10 Unique Fall Sailing Experiences Around the World

Last updated 11th July 2022

Fall isn’t just for leaf-peeping. It also happens to be one of the best times of year for a sailing adventure. You’ll encounter fewer crowds at many destinations and can take advantage of the many sailing packages and offers that make an aquatic adventure more affordable. Whether you’re looking for a long weekend getaway close to home or a far-flung vacation on the other side of the globe, read on for ten unique fall sailing experiences around the world.

Burlington, Vermont

On the western edge of the Green Mountain State, the quaint city of Burlington, Vermont, sits on the shores of picturesque Lake Champlain and embraces all things fall. Go for a jaunt on the lake with Hotel Vermont’s Let’s Go Sailing Package. You’ll be surrounded by the breathtaking changing colors of the foliage with a 2-hour sailing excursion and a picnic lunch from Juniper, packed with fresh, local foods. After a day on the water, head to Foam Brewers—a newbie among Burlington breweries—started in 2016 by an eclectic group with a shared appreciation for brewing, science, art, music and culture. With live music every weekend, the brewery is located next to Lake Champlain and serves up a rotating selection of seasonal beers.

The Beaches of Fort Myers & Sanibel, Florida

Before snowbirds flock to Florida for the winter, November along Florida’s Gulf Coast is quiet on the beach but vibrant in the streets. Known as Sanibel Island’s sleepier sister, Captiva Island will host the famed Hobie16 World Championship starting November 1, 2019—the first time since 1984 that the United States has hosted the event. Over one thousand sailors from around the globe will descend on the 2-mile long island for 16 days of sailboat races and events set just off the coast, affording spectators a picturesque view to watch the competition. Though rates skyrocket during the winter season, the area’s top resorts are offering special packages and prices during the iconic event, such as a $169 per night guest room at Sundial Beach Resort, and rooms just a mile away from the competition at Tween Waters starting at $200 per night.

Off the coast of Fort Myers, Florida, America’s number one sailing school operates sailing lessons by women, for women. With its “Fast Track to Cruising” course, Offshore Sailing School’s week-long experiential sailing vacation teaches women how to command a ship. Package Rates: Single private cabin $5685. Two traveling together, sharing room ashore, but taking private cabins aboard, $5245 per person. Two traveling together and sharing room ashore and cabin aboard, $4710 per person. (rates vary depending on the date).

Newport, Rhode Island

Often called the “sailing capital of the world,” it’s no surprise that Newport offers unparalleled sailing experiences to enjoy when the crisp, fall, New England air starts to set in. Dive head first into Newport’s prestigious sailing heritage at 12 Meter Charters and get a first-hand feel for what it’s like to race aboard a retired 12-meter class racing yacht. With guidance from a professional sailing crew, a simulated race is something every age can enjoy. 12 Meter Charters also offers an array of sailing packages for those looking to take in Newport’s stunning ocean views, seafood, architecture and history by way of the sea. Book the Air & Sea Sail which includes the Newport Mansion Helicopter Tour along with a 2-hour harbor sail. For foodies, the Eat, Stroll & Sail package includes a ticket to Newport’s Neighborhood Food Tour as well as a 2-hour harbor sail.

Kennebunkport, Maine

In the crisp days of fall, the Kennebunkport area offers some of the best of New England’s charms. Feel the salt-tinged sea breezes and take in the colorful foliage in this historic Maine village that straddles the Kennebunk River. Set sail along the coast on the Schooner Eleanor, a 55-foot traditional schooner that cruises the colorful coastline from Cape Arundel to Cape Porpoise, showcasing the gorgeous leaves contrasting against the brilliant blue ocean. Cottages at Cabot Cove are captivatingly cozy and quintessentially coastal, this magical enclave of 16 petite cottages is a departure from traditional inns, Bed and Breakfasts and hotels in Kennebunkport, Maine. All beautifully decorated by a different interior designer, the cottages offer a variety of sizes, amenities, and views of the cove and the gardens. Must book this package at least two weeks in advance.

The Galapagos: Central Islands

Escape the cooler temperatures of fall and climb aboard the M/Y Le Grande Daphne for a 10-day sailing adventure through the always-warm Galapagos Islands with small-group adventure tour operator Intrepid Travel. The Ultimate Galapagos: Central Islands (Daphne) tour is offering six departure dates this fall, and docks at six ports throughout the Galapagos Islands. Kids will love the certain wildlife sightings, snorkeling opportunities, black-sand beach walks, zodiac boat rides to get up close and personal with animals and walks across actively volcanic landscapes.

Phuket, Thailand

Looking for a far-flung sailing adenture? Join Intrepid Travel for a Phuket Sailing Adventure, which departs five times this fall and visits some of the world’s most idyllic beaches. Set sail on the calm waters of the Andaman Sea and feast on delicious Thai dishes, stroll white sand beaches, swim and snorkel in turquoise waters and kick back to relax.

The Islands of Tahiti

While there is an abundance of exciting activities and stunning scenery throughout Tahiti, the 118 islands and atolls that comprise the chain can best be discovered by sea. Guests can embark on a voyage to explore the French Polynesian islands with various special packages this fall.  Visit five Tahitian islands with The Bora Bora Dream, Land and Sea package for an intimate cruise through the islands of Tahiti, Bora Bora, Raiatea, Tahaa and Huahine. This package includes round-trip international air from Los Angeles, inter-island air, a 7-night cruise with all meals,  a visit to Tahiti’s only UNESCO World Heritage Site, a private island tour and more. This package is valid for travel from 9/1/19 – 12/6/19.

St. Maarten/St. Martin

Tucked away deep in the heart of the Caribbean among pristine, crystal blue waters is St. Maarten: host to the annual Heineken Regatta. Fueled by strong, cooling northeast trade winds, sailing weather is at its peak in autumn. Several incredible experiences are available to sailors of all skill levels. For those looking to stretch their sea legs, the 12 Metre Regatta offers an authentic experience pitting racing-class 12-meter yachts against each on a professional America’s Cup course. More laidback excursions include a private catamaran day charter or a fully customizable sailing excursion based on your length of stay and skill level from The Moorings.

British Virgin Islands

The British Virgin Islands is an alluring archipelago composed of over 60 islands and cays—making it the ideal island-hopping destination. Known as the Sailing Capital of the Caribbean, the best way to experience the islands is by boat. Each island is unique in itself: While Anegada is known for its decadent spiny lobsters, Norman Island boasts underwater caving and Jost Van Dyke is famed for its white-sand beaches. Companies such as The Moorings offer a crewed sailing experience that comes set with a gourmet chef, professional captain and sleeps as many as 12. Staying on a yacht is perfect for larger family vacations, and takes the stress out of planning; the captain knows all the best snorkeling spots and provides seamless transportation to all the islands you wish to see and more. This year is The Moorings’ 50th anniversary and they’ll be holding a 7-day group yacht charter in BVI from November 9 to 16 with a lead crew, expertly-planned itinerary, exclusive onshore meals and fun activities for everyone on board.