Flotilla Sailing Vacations

Flotilla Cruises Offered by Colgate Sailing Adventures™

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. To celebrate Offshore Sailing School’s 55th Anniversary in 2019, the Colgates are once again joining participants on a spectacular Anniversary Celebration in the British Virgins Islands. This cruise will fill fast, join the Colgates for a great time under sail!

Euro-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 Europe and the West Indies. They just returned from Greece where all had a terrific time, you can read the blog here. And here is a great story about the Atwaters that appeared in a June issue of WindCheck Magazine. In the first photo above, Heather and Nate are with the entire Greek Islands flotilla cruise group. The Atwaters put the crews together and make sure the itinerary takes you to fun places while avoiding weather issues. If you haven’t done one of these cruises yet, 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


Dutch Jongkind — BVI Expert Joins Steve and Doris Colgate for the Insiders Cruise to the British Virgin Islands

Dutch has been an Offshore Sailing School senior instructor, conducting Fast Track to Cruising Courses on monohulls, catamarans and power cats in the British Virgin Islands for the past four years and is now Caribbean Branch Manager. Those of you who have taken a course with Dutch, know how much fun a week of sailing with him will be! Dutch lead Croatia and British Virgin Islands flotilla cruises in 2016 and has put together a terrific itinerary with lots of fun-filled shore stops for Dutch’s Insider’s Guide to the British Virgin Islands in February 2019. You absolutely don’t want to to miss this celebration of Offshore Sailing School’s 55th anniversary and 46 years of conducting flotilla cruises!

Upcoming Colgate Sailing Adventures™ Flotilla Cruises

2018 cruises sold out early, some as soon as the dates were posted. When this happens you can put your name on a waitlist for a $200 refundable deposit. The fleet for each of these cruises is usually just four 4-cabin boats with 15 cabins available to sell. For the Grenadines and West Indies two-leg cruises, and the Croatia two-leg cruises, you may sign up for both legs and enjoy a special discount. If you are interested in joining one or more of these fabulous flotilla sailing holidays, act quickly because, as you can see, they sell out fast!

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.

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 vacations.

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 on all our Colgate Sailing Adventures. 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 participation 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