Contact us: | (732) 449-7248

Summer cruising on the Chesapeake Bay includes fantastic anchorages, numerous towns to explore, great restaurants and their famous Maryland crabs. Based in Annapolis, we have easy access to Baltimore, St Michaels, Oxford, and all the best the Chesapeake has to offer. n A world-renowned sailing destination, the Chesapeake Bay is the largest estuary in the United States, spanning 200 miles from the Susquehanna River in the north to the Atlantic Ocean in the south.

Cruising conditions are fantastic, with generally reliable winds, perfect for exploring the many sheltered harbors and waterways of the Maryland shore. Ashore, the area is rich in history and its maritime heritage is showcased in quaint, old-fashioned fishing and crabbing towns. The region is renowned for fine dining and fresh seafood, and after a stroll through the historic colonial streets of downtown Annapolis , or a visit to the US Naval Academy there’s nothing like diving into a platter of steamed crabs.

Our favorite destinations & anchorages:
– Annapolis
– Baltimore
– St. Michael
– Oxford
– Chester River
– Rhode River

Interested? email us for special deals and discounts

Sailboat for charter in Maryland | Irish Rover Sailing