2022 Sailing Adventures with American Sailing

By: Charter, Destinations

Do You Need Sailing Vacation Inspiration

This year, join American Sailing as we sail to destinations near and far. From the tropical waters of the British Virgin Islands to the culturally rich anchorages of Croatia we encourage you to go sailing with us.  Join groups of American Sailing Members in New England and the Chesapeake Bay aboard Arabella or hop on a flotilla in the Mediterranean.  

It’s finally time to embrace our freedom and get back out on the water. 

Where We Are Sailing In 2022

Sail with American Sailing in Croatia

American Sailing has scheduled two luxury charters in Croatia aboard Cataleya. At 30 meters, this luxury sailing yacht will be home to 18 total members for a week-long cruise of Croatia.  This sailing adventure is an opportunity for ASA Members to sail a bucket list destination with other like-minded travelers.

S/Y Cataleya

Discover New England Aboard Arabella

Visit Martha’s Vineyard, Nantucket, Newport, and Cuttyhunk aboard Arabella this summer.   Sample the seafood, get a dose of New England, and discover the islands off the coast of Massachusetts with American Sailing members. A group of sailors touring the islands on a 157-foot sailing should be on your bucket list.

S/Y Arabella

Sail The Chesapeake Bay

Tour the Chesapeake Bay and go to the Annapolis Sailboat Show. You will board the 157-foot Sailing Yacht Arabella in Annapolis and tour the Chesapeake Bay for 6 days and upon your return, you will be ready to attend the Annapolis Sailboat Show. Fall is the perfect time to visit the tranquil waters of the nation’s most famous bay. From the Southern charm of Annapolis’ history-soaked streets to the quiet eastern shore towns like St. Michaels, Oxford, and Baltimore’s inner harbor, you’ll enjoy the unique flair of this special region.


Seek Out The Sun This Winter In The British Virgin Islands

You’ll dip your feet in the warm water, you’ll sip on fine rum and you’ll work on your tan on the deck of Arabella. Meanwhile, you’ll discover that you have 20 new best friends who all love to sail. Visit Cooper Island, Virgin Gorda, Jost Van Dyke, and plenty more anchorages as you crisscross the Sir Francis Drake Channel in the British Virgin Islands.


Join an American Sailing Flotilla in the Mediterranean

Flotilla sailing charter vacations bring together a fleet of sailboats, each operating independently with its own crew, along with a lead boat and flotilla leader who knows the local area well. By joining a flotilla, you can enjoy the freedom of skippering your own boat but have comfort in knowing that support and advice are on hand to help with navigation and local weather.

Join us in:

Join American Sailing on a Flotilla in Turkey

The southwestern coast of Turkey is not only absolutely safe but is a sailor’s paradise with great sailing, friendly locals who will give you a warm welcome, stunning scenery, mind-blowing history and, like anywhere else in the Med, great food, and delicious local wines.


Join American Sailing on a Flotilla in Mallorca

This trip will be a combination of fun sailing fellowship with some entertaining land tours during which you will discover majestic caves, vistas from a monastery, high up a mountain peak, and a stunningly beautiful national park island with an intriguing history.


Join American Sailing on a Flotilla in Sardinia

Sardinia is the largest island in the Mediterranean, located just south of French Corsica and, until the mid-1900’s, it was for the most part unknown, until the Agha Khan started developing what is now the Costa Smeralda or Emerald Coast, a playground for the super-rich but, still it remains to this day to be discovered by American tourists and sailors.


Join American Sailing on a Flotilla in Greece

If you ever wanted to sail the Ionian Sea and the waters where Homer’s heroes sailed in ancient times, then this flotilla is for you. The Ionian Sea is located on the west side of Greece and south of the Adriatic Sea. We offer you a flotilla with a wonderful combination of sailing fun and fellowship, mythical legends and ancient history, legendary Greek hospitality, and gastronomy.


Join American Sailing on a Flotilla in Montenegro

The southwestern coast of Turkey is not only absolutely safe but is a sailor’s paradise with great sailing, friendly locals who will give you a warm welcome, stunning scenery, mind-blowing history and, like anywhere else in the Med, great food, and delicious local wines.


Join American Sailing on a Flotilla in Croatia

Although we change the routes a bit every year with new anchorages or different small ports, it still is an ideal flotilla to discover the islands of Dalmatia. It is a great way to enjoy fun sailing fellowship and experience different cultures and ancient history. Like with all of our other flotillas, this one is a foodie’s and wine lover’s dream as well.


Join American Sailing on a Flotilla in Tuscany

We have exciting experiences in store for you in Tuscany. Sail its azure waters with us to the islands of Elba and Capraia and discover the typical ports of Porto Azzurro, Portoferraio, Marciana Marina and Capraia. Walk in the footsteps of Napoleon Bonaparte who was banished here for a short time before finally being defeated in Waterloo. Discover the rich Tuscan gastronomy and take this opportunity to spend some time, before or after the cruise, to explore more of this unique region. Book early as this will fill up fast!


Join American Sailing on a Flotilla in Seychelles

The Seychelles, the Garden of Eden in the middle of the Indian Ocean. These islands are about 1,000 NM off the African coast and NE of Madagascar, but this trip of a lifetime will reward you with unforgettable memories. Sailors are starting to discover these wonderful islands with their unique fauna and flora, translucent blue waters, and friendly, hospitable people. It literally is a melting pot of Africans, Europeans, and Indians. English, French and Creole are the official languages.


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