Bareboat Chartering Time

The British Virgin Islands

Spiced with tales of pirates and yellowed treasure maps, the British Virgin Islands are easily the most popular bareboat charter destination in the world. They are also a first-timer's paradise. Stretching 45 miles long by 15 miles wide, most of the BVI can be covered in an afternoon's sail, and the islands are so close together that they can basically be navigated by sight.

The area is dotted with great anchorages, many with mooring buoys one charter company even touts more than 16 anchorages within an hour's sail of Tortola. Both power and sail monohulls and catamarans are available from a multitude of charter companies, and the weather in the region is uniformly balmy. Frankly, the only downside to the BVI is that they are so popular.

Snorkelers will find shallow reefs alive with brightly colored tropical fish that want to peer into your mask, and you can swim into caves made famous in Treasure Island. The infamous Baths, on Virgin Gorda, are a series of sunlit pools and grottos set between enormous boulders, which seem as if they've been tossed by giants into the water's edge.

Bitter End Yacht Club (800-872-2392, beyc.com) is a perfect overnighter, with fun restaurants and watersports to enjoy.

Pusser's Marina Cay (284-494-2467, pussers.com) has quiet moorings and a lively restaurant.

Peter Island Yacht Harbour  (800-346-4451, peterisland.com) has ample dockage and full resort facilities ashore.

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The Abaco Out Islands, Bahamas

Lying on the northeastern edge of the Bahamas Bank, the Abacos Out Islands are a string of cays sheltered by a long barrier reef, providing protected waters and a fascinating variety of islands to explore. Populated centuries ago by Loyalists fleeing the American Revolution, they bear names such as Man-O-War Cay and New Plymouth.

The villages are reminiscent of Cape Cod, with narrow streets and waterfront clapboard buildings.Marsh Harbour is the hub of Abacos action, with several charter companies offering both power and sail. The world-famous candy-striped lighthouse of Hopetown are nearby. Man-O-War Cay is dry, so bring your own bottle, and be sure to stop at Albury's sail loft for duffel bags and canvas goodies.

Besides pleasant weather, the drawing cards for the Abacos are miles of empty beaches (where you'll find conch shells with scarlet edges), good anchorages and great snorkeling. It takes some time to adjust to cruising all day in water just 10 feet deep, but you soon learn not to panic when you can clearly see starfish on the ocean floor.

The Abaco Beach Resort (242-367-2158, abacobeachresort.com) has a fine marina and resort facilities.

Treasure Cay Beach Marina & Resort (242-365-8250, treasurecay.com) is acclaimed for its flawless beach and marina.

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San Juan Islands, Washington

The San Juan Islands, some 60 miles north of Seattle, are a democratic archipelago: there is something for everyone! With more than 200 rocky islands (750 if you count the small ones at low tide), a dozen undisturbed state parks, lush forests and charming small villages, the San Juan Islands are reminiscent of Maine. There are several bareboat charter companies based on the mainland in Anacortes and Bellingham with quick access to these cruising grounds.

Friday Harbor on San Juan Island is the social and political center of the region, with a small-town feel and quaint shops. Fossil Bay on Sucia Island shows the Ice Age evolution of this island chain, with fossils embedded in rocks worn smooth by glaciers. Teddy Roosevelt once stayed in the Victorian-era hotel at Roche Harbor on the opposite side of San Juan Island, and there is ample anchorage near the property.

The Friday Harbor Marina (360-378-2688, portfridayharbor.org) is good for provisioning and makes a great base for exploring.

Rosario Resort & Marina (360-376-2152, rosarioresort.com), on Orcas Island, has a protected marina and resort facilities.

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Chesapeake Bay

Stretching more than 200 miles from mouth to headwaters, the Chesapeake Bay is one of the great American charter areas. Less a bay than a semiprotected waterway, the more than 3,000 miles of shoreline are dotted with creeks and hidden anchorages, and the gently rolling scenery is not only beautiful, but also marked with history at every turn. While the exact numbers are debatable, there are at least 230 harbors and 40 major rivers along this bay.

Annapolis is the area's boating capital and the base for several bareboat charter companies from which to launch a multitude of adventures. Across the bay, you can explore the Chester River, lined with plantation homes leading to the red-brick landscape of Chestertown. St. Michaels, on the Miles River, has a superb maritime museum with guest moorings and a lovely, sleepy town. Tangier and Smith Islands provide glimpses of fishing villages that haven't changed for a century”the odd English dialect spoken here dates back to the 1600s.

St. Michaels Marina (410-745-2400, stmichaelsmarina.com), set in the heart of downtown.

Port Annapolis Marina (410-269-1990, portannapolis.com) is a full-service marina located on Annapolis's Back Creek.

Chesapeake Harbour Marina is located on the Severn River in Annapolis (410-268-1969, chesapeakeharbourmarina.com).

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Florida's Gulf Coast

This is a still undiscovered bareboating paradise that has great weather, uncomplicated cruising and almost too many destination choices. Several charter companies are located in the area between Sarasota and Tampa Bay with an eclectic range of both power and sailboats.

Charterers have a choice of sailing in the open ocean or exploring the Intracoastal Waterway, which is really a misnomer since in this region it consists of connected bays and sounds. Pine Island Sound, for example, is protected by Captiva and Sanibel Islands, famed for the incredible shelling to be found on their beaches.

One of Cabbage Key's claims to fame is its bar, literally papered with thousands of signed dollar bills and allegedly the home of the cheeseburger that inspired Jimmy Buffett's Cheeseburger in Paradise.Farther north, bareboaters can explore Charlotte Harbor, Gasparilla Sound and the islands north of Clearwater. Heading south leads to the Ten Thousand Islands and eventually the Florida Keys.

Longboat Key Club Moorings (941-383-8383, longboatkeymarina.com) has an ideal location offering direct access to Sarasota Bay.

South Seas Island Resort & Marina (239-472-5111, southseas.com) a charming marina, is an easy walk to the shell beaches.

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Chris Caswell is the editor of CharterSavvy, the online magazine devoted to bareboat chartering worldwide. For your free subscription, visit chartersavvy.com.