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

“Had a great time experiencing all the beautiful beaches in Anguilla. The sandwiches were fresh and tasty. The drinks were plentiful...especially the Rum Punch. This is a don't miss day trip. The crew was friendly and knowledgeable.”

Check Availability →Read our full review →

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…”

Check Availability →Read our full review →

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 my second time visiting Sint Maarten and my second time on Qualiy Time! From the time we entered Bobby’s Marina til the time we returned , we enjoyed every moment! I was so excited to share this experience with friends and family who…”

Check Availability →Read our full review →

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.”

Check Availability →Read our full review →

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

“Great tour a time was had the staff were helpful and friendly the second helper was also a Dj made my experience a day I’ll never forget was my birthday 🎂 experienced so many other beaches I can’t swim I got a life jacket and…”

Check Availability →Read our full review →

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

“We had an excursion booked with Captain Bob that was cancelled last minute due to “health reasons” so imagine our surprise when we saw Captain Bob taking people out when we arrived at the dock. We booked last minute with Captain Read more”

Check Availability →Read our full review →

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…”

Check Availability →Read our full review →

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…”

Check Availability →Read our full review →

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.”

Check Availability →Read our full review →

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

“The requests for travel documents should be an easier process and preparation for this should have been specific at time of booking. It was not easy to communicate with Sam , and although email was where he was responding to, there Read more”

Check Availability →Read our full review →

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.”

Check Availability →Read our full review →

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…”

Check Availability →Read our full review →

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”

Check Availability →Read our full review →

More Anguilla Day Trips

Explore St Maarten

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