Sailboat Charters Chesapeake

Plan a sailboat charter on the Chesapeake Bay aboard one of South River Boat Rentals’ fleet vessels today and experience sailboat charters on one of the world’s chartering / cruising waters, the Chesapeake Bay.

Whether you choose the hands-on experience of a bareboat charter or want to relax with a captain on board, sailing / cruising the Chesapeake is an unparalleled experience.

The Chesapeake Bay is considered one of the finest cruising experiences in North America let alone the world. We have miles of navigable, open water, secluded coves, and harbors, nestled in quaint towns to enjoy! Bring your family and friends or escape for a romantic, private cruise or corporate outing. Contact us today and let SRBR make your sailing charter on the Chesapeake Bay and experience you remember forever.



Call 1-410-956-9729 or fill out the quick form below and member or our team will respond promptly.


O’Day 272

1/2 Day: $400 | Full Day: $600

Capacity: 6 Max

33' Hunter

1/2 Day: $450 | Full Day: $700

Capacity: 8 Max

36' Lancer

1/2 Day: $500 | Full Day: $900

Capacity: 12 Max