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Anguilla / Day Sails/Boat Trips

By Tess Hokin, James Henderson

A yacht trip to an isolated beach or an offshore island is the highlight of a visit to Anguilla for many visitors. There are quite a few uninhabited cays, with beach bars to which there are regular trips, including Sandy Island, Prickly Pear and Gorgeous Scilly Cay. Lunch and drinks are generally included in the excursions. There is just one sailing excursion, but there are a number of motorboat excursions that go to these islands as well. Each of the hotels has its own operator, so it is probably easiest to go through them.

Chocolat - a 35 ft Edel Catamaran, with 4 private cabins & 2 private heads which goes out with max 12 guests only and offers a 6 hour day sail including lunch and drinks. Trips include Prickly Pear and Sandy Island for swimming and snorkelling (gear not included), a sunset cruise and a round the island cruise. The boat is also available for private charter.

Prickly Pear Cay - lovely uninhabited cay with wonderful beaches and some good snorkeling. Popular stop for yachts and day trippers from St Martin. There are two beach bars serving food, one of which offers special packages to include snorkeling equipment, kayaks and sun loungers. Boats leave from Sandy Ground for the 15 minute trip.

Banana Boat Cruise to Prickly Pear - Sundays to Tuesdays departing from Johnno’s, Sandy Ground at 9am returning from Prickly Pear Island at 3pm. Includes open bar on board, snorkelling gear, beach chairs with umbrellas.

Sandy Island - a tiny desert island a couple of miles offshore, dotted with a couple of palms, beach bar which serves BBQ lunch and provides a free boat service from Sandy Ground. Occasional live music on Sunday afternoons. A great spot to chill out and snorkel. Bar closed Saturdays and mid August for 1 month, limited hours in the summer. Sandy Island is entirely made of sand and it has been known to be washed away in hurricanes, but gradually it sifts back.

Gorgeous Scilly Cay, Island Harbour - set on a small cay located off Island Harbour, reached by the free boat service which picks up guests for the short journey – just wave from the pier. Run by Eudoxie ‘Gorgeous’ Wallace, it is famous for its lobster lunch and strong rum-punches. On Wednesday and Sunday afternoons there is live music, closed Monday. Closed September-October.

There are also a number of charter companies such as Funtime Charters and Gotcha Garfield's Sea Tours, which you can hire to take you around to secluded beaches and offshore islands like Little Bay and Dog Island, or to simply tour the island, snorkel and have a cocktail. 

If like the idea of a glass bottom boat trip, take a tour of Shoal Bay's reef with Junior's Glass Bottom Boat and experience the excitement of snorkeling over the reef from the comfort of a canopy-covered boat.

To explore Anguilla by land, see our Things to Do and Places of Interest guides.

Browse Day Sails/Boat Trips on other islands

Anguilla | Antigua and Barbuda | Barbados | British Virgin Islands | Dominica | Dominican Republic | Grenada & Carriacou | Jamaica | Nevis | St Barthélemy | St Kitts | St Lucia | St Martin/St Maarten | St Vincent and the Grenadines | Tobago

Or read our other island guides

Anguilla | Antigua | Aruba | Bahamas | Barbados | Bermuda | Bonaire | British Virgin Islands | Cayman Islands | Cuba | Curacao | Dominica | Dominican Republic | Grenada and Carriacou | Guadeloupe | Haiti | Jamaica | Martinique | Montserrat | Nevis | Puerto Rico | Saba | St Barthélemy | St Eustatius | St Kitts | St Lucia | St Martin/St Maarten | St Vincent and the Grenadines | Tobago | Trinidad | Turks & Caicos Islands | US Virgin Islands

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Anguilla’s weather

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When to go and weather

Looking for inspiration?

  1. Try Cove Bay for one of the Caribbean's best white sand beaches
  2. Dine at the fantastic Blanchard's
  3. Stay at the beautiful Cap Juluca
  4. Play at the Temenos Golf Club, designed by Greg Norman
  5. Take a boat trip to the stunning unihabited Prickly Pear Cay

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