Top 11 Boston Drinks Tours

1.Boston to Martha’s Vineyard Day Trip with Optional Island Tour

★★★★★★★★★★4.5 · 3,162 reviews · 12 hours (approx.) · from $129Our pick

Ride from Boston to Falmouth in a small air-conditioned minibus, then sail to Martha’s Vineyard for 5.5 to 6 hours. Explore on your own or add a three-hour island tour with stops at Edgartown and Gay Head Light. Guides such as Johnny Boston, Tom, Elaine, and Jonathan are part of the experience.

“Nice scenery but it was boring The driver was ok personality wise but he drove too fast for us to see what he was talking about.”

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2.Boston Freedom Trail History Pub Crawl Small-Group Tour

★★★★★★★★★★5.0 · 996 reviews · 2 hours 15 minutes (approx.) · from $60Top rated

Meet your Boston guide at the Samuel Adams statue by Faneuil Hall for a 2-hour-15-minute pub crawl through the Freedom Trail area. Guides such as Maddie, Julie, Sam, Anna, and Arielle mix colonial and Revolutionary history with local beer, cider, cocktails, or nonalcoholic choices. Drinks are bought separately.

“A fun night with our guide Arielle! Not too much walking and some interesting locals drinks - but fun and facts about Boston’s history …. Was a great evening!”

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3.Martha’s Vineyard Day Trip with Optional Island Tour

★★★★★★★★★★4.6 · 573 reviews · 13 hours · from $129

Travel from Boston to Martha’s Vineyard by minibus and ferry, then choose three hours with a local guide or explore independently. Expect Oak Bluffs cottages, Edgartown shops, Gay Head Cliffs, Aquinnah Lighthouse, island tips, snacks, and about six hours on the island.

“Martha’s Vineyard is so beautiful. Great food and drinks too. We were lucky to have 2 wonderful guides. Jonathan picked us up from the hotel and drove us to Cape Cod to catch our ferry. He was witty and very knowledgeable. He even had snacks and water for us. Then we had Tom as our guide on the island. He also had a wonderful personality and was full of interesting stories. I highly recommend this trip with the island tour to everyone”

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4.Martha’s Vineyard Day Trip with Optional Island Tour from Boston

★★★★★★★★★★4.5 · 407 reviews · 13 hours (approx.) · from $130

Travel from Boston to Martha’s Vineyard by coach and ferry, with hotel pickup, live commentary, snacks, maps, and about six hours on the island. Choose free time in Oak Bluffs or add a three-hour island tour. Guides such as Keith, Rory, Matt, and Paul are praised for their local insight.

“Tour operator refused to pick us up and lied about the situation to Vistor. This is a dishonest and unprofessional company, don’t do business with them!!!”

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5.Cocktails & Cannoli: Boston’s North End Dessert Tour

★★★★★★★★★★5.0 · 309 reviews · 2 hours (approx.)

Walk Boston’s North End with Pat, Sarah, Deuce, or another local guide while sampling four desserts and three cocktails. You’ll compare cannoli from two famous pastry shops, visit Paul Revere’s House and Old North Church, and cover about 1.5 miles in two to two and a half hours.

“FANTASTIC! Exceeded expectations! Pat is full of information and made the tour so fun! You cannot go wrong with this one!”

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6.Harbor Champagne Sunset Sail from Rowes Wharf

★★★★★★★★★★4.8 · 299 reviews · 2 hours · from $82

Spend two hours aboard Schooner Adirondack III or IV, sailing from Rowes Wharf past Boston Fish Pier, Castle Island, the Navy Yard, and the Inner Harbor Islands. The crew, including hosts such as Steve and Therese, shares local stories while you enjoy a drink or picnic as the sun sets.

“We enjoyed our 4th of July sail. The crew did a great job catering to us all. My 11 year old son really enjoyed the sailing talk the crew gave. It was so fun!”

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7.History Pub Crawl Tour Along the Freedom Trail

★★★★★★★★★★4.9 · 279 reviews · 2 hours · from $48

Meet at the Samuel Adams statue by Faneuil Hall for a two-hour walking pub crawl with an English-speaking local guide. Visit four nearby Boston bars, buy local beers, and hear lively stories about taverns, the Boston Massacre, and beer’s role in American history.

“We had a great guide, Paxtin. He made sure everyone was happy. We had a great time even though it was raining. Nice group of people too.”

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8.Signature Boston Guided Brewery Tour with snack

★★★★★★★★★★5.0 · 271 reviews · 3 hours (approx.) · from $119

Spend about three hours visiting Boston-area breweries such as Night Shift, Dorchester Brewing, and Winter Hill. Your guide explains brewing, selects tastings, provides a snack, and handles transport from downtown. Guides including Adrian, Bill, Travis, and Raj have earned praise for making the tour fun and easy to follow.

“Travis was extremely knowledgeable about the tour and beer itself. The tour was fun and very enjoyable. Recommend Travis as your guide if you’re planning on a brew tour.”

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9.Martha’s Vineyard Day Trip with Optional Island Tour

★★★★★★★★★★4.6 · 123 reviews · from $120

Travel from Boston to Woods Hole by comfortable minibus, cross by ferry to Martha’s Vineyard, then explore on your own or add a 3-hour island tour. Guides such as Keith, Matt, Rory, and Harry share local history, town highlights, photo stops, and practical tips.

“I had a wonderful time on this day trip to Martha's Vineyard. The tour company was very accommodating. The tour guides were pleasant, knowledgeable, and entertaining. Everything went smoothly. I would definitely recommend New England Excursions.”

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10.Boston Seafood Private Tasting Tour

★★★★★★★★★★5.0 · 102 reviews · from $173

Spend 2½ hours walking from Independence Wharf toward the Rose Fitzgerald Kennedy Greenway, hearing Boston stories and sampling New England seafood. Your private guide may include lobster rolls, clam chowder, fried oysters, quahogs, crab cakes, or stuffed scallops, with guides such as Nabil, Tim, Molly, and Lucy praised for their local insight.

“Our tour guide was delightful, respectful, and clearly loves his work! It was a nice way to spend the afternoon learning things we never knew about Boston and eating some of our favorite seafood treats from the city.”

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11.2 Hour Historic Pub Crawl in Boston

★★★★★★★★★★5.0 · 45 reviews · 2 hours (approx.) · from $35Best value

Meet at Faneuil Hall Marketplace at 6:30 pm for a guided walk through several historic Boston taverns, including the Green Dragon and Dirty Nelly’s. Guides such as Cady, Tim, and Tony have led lively groups, while drinks are purchased separately. The evening ends at Bell in Hand, America’s oldest tavern.

“Just mehhh...nothing special. Had a great time with the new people/friends we made more than the tour itself.”

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