How to Charter Your Own Yacht

Bt Thumbnail DefaultBt Thumbnail Default

Live out a Jimmy Buffett song, if only for the week

Meandering around the Caribbean in your own yacht sounds fantastic. of course, it also sounds expensive and complicated. The truth is, chartering a boat often costs the same as or less than a traditional big-ship cruise or beach-resort stay. With a little sailing know-how--or the assistance of a trusty captain-for-hire--anyone can rent a boat and cruise to secluded dive spots, rollicking bars, and hidden coves.

Dare to go bare: You need a driver's license to rent a Dodge Neon, but there's no official certification required to hire a 50-foot yacht. Instead, a charter company will ask you to list your experience, including sailing lessons and previous yachting trips, on a résumé. Based on that, and how you perform during an onboard briefing and Q&A session, the company will decide whether your group can handle the boat you've chosen (smaller ones are easier), where you can go (some places are tougher to navigate), and whether you need a professional captain. If two or three people in your group know how to hoist the main and get on and off the dock safely, chances are you'll get to man your own craft, also known as bareboating. If you've never sailed or your skills are rusty, the company might make you hire a skipper for some or all of the trip. The extra cost is around $150 a day. A good pro will bring you up to speed on the specifics of the boat and help you steer clear of dangerous reefs and lame restaurants; his or her presence should also help you relax. You'll still be the captain in terms of deciding where to sail each day, and whether passengers can start downing piña coladas at noon.

Choosing an agency: It's possible to charter a boat through a small company, but most people report a wider selection, fewer headaches, and comparable prices with a larger operation or an established broker. Sunsail and The Moorings are the Hertz and Avis of the industry, renting fleets throughout the Caribbean (and nearly everywhere else sailing is popular). Ed Hamilton & Co. is a trustworthy broker that arranges charters with hundreds of boats in the Caribbean. Before making a reservation, do some research and ask a lot of questions. Get client referrals, ideally from people who have sailed on the ship you're interested in. If you're hiring a crew, ask about the captain's credentials and personality. Also, inquire about the age of the boat, the sleeping arrangements, the amenities onboard--some come with hot tubs, kayaks, and DVD players--and the procedure if something goes wrong. (The main sail tears while you're at sea. Now what?) Make sure any deposit you pay is held in an escrow account until just before departure, so that in the event of a worst-case scenario you can get your money back as easily as possible.

Prices and particulars: Most rentals have a five- or seven-day minimum. Prices are determined by season (rates go up when temperatures in the U.S. go down) and a boat's size, age, amenities, and staff. Typical rentals range from about 32 feet (four to six passengers) to 52 feet (10 to 12 passengers). Fill the boat with friends and the starting price in spring or summer for a ship with a skipper and a cook averages out to about $200 a night per person, with food and drinks included. Bareboating can start as low as $50 per person per night, and the charter company will stock the larder based on your preferences--lasagna, quiche, burgers, veggie dishes, Heineken, Bacardi--for about $25 per person per day extra. Nearly all boats have barbecue grills, and fresh fish should be easy to come by.

Dropping anchor: Consensus says the best spot for a beginner to get his sea legs is in the British Virgin Islands, where the winds are consistent, the waters are deep and sheltered, and there's plenty to do ashore. With dozens of islands concentrated in a relatively small area, most sailors spend their days swimming, snorkeling, and exploring the bars, shops, and beaches of yet another small port. Over the course of a week, you can snorkel in the caves at deserted Norman Island, which supposedly inspired Robert Louis Stevenson's Treasure Island; check out the giant boulders at the Baths on Virgin Gorda; and lounge on white-sand beaches and sip Painkillers--concocted with pineapple and orange juice, cream of coconut, dark rum, and nutmeg--at funky joints such as Foxy's Tamarind Bar and the Soggy Dollar Bar on Jost Van Dyke. If you're ever looking for advice on where to sail next, tie up for the night, or go bonefishing, use the time-honored tradition of sailors all over the world: Ask at the bar.

Don't drop anchor right next to another yacht--the whole point of a charter is privacy.

1. When someone waves at you from a nearby boat, he or she may be trying to tell you something. Don't simply wave back.

2. It's not so uncommon for a boat to be drifting halfway between Norman Island and St. John with everyone onboard fast asleep. Before you set out, be sure you've learned how to anchor properly.

3. If anyone within eyesight appears to be offended, put your swimsuit on.

4. Always remember to tip the crew--in cash.



  • Sunsail 800/797-5310,

  • The Moorings 800/535-7289,

  • Ed Hamilton & Co. 800/621-7855,
  • Lodging


  • Foxy's Tamarind Bar Great Harbour, Jost Van Dyke, 284/495-9258

  • Soggy Dollar Bar Sandcastle Hotel, White Bay, Jost Van Dyke, 284/495-9888
  • British Virgin Islands Tourist Board Road Town, Tortola, 284/494-3134,

    Related Content