Ideal Winter Sailing Charter Escapes

Baby It’s Cold Outside! Warm Winter Sailing Destinations

There’s a reason boating magazines are popular in the winter: that’s when more people are tucked inside reading and dreaming about time on the water. But you can do more than dream during these short cold days. You can plan for a winter sailing charter next year, or if you’re super flexible, you can jump on last-minute deals now and get to work on those tan lines. Here are ideas for eight great winter charters to take the chill off:

anegada sunrise
Sailboats at an anchorage in Anegada in the British Virgin Islands, a popular sailing vacation destination. Photos by Zuzana Prochazka

British Virgin Islands

There’s nothing like the BVI for newbies and old salts alike. With line-of-sight sailing, short distances, consistent winds, lots of beach bars and tons of shopping, what’s not to like? The BVI are perfect for “Chartering 101” so that first-timers can build skills, but others return to islands like Virgin Gorda, Anegada, and Jost Van Dyke year after year and always find new coves to explore. A candlelight dinner at the Bitter End Yacht Club, lobster on the beach with your toes in the sand, and cocktails at Cow Wreck Beach are great ways to forget your worries.

US Virgin Islands

So close to home that you don’t even need a passport, the US Virgin Islands are an exotic destination where you can speak English, pay with US dollars, and even use your cellphone without extra charges. Fly into St. Thomas and explore the coastline or head over to the spectacular coves of St. John, most of which is a watery national park. Toast with a tropical drink in the main port of Cruz Bay or go diving, snorkeling, and hiking all over the island. And if that sounds like too much work, just sit on deck and take in the colors of the water to lift your mood.

hope town lighthouse
A welcome landmark for sailors in the Abacos, Bahamas, the Hope Town Lighthouse.

Abacos, Bahamas

The Abaco Islands of the Bahamas are near the Florida coast and are just a short plane hop from Fort Lauderdale or Miami. The Abacos are tiny and clustered, forming what’s almost a protected lake where you can sail with minimal worries. Climb the steps of the famous Hope Town lighthouse, tuck into conch chowder in Little Harbor, or have a cheeseburger in paradise at Nippers on Great Guana Cay. Fly into Treasure Cay where most of the charter companies have their bases, change your boots for flip flops, and don’t look back.

Exumas, Bahamas

Farther down the Bahamas Island chain are the Exumas with hues of blue that you’ll never forget. Fly into Nassau and cross the infamous coral head bar to cruising grounds that include snorkeling on old plane wrecks, feeding pigs on the beach at Major Cay, running from iguanas on Alan Cay, and swimming in Thunderball Cave where an old James Bond movie was filmed. The Bahamas are spectacular but can be challenging due to shallow waters filled with keel-grabbing coral heads, so solid sailing skills and a good lookout will be necessary. But the clear water and the white sand will visit your dreams all the way until summer.

st lucia
Rodney Bay in St. Lucia, where sailors can spend a week exploring the coves and still not see it all.

St. Lucia

Pack your bags for Rodney Bay on the island of St. Lucia. This giant marina and anchorage are where charterers mingle with full-time cruisers and where you can spend an entire week in the coves of one island and never see it all. Relax in the trampoline of a catamaran looking up at the Pitons, the iconic twin volcanic plugs that are St. Lucia’s trademark. Hike up to Fort Rodney or tuck into a unique blend of Caribbean French cuisine that will have you buying local cookbooks. Grab a mooring at Marigot Bay, have a beer at the St. Lucia Yacht Club, or go shopping at Les Castries. One island, one week, a million choices.

Grenada up to the Grenadines

Many of the major charter companies have bases on the island of Grenada, and some are right in the main town of St. Georges. Flights from the US are affordable, and there’s much to visit from local chocolate factories to rum distilleries. Sail up to the Grenadines, check in at Union Island, and head to the Tobago Cays where you can snorkel with turtles or ask a local to throw a BBQ on the beach. Don’t forget to dive or snorkel Grenada’s Molinere Underwater Sculpture Park which is world-famous and very Instagram-worthy.

grenadines sailing
A sailing charter catamaran in the Grenadines. 

Florida Gold Coast

If you’d rather just stay on the mainland, head to Florida’s Sun Coast where you can watch the sunset over the water every happy hour. The cruising grounds stretch from Punta Gorda in the north to Sanibel and Captiva islands in the south. Fly into Ft. Myers and drive up to the Southwest Yachts base. The waters are protected but shallow without much room for long beam reaches, so exit via one of the cuts and hoist the canvas on the outside for a day of sailing. Then, come back in, drop the hook or secure a spot at one of the many marinas, and relax with an umbrella drink.

Farther Afield

There are other terrific destinations to try in winter including Mexico’s Sea of Cortez, but there the notorious nortes (northerly winds) may send you scampering for a fleece in February. In the South Pacific, Tahiti’s tropical temps are in the 80s year-round. December to February is the rainy season, so you may get lucky, or you might spend a week in the salon playing cards.

The Caribbean is close to the US and is serviced by many flights. It’s usually a safe bet for wintertime getaways, but it’s also busier during this season; so, make long-term plans for next year or watch for fire-sale offers from the big charter companies. The Moorings, Sunsail, Dream Yacht Charter, Navigare, and Horizon (charter list here) all have boats throughout these islalnds. Visit their websites and sign up for special-offer emails. In just a few weeks, you could be soaking up the sun rather than shoveling the driveway.

~By Zuzana Prochazka

More charter ideas.