Embark on one of America’s most iconic passages—from the turquoise shallows of Key West to the historic harbors of the Chesapeake Bay. This course is your trusted guide for a safe, strategic, and scenic coastal cruise.
Sailing from Florida to the Chesapeake Bay is a bucket-list voyage for many coastal sailors. This route offers a perfect blend of urban ports, remote anchorages, and ever-changing conditions that keep every mile interesting. Whether you’re traveling solo, as a couple, or with a crew, this course provides the detailed guidance needed to cruise with confidence.
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ONLINE COURSE OVERVIEW
This comprehensive course walks you through the classic coastal cruising route from Key West to the Chesapeake Bay, combining offshore sailing with protected ICW segments. You'll get practical, experience-backed advice for every leg of the journey—waypoints, fuel stops, anchoring spots, and timing tips included. Whether you stick to the ICW or brave offshore stretches, you’ll finish the course with a full route plan that adapts to your boat, pace, and conditions.
Who is this online class for?
This series is for coastal cruisers planning their first long passage or looking to level up their route planning. It’s ideal for cruising couples, liveaboards, snowbirds, and anyone on a sailboat or trawler traveling at 5–7 knots. You should have basic navigation and boat-handling skills—this course builds on them with real-world strategies.
What Will I Learn?
In this series, sailors can expect to learn how to plan, time, and adapt their journey up the Atlantic coast. You'll master when to go inside versus offshore, how to handle weather windows, and where to stop for fuel, rest, or provisioning. You’ll also learn techniques for tide timing, bridge schedules, and handling high-traffic areas.
List of Topics:
- Route segments and safe harbors from Key West to Norfolk
- Timing offshore runs vs. ICW stretches
- Fuel planning, marina stops, and anchoring tactics
- Bridge schedules and lock navigation
- How to handle shallow inlets, tides, and swing room
- Managing Gulf Stream impact and coastal currents
- Local knowledge tips and alternate route options
- Avoiding common mistakes on a long coastal trip
Coastal Cruising Confidence
Plan smart, sail farther
Set sail on one of America’s most legendary passages from sun-drenched Key West to the historic charm of the Chesapeake Bay. This class equips you with the skills and knowledge to cruise this iconic coastal route with clarity and confidence. Whether you’re plotting offshore jumps or hugging the ICW, you’ll learn to time tides, navigate bridges, and choose the best harbors, all while building a safe, efficient, and unforgettable cruising plan.
Smart Passage Planning for Real Cruisers
Led by experienced cruisers and route-planning pros, this course breaks down the full journey from Florida to the Chesapeake into manageable segments. With detailed guidance on timing, routing, fuel stops, anchoring, and weather strategies, you’ll learn how to adapt to your boat, your crew, and real-life conditions. Expect local tips, common pitfalls, and flexible route options that make your passage smoother, safer, and more enjoyable.
A Must for Coastal Sailors and Slow-Speed Voyagers
Perfect for cruising couples, liveaboards, or snowbirds aboard sailboats and trawlers, this class bridges the gap between theory and real-world passage planning. If you travel at 5–7 knots and want to make the most of each leg while avoiding stressful surprises, this is your go-to guide. Whether it’s your first time north or your fifth, you’ll walk away with confidence, clarity, and a plan you can actually follow.
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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