Calypso Sailing Life

 Learn - Sail - Live 

Calypso Sailing Life's mission:

Help people achieve their dreams to sail and even sail away!

We provide consulting to help you explore your options to achieve your sailing goals. We offer certification training through our partnership with NauticEd and American Sailing. And, we provide coaching on your new-to-you boat (or ours) to learn its systems and gain confidence to enjoy a safe sailing life.

Learn to sail and live your dreams. 

Experience sailing with us in these locations:

US Atlantic Coast ☼ Florida ☼ Bahamas ☼ Turks & Caicos ☼ Spanish Virgin Islands ☼ US Virgin Islands ☼ British Virgin Islands ☼ Antigua ☼ St Martin ☼ St Lucia ☼ St Vincent and the Grenadines ☼ Grenada ☼ Trinidad & Tobago

Learn to Sail

Hoist those sails! Take the helm! May you have fair winds and following seas.

Learn how to sail the most stable, comfortable sailing vessel around: a cruising catamaran. We'll teach you the ropes and you'll be chartering your own boat in no time. Or if you own a new-to-you boat, we can help you gain the confidence to live your dreams!

As a NauticEd Sailing School, we can help you can earn verified practical competence certifications and endorsements giving confidence to you, your bareboat charter company, and your marine insurance company.

Sail the World

A weekend, a week, or longer. Sailing the trade winds in a beautiful catamaran. Snorkeling crystal clear waters teeming with fish and coral. Walking isolated beaches and sipping sundowners with friends and family. What are you waiting for?

Check out our Try-A-Catamaran learning charter for scheduled options. Or Contact Us to schedule your own private charter.

Get Advice & Assistance

Planning to buy a new boat and don't know where to start? Need help to qualify for insurance? We can help. We'll help you identify great sailboat options for your intended lifestyle and qualify to keep your investment protected.

Contact us for more information: