Chesapeake Bay sailing
Embark on the waters of the Chesapeake Bay
Offered May through October, starting 2027
Weekend Adventure - $4900
Friday 1pm to Sunday at 4pm
3 Days, 2 Nights
Five Day Adventure - $7900
Monday 10a to Friday 4p
5 Days, 4 Nights
Ready to learn?
From the birthplace of the Star Spangled Banner, to the war of 1812, the Chesapeake Bay is chalked FULL of history to explore and learn.
Monday: Set the Sails!
Get settled into the cabins, go over the rules of the boat, assign roles for the week. Set sail at Herrington Harbor North, and enjoy that first feeling of being at the helm with the salty Bay air blowing gently by! Expect to see bald eagles flying above!
Tuesday: The town that fooled the British
We will sail to St. Michaels, the town famous for fooling the British in 1813! Explore the Chesapeake Bay Maritime museum, stroll historic streets, and get some fresh bay seafood.
Wednesday: Time at the helm
This will be a day to learn lots of sailing skills! From navigation, sailing under bridges, keeping a straight course, and anchoring, there is a lot to tackle.
Thursday: Activity day on the Chesapeake!
Get your swimsuits, because it is time to have fun! Mill Creek is a great place to kayak, jump in for a swim, and enjoy the Bay. Don't miss Cantler's Riverside....they have the best crab cakes in town!
Friday: Time for Downtown Annapolis
Come enjoy the Capitol of Maryland with its historic streets, tour the Naval Academy, and enjoy the quaint feel of downtown Annapolis.
Saturday: Sail back to Herrington north
Wrap up the week by testing what you've learned: make your sail back to Herrington Harbor North! You may be pleasantly surprised at how you can handle a yacht by this day.