Trip Planning 101

John and I travel a lot. Whether it’s a local day trip Portsmouth or driving cross country, we love to go on adventures and plan well so we get the most out of our trip.

Right now we’re planning our honeymoon to Oregon which is awesome but is also proving to be time consuming and a little frustrating. We’re already caught up in the all too common downfalls of planning a trip:
– We’re not familiar at all with the area so we need to rely on great internet research to guide us.
– There is so much to do there, how can we possibly see it all?
– It’s gotta be budget friendly (even though we’re on our honeymoon).

Here is our Honeymoon Planning Command Center:

So I wrote up a little guide on trip planning 101. This translates for any length trip, any budget, and any destination.

Step 1: Hit the Net

Don’t know what to do at your destination? Want to find cool restaurants? Do you plan to do any side or day trips? How can you find fun things to do that may be quirky or offbeat?

You can find all of this information online with a little bit of effort and time. I’m not talking an afternoon, I’m talking hours of leg work here. Examples: it took us 9 months to plan our cross country road trip, we’ve already spent 2 weeks planning our honeymoon. It’s daunting, I know, but so is the interweb. You really need to put the time in to find what’s helpful and relevant among so much information.

So, where to start?

Location Basics: I always use Google Maps to orient me to a city or area. I then take my search to a specific city website or tourism website. These kind of sites usually have a ton of great information about things to do and see, places to visit, public transportation, event calendars, and local flavor.
Some good examples: Portland, OR, Cambridge, MA, SXSW.

Food & Hotels: I go to Yelp (obviously). You can search by city, neighborhood, address, price, cuisine, public transit accessibility, and caliber of review. Essentially you can use their flexible criteria to find any experience at any price point, pretty amazing.

Side Trips/Fun Activities: This really all depends on your own interests. When we plan a trip we always use the following sites: Factory Tour USA, Beer Mapping for brewery tours, Nerdy Day Trips, and Roadside America and Atlas Obscura for quirky must-sees.

For side/day trips review the map of your destination then examine the surrounding towns. Pick a few and start this process all over again just on a smaller scale. Examples: Come to Boston, do a day trip to Providence; Go to Vegas, do a day trip to the Hoover Dam; Visit San Diego, do a day trip to Santa Monica. Of course you’ll probably need a rental car for a day trip. I find that rentals are ridiculously cheap these days, especially if you search and book on or

Step 2: Map It Out

Once you have a list of everything you might possibly want to to on your trip add it all to one single Google Map. We do this for every trip we go on, big or small. We have our own archives if you ever want us to share but you can also search existing user created maps on Google which are extremely useful.

Google has a feature called My Maps where you can create new maps and plot all of your interest points. This tutorial will teach you everything you need to know to get started if you’ve never used this feature before.

Here is our Oregon Honeymoon Map, so far:

This covers the cities of Astoria and Portland, and our drive down the coast from one to the other.

Step 3: Divide and Conquer

Once you have your map all the dots will undoubtedly be overwhelming. This is where you must divide and conquer. I start by drawing lines across and through naturally occurring clusters. Then, depending on how many days or hours we have in one place, I try to knit together activities within the clusters to form an organized and commute-efficient day.

Once I have a day planned I then chart it all out in Excel to formulate a whole trip itinerary. If you’re only traveling for one day this might not be necessary but if you’re going somewhere for a week, like we are to Portland, this Trip Itinerary is essential.

Here’s our trip itinerary for Portland (so far):

That’s pretty much it! If you have any tips or tricks to share, or any additional ideas, please comment and let me know! Happy travels!

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.

10 thoughts

  1. Thank you for making me feel less self-conscious about planning in a similar way. I have been mocked in the past for my vacation planning spreadsheets – good to know i’m not alone!

  2. I’d suggest using TripIt, if you don’t already. It’s an amazing website that lets you organize your travels by combining everything into one master itinerary. And, for many reservations (most airlines, hotels, car rentals, OpenTable, etc.), you can email the reservation to them and they’ll automatically import it into your itinerary. Then the itinerary can sync up with your Google Calendar, iCal, Outlook, or other calendar program. I’ve found it invaluable for trips both short and long.

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