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A few weeks ago, I wrote an article for this site discussing some of the wonderful and lesser-known small-ship options in Alaska, a region where small vessels are a particularly good bet and able to go where the megaships can't. Now we turn our attention to the , where the cruise season is set to start in little more than two months.

The Caribbean is a different animal from Alaska. Covering over a million square miles, it's a place where the challenge is often getting from island to island rather than being able to squeeze into port. In the Western Caribbean, the distance between cruise ports is particularly notable, with nearly 400 miles separating the big ports of and -- a distance that argues for a large ship with diversions to help get you through a long sea day. The Eastern Caribbean, on the other hand, offers dozens of beautiful ports and anchorages within easy sailing distance of each other, and is thus a primo destination for small ships -- though not for as many of them as you'd expect. For that, blame a combination of factors: the different regulations required for ships sailing internationally, the distance of the Eastern Caribbean from U.S. coastal regions (making it no easy jaunt to move ships seasonally), the difficulty of finding customers and carving out a niche, the competition from lower-priced big-ship cruises, etc.

The Barefoot Empire That Was

Ten years ago, the story was a lot different. Those were the days when anyone looking for an alternative to megaships in the Caribbean only needed to know three words: Windjammer Barefoot Cruises. The line ruled the small-ship Caribbean roost for three decades, and its 2007 collapse left a hole in the small-ship market that has yet to be filled and probably never will be, since today's operators are working with more difficult economics and since they tend to -- how do I say this? -- obey the law.

Back in the day, Windjammer's fleet of old-fashioned tall ships (plus one shady-looking cargo/passenger vessel that kept them supplied) prowled the Caribbean like pirate vessels, scooping up passengers at different island ports and taking off on itineraries that were only kinda-sorta thought out ahead of time. The line lived on the edge, keeping its ships just about legal and its crews just about paid while accumulating a loyal cohort of repeat guests drawn by its outsider image and promise of unstructured, few-holds-barred fun. And y'know, it was fun -- terrific fun, and I miss it. But good luck finding anyone willing to replicate the experience today. Their insurance companies would surely object. The rumor mill used to have it that Windjammer avoided that kind of thing by just not having insurance, which could explain a lot. In any case, they're gone (taking a lot of passenger deposits with them, by all accounts), and we live in the present, so let's move on.

Today's Sailing Ship Options

Aside from a few small motor-only luxury ships (such as those operated by Seabourn, SeaDream, and French line Ponant Cruises), all the small cruise ships operating in the Eastern Caribbean are sailing ships -- which is completely appropriate because if ever there was a region made for sailing, it's the Caribbean, with its blue waters, vast skies, and reliable trade winds. Here's a rundown of your options.

Canadian Sailing Expeditions (www.canadiansailingexpeditions.com): Founded in 2000, Canadian Sailing Expeditions operates the 245-foot, 77-passenger square-rigged barquentine Caledonia. Built in 1949 as a commercial fishing boat, the ship was rebuilt for passenger service in 2002, a process that added cabins, masts, and sails (the ship had previously sailed under diesel power alone) and brought everything into compliance with international safety-at-sea regulations. Interiors are more utilitarian than stylish (or even Windjammer swashbuckler style), but cabins are relatively roomy as sailing ships go. Four different 6-night itineraries are offered in the Eastern Caribbean for 2009-2010: Itinerary A sails between Tortola and St. Maarten, visiting Jost Van Dyke, Salt Island, Virgin Gorda, and Anguilla. Itinerary B sails between St. Maarten and Antigua, visiting St. Barts, St. Kitts, Nevis, and Montserrat. Itinerary C sails between Antigua and St. Lucia, visiting Guadeloupe, Les Saintes, Dominica, and Martinique. Itinerary D sails between St. Lucia and Grenada, visiting Bequia, Mayreau, Union Island, and Carriacou. Rates start around $2,100 per person, double occupancy. In summer, Caledonia offers cruises around Atlantic Canada (including Newfoundland), concentrating on outdoorsiness and wildlife.

Classic Cruises of Newport (www.cruisearabella.com): Newly launched in 2001, the three-masted staysail schooner Arabella is a sleekly modern tall ship that carries 40 passengers in yachtlike comfort, with a hot tub on deck, kayaks and snorkel gear for off-vessel fun, and cozy cabins with portholes. From December through May she offers three different 6-night Caribbean itineraries. Her U.S. & British Virgin Islands cruise sails round-trip from the village of Red Hook on St. Thomas, visiting Tortola, Norman Island, Coopers Island, Virgin Gorda, and Jost Van Dyke. Her Spanish Virgin Islands itinerary also sails from St. Thomas, visiting Vieques, Culebra, St. John, Tortola, and Jost Van Dyke. Her St. Bart's/St. Kitts/Nevis itinerary sails from St. Martin to St. Kitts, visiting St. Barts, St. Eustatius, and Nevis. Rates start from $1,395 per person (double occupancy), December-April, but drop as low as $1,050 in May. In summer and fall, Arabella sails in New England and on Chesapeake Bay.

