If you’re looking for charming cobblestone streets, sailboats, seafood, and breweries stop what you’re doing and book the trip to Maine. Whether you have a week or just a few days, Maine will not disappoint you. If you’ve been following me for awhile, I think you know that I’m not a huge planner. I love to arrive with a handful of ideas and let the destination take me the rest of the way and that’s exactly what we did . If you are more of a Type A person, this itinerary will still help guide you in your research and planning process!

DAY 1

Fly into the Portland International Jetway and jump in an Uber to meet your Outdoorsy host (Ubers in Portland are cheaper compared to cities like Atlanta, Minneapolis, L.A., New York, etc. so that’s a plus)! Once you arrive and get settled into your van (or hotel room if you’re gonna go that route), head to Old Port and start exploring!

Old Port has European charm in the best way. You’re gonna want to spend a lot of time here diving in and out of shops, trying local brews, and eating! We parked at the Park & Ride (because it was free) and it was an easy walk but I’ll warn you, the Park & Ride is a little sketchy so if you wanna park somewhere safer that’s an option too!

DAY 2

You’ll start with breakfast at Becky’s Diner on Commercial Ave. Make sure you get there early, we were there around 7ish and there was already a 15-30 minute wait. This place is exactly what you imagine when you think of an old-school diner. The food is great, the coffee is actually incredible (not your average diner coffee), and the service is unmatched.

After breakfast take a drive to the Portland Headlight and check out the lighthouse you think of when you think of Maine. This is a quick and easy drive from Becky’s and parking is pretty cheap, $5 for two hours.

Next, you’re gonna start your drive up the coast! Cute towns to stop in and check out include Freeport, Bath, and Boothbay! Wiscasset looked pretty cute too but when we drove through there was some sort of event going on and we couldn’t handle the traffic, we needed to get out😂

Depending on what time you get going on Day 2, Boothbay will either be your lunch or dinner stop. For us, it was lunch! We ate at Kaelers and sat outside so we could watch the boats come in and out of the harbor. Afterward, we explored the town. It’s another cute little touristy town with lots of shops, restaurants, bars, etc. so you won’t be bored.

Finally, we ended our day with a sunset cruise and it was one of my favorite things we did on the trip so don’t skip it! We saw lighthouses, islands, seals, and more boats, it was a really great time. Our only regret was not eating BEFORE we got on the boat… by the time we got back most kitchens were closed or closing soon so we ended up not having dinner on night 2. Be better than us😅

DAY 3

Breakfast! Depending on where you are, breakfast will vary. We drove back to Portland for breakfast because we wanted to try Dutch’s at the recommendation of our Outdoorsy host but unfortunately, after a bit of a wait, we learned that their computer system was completely down so we didn’t get to eat there.

We grabbed coffee at Dunkin (which if you know me you know that I HATE getting something on vacation that I can get at home but at this point, we didn’t have time to go somewhere and sit down) and headed back to the Portland Headlight to see it in sunshine! When we first visited, it was a really foggy day so we wanted to see it in different weather.

Finally, we did some last-minute shopping in Old Port before we dropped the van off and headed to the airport!