Anguilla Yacht Charters

An Anguilla yacht charter reaches one of the most exclusive cruising grounds in the Eastern Caribbean - a sixteen-mile island with more than thirty white-sand beaches and three uninhabited cays.

Anguilla has no cruise port, so most of the best anchorages can only be reached from the water. The beaches stay uncrowded even during peak season.

Most itineraries focus on the leeward islands - Shoal Bay, Meads Bay, Rendezvous Bay - with day runs out to Prickly Pear, Sandy Island, and Scilly Cay for snorkeling and lunch.

Nearby islands include St. Martin, which lies twelve miles south, and St. Barts, which is a comfortable sail beyond.

Why Charter a Yacht in Anguilla

A private crewed yacht is the only way to fully see Anguilla.

Several of the island's best beaches have no road access, and the offshore cays sit too far out for day boats from neighboring islands to reach.

With an anchored yacht, guests can step onto Sandy Island before the first ferry of the day, swim at Little Bay with the beach to themselves, and reach restaurants like Scilly Cay or Blanchards by tender straight from the anchorage.

A single week aboard can pair Anguilla with day sails to St. Martin and St. Barts.

Anguilla’s Best Beaches and Anchorages

Most of the working anchorages are located on the leeward coast.

Shoal Bay East runs two miles along the northern shore and is the island's signature white-sand beach.

Meads Bay is on the western coast and is where several of Anguilla's better-known beach restaurants are.

Rendezvous Bay is a long and sheltered strip, which opens south toward St. Martin across the channel.

Maundays Bay is a smaller crescent edged by the Cap Juluca resort. Barnes Bay is a good snorkeling site along its rocky points. Little Bay on the north coast is reached only by water.

The Offshore Cays: Prickly Pear, Sandy Island, and Scilly Cay

Anguilla has seven offshore cays, but the most popular ones are Prickly Pear, Sandy Island, and Scilly Cay.

Prickly Pear is a pair of uninhabited islets six miles northwest, surrounded by reef and shallow turquoise water, perfect for snorkeling.

Sandy Island is a single strip of sand with a beach bar, sitting alone in open water a mile off Road Bay. Scilly Cay lies off Island Harbour on the east coast and is known for its grilled lobster at a long-running open-air restaurant.

Things to Do on an Anguilla Yacht Charter

Beyond the beaches and cays, you can do watersports from the yacht or take in the island's food and music scene onshore.

Snorkeling and Diving in Anguilla

The protected reefs around Prickly Pear, Little Bay, and Shoal Bay Harbour hold healthy coral and reef fish, with seven designated marine parks across the island.

Divers reach wrecks and walls within short tender or yacht runs from the main anchorages.

Beach Bars, Dining, and Island Life

Anguilla is known as one of the strongest dining destinations in the Caribbean.

The range covers barefoot beach bars at Sandy Ground and Meads Bay, family-run grills on the cays, and several internationally recognized resort restaurants.

Day Trips to St. Martin and St. Barts

St. Martin is twelve miles south and offers the duty-free shopping and dining scene of Marigot and Philipsburg. St. Barts lies a longer but comfortable sail beyond, with the harbor at Gustavia a regular stop on weeklong routes.

Luxury Charter Yachts Available in Anguilla

Ritzy Yachts’ fleet covers four main categories. Sailing catamarans are well suited to the shallow waters around Anguilla's cays and remain the most popular choice for groups of up to 12 guests..

Motor yachts offer speed and range, useful for guests adding St. Martin and St. Barts to a single week.

Monohull sailing yachts suit traditional sailors.

Crewed superyachts above 100 feet are typically chartered on a plus-expenses basis with full crew, chef, and tender.

How to Get to Anguilla

Most Anguilla yacht charters begin on St. Martin. Guests fly into Princess Juliana International Airport (SXM), then reach Anguilla by yacht or by a short ferry from Marigot or Simpson Bay.

The crossing is about twelve miles, and many guests board the yacht in St. Martin and sail over as the first leg of the trip.

What's Included in an Anguilla Yacht Charter

A crewed charter includes the yacht, captain, chef, and crew. Sailing yachts and catamarans run all-inclusive, with meals, standard bar, fuel, and water sports covered in the base rate.

Larger motor yachts and superyachts typically operate on a plus-expenses basis, with an Advance Provisioning Allowance (APA) collected before the charter to cover fuel, provisioning, dockage, and other onboard expenses.

At the end of the charter, the captain provides a detailed account of the APA expenses. Any unused funds are refunded, while any additional expenses are settled at that time. Crew gratuity is customary at 15 to 20 percent of the charter rate across the Caribbean.

Anguilla Yacht Charter Prices and How to Book

Pricing varies by yacht, size, season, and group.

Ritzy Yachts provides a tailored proposal based on your group, preferred cruising area, travel dates, and charter preferences.

We recommend the yachts that best fit your needs, while the final itinerary is planned with the captain based on your preferences, weather, and local cruising conditions. We also handle the charter contract, APA, and all pre-departure coordination with the crew.

Best Time to Charter a Yacht in Anguilla

The Caribbean charter season runs from December through July.

December through April is the peak season, with steady trade winds, dry weather, and the calmest water.

May through July is the shoulder season. Demand drops, the air is slightly warmer, and charter conditions stay strong. Hurricane season peaks from August through October.

Ritzy Yachts books Anguilla charters across the full December to July window.

Ready to Charter a Yacht in Anguilla? Plan Your Charter with Ritzy Yachts

Ritzy Yachts brokers design each Anguilla charter itinerary around the group, the dates, and the anchorages guests most want to include.

Speak with one of our brokers to start the proposal.