Coastal Cruising from the Chesapeake to Florida - Online Class

4:30 PM PT / 7:30 PM ET

Coastal Cruising from the Chesapeake to Florida

with 

Jeff & Jean

 | 

Two Can Sail
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.
90-Minute Live Session
On Demand Replay Available
Live Q&A
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.
FREE
39
Coastal Cruising from the Chesapeake to Florida

Online class 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

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!

Get the class Bundle

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!