Anguilla Yacht Charter

Anguilla isn't the base; it's the prize. For clients looking to decompress from the bustle of St. Martin or the scene of St. Barths, this long, flat sliver of British territory offers a masterclass in barefoot luxury. This is a destination defined not by what it has, but by what it lacks: no cruise ships, no casinos, and no crowds, leaving only world-class beaches and an unexpectedly serious culinary reputation.

The cruising ground

From the deck, Anguilla presents a low-slung profile, a 16-mile-long limestone and coral island that barely seems to rise from the turquoise water. This isn't the dramatic volcanic topography of its neighbors. The magic here is at sea level and below, along a coastline blessed with more than thirty white-sand beaches and a necklace of uninhabited offshore cays.

Operationally, we treat Anguilla as a leeward cruising ground. The constant ENE trade winds mean the island's south and west coasts are almost always in the lee, providing calm, protected anchorages. This is where you'll find the headline beaches: Meads Bay, Rendezvous Bay, Maundays Bay. The water is gin-clear, the holding is excellent in sand, and the entire experience is geared towards easy access from your yacht's swim platform.

The northern and eastern coasts face the Atlantic and are generally left alone, save for a few spots like the magnificent Shoal Bay East, which is tenable in settled conditions. The real draw for a yacht, beyond the main island's coastline, is the collection of cays. Sandy Island, Prickly Pear Cays, and Dog Island are essential stops that transform a visit from a simple beach tour into a proper cruising itinerary. It’s a compact area, easily covered in two or three days, making it the perfect, tranquil centerpiece to a more dynamic week-long charter based out of St. Martin.

Bases and clearance

Let's be clear: Anguilla is not a charter base. There is no significant fleet of crewed yachts stationed here. Your charter will begin and end in St. Martin (usually the Dutch side, Sint Maarten, for its larger marinas like IGY Isle de Sol or Yacht Club Port de Plaisance), which is a short and pleasant cruise away.

Clearing into Anguilla is a straightforward process handled entirely by your captain. The sole port of entry for yachts is Road Bay, the large, protected harbor at the village of Sandy Ground. The Customs, Immigration, and Port Authority offices are all located here. While the captain manages the paperwork—passports, ship's documents, crew list—you and your guests are free to remain on board or take the tender ashore to one of the casual beach bars that line the bay.

There are two key costs involved, both covered by your APA. First are the standard clearance and immigration fees, which are nominal. Second is the Anguilla Marine and Parks cruising permit, which is mandatory for any yacht wishing to anchor or moor anywhere other than Road Bay. The fee is calculated per foot, per day (currently around $0.50 USD/ft/day), making it a minor operational expense. For a 150-foot yacht, you're looking at approximately $75 per day to have the freedom of the island's best anchorages. The captain settles this upon arrival, ensuring you are free to move as you please.

Where to drop the hook

Anguilla's value is measured in anchorages. Each bay offers a slightly different character, and the proximity allows you to sample several in a single day.

• Road Bay (Sandy Ground): This is your operational hub and a fantastic anchorage in its own right. The holding is firm sand in 15-25 feet of water. It’s a working bay but also the heart of the island's casual nightlife, with institutions like Johnno's Beach Stop. It's the perfect place to arrive, clear in, and then use as a base for exploring the island by land via a pre-arranged taxi.

• Meads Bay: This is the A-list address. A wide, two-mile arc of perfect sand, home to premier properties like the Four Seasons and Malliouhana. We anchor here and guests tender in for lunch at a world-class spot like Blanchards or for sunset cocktails. The bay is quite open, so it's best enjoyed in settled weather, but on a typical day, it’s a sublime spot for an afternoon of swimming and paddleboarding off the yacht.

• Rendezvous Bay: Looking directly across to St. Martin, this bay offers an impossibly long and tranquil stretch of sand. The main draw here is the legendary Sunshine Shack, a beach bar that serves up some of the best BBQ and rum punch in the Caribbean. It’s the ideal daytime stop for a completely casual, feet-in-the-sand lunch.

