Choosing the Best Charter Option

Not quite ready to skipper but still want to charter? Don’t worry, there are plenty of other options to get you out there.
Built for fun: Most crewed charter vacations are aboard well-appointed catamarans or larger monohulls, and water toys such as snorkel gear, stand-up paddleboards and kayaks are typically included. Dream Yacht Charter

Maybe you’re not quite ready for a bareboat charter. Or perhaps a potential charter in a new, more challenging location has you nervous. Or it could be that you’re just looking for a different kind of sailing vacation. Whatever your reasons, there are plenty of ways to get out on the water, all over the globe, regardless of your experience level. Let’s take a look at what’s available beyond the bareboat charter.

Learn-to-Sail Trip

If you’re new to sailing or want to improve your skills to become a more competent and confident skipper, consider checking out one of the learn-to-sail courses offered through many sailboat charter companies. This lets you earn certifications that could be useful for a future bareboat charter while enjoying a vacation destination.

The American Sailing Association, which offers sailing instruction and certifications, has affiliated schools all over the world, and many of these schools also have a charter fleet. This allows students to make a vacation out of learning to sail.


Barefoot Yacht Charters, located in St. Vincent and the Grenadines, has been doing this for more than 20 years with its Barefoot Offshore Sailing School. “BOSS gives a unique balance of an extraordinary vacation in a gorgeous tropical environment, combined with a good learning curve for sailing skills,” says Marissa Barnard of Barefoot Yacht Charters. “In addition to basic sailing courses, we also offer an offshore course, which includes overnight passagemaking between St. Lucia and St. Maarten.”

Hire a Captain

Perhaps you’re completely new to sailing, or the boat that you would like to charter is beyond your skill set. Consider hiring a captain for all or part of the trip. Most charter companies make it easy to do this at the time of booking. Just a little rusty? The Moorings offers its complimentary Friendly Skipper option on any bareboat charter. With this program, a captain joins your crew for a four-hour refresher course at the beginning of your charter.

If you’re more comfortable at the helm of a powerboat, there are charter companies with modern power fleets available in many cruising destinations, like MarineMax in the BVI. MarineMax

Join a Flotilla

Long a popular vacation option in Europe, flotillas are catching on in the North American market — and for good reason! Basically, a flotilla is a small fleet of chartered boats and a lead boat. Aboard the lead boat are guides who are in charge of the event and are familiar with the local waters and sights. You can charter an entire boat, or often just a cabin. Flotillas are a great way to explore a new destination, particularly if it’s challenging or you just would like the reassurance of traveling with someone who has local knowledge.


The ASA has a full calendar of flotillas offered at affiliate schools around the world. These trips are targeted both at new sailors and those who have been sailing for years. Lenny Shabes, who is an experienced sailor and also chairman of the ASA, wanted to do a charter in the San Juan Islands but had heard so many horror stories — underwater obstructions, floating logs — that he was apprehensive about going it alone on a bareboat. “I was looking for camaraderie and the security of knowing where I was going, so a flotilla was the perfect solution,” he says. “Every morning the flotilla leader would brief us on where to go and where not to go, and what time and place to meet up again. It was reassuring to be cruising in this unfamiliar area, always in sight of other boats, and we met some great people who we still keep in touch with.”

For newer sailors, flotillas can provide a bridge between sailing-instruction courses and heading out on your own. By booking just a cabin, you have the opportunity to learn from the captain and the rest of the crew while gaining experience in an exotic or challenging location.

If you’re looking for a different sort of adventure, one of Sunsail’s themed flotillas might be right for you. Some upcoming offerings include Food and Wine Flotillas in Italy and Croatia, as well as a rum tour of the BVI. “The Food and Wine Flotilla introduces our guests to stunning scenery, fine wine and delicious, local Croatian cuisine,” said Nicolle Smirlis, marketing manager for Sunsail. “Due to the popular demand of flotillas in the Mediterranean, earlier this year we launched a new flotilla out of Palma de Mallorca, Spain.”


Once you decide that a flotilla vacation is in your future, Danelle Carnahan, of San Juan Sailing, which offers a full schedule of flotilla options throughout the Pacific Northwest, offers this advice: “Just relax, brush off your sea stories and enjoy getting to know your fellow cruisers.”

Stress-free sundowners: Whether you have a crew of nonsailors aboard, or you just want more time to relax, consider hiring a skipper for the trip. Sunsail


A stress-free sailing vacation where you can meet interesting people and travel to some out-of-the way places on a crewed catamaran sounds pretty perfect, right? A by-the-cabin charter is exactly this, and is ideal no matter what your sailing skill level. These charters “remove the barriers for nonsailors and allow them to enjoy island-hopping aboard a luxury yacht at a reasonable price point,” says Dan Lockyer, general manager of Dream Yacht Charter. “But they also appeal to experienced sailors who enjoy being on the water but want to kick back and relax.”

By-the-cabin charters include a captain, and typically a chef as well, and take place on a well-appointed catamaran, or a larger monohull with separate cabins with en suite heads. Worried about whether you’ll like the other guests? Don’t be, says Lockyer. “These trips appeal to people with a similar mindset, which makes for a good group dynamic.”


Motor Up

Let’s say you have plenty of experience on the water, but it just happens to have been at the helm of a powerboat. Or perhaps your crew just isn’t interested in sailing. A charter aboard a trawler or a power catamaran might be just the thing. Powercats have started to appear in more charter fleets around the world. They offer the space and stability of a catamaran, with the ease of a powerboat. “Most poweryacht charterers are people who already own or have owned a poweryacht in the past,” says Barb Hansen, co-owner of Southwest Florida Yachts. “Other power charterers might be people who have been through our power-cruising school and are chartering for the first time. Their ultimate goal might be to own a boat or just to keep chartering for a while.”

Calling All Salts

If your call to the sea consists more of square rigs and sea shanties, consider a sail-training vacation aboard a tall ship. There is a wide variety of tall ships offering programs throughout the United States that ranges from overnight journeys to a semester at sea. Visit Tall Ships America’s website ( for more details and to find a program that interests you.

From learning sailing skills while cruising the Med to making new friends on a voyage through the islands, there is a way for you to get out on the water — no experience needed.

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Jen Brett is CW’s senior editor.