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Leeward Islands: An Idyllic Water-Oriented Playground

From Puerto Rico and the Virgin Islands (both US and British) to Guadeloupe, this collection of tropical islands offers a healthy variety of topography and culture. With reliable easterly trade winds and a tropical climate, these barrier islands between the Caribbean Sea and the western Atlantic form an idyllic water-oriented playground. There are excellent communication and travel options throughout the chain, though the islands further east provide a greater escape from civilization.

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Leeward Islands Overview

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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Antigua and Barbuda: Shoreside Adventures

Antigua is home to not one but two large-scale stadiums for cricket, a sport taken as seriously in the Caribbean as soccer/football is taken in Europe. The Sir Vivian Richards Cricket Stadium is a $60-million facility built in 2007 for Cricket World Cup matches, and today it regularly hosts the West Indies team.

Nelson's Dockyard is a well-known location on Antigua, but there are many inland shoreside activities as well.

Also on the island is Stanford Cricket Ground, which promotes shorter cricket matches known as Twenty 20. These are no small shakes, either; in 2008, the Stanford facility awarded a $20-million prize in a championship match.

Shirley Heights
Another location on Antigua that draws big crowds is Shirley Heights. It’s an honor on Antigua to earn a spot in the superb steel-drum band that starts the party just before sundown every Sunday and keeps it going well into the night. Guests dance the night away with outstanding views across the island, including a panorama of historic Falmouth and English Harbours, which are always dotted with large yachts. A barbecue is part of the fun, too, and of course the rum punch flows.

Frigate Bird Sanctuary, Barbuda
On Barbuda, one of the most interesting stops is the Frigate Bird Sanctuary, which is accessible only by boat. The most interesting time of year to visit is during autumn, when the frigate birds court. The males stand onshore and inflate the massive red pouches attached to their necks, straining their heads back as far as they can to make the pouches look as big and impressive as possible. The female frigates, meanwhile, circle above and choose their mates based on what they see from the sky. It’s a ritual worthy of the mile-high moniker, for sure.

On both islands, you can find international restaurants that cater to tourists in the resorts, but the best food is in the local eateries that serve conch fritters, jerk chicken, and other Caribbean favorites. Lobster is always fresh and delicious, and a good goat roti can easily help you forget about chicken for a few weeks. Also look for pumpkin and squash dishes, as both vegetables are grown on the island and have a nutty quality that can be hard to find in more northern climates. Wash it all down with a Ting—a grapefruit-infused version of lemon-lime soda that is a refreshing Caribbean specialty.

Antigua and Barbuda: 7 Day Charter Itinerary

Arriving in Antigua and Barbuda is much like arriving in any other port of call: You have 24 hours to clear Customs, including providing forms that can be downloaded prior to arrival. Cruising permits are required here along with regular port fees. Also expect to pay national park fees in popular Antigua locations such as Falmouth Harbour and English Harbour, including Nelson’s Dockyard (where the Customs houses for both harbors are located).

Antigua boasts 365 beaches, with enough nooks in the shoreline to offer solitude on most days.

These locations in Antigua’s southeast are good spots to begin a charter, as English Harbour offers a straightforward entrance while Falmouth Harbour’s entrance is clearly marked with buoys. Keep red to starboard on entry and you’ll do just fine. These harbors are also yachtie havens, with plenty of sailors and megayacht crew to chat with about weather, favorite anchorages, and the like. Spend a day milling about the cafés and bars, and you’ll have more information in hand than any cruising guide could ever offer.

Jolly Harbour
Cruising to the west from English or Falmouth Harbour, if you prefer to tie up at night and are willing to pay for services, you can set a waypoint for Jolly Harbour Marina. It’s the newest facility on the island and, as such, offers modern shopping, restaurants, tennis, and golf. A boatyard with a 70-ton Travelift is available for repairs and other work as needed, and a supermarket and liquor store cater to cruising yachts.

St. John’s
For even less-expensive supplies, including fuel and water, you can continue a bit farther north along Antigua’s west coast and instead stop at St. John’s—but keep in mind it is the island’s capital and often is crammed with cruise-ship tourists. They run on a regular schedule and can be avoided with a little research, but when they are in port, they dominate the local scene.

By the time you reach St. John’s, you will have circumnavigated almost half of Antigua—passing a number of inviting bays and beaches along the way. You can take as much or as little time as you like making your way to this point, anchoring for an afternoon or a few days in each one. There are enough nooks in the shoreline that you should be able to find solitude on most days as well as overnight whenever you’d like, almost always protected from weather. Listen to the daily forecast on Channel 6 at 0900 Monday through Friday (and occasionally on weekends).

St. John’s to Barbuda
From St. John’s, it’s about 30 nautical miles north to the island of Barbuda. The distance makes Barbuda inviting on a map, but in reality, the approach has scuttled hundreds of boats into wrecks. Barbuda is so flat that it can be hard to make out the contour of the land until you are right on top of the reefs. Up-to-date-charts and a reliable depthfinder will go a long way towards ensuring safe arrival. Also try to arrive from Antigua before noon, when the sun is either behind you or directly overhead to make the most dangerous reefs easier to see.

Much of Barbuda is still as nature created it, with Coddrington being the island’s sole town. It is home to fewer than 1,000 permanent residents. A single-runway airport is here, along with a few bed-and-breakfasts and the nearby Lighthouse Bay Resort. The resort offers spa services, horseback riding, and an open-air beachfront restaurant that serves gourmet cuisine in island style (expect some darn fine lobster).

The easiest way to reach Coddrington is via dinghy. You can anchor in Low Bay, carry your dinghy across Palm Beach to the lagoon, and then cruise across the lagoon to town. Basic supplies are usually available here in terms of galley provisions, and a handful of eateries offer the usual island cuisine such as conch and lobster. In season, you can also order deer, land turtle, and land crabs off the specials menus. A few bars offer beers and liquors, and at least one turns into a discotheque some nights.

After Coddrington, head just a few miles north up Barbuda’s west coast to the Frigate Bird Sanctuary, which is accessible only by boat along Eleven Mile Beach. Birdwatchers will be enchanted by more than 170 species of birds including more than 5,000 frigates, whose colorful mating rituals are on display each autumn. During any season, the frigates put on a show with their impressive four- to five-foot wingspans. They’re known as man-o-war birds because they use their size to overpower weaker birds in midair, stealing whatever food they may have. Watching an attack is almost like watching an air show, with nature handling the choreography.

Return to Antigua
You can circumnavigate the rest of Barbuda on your way back to Gravenors Bay, which is at the southernmost tip and makes an easy launch waypoint for returning to Antigua. Or, simply set a return course south from the sanctuary to Fitches Creek Bay or Parham Harbour on Antigua’s northeast side. If you can make it as far south as Nonsuch Bay, you’ll be in the company of megayachts that frequent the area as well as nearby Green Island, which is nice for day picnics and swimming. Try to avoid the tour boats at the height of the afternoon. Mornings and early evenings are the quietest here.

Green Island puts you within easy cruising distance of Willoughby Bay. If you’re itching to get off the boat, this is a good and private spot with charming villas. The area is generally regarded as one of the safest on the island thanks to the presence of Willoughby Bay Resort, an upscale facility that caters to high-finance professionals with a full-scale business center including a stock-trading floor.

The next large harbors west of Willoughby Bay are English and Falmouth Harbours—bringing your journey around Antigua and Barbuda full circle. If you missed it during arrival, spend a night having dinner at The Inn at English Harbour. Its hilltop gourmet restaurant is a little pricey, but the views are priceless, and you’ll have earned both after your circumnavigation of Antigua and Barbuda.