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Leeward Islands: An Idyllic Water-Oriented Playground

Puerto Rico
Well known as a vacation destination, particularly for American citizens who like the convenience of its U.S. Territory status and international airport, Puerto Rico is often overlooked by yachtsmen. In fact, this magical, mountainous island offers everything found elsewhere in the Caribbean, along with a hearty helping of Spanish culture and cuisine.

Puerto Rico is easy to get to and offers everything available elsewhere in the Caribbean, including yacht charter.

Fishermen, in particular, love Puerto Rico, which is home to some of the finest billfishing waters in the region. Several international tournaments are held here each year, and a large fleet of local sportfishing yachts is available for charter.

Yachts coming to San Juan, the island’s principal port, are greeted by the 16th century citadel Fort San Felipe del Morro, known as “El Morro”, at the entrance to the harbor. Several of the local marinas put yachtsmen within walking distance of the many historic attractions of Old San Juan.

Further west lies Fajardo, gateway to Puerto Rico’s natural splendors, including El Yunque Rainforest, home to exotic wildlife and waterfalls. Fajardo’s many marinas, including the huge Puerto Del Rey, serve as jumping-off spots for cruises to the beautiful beaches, spectacular snorkeling spots and abundant anchorages of Vieques and Culebra, the Spanish Virgin Islands, less than 15 nautical miles from the Puerto Rican coast.

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Cruz Bay on St. John, USVI

U.S. Virgin Islands

Thanks to their easy accessibility, the U.S Virgin Islands are the most popular destination in the Caribbean. Part of the island chain that includes the British Virgin Islands, the USVI trio – St. Thomas, St. John and St. Croix – have an appealing mix of sandy beaches, sapphire seas, tropical breezes, serious shopping and exciting nightlife. For yachtsmen, they also provide breathtaking cruising opportunities.

St. Thomas, the main island, features a fabulous mix of shopping and entertainment. Charlotte Amalie, the capital, is served by several marinas, including Yacht Haven Grande, flagship of the Island Global Yachting group, which offers both megayacht slips and trendy boutiques. Frenchtown, just off the main harbor, is the place to go for fine dining.

The pace is decidedly more laid-back on St. John, known for its 1960’s-style arts culture. A U.S. National Park, the island has 40 pristine beaches, and inland there are 22 self-guided hiking trails.

While most cruising itineraries jump from St. John to the BVI, those in search of something new can sail the 30 miles to St. Croix, the largest of the USVI. St. Croix Marine is the only marina here, and the mellow Caribbean towns of Mongoose Junction and Wharfside Village are the primary points of interest.

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Marina Cay on Virgin Gorda, BVI

British Virgin Islands
There are six good reasons why the British Virgin Islands are the most popular cruising grounds in the Caribbean: Jost Van Dyke, Tortola, Norman Island, Peter Island, Cooper Island and Virgin Gorda . This necklace of gem-like islands is strung along Drake Passage, a protected channel whose steady winds and spectacular views make it one of the world’s great sailing venues. Numerous bareboat fleets, both sail and power, are headquartered on Tortola, while virtually every luxury charter yacht passes through the BVI at some point in the season. There are several modern marinas, but stunning anchorages are among the BVI’s chief attractions.

The must-see spots get busy during the winter season, so it’s best to hit them early so you can stay and play all day. They include the wreck of the Rhone off little Salt Island, where divers delight in the bones of the 310-foot Royal Mail Ship that sank in 1867, and The Baths – a garden of giant, semi-submerged boulders at Virgin Gorda’s south end. Evening activities such as bending an elbow at Foxy’s on Jost Van Dyke and the “Willy T” floating bar off Norman Island are equally popular. But the BVI’s broad beaches and uninhabited, sandy cays provide a beautiful natural balance.

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A view of St. Maarten from the water

Saint Martin/Sint Maarten
Many yachtsmen treat the dual-nation island of Saint Martin (France) and Sint Maarten (Netherlands Antilles) merely as a way station to and from their Caribbean cruising vacations. That’s a shame, because this multicultural isle is a fun destination in its own right. Where else can you find an international airport, six superyacht marinas, fabulous food, duty-free shopping and 39 beaches all within 37 square miles?

The Dutch side of the island is where many of the marinas are located, within the sheltering shores of Simpson Bay Lagoon. A cab-ride away is the colonial city of Philipsburg, one of the Caribbean’s premier shopping destinations. By night, the action moves to the nightclubs and gambling casinos.

St. Martin is better known for its French cuisine, particularly in the fishing village of Grand Case. Orient Bay, one of the island’s best beaches, also has St. Tropez-style eateries. Adventurous visitors can venture inland to hike lush tropical hillsides or ride a zipline through the treetops at Loterie Farm.

Charter boats of every sort and size are based in Saint Martin/Sint Maarten due to its location as a Leeward Islands hub. Sandy Anguilla is only 10 nautical miles to the north, and it’s a 15nm run to chic St. Barths.

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The red roofs of St. Barths overlook Gustavia harbor.

St. Barths
The elite meet each winter season on the tiny, chic isle of St. Barthélémy, French West Indies—familiarly known as St. Barths. Movie icons, socialites, rock stars and royalty arrive for the island’s A-List New Year’s Eve celebrations and stay on to soak up the sun.

Even if your name has never appeared in the tabloids, you can still enjoy the principal pleasures of this French-accented retreat: world-class shopping, fine dining and 22 of the prettiest beaches in this part of the Caribbean. Not to mention the nightclubs, some of which, like famously frisky Nikki Beach, are located right on the sand.

While St. Barths has an airport (with a heart-stopping final approach), most visitors arrive by boat. St. Maarten, home base to several bareboat charter sailing fleets, as well as many of the luxury charter motor yachts in the Caribbean, is 15 nautical miles away.

There is just one marina on St. Barths: Port de Gustavia, at the foot of the island’s main shopping district. This state-owned yacht basin operates on a first-come, first-served basis, making it hard to plan ahead. Most boats anchor out in the holding ground off Gustavia or in secluded bays like Anse du Colombier at the island’s north end.

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English Harbor on Antigua

The island of Antigua offers yachtsmen a glimpse of history along with beautiful beaches and everything else you’d expect from its rich tropical setting. With an international airport, it’s also the perfect launch point for an itinerary in the mid- and southern Caribbean.

The largest of the English-speaking Leeward Islands, Antigua boasts warm, steady breezes; a winding coastline dotted with safe harbors; shell-laden beaches and a nearly unbroken coral reef. It offers both tranquil settings and exciting nightlife. Its quieter sister, Barbuda, located to the north, is a natural haven for sealife and birds.

English Harbour in Antigua is the site of the only working Georgian dockyard in the world. Admiral Nelson once hid his fleet in the harbor; today, Nelson’s Dockyard is an active yachting center offering berths from 30 meters up, and also features a museum dedicated to its namesake. Other popular marinas on the island include Jolly Harbor Marina, Catamaran Marina, Falmouth Harbour and Antigua Yacht Club.

While all types of charter boats are available here, both bareboat and crewed, thanks to the constant northeast tradewinds, Antigua and Barbuda are especially popular with sailors. Antigua Sailing Week in April is one of the largest sailing regattas in the world.

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