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For a memorable tropical getaway, consider bareboat chartering in the British Virgin Islands. (Courtesy of The Moorings)

Welcome to the World of Bareboat Chartering

An Expert’s Guide to ‘Sea’ More in Style

by Chris Caswell
March 17, 2022
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It was a flawless tropical morning and, rising early, I settled comfortably in the cockpit with a mug of fresh roast. Life was good.

Nearby, a white crescent of beach curved out of sight, and the overhanging palms glittered silvery in the early light. The only sounds were the soft shushing of wavelets onto the beach and the squawk of a distant bird. Life was very good.

A man on a small boat stopped next to me on his way to the beach.

“Great looking boat,” he said. I nodded amiably. He added, “I’ve always wanted to own one”.

“Me, too,” I replied.

You see, this wasn’t my boat.

As restrictions on travel are eased worldwide, bareboat chartering is again a wonderful way to get out on the water. For those in colder climes, it’s a chance to find warm water and palms blowing in tropical breezes. For Tampa Bay residents, it might just be a getaway from your home waters.

Bareboating does not (unfortunately) mean clothing optional. It means that your boat is supplied without a captain or crew: you and your friends or family handle everything from anchoring to cooking, and the choice is up to you where to go (or not go) each day.

Chartering in the British Virgin Islands (Courtesy of The Moorings)

As luck would have it, three of the largest bareboat charter companies are based in the Tampa Bay area: The Moorings, MarineMax Vacations and Sunsail. The Moorings, for example, has been in business for half a century with 20-plus locations worldwide from the British Virgins to the Mediterranean, and more than 400 yachts (both power and sail) from which to choose. There are also smaller companies in this area, such as the respected Southwest Florida Yachts in Cape Coral, offering yachts for exploring Sanibel and Captiva, as well as the Everglades and Tampa Bay.

Even if you own a boat, bareboat chartering allows you to sample cruising areas that would take months for you to reach otherwise. A few hours in an airline seat can put you in the Scottish isles, on the Italian Riviera or under a palm in Tahiti.

Pricing 

A bareboat charter compares favorably with a vacation at a fine resort hotel, especially when you factor in all those shoreside extras, such as resort fees and room service. Aboard a bareboat, your meals always have the best view (no waiting for seats!), and you have all the watery delights, such as snorkeling on coral reefs or exploring sandy beaches. It’s a chance for adventure – completely on your own terms.

Choosing Your Destination

If you haven’t bareboated before, pick a relatively benign area to dip your toes. The British Virgin Islands and the Bahamas are appropriate for novice charterers, with protected waters, short distances between harbors, well-marked navigation and predictable weather forecasting. Skip the swirling Hebrides off of Scotland until you’re experienced, and remember that foreign waters mean unfamiliar navigational aids and foreign languages to complicate your cruise.

Where you go should also be dictated by the time of year you have available, as well as the climate you desire. Winter eliminates much of Europe and parts of North America, while midsummer Caribbean can be steamy. The Pacific Northwest is temperate in the summer, cool in spring and fall, and wet in winter. Choose wisely.

Exploring The Bahamas (Courtesy of The Moorings)

No Captain Needed

If you’re an experienced skipper, you’ll learn everything you need during the comprehensive pre-charter briefing given out by each company. A representative will walk you through the boat and its systems, as well as provide a “chart talk” about everything from hazards to finding the best hamburgers.

Ian Pedersen, of The Moorings, notes, “If desired, we offer a ‘Friendly Skipper’ at no charge for a half-day to provide one-on-one instruction to familiarize yourself with your yacht or to brush up on your skills.”

If your boating resume doesn’t pass muster with the charter company, they’ll suggest you take a skipper for the duration, and this can actually be quite helpful. The skipper will take one of your cabins and you need to provide his or her food, so build that into your provisioning plan. The upsides are that you aren’t required to post an insurance waiver for damage, and the skipper we had in the Greek islands knew the best coves, his dockmaster friends gave us favorable slips, and we dined at bistros we would never have found.

Availability

You’ll find just about every boat available for charter that you’d find in your local marina. Catamarans have swept the charter industry, offering spacious accommodations with separation (no shared bulkheads to hear anyone snoring), plus ample space in the salon, cockpit and flybridge.

Catamarans (as well as monohulls) are available in all shapes and sizes in both power and sail, so you’ll need to do your due diligence, figure out how many people you need to handle, and what you’re comfortable skippering. Tip: Using convertible dinettes for sleeping is a pain to make and remake the beds daily. Try to get a private cabin for all aboard.

Choosing Your Crew

The U.S. Navy spends considerable time and money screening candidates for submarines, and you should devote as much time to everyone you plan to live with for a week in close quarters. Your family is one thing, of course, but too many charter crews result from a, “Hey, want to go on a charter?” at the yacht club bar.

Consider personal habits such as smoking and drinking, as well as common interests. If your invitees want to go ashore for happy hour every night and you like relaxing in the cockpit, a charter can be a breeding ground for conflict.

A power boat in Magens Bay, St. Thomas (Courtesy of The Moorings)

Do’s And Don’ts

Overpacking is the curse of even experienced charterers. An apocryphal story is told about a bareboater who lost his luggage enroute to the charter. He bought a bathing suit, two shirts and shorts when he arrived and, at the end of the charter, realized he hadn’t needed anything else.

Realistically (and depending on the area), take foulweather jackets, comfy clothes for the boat, and dressier clothes for going ashore (even in the casual Caribbean).

It all goes into a duffel bag, which can be stowed on board. Ask first, because some charter companies will store a hard suitcase, allowing you protection from the airlines. However, you would still repack into a duffel before your charter.

Don’t let finances get away from you. We always have a “kitty,” an envelope into which everyone contributes an equal amount. That is used for everything from mooring fees to ice-cream cones ashore, thus solving any issues of sharing costs. Just reload the kitty as needed.

Whatever and wherever you choose, remember that a bareboat charter is all about attitude. Go into it expecting fun, relaxation and excitement and that’s exactly what you’ll find.

Chris Caswell is an experienced bareboater and the author of Charter Smarter, the “bible of bareboating,” as well as publisher of CharterSavvy, a free online magazine about bareboating. When not bareboating the waters of Thailand, Tahiti or the British Virgin Islands, he and his wife, Rhea, hang their duffel bags in West Palm Beach.

Check out his other articles for TAMPA Magazines.

Tags: BahamasBareboat CharteringbareboatingBoating GuideCatamaransChris CaswellItalian RivieraLuxury TravelMarineMaxPower BoatingSailingScottish IslesSouthwest Florida YachtsSt. ThomasSunsailTahitiThe MooringstravelVacation Ideas
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