8 Cape Cod & the Islands Tours That Repay the Ticket

1.Whale Watching Tour in Gloucester

★★★★★★★★★★5.0 · 4,460 reviews · 4 hours (approx.) · from $48Our pick

From Gloucester, you’ll ride the 115-foot Hurricane II to Stellwagen Bank National Marine Sanctuary, one of the world’s best whale-watching grounds. Naturalists explain the wildlife, while the galley sells hot meals, snacks, and drinks. Allow about four hours, arrive 45 minutes early, and prepare for open-sea conditions.

“It was a beautiful day to be on the water, and we saw many whales and learned tons from the captain and first guide.”

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

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

Travel from Boston to Falmouth in a 24-passenger minibus, then sail about 35 minutes to Martha’s Vineyard. Choose free time in Oak Bluffs or add a three-hour island tour with Edgartown, Aquinnah, Gay Head Light, and all six towns. Guides such as Johnny Boston, Tom, Elaine, and Jonathan are known for lively local commentary.

“Johnny Boston is the man! He made the trip to and from informative and easy. Martha’s Vineyard was amazing even though a bit chilly today. Thx again to Johnny and the team for an awesome experience.”

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3.Whale Watching Trips to Stellwagen Bank Marine Sanctuary. Guaranteed sightings!

★★★★★★★★★★5.0 · 2,135 reviews · 4 hours (approx.) · from $45Best value

From Gloucester, 7 Seas Whale Watch takes you 3.5 to 4 hours toward Stellwagen Bank Marine Sanctuary. A naturalist explains whale behavior while the captain searches for feeding pods. Expect a spacious boat, restroom, galley, open decks, and a real chance of seeing humpbacks, dolphins, spouts, breaches, and tail slaps.

“We really enjoyed this trip! It was a first time for us and will be a cherished memory for our family! The boat crew were wonderful and made the trip experience very informative and exciting.”

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4.#1 Best 3hr Martha’s Vineyard shared Island Tour from Oak Bluffs

★★★★★★★★★★4.5 · 1,439 reviews · 3 hours (approx.) · from $65

Ride in an air-conditioned van with up to 14 people and a local guide through Oak Bluffs, Edgartown, Vineyard Haven, and Aquinnah. You’ll see the Flying Horses Carousel, Gingerbread cottages, lighthouses, Jaws filming sites, and the colorful Aquinnah Cliffs, with a brief stop for photos and exploration.

“The giide was EXTREMELY knoweldgeable about all things Marthas Vineyard. The excursion itself was well worth it. The communication at the pickup site between variius companies was a bit of a mess, and ur ticket doesnt make clear which company u r with. So we got off on the wrong foot, but it worked itself out thankfully.”

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

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

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

“Great trip to Martha's Vineyard. I would definitely recommend it. Trip was well organised. Pick up on time.”

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

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

Start with hotel pickup and live commentary from guides such as Rory, Keith, Matt, or Jimmy, then ride through Cape Cod to Woods Hole. After the ferry to Oak Bluffs, choose six hours on your own or add a three-hour island tour. Expect a long day, useful transport, and limited time at each sight.

“Guides were very knowledgeable about not only Martha’s Vineyard but Boston as well. Great job Matt and Jimmy! Had a great time!”

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7.Boston to Plymouth Day-Trip including Quincy, Plimoth Patuxet and Mayflower II

★★★★★★★★★★5.0 · 407 reviews · 11 hours (approx.) · from $165

Travel from Boston in a small air-conditioned mini-coach with a guide such as Chris Fisher. Visit Plimoth Patuxet, Plymouth Rock, the Forefathers Monument, Quincy, Scituate Lighthouse, and Mayflower II. The day includes admission fees, snacks, bottled water, coastal scenery, and free time for lunch in Plymouth.

“Wonderful trip. Two separate entry fees included, no lines. Water bottle and snack provided, multiple potty stops, some quick stops, also lengthy stops at main sites. Loved it.”

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8.Best of Martha’s Vineyard 3 hour Full-Island Tour

★★★★★★★★★★4.5 · 406 reviews · 3 hours (approx.) · from $65

This three-hour minibus tour covers Martha’s Vineyard with guides such as Paul, John, Jim, and Harry, many of whom grew up on the island. You’ll visit Aquinnah Cliffs, Menemsha Public Beach, Oak Bluffs, and Edgartown, hear stories about Jaws and island life, and make two short stops for views, food, photos, and restrooms.

“Our tour guide was exceptional. He knew the island, more information and history than I will remember but we had driven around prior to our scheduled tour. So, it was more exciting to see the sites again and to know the history. Thank you.”

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