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.

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

“When we arrived at the booth there were two parties in front of us. One was having trouble with chair rentals. There was only one employee and she was pretty laid back. My the time we got our kayaks we lost about 30 minutes of…”

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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

“This was a fun experience even if you aren’t a swimmer. I can recall the names of the crew, but they were great. My partner and friend said they didn’t see a lot of fish where we were though. The food was good, also.”

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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

“I wanted to see Anguilla while we were in St. Maarten. You don’t go into towns or anything but visiting the beaches and swimming in the water was perfect for me! The water was a little choppy as a hurricane had passed north a few…”

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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

“Ensure your tour operator knows what boat you are on as ship time and local time were different for us - our cruise gangway down was 8:30am which was 9:30 local time and same time of our departure. They confirmed they would wait. Read more”

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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 the best part of our vacation. My husband and son were celebrating their birthdays and they sang my praises all the way home for booking this for them. Ashton was AMAZING! He was entertaining, knowledgeable, resourceful and fun! I was sad as we…”

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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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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

“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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13.Mambo Sail Catamaran to Rendezvous Bay Anguilla

Discover the beauty of Anguilla with a full-day sailing trip on Mambo Catamaran, featuring stunning beaches, delicious onboard lunch, and snorkeling.

★ 4.5

“The service was great, and the crew always made sure they had drinks in your hand, whether it be rum punch, wine, beer, soda or fruit punch. We were told from the beginning that the ride to Anguilla would be choppy (as is expected sinRead…”

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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.