Liberty Fleet of Tall Ships (www.libertyfleet.com/tall-ship-cruise/bahamas.html): This clunkily named line was founded in 1995 and has since offered day sailings and multi-day cruises in Boston, the New England coast, Chesapeake Bay, and Key West. This year, the line's two-masted, 28-passenger schooner Liberty Clipper will winter in the Bahamas, sailing round-trip from Nassau and concentrating on out-islands such as the Berry Islands, Andros Island, Eleuthera, and Abaco Island. Liberty Clipper was launched in 1983 as a replica of a 19th-century Baltimore clipper. Though her hull is steel, she carries her old-fashioned air well, with a beautiful wooden deck and woody, period interiors. Cabins are small and offer bunk beds and a private marine-head style toilet/shower combos. For off-vessel fun, the ship carries snorkeling equipment, small sailboats and rowboats, and inflatable sea kayaks. Per-person rates are $950 throughout the season (double occupancy).

Sea Cloud Cruises (www.seacloud.com): If you're looking to sail like a captain of industry aboard his private yacht, circa 1900 to 1930 or so, look no farther than Germany-based Sea Cloud Cruises, which operates one (soon to be two) tall ships that emulate the look and feel of those classic vessels, and another that actually is one. The latter, the four-masted, 64-passenger Sea Cloud, was built in 1931 for Wall Street tycoon E. F. Hutton and his wife, heiress and businesswoman Marjorie Merriweather Post, and was outfitted with exquisite detail -- much of which was restored when German economist and seaman Hartmut Paschberg bought and refurbished the ship in 1978. She has cabins for 64 passengers, the luckiest (and richest) of whom can stay in Post's own museum-like suite, with its Louis XIV-style bed and nightstands, marble fireplace and bathroom, chandeliers, and intricate moldings. The other original suites are similarly if less sumptuously furnished. Standard cabins are comfortable, but lack the suites' time-machine quality. The larger, three-masted, 94-passenger Sea Cloud II is a modern reinterpretation of the classics, built in 2001. Her elegant lounge has rich mahogany woodwork, ornate ceiling moldings, leather club couches, and overstuffed bucket chairs, and she has several opulent suites, one with burled wood paneling and a canopy bed. The company is currently building the three-masted, 136-passenger Sea Cloud Hussar, which will set sail in summer 2010. This year, both Sea Cloud and Sea Cloud II will sail the Caribbean between December and April on 12 different itineraries, mostly in the eastern Caribbean. Of particular interest are those that visit Cuba -- which they can since Sea Cloud is a German line, though U.S. travel restrictions still apply to you if you're a U.S. citizen. (See here for exemptions and other info.) Weeklong cruises in the Caribbean start around $4,200 per person.

Stad Amsterdam (www.stadamsterdam.com): The square-rigged, three-masted, 28-passenger Stad Amsterdam was built between 1997 and 2000, its construction commissioned by the municipality of Amsterdam and the Randstad Holding company as part of Sail Amsterdam '95. Mixing classic and modern, it offers 14 small cabins with portholes, TVs, and lots of wood and brass trim; a large dining room that can also be used for presentations (the ship is often chartered for corporate events); and an open-air bar. Stad Amsterdam's winter itineraries had not yet been announced at press time, but in years past the vessel has sailed 6-night cruises from Martinique, priced from about $2,500 per person.

Star Clippers (www.starclippers.com): Star Clippers is the most visible of the sailing lines in the Caribbean, its ships regulars in the region for more than a decade. All in all, the line offers the best of two cruise worlds, with comfortable, almost cushy public rooms and cabins married to an unstructured, let-your-hair-down, hands-on ethic that means you can (if you want) help raise the sails, climb the masts, crawl into the bow netting, or chat with the captain on the open-air bridge. Company origins go back to the late 1980s, when Swedish-born industrialist and real estate developer Mikael Krafft spent more than $80 million to build the four-masted, 170-passenger twins Star Flyer and Star Clipper, using century-old blueprints married to the most modern materials, construction methods, and equipment. A decade later, Krafft launched the five-masted, 227-passenger Royal Clipper, the ship that currently operates all of the line's Caribbean itineraries. Done in a more luxurious style than the line's older ships, Royal Clipper offers roomier cabins, a small gym and spa, three pools, and fancy touches like marble bathrooms. But she sure can sail: Flying 42 sails that together stretch to 56,000 square feet, the ship is able to achieve 20 knots under sail power alone, or 14 knots under engine power. This winter, Royal Clipper offers two different 7-night itineraries between November and March, both round-trip from Barbados. Her Windward Islands cruises visit St. Lucia, Dominica, Antigua, St. Kitts, Iles des Saintes, and Martinique, while her Grenadines itineraries visit Grenada, Tobago Cays, St. Vincent, Bequia, Martinique, and St. Lucia. At the end of the season, in March, the ship also offers two 10- and 11-nigth British Virgin Islands cruises, visiting St. Barts, Norman Island, Sopers Hole, Jost Van Dyke, Virgin Gorda, Antigua, St. Kitts, Ile des Saintes, St. Lucia, and Dominica. Rates start around $1,685 per person, though the majority of sailings are priced from around $2,000.