• Maundays Bay: The picture-postcard, perfect crescent that fronts the Belmond Cap Juluca. The architecture is stunning against the white sand and blue water. We often anchor here just for the view, a swim, and the sheer beauty of the location.

• Crocus Bay: A more intimate and dramatic setting, flanked by limestone cliffs. This is a fantastic spot for snorkeling right off the boat. It's also home to da'Vida, a stylish restaurant and beach club that's perfect for a sunset dinner. The protection is excellent, making it a preferred overnight anchorage.

• Sandy Island: This is a must-do. A tiny spit of sand, a few palm trees, and a rustic-chic beach bar serving grilled lobster and potent cocktails. Your yacht will pick up a mooring ball a short distance away, and you'll spend the afternoon on what feels like your own private desert island, albeit one with a bartender.

• Prickly Pear Cays: A short cruise northwest of the main island, these cays offer a more adventurous day. A well-maintained mooring field protects the fragile seabed. The channel between Prickly Pear East and West is a superb snorkeling site, with calm, clear water and abundant reef fish. A simple beach restaurant on East Cay serves lunch to visiting yachts.

Weather and season

The charter season in Anguilla is dictated by the Atlantic hurricane season. The window is clear and non-negotiable.

The prime season runs from mid-December through April. During these months, you can expect the classic Caribbean dream: dry weather, low humidity, and consistent ENE trade winds blowing at a comfortable 15-20 knots. This breeze keeps things from getting too hot and provides fantastic conditions for sailing catamarans. Air and sea temperatures are perfect, hovering around 80°F (27°C).

The shoulder months of May, early June, and November can be excellent. The winds tend to be lighter, the anchorages are less crowded, and you often get the best of the island to yourself.

From late June through mid-November, Anguilla is effectively closed for charter. This is peak hurricane season. Insurance policies will not provide cover for named storms, and most yachts will have already departed for the Mediterranean or New England. Many island restaurants and hotels close during this period as well. We do not place charters in this region during these months.

The right yacht

The short distance from St. Martin and the focus on beach-hopping makes certain yachts a better fit than others.

• Motor Yachts (90 - 200ft): This is the dominant platform for Anguilla charters. Their speed is a major asset, turning the 12-nautical-mile crossing from Marigot, St. Martin, into a sub-one-hour trip. This maximizes your time at the destination. Large, hydraulic swim platforms and an extensive collection of water toys are perfectly suited to the island's lifestyle. Their often shallower draft allows captains to get closer into the bays than deeper-keeled vessels.

• Sailing Catamarans (55 - 85ft): An outstanding choice. The sail from St. Martin to Anguilla is typically a glorious beam reach, allowing you to shut down the engines and enjoy the journey. Once at anchor, their stability, enormous deck space, and low draft are huge advantages. They feel like a private floating beach club, with the trampolines forward being the best seat in the house.

• Classic Monohull Sailboats: While perfectly capable, they are less common for a dedicated Anguilla trip. The charter is less about the long-passage sailing experience and more about destination access. For clients whose primary passion is performance sailing, we’d build a different itinerary, though a stop in Anguilla can certainly be included.

Money

The financial side of an Anguilla charter is refreshingly straightforward.

• Currency: The US Dollar (USD) is the official currency for all charter-related transactions and is universally accepted on the island. There is no need for currency exchange.

• Charter Fees: For a one-week charter in the 2026 high season, you should budget accordingly. These are base charter fees, exclusive of running expenses:

  • Luxury Crewed Catamaran (60-70ft): $40,000 - $70,000 per week
  • Prestige Motor Yacht (100-130ft): $90,000 - $160,000 per week
  • Superyacht (150ft+): $200,000 per week and rising sharply with size, build, and reputation.

• Taxes: This is a significant advantage. Unlike the Mediterranean, there is no Value Added Tax (VAT) on the charter fee in Anguilla or St. Martin. This represents a substantial saving.

