All charters aren’t the same. There are luxury crewed charters usually on large motoryachts with a captain, chef and crew, and bareboat charters in which you’re the captain who makes all the decisions and manages the rented vessel on your own.

Crewed Luxury Charter

Crewed charters provide a staff to help you enjoy your vacation. Smaller boats (say under 60 feet) will usually have at least a captain and sometimes a chef. Larger vessels (60-200+ feet) will have a captain, mate or deck hand, chef and a steward.

Missy Johnston, owner of Northrop-Johnson Yacht Charters in Rhode Island is a certified charter broker who works with yachts 50-200 feet. She says these yachts usually carry 1-12 passengers and are part of a database called YACHTFOLIO, which specialized brokers access to find vessels offering charter in different parts of the world.

Brokers working with luxury crewed charters typically belong to one or many professional associations including AYCA (American Yacht Charter Association), CYBA (Caribbean Yacht Brokers Association), or IYBA (International Yacht Brokers Association). If you want to charter a large yacht, start by finding a broker via one of these organizations.

To experience a high-end charter, you first need to decide where you want to go. Most of these yachts run a circuit. For example, yachts work the Caribbean in the winter and then head up to New England or to the Mediterranean in the summer. The Med also splits into the western side (Spain, France and Italy) and the eastern side (Croatia, Turkey and Greece). Some yachts stay in the Pacific working French Polynesia, Fiji or East Asia, while others wander up to Mexico and Alaska. Not all yachts are flagged to legally work in all places so you need to decide what you want to see.

Bareboat Charter

When you charter a vessel that you will command without professional crew or a chef, it’s called bareboat chartering. Most bareboat chartering is done on monohull or catamaran sailboats but there are organizations (The Moorings, MarineMax Vacations) that charter powercats.

Dedicated charter companies have bases around the world and centralized booking systems that you contact directly. Finding a bareboat charter is child’s play. Check out Dream Yacht Charters, Moorings, Sunsail and Navigare, all of whom have a significant global presence. There are also excellent regional players like those in the British, U.S. and Spanish Virgin islands including Horizon, CYOA, Conch, Voyage and TMM . Then there are budget third tire providers and private brands in various corners of Europe and the Caribbean.

There are also river and canal charters with self-drive powerboats that crisscross France, Italy, Ireland, England and Germany where meander through vineyards and castles at a leisurely pace.

British Virgin Islands

For this adventure, let’s explore the magnificent British Virgin Islands in the Caribbean, possibly the most popular charter destination in the world. With manageable winds and short hops between islands, the BVIs are perfect for newbies but their sheer beauty, prevalent eating establishments and perfect weather bring back seasoned sailors again and again.

Not to be missed are the Baths on Virgin Gorda, Foxy’s famous watering hole on Jost Van Dyke and snorkeling at the Indians. A highlight is the island of Anegada. Once completely off limits to charter boats, the 11-mile island on the horizon is like a siren’s song. Up until a few years ago, Anegada’s entrance was not easy to navigate. You had to line up compass bearings and keep a sharp lookout for coral while avoiding Anegada’s eighteen mile-long Horseshoe Reef, a notorious boat eater. Today, the entrance is well marked with buoys and unless the weather is howling, there’s no reason not to visit this quiet paradise, even if just to get away from the party scene.

Take a taxi to the windward side to one of the beaches where you may be the only visitor – a rarity in the BVIs. In the afternoon, make reservations at the Anegada Reef Hotel for a perfect candlelit dinner as you enjoy having your toes in the sand and a forkful of lobster in a dish of butter. 

Salt Island is home to the wreck of the Royal Mail Steamship, the Rhone, which sank in 1867 during a hurricane. The hulk collapsed long ago and now lays mostly flat along the bottom with little vertical structure. It’s easy to snorkel the length of the ship out to the bow buried in 60 feet of water and see it well even without dive gear. The ship is an eerie sight as you follow the long drive shaft until the propeller comes into full view.

Trellis Bay highlights local artists and the Last Resort – an unlikely bar on Bellamy Cay in the middle of the bay. Founded by a Polish yachtsman named Wagner in the 1950s, this is a bar you can only visit by dinghy and even so, beware the coral heads that reach up for your outboard prop. Here you’ll find perhaps the best painkiller cocktails in all of the BVI.

No visit to the BVIs is complete without at least a day at Jost Van Dyke, home of the Bubbly Pool and Foxy’s Tamarind Bar. Hike to the Bubbly Pool, a tiny inlet with a constricted rock opening to the northeast swell. Periodically, the waves come crashing through and churn up the waters in the pool with a great force that turns the water into foam. It’s like taking a dip in a washing machine as the water tosses you about and turns even staid adults into squealing kids.

The BVI is a good place to visit about nine months a year, skipping August to October, which is hurricane season. Many sailors choose this destination as their first bareboat experience and none are disappointed.