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.

Join American Sailing and Caribbean Sail Training for a hands-on racing adventure in the British Virgin Islands. Sail aboard Spirit of Juno, a Farr 65 performance yacht, and become part of the crew during one of the Caribbean’s most exciting regattas. Whether you’re new to racing or a seasoned sailor, you’ll learn, compete, and experience the thrill of teamwork at sea.

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.

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.

4 days / 3 nights sailing from Marina del Rey to Catalina Island with stops in Avalon and Two Harbors. Enjoy a welcome dinner, beach yoga, hiking, paddleboarding, dinghy raft-ups, happy hours, and fully supported flotilla sailing with Naos Yachts’ newest fleet.

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.

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.

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.

Race the legendary St. Maarten Heineken Regatta aboard Spirit of Juno, a Farr 65 performance racing yacht. Train with your crew before putting your skills to work during four days of Caribbean racing. No racing experience is required—just come ready to sail faster, learn, and be part of the crew.

Experience the beauty of Italy’s Amalfi Coast on this unforgettable flotilla sailing vacation. Cruise alongside fellow sailors as you explore iconic destinations like Capri, Positano, and Procida, discover charming coastal villages, swim in crystal-clear waters, and enjoy authentic Italian cuisine. With expert guidance, a flexible itinerary, and the camaraderie of a small flotilla limited to just three catamarans, this is the perfect way to experience la dolce vita by sea.

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.

Explore Victoria, British Columbia, the San Juan Islands, and the Gulf Islands on a seven-day guided sailing flotilla with San Juan Sailing. Depart from Bellingham and cruise through sheltered waters to scenic anchorages, marine parks, charming island communities, and vibrant Victoria. Enjoy long summer days, abundant wildlife, daily route briefings, flotilla activities, and camaraderie with fellow sailors.

Celebrate BVI Sail Week with 7 days and 6 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!

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.