. It’s kind of difficult to walk these mega insane San Francisco hills when you are full of delicious Italian food!

Check this out. I took this photo on top of one hill looking over to another. If you look closely you can make out the crest of the other hill in the distance. Isn’t that insane? My poor quads.

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Stay tuned for Day 6, our second full day in San Francisco!

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