Charter Sailing Vacations: Frequently Asked Questions

Explore the Exciting World of Charter Sailing Vacations!

Q: What are the benefits of taking a charter sailing vacation?

A: A charter sailing vacation is one of the all-time greatest vacation options in the world! You have the opportunity to take a vacation in an idyllic setting that offers relaxation, freedom, exhilaration and plenty of fun, all in one experience. In today’s pre-packaged-TV world, taking a week or two to sail in an exotic location with family or friends offers a break and bonding experience unlike any resort, cruise or tour could ever begin to offer.

Q: Where can you charter a sailboat?

A: Almost anywhere the sailing is good! However, you will find more charter boats available in tropical destinations that can offer better and longer sailing seasons. The British Virgin Islands is probably the most popular sailing destination, although there are numerous other Caribbean islands available for chartering. Florida also has numerous charter locations, and the Pacific Northwest is a big charter destination as well. If you want to really go for a world-class adventure, you can also consider fabulous options in the Med, Asia and/or the South Pacific.

Q: It sounds like a really great idea … but what are the estimated costs?

A: Actually, it depends on the number of people who go, the size of the sailboat and the season, but rates are pretty comparable to ski and golf vacation. For instance, in the Caribbean, a 32’-35’ sailboat will run between $200 in low season to $400 a day in high season. On a big catamaran (where the costs can be split among several couples), the costs will usually range between $600 to $1200 per day. Ask the charter company about season dates and rates as it varies from region to region.

Q: Besides the boat charter itself, what other costs are involved?

A: Transportation to the destination (i.e. flights), provisioning (food) and security insurance (also called damage waiver) are the primary additional costs, along with “spending money.”

Q: When should you crew versus bareboat?

A: First, a brief explanation. “Crew” means you book your charter with a captain and possibly either a mate and/or chef who are responsible for handling the boat and often for the preparation of your meal. “Bareboat” means that you take full responsibility of the boat and all aspects of your adventure. Both have distinct advantages based on your level of sailing experience and what you want out of your vacation.

If you are an experienced sailor who has done some cruising in the past, bareboat may be the ideal choice for you. It provides the ultimate degree of freedom … there is just something great about being alone with family and friends on your own boat and going where you want to go, when you want to go.

But having a crew can add extra luxury and give you more of a carefree, "everything’s taken care of" vacation experience. Also, for those who are less seasoned, having a captain aboard can offer a great educational experience to help you gain confidence for going bareboat the next time around!

Q: How experienced do you really need to be in order to bareboat?

A: You need to be completely comfortable sailing a boat of similar size in similar sailing conditions. The charter companies allow you to try different types and sizes of boats, but they will ask you to complete a sailing resume to indicate your experience level on boats like the one you want to charter. Almost all of the charter companies will provide a skipper (for an extra cost) to help get you familiar with the boat and/or waters. In addition, all charter companies will provide a boat briefing to ensure you are familiar with the boat and its systems and a chart briefing to introduce you to the waters, cruising areas and how to get up-to-date weather info.

Q: What are some activities you can participate in when you charter a sailboat?

A: Sailing, snorkeling, swimming, exploring islands and sightseeing, plus simply kicking back and relaxing are high on the list! However, if you want a little more action, most charter companies can also arrange diving excursions or equipment rental, windsurfing rentals, fishing equipment along with many other destination-specific activities if you are interested. Crewed charter boats might even have a tender available that can provide more diving options, along with water skiing, etc. That’s one of the major benefits of a charter vacation … you can set the pace and do exactly what you want to do!

Q: Describe a typical day and night on board.

A: Probably much like a cruising day on any boat, although perhaps more relaxed. Wake up whenever … breakfast on board … maybe a refreshing morning swim … then you decide on the next destination which might include either a lunch stop or heading toward your next night’s location. Sometimes, you may decide to simply stay put and go nowhere!

Assuming you have a new destination, you’ll sail for a few hours, stop for lunch, swim, snorkel, etc. Then it’s sailing for a few more hours to that evening’s anchorage. Arrive and set for night. Then it’s more swimming, snorkeling, windsurfing, lazing back with a great book, etc. At sunset, maybe it’s cocktails on deck with some music. Perhaps you’ll have dinner on board in the cockpit, or you’ll wander up to a beachfront restaurant. And then it’s back to the boat where you can lounge beneath a canopy of stars, read, talk, play games … whatever! Repeat, repeat, repeat... As many who have experienced a charter vacation will tell you, it’s the life!

Q: Any special do’s and don’ts for chartering that you’d recommend?

A: Biggest do is: "JUST DO IT!" The biggest don’t is:

As a former employee of the charter industry who used to always take charter vacations myself, I was convinced that all vacations were that good! However, over the last few years, I’ve taken a number of different types of vacations and few of them compare to the freedom and relaxation of a charter sailing vacation.

Q: How do I take action?

A: Contact and research the charter companies. Take your time and ask lots of questions. Visit your nearest sailboat show as the charter companies often have displays there with knowledgeable staff on hand who can answer your questions and in some instances, actually show you some boats. You can visit with several different charter companies and have more individual attention to address your questions and walk you through their brochure, sailing locations, and explain how it works. Also, Most of the major sailing magazines will include advertisements and listings of charter sailboat companies. Another great source of information is other sailors who have taken charter vacations. And, if you are ready to dig in right now, do a website search and you’ll find a wealth of easily available information right at your fingertips!

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