Caribbean to Florida

with

Jeff & Jean

Two Can Sail

Learn how to safely and confidently sail from the Caribbean back to Florida—turning the “thorny path” north into a manageable and rewarding journey.

90-Minute Live Session

On Demand Replay Available

Live Q&A

Heading north from the Caribbean can feel more challenging but with the right strategy, it becomes an incredible sailing adventure. This course shows you how to work with weather windows, currents, and island-hopping routes to make your way back to Florida safely and enjoyably.

FREE

Caribbean to Florida

Online class overview

Learn how to safely and confidently sail from the Caribbean back to Florida—turning the “thorny path” north into a manageable and rewarding journey.

Who is this online class for?

This online class is ideal for cruising sailors who have already reached the Caribbean and are planning their return to the U.S. It’s especially valuable for couples and short-handed crews looking for a safer, more strategic way to head north. If you want to avoid unnecessary risk and make the most of your journey home, this online class is for you.

What will I learn?

You’ll learn how to plan a northbound route that works with—not against—weather patterns, currents, and geography. The online class teaches you how to break the trip into manageable legs, choose the right departure windows, and safely navigate key passages like the Mona Passage and Gulf Stream crossing. By the end, you’ll have a clear, step-by-step plan to get from the Caribbean to Florida with confidence.

List of topics:

Planning your departure from the Southern and Eastern Caribbean
Island-hopping north through the Windward and Leeward Islands
Navigating the Virgin Islands and staging for the next legs
Strategies for transiting Puerto Rico and the Dominican Republic
Understanding and managing the “Thorny Path” northbound
Crossing the Turks & Caicos and Bahamas safely
Staging and executing a Gulf Stream crossing to Southeast Florida
Weather routing, trade winds, and current management for a smoother passage

Mastering the Northbound Passage

CREATING A STRATEGIC JOURNEY

Sailing north from the Caribbean is often seen as one of cruising’s greatest challenges, but with the right approach, it becomes a well-planned and deeply rewarding experience. This online class helps you move beyond uncertainty and approach the journey with structure, giving you the tools to navigate the route with confidence, efficiency, and purpose.

WORKING WITH CONDITIONS, NOT AGAINST THEM

From managing trade winds and currents to selecting the right weather windows and routes, this online class breaks down the northbound passage into clear, manageable decisions. You’ll learn how experienced cruisers plan each leg, adapt to changing conditions, and safely navigate key passages like the Mona Passage and Gulf Stream. Instead of fighting the elements, you’ll understand how to work with them to your advantage.

A CLEAR PATH FROM ISLANDS TO HOME

When your passage is guided by strategy rather than guesswork, the journey north becomes smoother, safer, and far more enjoyable. You’ll leave this online class with a step-by-step framework for island-hopping through the Caribbean, staging key crossings, and making landfall in Florida with confidence. Whether sailing as a couple or short-handed, you’ll be prepared to take on the “thorny path” with clarity and control.

Your Host

Jeff & Jean

Jeff has been actively sailing for over 45 years and Jean has been sailing since she was 12 years old. Both Jeff and Jean have extensively cruised the Caribbean, Bahamas and Florida on their Skye 51. Jeff holds an Electrical Engineering degree and has worked with almost all forms of electronic navigation from B-52 Inertial Navigation systems to modern integrated Nav Suites. Jean is a retired Accredited Marine Surveyor, and was a member of the Society of Accredited Marine Surveyors and ABYC Standards Certified. Both Jeff and Jean are 100GT Masters and ASA Certified Sailing Instructors. Over 15 years ago, Jeff and Jean founded Two Can Sail to address the unique needs of couples cruising and to assist in couples realizing their sailing dreams. Together they help couples gain the perspectives and tools needed to safely pursue the cruising lifestyle while having fun and staying together!

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Online Class Registration

@ 4:30 PM PT / 7:30 PM ET (90 min)

Regular Price

ASA Member Price

On-Demand Access

All registrations include unlimited on-demand access to the recordings of the live online class. So if you are unable to attend live you can still register and watch at your leisure.

ASA MEMBER DISCOUNT

American Sailing Members can claim their discount in the Member Portal. If you’re not a current member then for only $59/year you can join or renew today!

Online Course
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- Caribbean to Florida
ASA Certification
ASA Online Achievement Seal
- ASA Online Achievement Seal
  *recommended
  $19.00
By completing this entire course you can earn an ASA Online Achievement Seal - an official ASA seal that can be entered into your ASA Logbook!
Official ASA Logbook
- ASA Logbook
  $29.99
The ASA Logbook is a living document that chronicles your certifications and can also be used to keep a record of any and all sea-hours accrued along the way. If you chose to earn an ASA Online Achievement Seal and don't have an ASA Logbook then you *must* chose this option and purchase one.
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