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The Islands You Never Knew

There aremany Caribbean islands that are just off the beaten path and are readily accessible for bareboaters looking for adventure, for something different or just to break out of the rut. Here’s a look at five islands you never knew you always wanted to visit.

It’s been said that in many popular bareboating destinations, you don’t need charts or a plotter because the boat already knows the way. This is partly because charter companies offer itinerary suggestions that many bareboaters follow to the letter, and partly because there is comfort in following the herd.

There are, however, many Caribbean islands that are just off the beaten path and are readily accessible for bareboaters looking for adventure, for something different or just to break out of the rut. Here’s a look at five islands you never knew you always wanted to visit:


Although it lies just a dozen miles north of the charter bases on St. Martin, Anguilla seems invisible to most charterers, who usually are intent on heading southeast to explore the jet-set delights of St. Barthelemy. There’s nothing wrong with St. Barts, save the price point, but Anguilla is a taste of the “old” Caribbean with a citizenry renowned for being friendly.

Laid-back and serene, Anguilla draws bareboaters who aren’t looking for a disco in every harbor. It has 33 spectacular beaches and is known as the wreck-diving hub of the Caribbean, with no fewer than seven wrecks that thrive with tropical fish.

Road Bay is one of my favorite anchorages, and though it has no moorings, there is plenty of room to swing at anchor and the bottom has good holding. Anguilla is British, and Road Bay is an easy entry point.

Looking just as Columbus saw it in 1493, Anguilla is a low flat island unlike the tall islands of nearby Saba and St. Barts. En route to Road Bay from St. Martin, be sure to stop at Sandy Island, which is exactly what your mind’s eye sees when it thinks “tropical”—palm trees, a fringe of reef to snorkel on, and a lone refreshment shack selling snacks and drinks.

From Road Bay, it’s about 5 miles out to Prickly Pear Cays, which rival the Tobagos in terms of beauty and snorkeling. Another few miles and Crocus Bay on Anguilla provides another good anchorage.

If you want to explore, rent a car and drive around the island, where you’ll see many colorful racing sloops derived from traditional workboats careened on the beaches. You’ll also find a remarkable array of small shops to browse, plus restaurants offering everything from French to Creole cuisine.

For nightlife, Johnno’s Bar on Road Bay hops until the wee hours, or you might enjoy an upscale dinner at Malliouhana Resort (with its 30,000 bottle wine cellar) or CuisinArt Resort (the name says it all).

Even a couple of days exploring Anguilla will leave you plenty of time to head to St. Barts, so don’t overlook this quiet island. 


Though it’s the second largest of all the British Virgin Islands, Anegada is often the forgotten stepsister of the BVI. For one thing, it is the only island that is removed some distance from the main archipelago, and for another, it’s surrounded by Horseshoe Reef, the third largest coral reef in the world. Before the advent of shallow-draft catamarans and chartplotters, navigating the reef was a no-go, and this mentality has been slow to change.

What bareboaters are missing is a true paradise with soft sand beaches, great snorkeling, colorful wildlife and great piña colada beach bars. If you haven’t savored the buttery-soft flavor of a grilled Anegada lobster, well, your life isn’t complete.

Anegada is about a two-hour sail from Virgin Gorda (15 miles) in a good easterly, and you’ll find that it is unlike any of the other BVIs because it is coral, rather than volcanic, and therefore low—a mere 26 feet at its peak—and flat, earning it the nickname “the drowned island.”

What it does have is a leisurely lifestyle, great beaches and seclusion not often found in more popular BVI anchorages. There is no harbor, but the most popular anchorage is on the southwestern side, where Pam’s Kitchen delivers freshly baked goods by dinghy each morning.

Grab a taxi to admire the flamingoes or to reach Loblolly Beach, which is great for snorkeling. Hire a guide to stalk bonefish on the flats, or just enjoy a rum punch in the shade of a beach pub. Two popular choices for the latter are Big Bamboo on Loblolly (dine on lobsters straight from the sea) and Cow-Wreck Beach Bar, where the house specialty is the Cow Killer, a drink renowned for its ferocity.

Tip: Leave early for Anegada so you reach the channel through the reef with good light. And don’t forget your polarized shades.


It would be like visiting New York City and never seeing Manhattan. Too many bareboaters start and finish their Antigua charters without ever venturing the 30 or so miles across to the island that forms the other half of the nation of Antigua: Barbuda.

True, Antigua has a beach for every day of the year (365 of ‘em), and you can easily spend a 10-day charter just hopping from bay to bay. But Barbuda is also a delight, with horses running wild, beaches that stretch more than 10 miles and a larger rookery for frigate birds than in the Galapagos. Barbuda is not about nightlife, but about nature and great beauty.

For sailors, the open water passage to and from Barbuda can be good fun, with a brisk beat in one direction and a booming reach in the other, depending on the wind.

Leave early from Antigua so you arrive at Barbuda with enough sun to make anchoring easy. Most bareboaters tuck into one of several coves near Cocoa Point, which provide good protection as well as access for snorkeling Palaster Reef just offshore. Even better, the pink sand beach at Cocoa Point is, according to connoisseurs of such things, the most beautiful in the Caribbean.

