Most North American sailors choose the Caribbean for a winter sailing vacation. There are good reasons: a well-developed chartering infrastructure; a variety of discrete cruising grounds to choose from; great sailing conditions; numerous flights to Caribbean locations; lots of charterboats.
Here are essential considerations when planning your charter.
1. The timing of your charter affects everything from the cost of the boat to the seasonal sailing conditions to the cost and availability of air arrangements.
2. Keeping in mind your comfort level and the experience of your crew, consider this: the Virgin Islands are the "easiest" cruising ground, requiring only short passages between islands and line-of-sight navigation. The waters of the main drag—the Sir Francis Drake Channel—are protected by islands on both sides. In the Leewards and Windwards, you leave the bunny slope; anchorages are farther apart, and passages between islands are unprotected.
3. Consider what size boat you need (and feel comfortable handling). The smallest charterboats available are two-cabin monohulls in the low-30-feet range; the largest are 50-foot sloops and catamarans with four to six cabins.
4. Consider your budget. The boats in some charter companies' fleets are less than three years old; other companies offer well-maintained older boats (and lower prices). Turn to page 97 for SAIL's annual listing of charter companies in the Caribbean and Bahamas to compare prices for a 40-foot monohull and a 38-foot catamaran in high and low seasons.
5. Do your homework. Get hold of a cruising guide to the area you're interested in; read the articles posted on sailmagazine.com (click on Charter Cruising) for personal takes; check out suggested itineraries on charter company Web sites.
6. Call the charter companies whose base locations, prices, and fleets interest you the most; expect to get information on boat availability, sailing conditions, and anything else you need to know.
7. Once you've chosen a company, a destination, and a boat, the fine-tuning phase begins. Here are some pointers:
- If you're hoping to use frequent-flyer miles in the winter, call right now.
- Most charter companies have either an in-house travel agency or agents they work with. They often offer good prices, and their experience in booking Caribbean flights means that they may be aware of better connections.
- Trip insurance is a good idea. Learn why in the charter section of sailmagazine.com.
- Most charterers choose to arrive at least a day before their charters start (and sometimes stay on a day or two at the end). Your charter company will be able to help you find a hotel that will let you have a room for less than a week.
- All charter companies will order provisions for you from an extensive list of supplies. You can also choose to self-provision, keeping in mind that it will cost you some time (and taxi fares). Ask about the availability of reprovisioning along the way before you make the decision; cruising guides have useful information on this.
- Pack light, in a soft-sided bag; you don't need much on a boat. The essentials: a bathing suit (maybe two), sunscreen, boat/water shoes, a T-shirt to snorkel in, something to wear ashore during the day (the islands are generally conservative), something to wear for dinner ashore (some resorts require that men wear jackets).
- Cell-phone calls are costly in the islands. Your charter company may be able to tell you how to get a better rate if you think you'll be making many calls.