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

“Jad & Jr gave us an excellent tour of Anguilla yesterday. My husband and I use this company in 2022 as well. You can’t go wrong with Billy Bones tours. The guides are well-versed on the island, take precautions and ensure safety, and make sure…”

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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

“Fantastic adventure. Emmensly enjoyed the sights, sounds and professionalism of the crew!! For a day to relax and catch the breeze, this is the day trip you've always wished for.”

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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

“The crew was amazing. There was a group of 6 of us. And we could not have asked for better weather, atmosphere, and fun. It was more than we expected and will definitely do it again.”

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5.Boomerangs Best of Anguilla: Swim with Turtles Adventure

Experience a full day of snorkeling, beach hopping, and delicious Caribbean cuisine on a stylish catamaran tour around Anguilla from St. Maarten.

★ 5.0

“Awesome trip!! The 4 stops in Anguilla for snorkeling and swimming were picture perfect. We were in water that was turquoise blue and crystal clear. The captain and crew made sure everyone was safe and the open bar and Caribbean luRead more”

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6.Anguilla – Discovery Speed Boat tour

Experience the best of Anguilla with a 7-hour speed boat tour from St. Maarten. Snorkel, relax, and explore secluded beaches with all-day drinks and lunch included.

★ 5.0

“We had a great time on our trip to Anguilla! Miguel and Coco were awesome!! Our safety is a priority to the crew as well as making sure we were all comfortable and having a great time! I even forgot that I couldn't swim for…”

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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

“The best excursion I’ve been on! Boy and Dona feel like friends by the end. The 2 of them were so knowledgeable and safe, yet super fun and laid back like it should be. They both knew so much about the island and they made…”

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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

“This was a wonderful experience. We were in town on a cruise stop. We were picked up right by the port sign. Communication with the operator was excellent. We had a great day away from the hustle and bustle. Would 100% book this again.”

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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

“Etienne was a fantastic captain, tour guide, bartender, local historian. Everyone on our trip said this was the best day of our vacation! We could not have asked for a better day.”

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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

“Was truly amazing! Sam was so nice and took us to some incredible beaches. Honestly, it's a must do in St. Martin...worth every last penny.”

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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

“Junior and coco made this experience exceptionally fun and safe. The expertise they give to the customers was great. I was able to overcome some fears I had. Thank you for a great 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

“⭐️⭐️⭐️⭐️⭐️ A Truly Unforgettable Sunset Sail with Yes Darling Charter Yacht! Our experience with Yes Darling Charter Yacht was nothing short of spectacular! We went on a sunset sail, and it turned out to be one of the absolute hiRead more”

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More Anguilla Day Trips

Explore St Maarten

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