Choose a Captain
Most charter companies will require a sailing résumé before renting you a craft. Though it’s not necessary to have owned a yacht, they will be looking for boating experience. If you’re a relative novice, a skipper may join you for a test run, or you can hire a captain for the whole trip, usually an extra $125 to $175 per day. It is advisable to have an experienced sailor on board for your first charter. You can also beef up your experience through an American Sailing Association–affiliated school (310/822- 7171; asa.com) or a learning vacation with the Offshore Sailing School (800/221-4326; offshore-sailing.com).
Pick Your Destination
There are endless bareboating alternatives, from the Great Lakes to the Grenadines. But be wary of bargains. There’s a reason why the low season costs less: stormy weather can ruin a sailing vacation. Wherever you go, book with an established company. Larger outfits can quickly send help if you need it. And consider destinations with established mooring fields. Securing a safe anchorage is the most difficult part of sailing for many bareboaters.
Keep it light, especially if you’re headed to a warm locale, and leave your suitcase at home. A soft duffel can be stored more efficiently. Make sure to pack extra bathing suits, sunscreen, a sun hat, and an extra pair of sunglasses, just in case one goes overboard. Finally, it’s worth bringing your own mask and snorkel (rentals can be ill-fitting). But fins can be rented easily from outfitters and even some charter companies.
Make sure everyone has a realistic idea of what to expect—tight quarters (little privacy) and few amenities. A pre-trip agenda laying out how many hours should be spent sailing and how many in port is a good idea. When you pick up your charter, opt for the extra insurance. Even small accidents like a winch handle dropped overboard can lead to serious additions to the final bill. Also, make sure everyone understands the basics of the boat and learns some key skills—how to tie a couple of good knots, for instance.
T+L Picks: Bareboat Charter Companies
Horizon Yacht Charters
(877/494-8787; horizonyachtcharters.com) specializes in the Caribbean, renting out of Tortola in the BVI, as well as several other island destinations.
(888/952-8420; moorings.com) has multiple outposts in the Caribbean, the Mediterranean, and the Pacific.
(888/350-3568; sunsail.com) rents worldwide, including in Australia’s Whitsunday Islands.