Flotilla Sailing Vacations — Colgate Sailing Adventures®

Steve and Doris Colgate sailing near the coast of Yugoslavia in 1989, pioneers in flotilla sailing adventures.

Doris and Steve in Yugoslavia 1989

In 1972, Steve and Doris Colgate introduced “flotilla cruises” to the United States market. After leading more than 70 flotilla sailing cruises worldwide with Offshore Sailing School alumni participating, the Colgates started a program called Colgate Sailing Adventures®. They turned the flotilla cruise helm over to longtime cruising sailors Heather and Nate Atwater. Since 2016 the Atwaters have hosted and led most Colgate Sailing Adventures® flotilla sailing holiday cruises in Italy, Greece, Croatia, Thailand, the Seychelles, Tahiti, Bahamas, Belize, British Virgin Islands, and all over the Caribbean. Read diaries from previous flotillas on our Blog here. Read the article from the Grenada flotilla that was published in WindCheck magazine.

Upcoming Colgate Sailing Adventures® Flotilla Cruises

Who Should Participate in a Flotilla Cruise:

Group of happy flotilla participants in Corfu, Greece, during the 2021 sailing adventure.

Corfu, Greece 2021

Offshore Sailing School encourages everyone who loves to sail, especially those who have earned US Sailing Bareboat Cruising Certification, to purchase a cabin as a single or couple and join these hosted sailing trips. It is important to realize, however, that the boats you sail on are not cruise ships. There are no elevators, medical facilities, and captained launches that take you to shore and back. You will sail with others on 40′ to  50′ monohulls and catamarans that require a certain level of physical ability and the desire to participate in handling the boat. Check out our Flotilla Cruising FAQs, and note these points below:

  • Flotilla cruises are hands-on activities that require unaided mobility, getting on and off boats, dinghies, and docks.
  • All participants must complete a Sailing Resume before being confirmed for the trip.
  • A Skipper and Mate are assigned to each boat based on the completed Resumes. In certain countries, each Skipper must have the International Proficiency Certificate, which is easy to get if you have US Sailing Bareboat Cruising Certification. Learn more about the IPC here.
  • All participants are expected to trim sails, steer, anchor, dock, pick up moorings, cook, and clean up.
  • All participants must complete a Sailing Resume before being confirmed in a flotilla. Please complete and submit online Resume here. 
    Flotilla leaders Nate and Heather Atwater guiding a sailing trip on a sailboat, experienced and trusted skippers

    Heather and Nate Atwater – Flotilla Cruise Leaders and Hosts

Join an Exotic Bareboat Cruise in Paradise

Colgate Sailing Adventures® Flotilla Cruises are led and hosted by Heather and Nate Atwater, or one of your favorite Offshore Sailing School instructors. You couldn’t pick a nicer or more accomplished sailing team than the Atwaters or Offshore instructors to lead our Colgate Sailing Adventures® Flotilla Cruises. Heather writes a blog during each cruise posted here, providing interesting recaps of these great adventures. WindCheck magazine has run several stories written by Heather in reports on the 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 the best sailing vacations you’ll find, why not now? Register for one of our sailing holidays today!

a frequent flotilla participant, with a historical Greek fort in the background during a sailing trip.

Mike Mahan – Frequent Flotilla Cruise Participant

Greece was a wonderful trip in 2021. 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

Make Every Sailing Vacation the Perfect Getaway

Flotilla sailboat vacations provide lasting friendships and take you to places you might never go on your own. Colgate Sailing Adventures®  flotilla sailing holidays are open to all sailors with sailing certifications or requisite experience. They sell out fast!

Discounts for Offshore Sailing School Graduates on Colgate Sailing Vacations® 

It is very important that anyone who wants to skipper or be an official mate on a Colgate Sailing Adventures® flotilla cruise, hold US Sailing Bareboat Cruising Certification provided by Offshore Sailing School, and carry an International Proficiency Certificate (IPC). Discounts are available that recognize these levels.  Please see each cruise for more details.

Couple enjoying their time onboard a monohull during a Caribbean flotilla cruise on a mooring ball, beautiful seascape in view

Michelle and Terry Brown

The trip was fantastic. Our cruise leaders did a great job putting the crews together. Our boat had a great time.”

Terry and Michele Brown – Salt Lake City, UT

Travel Information

For flights to/from most charter base locations where Colgate Sailing Adventures® flotilla cruise vacations start, we recommend you contact The Moorings in-house flight specialists at 866-649-2003. They successfully book flights for thousands of their charter customers.

Join a Flotilla Cruise Now!

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


This is Bareboat Chartering at Its BestMan steering a catamaran across clear blue waters, showcasing the thrill of flotilla cruising

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. 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 spouse or sailing partner. Individuals and couples are assigned to each boat based on sailing resumes required from everyone on the cruise.Couple making margaritas inside a sailboat, enjoying leisure time during a flotilla sailing vacation.

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 a Colgate Sailing Adventures® 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.  As stated earlier, each boat must have two bareboat cruising certified sailors aboard (the designated skipper and mate). Still, all participants should have minimum certification at the Learn to Sail level on boats of at least 26’ in length.  The minimum age for participating in our sailing vacations is 18. Fill out the form below and call or contact an Offshore Sailing School representative today.


Join a Flotilla Cruise Now!

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