Portland, Maine had been on our travel list for a while, so when we had a wedding to attend there, we knew we had to make the most of our four days in the city. What started as a wedding weekend quickly turned into a mini-Portland vacation filled with lobster rolls, breweries, cocktails, lighthouses, a harbor cruise and, of course, a food tour.
We flew direct from MSP to Portland on Friday, grabbed our rental car and headed to our Airbnb in the Parkside neighborhood. After dropping our bags, we immediately walked over to Bayside American Cafe for lunch. Naturally, I had to start the trip with a lobster roll. From there, we drove up to Bowdoinham for the wedding welcome party, making an important stop at Maine Beer Company along the way. After the party, Ryan and I headed back to Portland and walked over to Bramhall, a speakeasy in our neighborhood, for a few cocktails before calling it a night.
Saturday morning started with, you guessed it, another lobster roll. We drove to Becky’s Diner, where I ordered the lobster roll and clam chowder. The wait was long, but it was absolutely worth it. After breakfast, we headed back to Bowdoinham for the wedding, stopping at Mast Landing Brewing Company for a few pre-wedding drinks.
Sunday was our first real opportunity to explore Portland. We took it easy that morning before heading out on the Harbor Lights and Sights Cruise with Portland Discovery. I highly recommend this cruise if you’re visiting Portland. It’s a great way to get out on the water, see the city from a different perspective, check out lighthouses and spot seals. The cruise is narrated, so you also get plenty of information about what you’re seeing along the way.
After the cruise, we wandered around the wharf area and did a little shopping before grabbing an early dinner at The Honey Paw. And yes, I got another lobster roll. That evening, Ryan and I walked over to LFK Drink for a few cocktails.
Monday was our last full day, and we saved one of our favorite activities for the end: the Maine Day Ventures Maine Food Tour. If you know us, you know we LOVE food tours, and we always recommend doing one early in a trip. You inevitably learn something about the city that helps you plan the rest of your visit. This three-hour tour included five stops around Portland’s wharf area, with everything from fish tacos and chowder to lobster rolls, truffles and gelato. Come hungry!
After the tour, we continued our food and drink adventure with drinks and oysters at Boone’s in the wharf, followed by a lobster roll flight at Luke’s Lobster on the pier. We then took an Uber to Belleflower Brewing and Apres, which is a great little brewery district and an easy ride from the wharf.
We squeezed in one final cocktail at Independent Ice Co., which I highly recommend if you’re into whiskey, before ending our trip with dinner at Street & Co. Be sure to make reservations ahead of time!
Four days was nowhere near enough time to experience Portland, Maine. Between the food, breweries, waterfront, neighborhoods and all the places we didn’t have time to visit, we left already planning our return. If our first trip was any indication, Portland is a city we’re going to have to revisit, and next time, we’re staying longer.
If you’re interested in seeing more, I have our whole trip saved on a highlight on Instagram called Maine ’26.
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