The Caribbean · ANGUILLA TOURS
The 9 anguilla tours below are ordered by how consistently travellers rate them. Price, duration and the one thing to check before you commit sit on every entry.
Join Billy Bones for a seven-hour powerboat trip from Simpson Bay to Anguilla. Expect beach time at Sandy Island, Little Bay, Shoal Bay, and Meads Bay, with snorkeling gear, sandwiches, fruit, chips, and an open bar included. Captains such as Sammy, Junior, Lucas, Noah, and Miguel are praised for friendly, careful service.
“We had a good experience on the water. We got to see a number of different beaches. It was a nice experience.”
Spend about eight hours aboard a catamaran from Bobby’s Marina, sailing past Simpson Bay to Prickly Pear and Meads Bay in Anguilla. You’ll get snorkel gear, sandwiches, a barbecue lunch, an open bar, and Champagne at sunset. Crew names vary, but past trips have featured JP, Jasper, Tamara, Tyrell, and Captain Kay.
“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, taking care of thRead more”
Sail from Simpson Bay to Anguilla aboard Boomerang’s catamaran for about eight hours. You’ll visit Little Bay, Shoal Bay, Prickly Pear Cays, and Meads Bay, with snorkeling gear, paddleboards, floaties, an open bar, and BBQ lunch included. First mate Angelo has even been known to retrieve a dropped pair of sunglasses.
“Wonderful day snorkeling in Anguilla. We went to 4 different spots, every one a little different. The crew was attentive and professional. Thanks!”
Spend about seven hours crossing from St. Maarten to Anguilla by speedboat, with stops at Sandy Island, Little Bay, Shoal Bay, and Meads Bay. Your crew handles the route, snorkeling gear, floating devices, sandwiches, and open bar. Captains such as Sammy, Lucas, Nico, and Junior may lead the boat, but names vary by departure.
“Had an amazing day despite the bad weather. The beaches were beautiful and the snorkeling was great. Lucas always made sure we had a drink in our hands whether we were on or off the boat.”
Take a six-hour shared speedboat from Simpson Bay to Anguilla with stops at Sandy Island, Little Bay, Meads Bay, and Rendezvous Bay. Your crew handles the route, drinks, snorkeling gear, and French sandwiches. Captains such as Anthony, Ashton, Pascal, Alex, and Elias have earned praise for friendly service and careful boat handling.
“It is a nice experience. There is not a lot of food offered so come with a meal in your system. A full day in the sun.”
Board Tradition at Sandy Ground for a six-hour sail to the Prickly Pear Cays. You’ll get a safety briefing and a short tale of the boat’s cargo-trading and rum-smuggling past, then snorkel, swim, relax on the beach, and eat lobster lunch. Snorkel gear, beach chairs, lunch, snacks, and an open bar are included.
“Definitely take this tour as the boat, captain, mate, and crew were beyond professional, friendly, knowledgeable, safe, clean, etc. can’t say enough good things about it. Grilled lobster lunch was great too! And the cookies!”
Join Deb and the crew of Tradition Sailing Charters at 4:30 pm in Sandy Ground for a 2.5-hour sunset sail. You will cruise between Crocus Bay and Little Bay aboard a historic wooden rum-smuggling boat, with champagne cocktails, an open bar, soft drinks, water, and house-made hors d'oeuvres included. The boat carries no more than 12 people.
“Amazing service. Excellent drinks — started with passion fruit and mandarin vodka with Cointreau served in a brown sugar rimmed flute. Delicious rum punch? Of course! Beer and wine? Yes. Water and soda too. Food was a well-curated Read more”
Captain Sam takes your private group from Cole Bay to Anguilla by speedboat, with time for snorkeling, beach stops, and lunch. Your route can change with the weather and your interests. Drinks and gear are included, but bring a passport and US$35 in cash for clearance fees.
“Sam was an awesome guide. He offered to take us anywhere we wished in the area but we deferred to him and he had a great itinerary in mind. We hit all the nice spots on the island, had a reserved table on Pinel for lunch and some decent snorkel spots. I highly recommend them for anyone who can afford a private tour.”
Board Tradition at Sandy Ground for a relaxed 3-hour sail with Captain Deb and Laurie’s attentive crew. Learn the story of this 1978 West Indian cargo sloop, help raise the sails, then snorkel Little Bay among turtles and stingrays. Towels, swim aids, snorkel gear, and alcoholic and nonalcoholic drinks are included.
“It was a great way to spend time in Anguilla. Sailing in a boat with such rich history was a plus. The owners put great pride in hosting the adventure. The amazing lunch, drinks and service were top notch.”
Pick a reef, a river or a rum shop.
