Flotilla Holidays Sailing Vacations

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:

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!

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!

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). The IPC is a Certificate which will certify you to bareboat charter in several countries overseas. Discounts are available that recognize these levels. Please see each cruise for more details.

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.

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.

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.

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.

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.