Enjoy a week of brilliant sailing and relaxation through gorgeous Islands! Stay aboard a modern sailboat skippered by a certified Sailing Collective captain who will take care of your every need throughout the week from daily itinerary planning to shuttling passengers to shore for seaside cocktails and dinner. Don’t worry if you have never sailed before, The Sailing Collective captains are all professional sailing instructors and will teach you everything you need to know; and if you are a sailor, this sailing vacations will be a sailors dream come true! Sit back and relax as we sail each day to new and exciting locations where we will catch anchor or tie up along some of the Mediterranean's most historical ports.

Monohulls from $14,950

Catamarans from $15,800

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Past Journeys


Explore photos from our past journeys