Top 8 Boston Drinks Tours

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

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

Spend about 13 hours traveling from Boston to Martha’s Vineyard by minibus and ferry. Visit Oak Bluffs, Edgartown, Gay Head Cliffs, and Aquinnah, then choose three hours with a local guide such as Tom or Anthony, or explore independently. Hotel pickup, snacks, ferry tickets, and island discounts are included.

“It was convenient and organized. Johnny Boston picked us up from the hotel and is knowledgeable and witty it made the 2-1/2 hour trip to Cape Cod not boring at all. From Cape Cod we rode the ferry Nantucket for about 30 mins and a local guide Tom was already there waiting. Tom grew up there and knows the history by heart. It’s our first time and I’m glad I took the optional island tour. This is the highlight of our trip and my husband and I really enjoyed it. Thank you New England Tours for making it happen. I give this company 5 star rating. Don’t hesitate. Sign up…”

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2.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 round-trip boat tickets included. You get about six hours on the island, either independently or with a three-hour add-on tour. Drivers such as Rory, Keith, Matt, and Jimmy are known for lively local history, while the island tour varies by guide and vehicle.

“This was our 1st of 3 Excursions with Matt. I have never been on a more brilliantly lead Excursion. Matt is the best and knows his history. Would 100% do it again.”

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

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

Walk Boston’s North End with guides such as Pat, Sarah, Deuce, or Gabrielle, stopping for four desserts, three cocktails, and local history. You’ll skip long pastry-shop lines, compare rival cannoli, visit Paul Revere’s House and Old North Church, and cover about 1.5 miles in two to two and a half hours.

“Our group had the luck & pleasure of the expertise of lovely, entertaining & intelligent Gabrielle(a). She was witty & truly a great tour guide. This tour gives you an unexpected informative tour with features of the Northend few of us probably know. It was a marvelous take and thats all I'm going to say.”

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4.Boston: Harbor Champagne Sunset Sail from Rowes Wharf

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

Spend two hours aboard Schooner Adirondack III or IV, sailing from Rowes Wharf past the Boston Fish Pier, Castle Island, Fan Pier, the Navy Yard, and the Inner Harbor Islands. The crew, including guides such as Steve and Therese on some departures, shares local stories while you enjoy sunset views. Drinks are sold onboard, and you may bring a picnic.

“The crew was fun and amazing at answering our layman's questions about sailing.”

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5.Signature Boston Guided Brewery Tour with snack

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

Spend about three hours visiting Boston-area breweries by bus, with up to 16 beer samples, brewery equipment, brewing stories, and a snack. Routes may include Night Shift, Dorchester, Winter Hill, Samuel Adams, or Downeast Cider House. Guides such as Adrian, Travis, Andy, and Raj are known for mixing beer lessons with plenty of humor.

“The tour guide was phenomenal his beer knowledge was very interesting and made the tour memorable. A+++”

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6.Boston Historic Taverns Tour with Tastings and Ferry

★★★★★★★★★★5.0 · 156 reviews · 3 hours 30 minutes (approx.) · from $129

Start at Modern Pastry in Boston’s North End, then walk through Revolutionary-era sites, cross Boston Harbor by public ferry, and stop at two historic taverns for drinks and snacks. A guide such as Big Al or Alvin brings the stories to life. The 3.5-hour tour ends with a cannoli.

“Big Al was soo knowledgeable and funny..Loved it He was great with going at our pace,so we never felt rushed or too tired.”

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7.Boston: Martha’s Vineyard Day Trip with Optional Island Tour

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

Travel from Boston by comfortable minibus to Woods Hole, cross by ferry to Martha’s Vineyard, then explore at your own pace or add a three-hour island tour. Guides such as Keith, Matt, Rory, Harry, and Matthew provide local history, Boston context, and practical tips. Expect scenic views, shopping, beaches, and limited time.

“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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8.Boston Seafood Private Tasting Tour

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

Spend about 2.5 hours walking Boston’s Seaport and tasting locally sourced seafood. Your guide may serve lobster rolls, clam chowder, fried oysters, quahogs, scallops, or crab cake, while sharing stories about the waterfront and Boston Tea Party site. Guides such as Tim, Nabil, Molly, and Lucy have earned strong praise for their warm, lively commentary.

“Tim was such a lovely guy and the food that I tried tosay was amazing. Although it was super chilly I still had a great time.”

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