St Maarten

15 Best Anguilla Day Trips

The neighbor-island escapes: Anguilla getaway cruises to beaches that make St Maarten jealous, Prickly Pear’s sandbar day and Pinel Island by tandem kayak for the closer hop. Anguilla’s sand is the argument; the boat ride is twenty minutes of foreplay.

1.Anguilla Getaway Cruise

Discover Anguilla on a full-day powerboat tour from Sint Maarten, with beaches, snorkeling, delicious onboard lunch, and open bar — a lively, scenic island hop.

Most Popular★ 5.0

“This was NO CRUISE! This was a speed boat to the different beaches of Anguilla. Not what we expected. I do not recommend if you aren't a strong swimmer. The waters were rough and sometimes the boat wasn't able to get close to the shore.…”

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2.Pinel Island Adventure: Tandem Kayak Experience

Explore Pinel Island by kayak with this full-day rental from St Maarten. Enjoy stunning scenery, marine life, and flexible exploring at your own pace.

★ 5.0

“This was a wonderful adventure for my husband and myself. We battled the wind and waves to get out to Pinel Island. The hard work was worth a priceless day on any amazing beach, great snorkeling, and delicious food! The owner was very courteous and…”

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3.Ultimate Prickly Pear and Anguilla Experience

Experience a full day sailing from St. Maarten to Anguilla and Prickly Pear with snorkeling, delicious food, open bar, and sunset champagne toast.

★ 4.5

“Very good trip overall. We’ve been on this Eagle trip before and it was off the charts - Three islands and lots of food and drink going around with great music. The crew on this trip were so fun! They were all about your safety,…”

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4.Prickly Pear Catamaran Trip from St Maarten Including Lunch

Enjoy a full-day catamaran cruise from St. Maarten to Anguilla's Prickly Pear Cay, snorkeling, a buffet lunch, and island swimming for $135.

★ 4.5

“This was a lovely experience. The captain of the ship was delightful. He made us very comfortable and kept everyone informed and safe. The crew was terrific. . The boat was very clean. This was such a pleasant boat experience. The food was very very…”

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7.Speed Boat & Snorkeling Tour Pinel & Tintamarre Islands for CRUISE SHIP GUESTS

Discover St. Maarten’s best snorkeling and island sights on a small-group speedboat tour featuring Tintamarre, Pinel Island, marine life, and stunning views.

★ 5.0

“Our crew, Julian and Owen, were very welcoming. We saw turtles at Tintamarre, lots of fish at Creole Rock and our lunch at Lola’s was very delicious. Our crew did the best they could in the sudden change in weather. We had to navigate through…”

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8.Anguilla In Style

Experience Anguilla's best beaches and hidden gems on this 6-hour speedboat tour with guides who know how to make every moment memorable.

★ 5.0

“This was a very fun excursion. The captains were very nice and patient. I panicked getting into the ocean to snorkel and they were very helpful with calming me down so that I could enjoy my time in the ocean. You have plenty of time…”

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9.All-Inclusive Local Guided Pinel Island Tour

Discover the natural beauty of Pinel Island with an all-inclusive guided tour featuring snorkeling, hiking, wildlife encounters, and Caribbean cuisine.

★ 5.0

“We booked spur of the moment and we could not have made a better choice! My sister and I had an amazing time. We were treated like queens and Nick our tour guide went out of his way to make sure we had a fantastic…”

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10.Private Full-Day Cruise of St. Martin and Anguilla

Experience a private full-day cruise exploring St. Martin and Anguilla with customizable stops, snorkeling, and free drinks, led by expert guides.

★ 5.0

“This was the highlight of our two week vacation in St. Martin! We experienced such amazing beaches in this wonderful Anguilla tour. Jean-Claude was the BEST host and captain.... So very attentive and was very knowledgeable about the islands. 20 out of 10.”

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11.Private Speed Boat Charter to Anguilla

Discover Anguilla with a private speedboat, personalized itinerary, stunning beaches, snorkeling, and drinks—perfect for those seeking a tailored Caribbean adventure.

★ 5.0

“From sight seeing and snorkeling to eating and more sight seeing, Sam gave us a great overview of Anguilla and St Maarten and we had the most wonderful time.”

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12.Billy Bones Exclusive Private Charter to Anguilla

Experience a private speedboat tour from St. Maarten to Anguilla, visiting stunning beaches, snorkeling spots, and enjoying unlimited drinks with expert guides.

★ 5.0

“Capt Junior and 1st Mate Damian on Rum Rush 100%. The Aguilla tour was amazing. These two guys are very good. The island speaks for itself. Go to Billy's Bones, and request Capt Junior Gong and 1st Mate Damian if you want a good experience.”

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14.Yacht YES DARLING – Private Boat St Martin, St Barth & Anguilla

Experience Caribbean luxury with a private yacht cruise visiting St Martin, St Barth, and Anguilla. Enjoy stunning scenery, gourmet food, and personalized service.

★ 5.0

“We had a mother/daughter trip with a group of almost 20, and the Yes Darling Crew made our experience so wonderful! We had great drink service, and we enjoyed all of the destinations during our boat trip., We are all thankful for the gorgeous, fun-filled…”

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More Anguilla Day Trips

Explore St Maarten

Two nations, one island: jet blasts, catamarans and turtle bays.