About Sailing Season
The Chesapeake is a fantastic place to sail. We have hundreds of places to go, including quiet anchorages, picturesque marinas with pools and cookout grills, as well as first-class shopping and dining options.
The Chesapeake is a great place to learn, because the bay is big enough to sail for days but feels protected.
We have historic architecture combined with out-of-the-way idyllic anchorages.
The distances are just right, about fifteen to thirty miles, which makes multi-day sails easy to plan.
If you're looking for long offshore routes, we can also offer that too.
Highlights
Learn to do it all: Captain, Crew, Navigate, Cruise, Race, Live-aboard, Charter
On-the-water time is all hands on.
If your sailing trip is for learning, we specialize in a light touch.
We let you be the captain while keeping you safe.