Flotillas

Sail Thailand’s stunning islands on a guided 10-day flotilla with Whitecaps Sailing, featuring Krabi, Phi Phi, and Maya Bay.

Sail Italy’s Amalfi Coast, visiting Capri, Positano, and Procida on a guided flotilla adventure with fellow sailors.

Join American Sailing and Fairwinds Sailing Greece on a journey from Corfu through the Corfu Islands. Our local captains from Fairwinds Sailing will take us to their favorite anchorages and introduce us to Greece as seen through their eyes. Corfu Island is in the north Ionian Sea, between Italy and Greece (Greek “Ιόνιο Πέλαγος” – […]

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 […]

Explore Belize’s paradise islands on your own private luxury catamaran. Learn sailing from ASA certified instructors & crew. Snorkel, kayak, and fish in crystal clear waters. Enjoy gourmet meals & exotic drinks prepared by your crew. Experience a different destination every day on this ultimate sailing vacation!

Explore the Abacos on a guided flotilla—sail by day, unwind by night, with expert support and island freedom.

4-day Catalina flotilla from Marina del Rey to Avalon & Two Harbors—sailing, yoga, raft-ups, hikes & social nights at sea.

Sail Turkey’s stunning southwest coast on a guided flotilla with hidden coves, ancient ruins, calm seas, and unforgettable camaraderie.

Sail Croatia’s Dalmatian Coast from Trogir to Hvar and Vis on a week-long flotilla with turquoise waters and relaxed island sailing.

Sail through the Adriatic from Croatia to Italy on a guided flotilla adventure culminating in the legendary Barcolana Regatta in Trieste.

Sail the British Virgin Islands aboard a luxury catamaran while exploring paradise and earning ASA certifications.

Explore Greece’s Southern Ionian Islands on an 8-day guided flotilla with island hopping, crystal-clear waters, and Greek hospitality.

Sail from Bellingham to Victoria, the San Juan Islands, and Gulf Islands on a seven-day summer flotilla filled with scenic stops.

Celebrate Sail Week with a week of sailing, regattas, sundowners, and unforgettable adventures in the beautiful British Virgin Islands.

Race the St. Maarten Heineken Regatta aboard a Farr 65 with a training day, four days of racing, and a 12-person crew.