Flotilla Sailing Vacations

In 1972, Steve and Doris Colgate decided it was time to open new horizons for Offshore Sailing School alumni and introduced “flotilla cruises” to the United States market. The very first flotilla sailing holiday cruise they led was in August 1972 in the British Virgin Islands with 36 participants on a British Virgin Islands flotilla of six identical boats from The Moorings. In 1973 they headed to Greece with 40 eager graduates. Then the Coast of Maine, Turkey, Yugoslavia before it split, and then Croatia, France, Tahiti, Tonga, the San Juan Islands of the Pacific Northwest, Belize, the Windward and Leeward Islands of the Caribbean, St. Martin, St. Lucia, and the list goes on.

Cruise Leaders — Heather and Nate Atwater

You couldn’t pick a nicer or more accomplished sailing team than the Atwater’s to lead our Colgate Sailing Adventure Flotilla Cruises. In 2018 they finished the year with two fabulous sailing holidays– in Greece and Tahiti – where all had a terrific time. In 2019 they started out the year with two flotilla cruises in the St. Lucia, headed to head to Spain with a sold out crowd of eager sailors, and then to Croatia. Check out our blog for recaps on these great adventures. If you’d like to learn more about the Atwaters and out sailing adventures, WindCheck magazine ran two stories written by Heather. Read the article from our 2019 trip in Croatia and here is an earlier story from 2018. The Atwaters put the crews together and make sure the itinerary takes you to fun places while avoiding weather issues. If you haven’t participated in one of our best sailing vacations, why not now?


Greece was a wonderful trip. The location was fantastic. What a great way to see the islands. Great job by Nate and Heather. Always professional and always trying to provide good ratio of sailing time with fun and sightseeing. I love these flotillas. I plan to keep coming back.

Mike Mahan – Miami, FL
Abacos, St. Lucia, Italy, Belize, Greece Flotillas

Upcoming Colgate Sailing Adventures™ Flotilla Cruises

The fleet for each of these bareboat charter cruises is usually four to six 4-cabin boats with 15-20 cabins available to sell. If you are interested in joining one or more of these fabulous flotilla sailing holidays, act quickly. They sell out fast!

View a video recap of our 2019 “Dutch’s Insider’s Guide to the BVI” here.

Make Every Sailing Vacation a Smiling Vacation

These special flotilla sailboat vacations take you to places you might never go on your own and, best of all, they provide lasting friendships. Our flotilla sailing holidays are open to all sailors with sailing certifications or requisite experience, a Colgate Sailing Adventures® Flotilla Cruise is a super travel deal. Check out our Flotilla Cruising FAQs to learn more. Not yet a sailor? Sign up for one of our 2-day or longer certification courses, available in Florida and the British Virgin Islands and earn your passport to see the world under sail.

Required Flotilla Cruises Resume
Join a Flotilla Cruise Now!

Call 888-454-7015 or 239-454-1700

Email Sail@OffshoreSailing.com

Bareboat Chartering at Its Best

Our Flotilla Cruises are the best way to enjoy bareboat chartering. “Bareboat” chartering means you sail the boat, just like renting a car. But on these flotilla sailboat vacations, Offshore Sailing School charters a fleet of monohulls or catamarans and takes care of all the details. All you need do is sign up, pack your sailing clothes, and meet at the cruise departure location for these turn-key sailing holidays.

Bring a Friend or Loved One, Make New Friends

With private cabins, spacious main salons, cockpits and decks, these boats are ideal for socializing and enjoying the outdoors. You may purchase a single private cabin, or share a cabin with another sailor you bring with you on a flotilla sailing adventure. We assign individuals and couples to each boat based on sailing resumes required from everyone on the cruise.

Sharing and Sailing

Everyone shares in the fun and sailing while you’re on one of the best sailing holidays. In the evenings, stories and laughter abound as you relax under a canopy of stars while dining al fresco in the cockpit. Each morning your Cruise Leaders make the rounds to discuss the itinerary and navigation on each boat. In an Offshore Sailing Adventure flotilla, all the boats follow the same route and rendezvous in an anchorage or harbor designated by the Cruise Leader that day.

Who May Participate

Colgate Sailing Adventure® flotilla cruises are open to all sailors who have sailing experience that is at least equivalent to what is learned in US Sailing Basic Keelboat Certification courses. Most participants have taken the Offshore Sailing School Fast Track to Cruising® or Live Aboard Cruising course on large catamarans or monohulls. The most experienced aboard are designated “skipper” and “navigator”, tasked with taking charge in an emergency. They also are the “voice” of all aboard in communications with the Cruise Leader.

Sailors Who Enjoy the Company of Other Sailors

Colgate Sailing Adventures® flotilla cruise sailboat vacations are for sailors who enjoy the company of other sailors. All participants should have minimum certification at the Learn to Sail level (or equivalent experience) and experience on boats of at least 26’ in length. You also must be in good health with strength and ability to move about a cruising boat easily underway; able to get into a dinghy from the cruising boat and back onto it without assistance. As part of the flotilla sailing holiday, you must be willing to participate with others aboard – trimming sails, steering, helping with anchoring, docking, picking up moorings, and sharing cooking and cleaning up. Minimum age for participating in our sailing vacations in Greece and other destinations is 18. Call or contact us today for more information on flotilla sailing vacations.

The trip was fantastic. Whoever put the boat crews together did a great job, our boat had a great time.”

Terry and Michele Brown – Salt Lake City, UT


Join a Flotilla Cruise Now!

Call 888-454-7015 or 239-454-1700
Email Sail@OffshoreSailing.com