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With so many enticing choices, planning a boat charter vacation may seem overwhelming at first, especially if you're new to chartering. You can easily get bogged down in details and then overloaded with information. Here's how to streamline the process, starting with three simple basics.

Area

When it comes to chartering a boat, the world is at your fingertips. There are boats of all sizes and types available for charter in nearly every desirable destination. If you'll be operating the boat yourself, with you as skipper, and family or friends as your crew, first consider your experience level; some destinations offer easier boating, others more challenging. If you're new to cruising or chartering, pick a novice-friendly area. Do some quick research and look for areas with protected harbors, deep water, easy line-of-sight navigation (meaning you can see your next destination from your current location), short hops between ports, and few or well-marked navigational hazards. The British Virgin Islands is an example of a perfect first-time chartering location.

French canal charter

Photo: Stuart Pearce/Le Boat

Cruising the French canals

A perfect boating holiday? Charter a bareboat barge from Le Boat to explore the canals of Europe and ­Canada with friends or family.

Finally, choose your dates to coincide with the most optimum seasonal wind and weather conditions in that area, information that is easily found on charter companies' websites. If you're a seasoned skipper and crew, match your area with the type of boating you enjoy most: easy and relaxed or a little more challenging. Keep in mind that license or certificate requirements for bareboat skippers vary according to state and/or country laws. Most charter companies list qualifications required to bareboat in their areas. If you don't feel like shouldering any responsibility, simply choose your dream destination and opt to charter a boat with a one- or two-person crew, usually either a professional captain only, or captain and first mate/cook. (Sometimes you'll be given the option of paying for a captain by the day until you get used to handling the boat on your own.) You'll still be able to participate fully in every aspect of operating the boat if you like, but these experienced local pros will be ultimately responsible for boat and guest safety and will have lots of great inside local knowledge to ensure you have the best vacation possible. Check out our sidebar of top chartering destinations below to see which places may be great for your next vacation.

Great Destinations For First-Time Charters

A great way to take your first bareboat-chartering vacation is by exploring one of these beautiful and popular destinations. The following areas have accurate charts, GPS, and reliable aids to navigation, and offer mostly line-of-sight cruising and short distances between islands or coves. All require basic coastal navigation and anchoring skills, but moorings and marinas are also readily available. Charter companies based in these areas will provide thorough briefings before you depart to help you with local knowledge, itineraries, and navigational precautions.

Chesapeake Bay

Best season: mid-May to mid-October

Stretches about 200 miles into Maryland and Virginia from the Atlantic Ocean, with a serrated shoreline of more than 11,000 miles. There are about 500 harbors, uncounted coves, quaint villages, and islands to explore. A bareboaters' playground! And remember, the Chesapeake is world-famous for striped-bass fishing. May is the best time to catch a trophy-sized fish; summer and fall offer larger numbers of school-sized stripers.

Great Lakes

Best season: June to September

The five lakes that sprawl along the boundary between the United States and Canada touch eight states and two Canadian provinces — a great bareboat destination. With 10,000 miles of shoreline and 35,000 islands, the freshwater, tideless Great Lakes offer clear, deep water; beaches and sand dunes; charming towns; national parks; and forests, hiking trails, and unspoiled beauty. There are diverse fishing opportunities — walleye, perch, salmon, and more — depending where you visit.

Washington's San Juan Islands

Best season: June through early September

Roughly 60 nautical miles north of Seattle, they form an oval, with San Juan Island on the west with its back facing Canada's Vancouver Island and Orcas Island draped across the top of the cluster. The remaining islands lie between these two large islands and the mainland to the east. There are at least 150 named islands. While Seattle is famous for rain, the San Juans are in the "banana belt," protected from most storms and averaging 250 sunny days a year. Literally something for everyone — small coves, wildlife, villages, beaches set in pine forests, and protected waters suitable for boats of all sizes. Time your visit to enjoy fishing for a fresh salmon dinner (runs vary by species), or try hauling up some halibut.

Florida

Best season: December to April

Two bareboating areas, both providing the "faraway" delights of palm trees, white sandy beaches, wonderful weather, and great snorkeling, as well as a mix of resort marinas and quiet anchorages. The West Coast is primarily the protected Pine Island Sound area including the barrier islands of Sanibel and Captiva all the way up to the boating-rich bay that's home to Tampa and St. Petersburg, plus islands and parks. "Old Florida" architecture and Native American history.

The Florida Keys start at Biscayne Bay off Miami and curve south in a necklace down to Key West, the southernmost point of the United States. In between are some 1,700 cays, coral reefs teeming with tropical fish, warm water, and pleasantly warm trade winds.

Also, Florida is a mecca for anglers. From inshore to offshore, Gulf to Atlantic, just about every inch of Florida's waters are home to various gamefish. For more ideas visit our travel and destinations articles.

British Virgin Islands

Best season: December to April

With turquoise waters of a Caribbean paradise, the BVI is ideal for bareboaters still building their charter know-how and experienced boaters alike. Outside the U.S., but sharing a common language and hosting many American tourists, the BVI is the world's most popular charter destination, offering warm waters, white sand, and balmy tradewinds. Tortola, the main island, is where most bareboat charter bases are located. From there, most islands are just a half day's voyage away. Seas are generally calm in the lee of the many islands.