Wanderbird Expeditions (www.wanderbirdcruises.com): The 12-passenger Wanderbird is a 90-foot, Dutch-built trawler that fished the North Sea from 1963 until 1990 and is now based in Maine, where she's one of the weirder vessels among that coast's more characteristic schooners and sloops. On the outside, she could almost pass for a working research or fishing vessel, if she weren't so spic and span (and if you discount the sails, which provide auxiliary power). On the inside, she's got a woody, homey, yacht-like interior. Her cruises mix total relaxation (i.e., few planned activities) with nature observation and exploration, whale and bird watching, wildlife photography, and unusual touches like listening to and recording whale songs. She also carries two small boats and several kayaks for off-vessel exploration. For 2010, Wanderbird will be sailing three quarters of the way around North America, from Maine through the Panama Canal to Alaska. In between (from December through March), she'll be offering eight 6-night cruises from the island of Culebra, located about 19 miles east of the Puerto Rican mainland. Cruises will visit Vieques (known for its Bioluminescent Bay, where tiny dinoflagellates light up the water when they're disturbed by boats or swimmers) and the U.S. Virgin Islands of St. John and St. Croix, and will offer activities like snorkeling, kayaking, beachcombing, and wildlife watching focused on birds and giant sea turtles. Wanderbird's Caribbean cruises are all priced at $1,499 per person, double occupancy, for all cabins.

Windjammer Adventures (www.windjammeradventures.com): When I said above that no one would probably ever really recreate the Windjammer Barefoot Cruises experience, I didn't mean no one would ever try -- and in that vein, enter Captain Neil Carmichael. Back in April, the former Windjammer Barefoot captain (longtime master of the Polynesia) announced that he'd made a deal to acquire the 12-passenger schooner Diamante and reposition it from the Galapagos to the Caribbean for cruises that would emulate the old Barefoot ethic. Well, not so fast: According to Carmichael's own log on the WA website, he got screwed and no longer has possession of the boat -- or any boat, for that matter. So, while I'm not advising that anyone make a reservation with a boatless cruise line, consider this a heads-up: Carmichael swears (on his mother's grave, no less) that he will start his cruises this season, once he finds a vessel. He even posted his e-mail address if you want to call and talk. So, stay tuned -- and good luck, Capt. Neil!

Windstar Cruises (www.windstarcruises.com): Owned, for better or worse, by Ambassadors International (the company that so badly botched the now-defunct Majestic America Cruises, in the process ending the run of the legendary Delta Queen ships), Windstar remains a wonderful product, mixing an always-casual onboard vibe with beyond-the-norm itineraries and first-class service and cuisine. Its three ships are technically motor-sail vessels, combining 19th-century sailing-ship technology with modern engineering, adding up to ships that are huge by sailing-ship standards, with at least 21,489 square feet of computer-controlled staysails that furl and unfurl at the touch of a button. (The ships are able to travel at upward of 12 knots under sail power alone, though usually the sails operate more as a fuel-saving aid to the diesel engines.) On board, stained teak, brass details, and lots of navy blue fabrics and carpeting lend a traditional nautical ambience, and cabins and public rooms are more what you'd expect on a medium-sized cruise ship than on a sailing ship. Currently, the Windstar fleet is comprised of three ships, the four-masted, 148-passenger Wind Star and Wind Spirit and the five-masted, 312-passenger Wind Surf. For 2009-2010, Surf and Spirit will be in the Caribbean from November through March, offering 7-night cruises that sail round-trip from Barbados or St. Martin or between the two islands, visiting ports like St. Kitts, Nevis, St. Barts, Iles des Saintes, St. Lucia, Tortola, Jost Van Dyke, Virgin Gorda, Bequia, and Martinique. Per-person rates start around $1,859, double-occupancy.

One final note: Despite the fact that all of the ships here are real sailing vessels, none operates solely by wind power. Instead, each also employs engines in order to keep the ships on schedule and the generators running. If you want to go completely, traditionally engine-free, one option is to head north and sail a schooner along the Maine coast in summer. The Maine Windjammer Associatio and Maine Adventure Sails both represent multiple owner-operated vessels.

Talk with fellow Frommer's cruisers on our Cruise Forum.