Charter Tips

I was in St. Thomas the last week of March on a press trip organized around the annual International Rolex Regatta. The welcome party at the St. Thomas Yacht Club welcomed not only the racers, but gusty winds accompanied by rainsqualls. By the next day, when we press people were out on a spectator boat watching the downwind start of the first race, it was threatening to blow the hair off the

Thanks to the unusual nature of my job—I give thanks frequently—I’ve sailed on a lot of charterboats with (often) people I’d never met before in (sometimes) unusual weather patterns. It’s not unusual, however, that many of these boats have been catamarans, given the proliferation of cats in charter fleets worldwide. So I can claim a certain authority in saying that, in many circumstances in

Over my years as SAIL’s charter editor, I’ve worked with many bareboat-charter companies both as a charterer and as an editor. Truth is, the people you interact with in setting up a charter vacation and dealing with the details are almost invariably as helpful and knowledgeable as you could wish.When a friend who was planning a first-time charter came to me with questions, I seized the

HAVE A QUESTION ABOUT CHARTERING?Readers want to know: How to get there; when to go; what to pack. I’m not a travel agent—far from it—but I do have some practical experience to share, especially when it comes to the Caribbean.How to get there. San Juan, Puerto Rico, has long been the hub for travel from the U.S. mainland to the islands, and American

If you’ve done any sailing outside your home waters, you already know how invaluable a cruising guide can be. I suppose it’s possible to tough it out with just the chart and the chart checkout, but at the very least this means you’d be reinventing the wheel when it comes to choosing an anchorage, figuring out what time you should arrive there, finding groceries, and much more.Chris

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

This month’s contributor is Tom Reinke, who sails a Flying Scot with his wife, Mary. They love leading bareboat charters and turning over the helm to the officer of the day. If you’re new to chartering—or if your friends are—you’ll find his organizational ideas helpful.The primary objective of a charter is to have a good time, and that means different things to different people.

I was recently confronted with the not-unpleasant conundrum of how to make the best use of a one-week charter in a place (a) I’d never sailed before, (b) I am unlikely to return to, and (c) that is too big to sail and see it all in a week. What I consider to be “best use” involves a pleasant amount of sailing (but not dawn to dusk) and a reasonable amount of time to see the sights ashore and

Caribbean. Everyone likes to save money—and why not. If you must have some time in the tropics and can’t wait for the summer specials in the Caribbean and the Bahamas to kick in (see May SAIL for a rundown)—and if you’re flexible about dates—you’ll find that most bareboat companies in the Caribbean are offering last-minute online specials. The list on sailmagazine.com links to company Web

The word is “most.”Most bareboat-charter companies are able to hire a skipper for you at most or all of their bases and most can also find an instructional skipper, should you want to brush up your basic sailing skills or acquire cruising-specific knowledge. Most of the time it goes well. You not only pay the skipper, but are also expected to provide a cabin on your boat for him/her as