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Call: (888) 454-7015

Learn to Cruise a Sailboat You Can Live On

Picture yourself at the helm of a yacht you can live on, cruising with family and friends in the Caribbean, Greek Islands, South Pacific, and Croatia. Imagine the thrill of confidently taking family and friends for a sail on your own spacious cruising catamaran or monohull. All these exciting sailing adventures can be yours to enjoy, when you Learn to Cruise on liveaboard sailboats.

The Ultimate Cruising Course

OSS 110 – Ultimate Cruising Course just announced! Learn to sail, then learn to cruise on a brand new 44′ monohull and band new 40′ catamaran in one week!  This special 7 day course is only offered two weeks later this year, at ‘Tween Waters Island Resort & Spa on Captiva Island, FL.  Check it out now!

Take Command of a 40-50′ Yacht While Learning and Living Aboard

Offshore Sailing School learn to cruise courses – OSS 103, 104 and 114 are taught on 40’ to 50’ monohulls and catamarans. These next step up from Basic Keelboat OSS 101 sailing lessons  provide skills and knowledge to competently and confidently handle large monohulls and catamarans under sail and power.  In five days, you can earn US Sailing Basic Cruising Certification and US Sailing Bareboat Cruising Certification, ready to skipper a yacht up to 50′.


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 45′ catamaran (OSS 101/103/104/114)  – learning how to handle big sailing yachts.

Stay Ashore or Live Aboard Schedule Options

While most students opt for the immersive Fast Track to Cruising® live-aboard experience, a stay-ashore version of the cruising course is available in certain locations. Some students prefer the stay-ashore version in late summer when the water and air can be very warm, and an air-conditioned room is the perfect end to each day of the course. If you are traveling with family or friends who just want to enjoy the resort and not participate in sailing lessons, the stay-ashore schedule works well for all in our party.  Call 888-454-7015 for stay-ashore date and location availability.

Do You Have Basic Sailing Experience Equivalent to OSS 101 Certification?

You may be able to test-out of the first two days of the Fast Track to Cruising® course if you have basic skills and are comfortable steering and maneuvering sailboats (keelboats with jib and mainsail) at least 20’ in length. Ask your Sales Associate for details.

Specially-priced Family Cruising Package

Our special family Fast Track® to Live Aboard Cruising Course is available for two adults and two family kids* between the ages of 12 and 25 learning together. This family sailing adventure is a perfect opportunity to reunite family members. learn the skills to bareboat charter together, and enjoy countless boating vacations in the future! Call 888-454-7015 for availability and pricing.

*Fifth family child between age 12 and 25 may be added for additional fee.

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 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.

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 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.

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.