9 Must-Visit Caribbean Islands

A fruity rum drink is calling your name from the deck of a catamaran. Consider this your step-by-step, island-by-island guide to fun on the high seas.

Chatham Bay on Union Island

(José Mandojana)

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 over-crowded 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.

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.

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).

Packing & 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.

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.

HIDDEN CARIBBEAN

Get Inspired with more from BudgetTravel.com


Note:This story was accurate when it was published. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.
 

Budget Travel Real Deals


  • From $1,078
  • From $1,199

See more deals »

Video


Our newsletter delivers vacation inspiration straight to your inbox.

Check Prices