Warm waters, sheltered coves, consistent winds and a seemingly endless array of islands — the Caribbean was made to be sailed. But that doesn't mean all parts were created equal, which is why sailors tend to gravitate to five regions: the British Virgin Islands, St. Martin and Antigua, St. Lucia, St. Vincent and the Grenadines, and Grenada. Each has its draws. The Virgins, for example, have the best sailing infrastructure (most charters, well-defined routes and moorings), but that means the islands can be overcrowded in high season (December to mid April). On the flip side, Grenada and St. Lucia are less crowded, but the sailing often involves longer passages over open water, which can make landlubbers a bit squeamish. St. Martin and Antigua are great bets for pristine beaches, but power boaters have figured that out as well, so you'll have (loud) company. That leaves St. Vincent and the Grenadines. Sparely visited and with occasionally choppy seas, this country's collection of tiny, uninhabited cays and lush green islands feels like the Caribbean 30 years ago — all charming ports, undeveloped bays and untracked beaches.
Slideshow: 9 Must-Visit Caribbean Islands
To hoist your own sail, you've basically got two options. You could captain a private charter boat, otherwise known as bareboating. Or you could skip the sailing courses, the charts and the nail-biting passages around unfamiliar reefs, and rent a boat with a skipper. (Can you tell which way we're leaning?)
When it comes to the actual selection of your boat, there are more than enough charter operations to help you along. The default operators are The Moorings (moorings.com) and Sunsail (sunsail.com); the two chains have new boats, branches in most sailing centers, and prices that reflect the premium service (a week with a skipper will cost you about $210 per person per day, not including food). If you'd prefer lower prices, go with a smaller, local company, such as Barefoot (barefootyachts.com) or Horizon (horizonyachtcharters.com); they have older boats, more laid-back service standards (island time, mon), and rates of $125-$150 per person per day — or as little as $200 a day for a crewed boat, plus a cook and food.
If all this sounds baffling, you may want to start your search with a charter broker like Ed Hamilton & Co. (ed-hamilton.com). Brokers help answer pressing questions about the best type of boat (a catamaran, because it's more stable) or the ideal season (late April through June for the best combination of deals and weather). Then they'll pair you with a private owner and captain at rates starting at around $155 a day. Our photographer used Captain Eric Stahl and his boat Tachyon (tachyonsailing.com).
Related: Secret Hotels of the Caribbean
Packing and provisioning
A key rule of the sea: If you feel like you've packed too little, you've still probably overdone it. Space is tight on a boat, so bring only the absolute basics and stuff them into a soft duffel (preferable to a wheelie bag for easy storage). Most sailors like to bring a guidebook, but not of the Lonely Planet variety. The Sailors Guide to the Windward Islands (cruisingguides.com, $30) is the true boater's companion for these parts. It covers all you need to know about anchorages, restaurants, and water-sports outfitters.
Five don't of sailing the Caribbean
On the topic of food, sailors have three options: Hire a cook (from about $110 a day); buy a provisioning package from your rental outfit so you arrive to a fully stocked boat (about $30 per person a day); or simply do the stocking yourself. The decision is yours, but remember, this is a vacation after all.
DAY 1: St. Vincent to Mustique: The private island of Mustique, about three hours from St. Vincent, is the most upscale in the Grenadines; Mick Jagger and Elton John both vacation here. What better place to begin your yacht trip? Moor near the famed Basil's Bar and head up the hill to Firefly (fireflymustique.com) for a sunset cocktail and an incredible view of your boat anchored in the harbor below.
DAY 2: Mustique to Mayreau: Thanks to the perfect crescent of white sand and the beachside bar at Salt Whistle Bay, about four hours from Mustique, most travelers don't venture to the village atop Mayreau, the smallest inhabited island in the Grenadines. But those who make the 20-minute climb are rewarded with a picturesque stone Catholic church and a stunning 360-degree view of the Caribbean.
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DAY 3: Mayreau to Tobago Cays: The setting for Pirates of the Caribbean: The Curse of the Black Pearl, the uninhabited Tobago Cays are about as idyllic as the Grenadines get. Longtime skipper and Sunsail manager Simon Carey recommends a picnic on Baradal Island's U-shaped beach, then swimming with the green turtles often seen at the nearby reserve.
DAY 4: Tobago Cays to Mopion to Petit St. Vincent: A solitary thatched umbrella stands at one end of the 50-foot-long curve of sand that is Mopion island. Stop for a snorkel then move on to Petit St. Vincent. There isn't much here — besides miles of palm-fringed beaches — so guidebook author Chris Doyle suggests radioing the nearby Palm Beach Restaurant & Bar; the staff will shuttle you from your yacht to a table on the beach.
DAY 5: Petit St. Vincent to Union Island: On your way into the harbor at Union, about two hours from PSV, stop for a rum punch at Happy Island, an artificial landmass created by one man — Janti — from a mountain of conch shells. Then continue on to Union. For dinner, Doyle recommends the fresh conch and French-Creole fusion fare at West Indies Restaurant.
DAY 6: Union Island to Petit Nevis to Bequia: According to Carey, the waters off Petit Nevis, about five hours from Union Island, are one of the area's best-kept secret snorkeling destinations, rivaling even the Tobago Cays. Following a swim, sail north to Bequia, famous for its boat building, to sample a conch roti at a picnic table at the Green Boley Restaurant & Bar. Top it off with a cocktail at Jack's Bar, a tented open-air establishment on Princess Margaret Beach.
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DAY 7: Return to St. Vincent: Most charters are due in port by noon — just in time to take in St. Vincent. If you can't make the trip up the island's still-active volcano, La Soufrière (about five hours round trip and worth it), then head over to Montreal Gardens (montrealestgdns.f9.co.uk), which are surrounded by banana plantations and rain forest, all cut with walkways and shaded by tree ferns.
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