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. After leading more than 100 flotilla sailing cruises all over the world, the Colgates turned the flotilla cruise helm over to Heather and Nate Atwater who for the past four years have led at least four to six Colgate Sailing Adventures® flotilla sailing holiday cruises each year. Read diaries from previous flotillas on our Blog here.

Important Notes:

  • All flotilla participants must be fully-vaccinated against the COVID-19 virus before embarking on a flotilla trip.
  • These trips are hands-on activities that require complete, unaided mobility getting on and off docks, boats, and dinghies.
  • All participants must complete a Sailing Resume before being confirmed on the trip, including answering questions regarding existing medical conditions that may hinder their full participation.
  • A Skipper and Navigator will be assigned to each boat based on the completed Resumes.
  • All Skippers on European charter trips must also have their US Sailing IPC, International Proficiency Certificate. Learn more about the IPC here.
  • For flights to/from the British Virgin Islands, we strongly recommend you contact The Moorings’ in-house flight specialists at 866-649-2003. They successfully book flights for thousands of their charter customers.

Join the Atwaters on an Exotic Bareboat Cruise in Paradise

You couldn’t pick a nicer or more accomplished sailing team than the Atwaters to lead our Colgate Sailing Adventures® Flotilla Cruises. Since taking charge In 2018 they have sailed with Offshore Sailing School graduates in Greece, Tahiti, St. Lucia, Spain, Croatia, St. Martin, Bahamas, Italy, and more. Check out our blog for recaps on these great adventures. WindCheck magazine has run several stories written by Heather: 2020 trip in the Apostle Islands of Lake Superior, 2019 trip in Croatia, and an earlier story from 2018. If you haven’t participated in one of our best sailing vacations, why not now? Register for one of our sailing holidays today!

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, Croatia Flotillas

Upcoming Colgate Sailing Adventures® Flotilla Cruises

  • Thailand – (catamarans) April 22 – May 2, 2023
  • Grenada – (catamarans) November 4-11, 2023
  • Belize (catamarans) February 3-10, 2024

Make Every Sailing Vacation a Smiling Vacation

Flotilla Cruise sailors

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

These special flotilla sailboat vacations take you to places you might never go on your own and, best of all, they provide lasting friendships. Colgate Sailing Adventures®  flotilla sailing holidays are open to all sailors with sailing certifications or requisite experience. Most are Offshore Sailing School Fast Track to Cruising® or Live Aboard Cruising course graduates. The most experienced aboard are designated “skipper” and “navigator”, tasked with taking charge in an emergency. Each flotilla cruise fleet is usually four to six 4-cabin boats with just 15-20 cabins available to sell. They sell out fast!  Check out our Flotilla Cruising FAQs to learn more. 

Join a Flotilla Cruise Now!

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


Bareboat Chartering at Its Best

Colgate Sailing Adventures® flotilla sailboat vacations are the best way to enjoy bareboat chartering – you sail the boat,and Offshore Sailing School takes care of all the details. Just 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. Purchase a single private cabin, or share a cabin with a sailing partner. Individuals and couples are assigned to each boat based on sailing resumes required from everyone on the cruise.

Everyone shares the fun and sailing 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.

For 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 is 18. Fill out the form below and call or contact s today for more information on flotilla sailing vacations.


Join a Flotilla Cruise Now!

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