Caribbean to Florida
with Jeff & Jean | Two Can SailLearn how to safely and confidently sail from the Caribbean back to Florida—turning the “thorny path” north into a manageable and rewarding journey.
Heading north from the Caribbean can feel more challenging but with the right strategy, it becomes an incredible sailing adventure. This online class shows you how to work with weather windows, currents, and island-hopping routes to make your way back to Florida safely and enjoyably.
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ONLINE CLASS OVERVIEW
Join experienced cruising couple Jeff & Jean as they guide you through the real-world process of sailing from the Caribbean back to Southeast Florida. Drawing on decades of offshore and coastal cruising experience, they break down the northbound route into practical, achievable legs—combining day sailing, strategic overnight passages, and smart weather planning. Starting in the Southern and Eastern Caribbean, you’ll learn how to time your departure and work your way north through the island chain, including key stops like the Windward and Leeward Islands, the Virgin Islands, Puerto Rico, and the Dominican Republic. Special attention is given to navigating the “Thorny Path” in reverse—helping you understand how to safely move against prevailing easterly trade Winds. From there, the course walks you through crossing the Turks & Caicos and Bahamas, staging for a Gulf Stream crossing, and making a safe landfall along Southeast Florida. Along the way, you’ll discover when to day sail, when to make overnight hops, and how to choose the safest and most efficient routes based on conditions.
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 HOSTs
Jeff & Jean
Jeff and Jean assist couples in realizing their sailing dreams with their company Two Can Sail. As Licensed Yacht Brokers they work with one couple at a time to provide cruising lifestyle training including; boat shopping/purchase and personal training aboard the couple’s boat. Jeff has been actively boating over 50 years, sailing as Captain since the age of 15. Jean has been sailing since she was 12 years old on vessels ranging from sunfish to 80’ schooners. Jean was an Accredited Marine Surveyor (AMS) and was a member of the Society of Accredited Marine Surveyors (SAMS) and ABYC Standards Certified. Jeff holds an Electrical/Computer Engineering degree and has worked with almost all forms of electronic navigation. Both Jeff and Jean are 100GT Masters, ASA Certified Sailing Instructors and together have sailed over 260 different models of sailboats including 61 models of cruising catamarans.
ONLINE CLASS REGISTRATION
@ 4:30 PM PT / 7:30 PM ET (90 min)
Regular Price
$39
ASA Member Price
$29
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!
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