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Learn to Cruise

Picture yourself at the helm of a beautiful sailboat, chartering in the Caribbean, Greek Islands, South Pacific, and Croatia. Imagine the thrill of confidently taking family and friends out on your own cruising catamaran or monohull. All the learn to cruise courses below are taught on 43’ to 50’ monohulls, and give you the skills and bareboat charter cruising certification to embrace the sailboat cruising lifestyle with ease!


OSS 101/103/104 and OSS 114 – Fast Track to Cruising® Courses

If you are not yet a sailor or have minimal experience, Fast Track to Cruising Courses® start with two days of sailing lessons on a Colgate 26 while staying ashore at night, then five or six days either on a 43’ to 50’ monohull (OSS 101/103/104) or 40′ to 48′ catamaran (OSS 101/103/104/114)  – learning how to handle big sailing yachts. In most of our locations, you may also take the entire course while staying ashore. If you have basic skills and are comfortable steering and maneuvering sailboats at least 20’ in length, you can skip the first two days on the Colgate 26 and enroll in one of following sailboat cruising course options, all culminating in receiving US Sailing Basic Cruising and  Bareboat Cruising certifications.

OSS 103/104 Basic Cruising and Bareboat Charter Cruising Certification Courses

These two courses are offered together in one week, taking you from the basics of cruising through the skills needed to skipper a large cruising yacht. If you prefer to sleep ashore in a hotel room each night, consider one of the Bareboat Cruising Certification Courses at our Florida catamaran sailing school or monohull sailing school.

Live Aboard Cruising Courses provide total immersion in the cruising lifestyle. You sleep on the boat for your live aboard sailing lessons, while sharing all the tasks with your classmates, and learn while sailing to different destinations each day.

Bareboat Cruising Courses provide other benefits, especially during warm summer months in Southwest Florida. You cover the same curriculum as the Live Aboard version, but you will have increased docking and maneuvering in tight quarters when you return to the resort to eat and sleep each night. You will enjoy the resort amenities, dining options, and sleep well in your air-conditioned room, which is not always guaranteed when you sleep aboard. Our generators use sea water to “cool” the system, but in summer months in Southwest Florida, the water stays too warm to be used reliably and effectively to cool cabins at night.

Navigation Courses and Passage  Making Courses

The next step after learning to cruise sailboats is learning to sail far from land. OSS 105/106 Fast Track to Coastal Passage Making is a an 8-day journey that starts with two days of Coastal Navigation instruction while staying ashore, then six days learning the nuances of sailing longer distances but not too far off shore. The final step in the Fast Track program is OSS 107/108 Fast Track to Offshore Passage Making – a 10-day program that starts with four days of Celestial Navigation while staying ashore, then six days heading off shore and out of sight of land.

Join a Colgate Sailing Adventures® Flotilla Cruise

Offshore Sailing School organizes flotilla cruises all over the world, for our graduates and competent sailors who love to explore under sail. These hassle free sailing vacation adventure cruises are lead by our experienced team – Nate and Heather Atwater. No research of the exotic destination is necessary. Just sign up, pack your bag, meet your crew mates and the Atwaters for a flotilla cruise vacation in amazing ports all over the world.

International Proficiency Certificate (IPC) for Chartering Overseas

If you plan to charter in Europe or other areas overseas, you may be required to show your certification credentials and an International Proficiency Certificate. The IPC is issued by US Sailing for a nominal fee, once you have obtained US Sailing Basic Keelboat, Basic Cruising, and Bareboat Cruising certifications. For more information, view details on US Sailing organization’s website here.