Codrington is a sleepy hamlet that doesn’t really come alive, if you can call it that, until evening. There are several restaurants and a supermarket, but because the village is far from the anchorages, it’s difficult to restock on Barbuda, so plan ahead.

The reefs provide wonderful snorkeling, and don’t be surprised to spot an eagle ray gliding along the seafloor. Several of the southern reefs near Cocoa Point have shipwrecks to explore and, since spearfishing is forbidden, the fish are plentiful and unafraid.

Exploring on land is easiest by taxi. Many drivers either wait near the anchorage areas or monitor VHF-16.


These islands are what most bareboaters peer down upon as they fly into the Caribbean to the usual charter destinations. But they are easily accessible in several ways—if you know how.

Bimini, of course, is an island of legends just 50 miles off the Florida coast. For hundreds of years, it has drawn larger-than-life characters: rum-runners and smugglers, pirates and politicians, heroes and villains.

From charter bases in Florida, Bimini is an easy sail, just as it was when Ernest Hemingway settled there to write To Have and Have Not. A big-game fishing Mecca for decades, Bimini is actually two (or three, depending on who is counting) islands. The islanders mostly live around Bailey Town, while the hotels and marinas are in Alice Town, where you can buy sweet Bahamian bread. The End of the World Bar has the best sunset views. The Bimini Big Game Club is where anglers gather to tell tall tales.

On the water, you can chase conch on Gun Cay, sail south to the wreck of the Sappona to snorkel over a sunken freighter, and can choose from several beautiful anchorages.

The Berry Islands require a longer charter (unless you start in Nassau), but are known for their tropical beauty. Many of the dozens of small islands and cays are privately owned as second homes, and the Berrys have more resident millionaires than any other place in the world. Cruise lines own another two islands, so avoid these like the plague if you see a big ship. The rest have great snorkeling and diving, earning them the nickname “The Fish Bowl of the Bahamas.”

Be prepared: the Berry Islands have no resources, so bring all the food, fuel and water you need. 


I know exactly why I never go to Little Harbour when I’m bareboating in the Abacos. I’m lazy.

The entire Sea of Abaco is surrounded by so many delightful islands that sailing 20 miles south seems like such a long haul when, hey, there’s another wonderful island right over there!

So Little Harbour, which is really a part of Great Abaco Island where you probably started your charter, gets short shrift from bareboaters. But it deserves better.

First, it’s the gateway to the Pelican Cays Land and Sea Park, which is akin to swimming in an aquarium. Anchor off Sandy Cay and then snorkel at leisure amongst hordes of fish. This natural preserve also has a multitude of sea creatures and birds, so don’t be surprised if you are surrounded by a school of porpoise or if a sea turtle waves its lazy flipper at you.

Little Harbour is a pleasant anchorage where you can pick up a mooring buoy, and the village ashore has been a community of artists for half a century. The Johnston family was the first of these artist/settlers, and the family foundry, which still casts life-sized bronzes of local marine life, is worth a visit.

The beach is delightful, and at the foot of the cliffs there are caves to explore that were reportedly used by pirates. Sample the aptly named Blaster (a rum punch) and a grilled burger at Pete’s Pub and Gallery (run by a Johnston) or snorkel the coral reef along North Beach.

A tip: check the bottom carefully if you are anchoring; anchors don’t like the slippery eel grass found in some areas.

Why the Caribbean in the Summer?

There is an old wives’ tale, or perhaps an old bareboaters’ fable, that one should never charter in the Caribbean during the summer. Something about frying your brains or tempting hurricanes or somesuch.

It is—if I may use a technical term—pure hokum. I love summer charters in the Caribbean for several reasons.

First, about that heat. In the BVI, the coolest month is January, which averages 82 degrees. The summer months of July, August, and September average 88 degrees. You can’t tell a six-degree temperature difference if you stick your toe in a warm bathtub. Case closed.

Hurricanes? The season runs from June through November, but hurricane forecasting is now very good and, hey, that’s what travel insurance is for.

Rain? Yes, it rains more in the summer but remember: it’s warm rain.

There are, in fact, several great reasons to charter in the Caribbean during summer. First, a bareboat charter is less expensive. Booking a charter in “low season” can knock 25 percent off the top, and sometimes charter companies will give you 10 days for the price of seven. Airfares, hotels and car rentals are at their cheapest, and even the required BVI Cruising Permit ($2 per person per day in winter) drops to just 75 cents.

Summer is far less crowded, so you don’t have to race from harbor to harbor to fight for a mooring ball. And because there are fewer cruise ships, you won’t be buried by tourists at the popular spots (like the Baths in the BVIs), at restaurants or in shops. Of course, it’s also easier to take the kids in summer when they’re out of school.

The weather, in my opinion, is better in the summer. The winter winds can blow steadily at 25 knots, which is just too much work for a vacation. In the summer, count on a steady 15 knots—plenty for a fun sail and good air conditioning at anchor. In addition, winter storms in the North Atlantic can send swells into the Caribbean, making many anchorages too rolly to be comfortable.

Finally, the days are longer. You have more time to sail from place to place, more light for snorkeling, and more minutes to enjoy a leisurely happy hour.

Summer charters: cheaper, less crowded, better weather. Easy choice.

Photos by Bill Springer, Bahamas Tourism & Meredith Laitos



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