Top Portland Holidays

See a new vantage on Portland and the Maine coast—and enjoy a relaxing excursion out on the water—on this sailing tour. Make your own way to the Maine State Pier, and hop aboard a traditional, Maine-built windjammer. Once you set sail, soak up the sea breezes, look out for seals, and even take a turn at hoisting the sails or behind the ship’s wheel.

Taste your way through the Portland area’s craft alcohol scene with a 3.5-hour, small-group tour of two breweries and a meadery. Sample a flight of the brews on tap at Maine Beer Company, and get an insider’s perspective on the state's cutting-edge craft brewing. Enjoy a tasting at Rising Tide Brewing Co., in the heart of Portland’s East Bayside neighborhood, then try Maine Mead Works' dry brews. Kick off the evening with a fun, small group of fellow drinks lovers, and finish your tour at The Craft Beer Cellar.

Explore the lighthouses of the South Portland Greenbelt Pathway by bicycle with this guided tour. You'll visit Bug Light, Point Ledge Light, and Portland Head Light with a local guide. You'll also have the chance to stop at a local food truck for a lunch of lobster rolls before returning to your starting point.

Portland, Maine is regarded as one of the country’s top brewing capitals—and this tour will whisk you to three of its highlight breweries. With just a small group for company, you’ll explore local legends Shipyard Brewing, will visit one of the city’s newest breweries, and will stop by a traditional brewpub. You’ll also go behind-the-scenes and learn how beer is made, and will enjoy numerous bites and sips.

Board your boat, the Elizabeth Grace, near the Portland ferry terminal and cruise around Portland Harbor at sunset, when Casco Bay and the coast of southern Maine are the most romantic. See lighthouses, historic forts, and stray groups of swimming seals and enjoy local craft beer from the boat. As the sun sets, turn toward Portland to see the town light up before returning to harbor.

Brewery hop at brunch time with this fun daytime tour that takes visitors to some of Portland's best breweries! You'll start off at Bissel Brothers Brewing Company, known for their hoppy ales, before continuing on to Rising Tide Brewing, a husband-and-wife-owned operation, and on to Lone Pine Brewing Co. Although beer is what's on the menu for brunch, you'll get a breakfast-themed hand pie to soak up some of your libations.

Food lovers can explore Portland's historic Old Port independently, but to uncover the best places serving traditional local fare, you really need a guide to lead the way. Taste the best that Portland has to offer on this guided foodie walking tour, complete with stops at up to seven different eateries—and enough tastings to replace a meal. Along the way, your guide offers some stories about Portland's food scene, so you can get familiar with the local culinary stalwarts.

Go beyond the sights of Portland, Maine and take a day trip to Salem, Massachusetts. The town of Salem is known for its famous witch trials that took place in 1692. Learn about the history of Salem on a guided tour through the town and see several landmarks including the Salem Witch Museum, the memorial, and Phillips House. On your way to Salem, stop in Kennebunkport to explore the historic village.