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Image: Chatham Bay on Union Island
Jose Mandojana via Budget Travel
Renting a caraman — with or without a crew — is a good way to get around reefs and beaches like this one on Chatham Bay on Union Island in the the Grenadines.
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updated 3/4/2011 11:59:13 AM ET 2011-03-04T16:59:13

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

Casting off
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.

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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.

The Route
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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Copyright © 2012 Newsweek Budget Travel, Inc.

Photos: Caribbean way of life

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  1. Barbados

    This undated photo courtesy of the Barbados Tourism Authority shows Harrismith Beach, Barbados. Sun, surf and sand are the main draws on this tropical Caribbean island. (AP) Back to slideshow navigation
  2. Barbados

    This undated photo courtesy of Barbados Tourism Authority shows The Watering Hole rum shop in Barbados. The rum shops on the island are good places to sample local food and drink, watch a game of dominos, or just get to know the friendly and hospitable Bajans. (AP) Back to slideshow navigation
  3. St. Lucia

    Developed, beautiful and situated in the Eastern Caribbean, St. Lucia is accessible from Europe and Canada, and reachable -- albeit not as easily -- from the United States. St. Lucia is known as a romantic destination. The island gets plenty of visitors, including wedding parties. (Holger Leue  / Lonely Planet Images) Back to slideshow navigation
  4. St. Lucia

    Cocoa pods lie on the ground ready to be processed at Fondoux Plantation in Soufriere, St. Lucia. Cocoa is one St. Lucia's main produce alongside the more obvious banana crop. (Chris Jackson / Getty Images) Back to slideshow navigation
  5. St. George's

    The capital of Grenada, St. George's is considered one of the prettiest harbor towns in the Caribbean. Grenada's unique layout includes many finger-like coves, making the island a popular sailing destination. (Richard Cummins  / Lonely Planet Images) Back to slideshow navigation
  6. The Cayman Islands

    The Cayman Islands very popular attractions, Stingray City and the nearby shallows known as the Sandbar, provide the only natural oportunity to swim with Atlantic Southern Stingrays. (David Rogers / Getty Images) Back to slideshow navigation
  7. Stingray City

    The Cayman Islands very popular attractions, Stingray City and the nearby shallows known as the Sandbar, provide the only natural oportunity to swim with Atlantic Southern Stingrays. (David Rogers / Getty Images) Back to slideshow navigation
  8. St John's

    In high season, up to five cruise ships visit St John's, Antigua, each day. The boats unload mostly American and European passengers who fan out across the island visiting the casinos and beaches. Antigua is easily accessible, and can offer good values for tourists. (Chris Jackson / Getty Images) Back to slideshow navigation
  9. Antigua

    Antigua, located in the Northeastern Caribbean, is a popular tourist spot. While there are high-end, stylish hotels, the island also features a large number of mid-priced options. Visitors will find beach bars, restaurants, casinos and shopping. (Richard I'Anson  / Lonely Planet Images) Back to slideshow navigation
  10. Antigua

    People walk along an area known as Devils Bridge in Indian Town Point, Antigua. Antigua is a wintertime destination for many visitors from the north. (Joe Raedle / Getty Images) Back to slideshow navigation
  11. Dominica

    Not as well known as other Caribbean islands, Dominica is green, fertile and mountainous. Visitors will find some opportunites to scuba dive, but watersports are not its main draw. The island does, however, offer a slew of rainforest trails -- great for hiking and sightseeing. (Greg Johnston  / Lonely Planet Images) Back to slideshow navigation
  12. Dominican Republic

    An old church building is seen in La Romana, the third-largest city in the Dominican Republic. (Wayne Walton / Lonely Planet Images) Back to slideshow navigation
  13. Belize

    Belize gets more than 850,000 visitors each year. The hot spot allows watersports such as kayaking and snorkeling, as well as inland activities like hiking and birding. The Mayan ruins of Altan Ha, pictured, are easily accessible from Caye Caulker. (Andrew Marshall / Lonely Planet Images) Back to slideshow navigation
  14. La Tortuga

    A fisherman repairs his nets on Cayo Herradura, off the island of La Tortuga in Venezuela. The country offers visitors a variety of activities to choose from, but remains undervisited -- especially compared to its South American neighbors. (Lynne Sladky / AP) Back to slideshow navigation
  15. Cuba

    Cuba blends the fantastic attractions associated with other Caribbean destinations with an amazing history. Tourists can stroll white sand beaches, take in the incredible architecture and party into the early-morning hours. (Javier Galeano / AP) Back to slideshow navigation
  16. St. Barthelemy

    St. Barthelemy is a vacation spot of stars and millionaires. Trendy, chic and sexy, St. Baarths is safe for tourists, but expensive to visit. About 8,700 people reside on the island. (Mark Mainz / Getty Images) Back to slideshow navigation
  17. Puerto Rico

    A man climbs to a 40-foot waterfall at the south side of the Caribbean National Rain Forest, commonly called El Yunque, near Naguabo, Puerto Rico. Most visitors hike the well-marked paths in the northern half of the park's rain forest but the trails in the south allow hikers and nature lovers to explore the only tropical forest in the U.S. national forest system. (Herminio Rodriguez / AP) Back to slideshow navigation
  18. Puerto Rico

    The cupola of San Juan Cemetary as well as colorful homes sit next to the ocean in Old San Juan, the original capital city of San Juan, Puerto Rico. The old city is a historic district of seven square blocks made up of ancient buildings and colonial homes, massive stone walls and vast fortifications, sunny parks and cobblestoned streets. (Joe Raedle / Getty Images) Back to slideshow navigation
  19. Puerto Rico

    Men play dominos in Old San Juan, Puerto Rico. Old San Juan is a well-preserved colonial city that allows tourists a peek into the past. (Joe Raedle / Getty Images) Back to slideshow navigation
  20. Guadeloupe

    Guadeloupe isn't as developed as some other Caribbean islands, but it offers a variety of beaches -- some active with watersports, some secluded. The island also offers beach bars, restaurants, mid-range hotels and other tourist amenities. (Marcel Mochet / AFP - Getty Images) Back to slideshow navigation
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    Above: Slideshow (20) Caribbean way of life
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    Slideshow (12) Picturesque Puerto Rico

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