When it comes to fishing, BVI is known not only for the big game in nearby offshore waters, but also a healthy stock of snapper that will be more than happy to keep the kids entertained all day long. Just remember, your vessel must have a BVI fishing vessel registration number, and each individual 18 years or older who will fish needs to purchase a license ($45, good for 30 days).

— Chris Caswell, Anne Morley and Lenny Rudow

Boat

There are boats available in all sizes and types, power or sail. Would you prefer a monohull or multihull? How important is comfort? Speed? Performance? Answer these questions, and you've considerably narrowed the search. Next, take a head count of family or friends joining your adventure. How many people are you? If you're a couple only, there are smaller boats available. More people? Great. Most mid-size charter boats can take between four and eight passengers. Decide how many cabins and beds you need, as well as how many heads and showers will suit your particular group. Some boats of even larger size typically have one or two heads.

Easy to operate catamaran

Easy-to-operate power or sailing cats are great for comfortable chartering. Book one as either a bareboat (no crew), or hire crew for a day or two — or more! — to learn the ropes yourselves. (Photo: George Kamper/The Moorings)

Once you know these parameters, determine the approximate size boat you need. Many chartering websites let you enter these parameters, then present you with a list of appropriately sized boats. On most charters, other than sleeping, very little time is spent belowdecks, even for showering (many charterers in the tropics prefer showering on the stern swim platform anyway). So check the cockpit configuration as well as deck space for lounging and relaxing. Is there adequate space for the number of people you have?

Tip

BoatUS Members receive exclusive discounts and other benefits with several charter companies including The Moorings and Le Boat. Log into your BoatUS account and click "resources" to access information and discount codes.

Finally, pay attention to the extras that do or don't come with the boat, such as any water toys you may like — kayaks, sailboards, or paddleboards (sometimes those can be rented from the charter company). An adequate dinghy and snorkeling gear are usually included with the boat. Once you have your parameters set, choose the boat in your desired location that will be right for you.

Consider A Bareboat Flotilla

To further hone your skills or just have a blast with other boaters, think about joining a flotilla. On these trips, a group of powerboats and sailboats travels in company with a professionally crewed "lead boat" that guides the flotilla, provides daily skippers' briefings, and is prepared to assist boats with anchoring, docking, or mooring, or in urgent situations, if needed. Boats in the flotilla may be either bareboat or have a company-appointed skipper on vessels requesting or requiring one.

An excellent choice are flotillas such as those run by Sunsail, which rates the level of qualification required for each destination on its website. The company also offers a "Flotilla Starter" trip combining a vacation with learning the basics in a fun, relaxed environment. sunsail.com/flotilla-sailing

Another great option: Join our annual BoatUS flotilla with The Moorings in the BVI for power and sail. The next one is May 16–23, 2020, and BoatUS members get exclusive discounts and other benefits. hsinfo.moorings.com/boat-us-flotillas

Parts of this sidebar were excerpted with permission from "Five Easy Places" by Chris Caswell, from the website CharterSavvy.com.

Cost

Everyone has a budget, and you can easily choose a boat that will suit yours. You might be surprised to find that a boat vacation can be far less expensive than an equivalent land-based vacation in whatever idyllic spot suits your fancy. Prices for boats vary widely, but here are some things to keep in mind.

Almost always, prices quoted are for the whole boat, for the whole week (usually excluding provisions and fuel). You can divide the cost for the week among the people in your charter party. Larger boats are more expensive per week than smaller ones, but because you'll divide the price among your group, the more people you have, the less it will cost per person.

Northwestern Explorations flotilla

The Pacific Northwest offers scenic cruising around the San Juan and Gulf islands. Or you can go farther afield to Desolation Sound and Princess Louisa. Charter companies like NW Explorations offer many chartering options. (Photo: Stacey Nedrow-Wigmore))

Catamarans are generally more expensive than monohulls overall, but provide much more living space than monohulls of the same size. New boats are pricier than older models. Some people prefer new boats and are willing to pay more for them. But if you're on a budget, remember: As long as a boat is maintained and fully equipped, age only makes a difference when it comes to price. Older boats almost always are priced lower than new ones.

Other factors influencing cost are the charter region, season (high-season rates are sometimes higher than in the area's "fringe" or low seasons), and what's included in the total price. Is it "all inclusive" (meaning it includes expenses such as food, fuel, harbor fees)? Or is it "plus expenses" (meaning food, fuel, and other fees are not included and you pay them along the way during your charter)? For foreign charters, most companies list rates and charge fees in local currency, which may fluctuate a little depending on variations of the exchange rate at the time. Once you book your boat, the company you choose will personally lend an expert hand to guide you through all the other details of your charter.

Author

Anne Morley

Contributor, BoatUS Magazine

Anne has worked in the charter industry for many years as a charter-boat owner and operator, and has sailed on chartered boats as either paying passenger or paid crew in most of the world’s top chartering locales.