California to Oregon Road Trip | Day 1: San Diego

Hold on to your hats, our latest road trip recap posts begin today! Here’s how it’s going to go down – I am going to break up each post by day (10 in all) which conveniently enough is also by location. That way they will be easy to look up or reference back to later. I will post once, maybe twice, per day for the next two weeks to get them all in. Enjoy!

To recap, 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:


Our journey began in Boston, obviously. A 5am bleary eyed cab ride brought us to Logan Airport where it finally set in – vacation! Our prior two road trips began in Massachusetts but this one felt different right away because we weren’t hitting the road from our house. The flight was quick thanks to JetBlue making a 6 hour flight as comfortable as possible (read: tv and snacks). We got to San Diego at 11AM PST and, after a tiny bit of confusion, picked up our rental car. Now it felt like a road trip!


Our first stop was to get bagel sandwiches at a little place we discovered when we were in San Diego back in December, and then we were off to Cabrillo National Monument.


The Visitors Center and Museum gave a good history lesson on the area. Juan Cabrillo, the first European to step foot on the west coast, landed at this spot in 1542 and began to explore what is now California. It was made a national monument to Cabrillo in 1913.


The drive to Cabrillo takes you through Point Loma which is home to several military installations including the Point Loma Naval Base (which is HUGE). The area is gorgeous and climbs up through the hills until you get to the monument…and this view overlooking the San Diego Bay and San Diego:


It was so gorgeous up there.


The views across the bay and over to San Diego were crystal clear.


Just across the way you could see the statue of Juan Cabrillo which we walked over to.



The Cabrillo National Monument area has some pretty typical Californian flora and fauna including the first cactus we saw:


But the most spectacular thing about Cabrillo is the tide pools. They are located down the hill and on the opposite side of the peninsula.


I was totally in my element here; I took about a million pictures.


The tide was in when we were there but it was still amazing. Such a peaceful place. The sound of crashing waves and seabirds is something I could listen to for hours.



John was pretty zenned out too.


The rock formations were fascinating. It’s so cool what ages of water and erosion will do, isn’t it?





Done exploring, we decided to head to our hotel in Coronado.


Coronado is connected to San Diego by the San Diego-Coronado Bridge.


It’s pretty awesome to drive over, the views are awesome. Where San Diego is a bustling city, Coronado has a quieter, more residential but resort-like feel to it.


We decided what better way to kick off our trip than to stay in the absolute best hotel in the area: the Hotel Del Coronado.


Hotel Del is a beachfront luxury resort that opened in 1888. It has hosted presidents, royalty, and celebrities, and has been named one of the best resorts in the world over and over again. Some Like It Hot was filmed here and it is also said that L. Frank Baum based his design for the Emerald City from the Wizard of Oz on the hotel.


In 1977 it was named a national historic landmark, understandably so.


John and I loved the elegant resort feel of The Del. We’d never stayed in a place like this and it was really something.


The grounds were immaculate too; everywhere we went was lush, green, and bursting with life.


Two of my favorite things on the grounds of Hotel Del were the herb garden used for all the resort restaurants and all the wild bunny rabbits running around.


In general, all of Coronado was simply lovely. This was the perfect place to begin our vacation!


After touring around the Hotel Del we decided to walk to downtown Coronado for some dinner. We went to Leroy’s Kitchen and Lounge which had excellent Yelp reviews.


It’s no wonder – their food was amazing. I had the quinoa fried rice (which I’ve since made at home and cannot wait to share the recipe with you!) and the grilled halibut. Both were fantastic!


After dinner we walked around downtown and then took a stroll on the beach behind the Hotel Del. It was a little overcast but the view was still pretty amazing.


As the sun was setting we were getting ready for our final activity of the night…


Smores on the beach!! Hotel Del offers all these amazing little add-ons when you stay there so John booked the Smores on the Beach package for us. Sweet, right? They set you up with a fire pit, chairs, and smores ingredients and let you hang out for two hours. We watched the sun set and the lights on the Del come up. It was super romantic and the perfect way to end our first day of vacation.


Stay tuned for Day 2 where we explore Joshua Tree National Park and Bakersfield, CA!

Author: Domestocrat

I'm a lady who enjoys photography, football, cooking, long drives with the windows down, This American Life, kettlecorn, hot yoga, pop punk, my nephews, my cat Reggie, and my home: Boston.

12 thoughts

  1. I love hearing about your roadtrips! Can’t wait for all of your recaps! San Diego looks awesome – I haven’t been since HS. I’ve always wanted to go back to Hotel Del Coronado as an adult. Amazing!

  2. We live in San Diego and are planning a similar road trip. We will skip the sights in SD since we live here, and focus more time in Oregon. Any tips or recommmendations are welcome!

  3. What a great road trip! San Diego is the perfect place to stop. I’ve heard there are many cute little shops and great restaurants to dine at. Definitely a good place to get out and stretch your legs.

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