• Onshore Spending: Be aware that Anguilla's restaurant scene is high-end and priced accordingly. A dinner for eight guests with wine at a celebrated restaurant like Veya, Blanchards, or Hibernia will be a notable charge against your APA, but it's an integral part of the Anguilla experience.

APA and the small print

The Advance Provisioning Allowance, or APA, is the standard system for handling all your on-board expenses. We recommend budgeting 30% of the base charter fee for a week-long trip that includes Anguilla.

This APA is transferred to the yacht before the charter and managed by the captain like a transparent escrow account. It covers all variable costs:

• Fuel: For the yacht and its tenders. The distances are short, so this is not a major cost driver compared to a Med charter.
• Food & Beverage: All your meals, snacks, and drinks on board, provisioned to your exact preferences.
• Port & Clearance Fees: This includes the Anguillan cruising permit and customs charges.
• Communications: Satellite internet and phone usage.
• Shore-side Logistics: Any taxis or activities arranged by the yacht.

The captain will maintain a running tally of all expenditures with full receipts. If there is a surplus at the end of your charter, it is refunded to you immediately. If your expenses exceed the APA (perhaps due to extensive fine wine requests or multiple high-end dinners ashore), the difference is settled via credit card before you disembark. The system is efficient, transparent, and ensures the charter is tailored perfectly to your tastes.

How we'd plan a week

The classic "Leeward Islands Trio" of St. Martin, Anguilla, and St. Barths is a perfect week-long charter. It offers three distinct island experiences in one seamless itinerary. This is how we'd structure it:

• Day 1: St. Martin Start: Arrive at Princess Juliana Airport (SXM) and be whisked to your yacht at Isle de Sol Marina. After settling in, we'll make the short cruise to Grand Case on the French side, the culinary capital of the Caribbean. Anchor off the beach for your first sunset and choose between a fine-dining French restaurant or a famously good "Lolo" BBQ shack for dinner.

• Day 2: The Anguilla Escape: A leisurely morning cruise north to Anguilla. The captain handles clearance in Road Bay while you enjoy a mid-morning coffee. We then move to Meads Bay. The afternoon is for swimming, paddleboarding, and enjoying the yacht's toys. As evening approaches, tender ashore for cocktails at the Malliouhana before returning to the yacht for dinner under the stars.

• Day 3: Cays and Cliffs: Today is for exploring Anguilla's outer islands. We head to Sandy Island for the quintessential beach bar lunch. In the afternoon, we cruise to the protected waters of Crocus Bay. Snorkel the cliffs, enjoy the quiet anchorage, and perhaps have dinner ashore at the elegant da'Vida restaurant.

• Day 4: World's Best Beach: We reposition to Shoal Bay East, a two-mile stretch of powder-fine sand that frequently tops global beach rankings. The crew will set up a beach camp for you. After a long, lazy lunch on board, we'll head back to Road Bay for the evening, giving you the option of one last Anguillan fine-dining experience at Veya or Blanchards.

• Day 5: The Shift to St. Barths: An early departure for the 20-nautical-mile sail down to St. Barths. You'll feel the energy shift the moment Gustavia's red-roofed harbor comes into view. Clear customs, then spend the afternoon exploring the chic designer boutiques before returning to the yacht for cocktails overlooking the megayacht-filled port.

• Day 6: Seclusion and Scene: Anchor off Anse de Colombier, a stunning, protected bay accessible only by boat or hiking trail. Enjoy a quiet morning of swimming and snorkeling in this marine park. In the afternoon, we move to the iconic Baie de St. Jean to watch the planes land over the hill and soak up the scene at Eden Rock. The evening is for dinner and people-watching at one of the island's hotspots like Bonito or L'Isola.

• Day 7: Final Farewell: Enjoy a final breakfast on the aft deck in St. Barths. One last swim, and then a short, final cruise back across the Anguilla Channel to Sint Maarten for your afternoon flight home, completing a journey through three unique Caribbean cultures.