Expert Advice

What It's Really Like to Own a Boat in Charter

by Paul F. Jacobs, Posted October 7, 2014
My wife, Nancy, and I are big-time charterers. We love to sail, we love to travel, and we love to do the two of them together—so much so that after several years of chartering once or twice a year, we were looking to increase that to four or five times a year. In our travels we’d heard about owning a charter boat in a fleet

Charting a Charter

by Amy Ullrich, Posted August 8, 2008
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
In the October issue of SAIL, we take you on charter adventures in the Spanish, U.S. and British Virgin Islands. You may have sailed there a dozen times before, but there are always new gems to discover. We asked our panel of Island Experts to divulge their best Virgin Island charter secrets. Here's what they came up with

The Practical Side, Please

by Sail Staff, Posted August 10, 2008
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

School's in Session

by Rebecca Waters, Posted November 11, 2010
If your goal is to be able to charter a boat in your dream destination, nothing will prepare you better than a sailing course taught on a charter boat. Working on a charter boat, your instructor can walk you through the entire charter process, from chart briefing and provisioning to the final return. And who’s to say your class can’t be in that dream locale?“We use charter boats to teach

Your New Best Friend

by Amy Ullrich, Posted August 11, 2008
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

The Family Way

by Peter Nielsen, Posted March 11, 2011
Before I actually took my family on a flotilla vacation, I couldn’t understand why anyone would take their family on a flotilla vacation. The mere thought of sailing along in a group of a dozen boats, being herded like sheep into marinas by some officious lead skipper, not to mention the forced jollity with total strangers, filled me with horror. After all, one of the reasons I go sailing is to

Charter Cats

by Amy Ullrich, Posted August 20, 2008
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
Any bareboat skipper who’s experienced a restless night at anchor knows that bareboating can sometimes be stressful. And while some veteran bareboaters positively enjoy planning trips and controlling ships, others know how glorious it can be to give up the helm and embrace the vacation. That’s when they try out crewed yacht chartering.
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
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