Upcoming Cruises and Flotillas

Embrace the adventure of a lifetime and journey from the British Virgin Islands to Bermuda on the majestic Arabella. Don’t miss this unparalleled blend of adventure and luxury at sea.

Embrace the adventure of a lifetime and journey from the British Virgin Islands to Bermuda on the majestic Arabella. Don’t miss this unparalleled blend of adventure and luxury at sea.

Sailing the waters around La Paz, Mexico, is a truly magical experience. Nestled in the Sea of Cortez, often referred to as the “Aquarium of the World,” La Paz offers crystal-clear turquoise waters, calm seas, and stunning, unspoiled islands just offshore. With no Pacific ground swell, the waters are as smooth as a lake, making for relaxed and enjoyable sailing conditions.

Welcome aboard Cataleya a 30 meter luxury sailing yacht which will be your home for 8 days as you explore the Dalmation coast of Croatia. This trip will include stops in Split, Hvar, Korcula as well as a few anchorages that are the secrets of the captain and the crew. Join us on a once-in-a-lifetime sailing vacation.

Join fellow boaters in exploring the highlights of the San Juan Islands during the early summer. This flotilla is timed to beat the crowds and enjoy the long hours of daylight during the summer solstice. The San Juan Islands boast sheltered waters, magnificent marine parks, quaint villages and welcoming marinas. Wildlife abounds on the land and in the sea, with deer, bald eagles, otters, seals, sea lions and orca whales commonplace.

Enjoy seven days and six nights of sailing alongside fellow boats for one epic flotilla experience. Explore the iconic baths, get in on a small boat regatta at the famous Bitter End Yacht Club, and swim to shore to visit the iconic Soggy Dollar Bar. It’s going to be an action-packed sailing adventure!

Join a unique three-day sailing vacation in Denver, Colorado, that combines hands-on marine diesel engine training with outdoor adventure. Enjoy expert instruction, meals, included tools, and an evening sail on scenic Chatfield Reservoir.

Set sail on the Harmony Cruise, an affordable 8-day island-hopping sailing adventure through the stunning Aegean Sea. Departing round-trip from the Athens area, this relaxed, social voyage blends swim stops, historic harbor towns, and open-water cruising aboard a traditional Greek gulet. Designed for travelers who want the magic of exploring Greece by boat without the high price of luxury cruises, this journey offers authentic sailing, beautiful coastal scenery, and unforgettable moments at sea.

Imagine this: You’re on the deck of a magnificent 157-foot yacht, the Arabella, cruising the crystal-clear waters of New England. The wind whispers through the sails, the sun warms your skin, and the breathtaking coastline unfolds before you.
This isn’t a dream; it’s your reality with the American Sailing’s Grand Tour of New England aboard Arabella.

Set sail on the Greek Island Hopper Flotilla, hosted by Fair Winds Sailing Greece, and experience the beauty of Corfu and the surrounding Ionian islands. Guided by local captains, you’ll visit favorite anchorages, UNESCO World Heritage sites, and charming island towns while enjoying the perfect blend of sailing, culture, and relaxation. Sail aboard modern monohulls or catamarans, share meals and onshore excursions with fellow sailors, and discover Greece as seen through the eyes of those who know it best.

Embark on a 8-day luxury sailing adventure aboard Chronos Yacht, exploring Mallorca to Menorca with American Sailing. Enjoy personalized service, secluded coves, and stunning coastlines with a small, passionate group. This intimate voyage offers full-board luxury, breathtaking views, and unique experiences in the heart of the Balearic Islands. Set sail for an unforgettable journey this fall.

Join Caribbean Sail Training in Antigua for an unforgettable offshore sailing adventure aboard the legendary S/Y Spirit of Juno. This hands-on expedition combines real-world seamanship, offshore passagemaking, and exploration of some of the Caribbean’s most remote and beautiful islands. Designed for sailors looking to build confidence on larger yachts, you’ll gain practical offshore experience while discovering a side of the Caribbean few ever see.

Join American Sailing Vacations and Cruise Abaco for a week of clear, warm waters, white-sand beaches, and unforgettable sailing through the Abacos. This flotilla offers the perfect mix of freedom and fun — explore the Out Islands by day and share sundowners with new friends each evening.

Experience the magic of Sicily on a breathtaking sailing journey through the Aeolian Islands. Departing from Palermo, this refined Mediterranean voyage blends volcanic landscapes, turquoise swim stops, charming coastal villages, and unforgettable nights under the stars. Designed for travelers seeking both adventure and elegance, this weeklong escape offers an immersive taste of Italy’s culture, cuisine, and timeless rhythm of life at sea.

Sardinia & Corsica Aboard CHRONOS is a luxurious Mediterranean sailing adventure through the breathtaking coastlines of Sardinia and Corsica aboard a stunning 54 meter classic yacht. Explore the crystal clear waters of Costa Smeralda, La Maddalena National Park, and the legendary harbor town of Bonifacio while enjoying elegant dining, spacious decks, and unforgettable sunsets under sail. With only 12 cabins available, this exclusive September 4–11, 2027 voyage offers the perfect blend of authentic sailing, relaxed luxury, and timeless Mediterranean charm.