On the island of St. Maarten, visitors may take a bus to pass across the open border between the Dutch side and the French side, while farther south, the only link residents of Montserrat have to the outside world is the shuttle flight to neighboring Antigua. At best, you can enjoy breakfast, lunch and a sundowner on three different islands by ferry. At worst, prepare to run the gauntlet of delayed flights, high fares and immigration officials often resistant to arriving passengers’ charms.
Take a Cruise
Arguably the simplest, cheapest way to see a handful of Caribbean islands without assuming the logistical responsibility of planning an itinerary is to join one of the many cruise lines plying the eastern, western and southern Caribbean routes. All the major cruise lines organize seven-night eastern Caribbean cruises, which allow passengers to visit islands including the Bahamas, St. Maarten, St. Thomas and Puerto Rico, with all meals and accommodation included. Some extended southern Caribbean cruises visit at least 10 islands, but western Caribbean cruises focus more on Central American ports. A cruising drawback is that passengers spend only a day in each port, which is hardly enough time to appreciate an island.
Pick an Area
Certain clusters of Caribbean islands lend themselves more readily to island hopping than others. The northern Leeward islands presents an arc of vastly different islands close together. From St. Maarten, visitors can see six neighboring islands on a clear day. Regular shuttle flights run on Winair, LIAT airlines and other island carriers among the Leeward islands, while visitors to the U.S. and British Virgin islands can fill a vacation with day trips by ferry among eight islands. Even the larger Windward islands operate a ferry service. Starting in Guadeloupe, visitors can take the high-speed Express Ferry to the offshore islands of Marie Galante and Les Saintes, or head down the island chain to Dominica, Martinique and St. Lucia. Prices for the approximately two-hour crossings are extremely competitive, but conditions sometimes are challenging.
Small Plane Network
As the leading carrier in the region, LIAT airlines covers 21 islands from the Dominican Republic to Trinidad and Tobago. Unfortunately, the company no longer operates its 30-day AirPass with unlimited stopovers, but passengers can book flights among multiple destinations with CaribJet, incorporating other carriers. Caribbean inter-island flights are expensive, with a roster of departure fees and fuel surcharges, and most return through the major transport hubs. For this reason, "The Daily Telegraph" recommends travelers base themselves on an island such as Antigua, which functions along with St. Maarten and Puerto Rico as a focal point for inter-island flights.
The Caribbean remains one of the prime yacht grounds in the world, with travelers able to pick up a bareboat yacht with or without a captain at several points throughout the island chain -- and even drop it off at another island. This is island hopping at its most leisurely, but most visitors tend to cruise a distinct area rather than leave a trail of foam from north to south. The main yachting bases are in Tortola for the Virgin islands; St. Maarten for the neighboring islands; Antigua and St. Lucia for the Windward islands; and Grenada for St. Vincent and the Grenadines. Bear in mind that heading windward -- as in sailing down the chain against the wind -- can make for a grueling experience. For this reason, many island-hopping cruisers tend to sail up the chain and leave the boat at another base.