Boating

Annapolis Bay Charters Inc.

Annapolis Bay Charters is the original sailboat rental business in the Chesapeake Bay area. Enjoy a sailing charter vacation in and around the breathtaking coastal waters. Our agents help you choose t...

Boating

Annapolis Sailing Cruises: Schooner Woodwind

Sail the Chesapeake on a 74-foot schooner! Raise the sails, steer the boat, or sit back and relax on a two-hour sail. Special, longer event cruises, too. The Woodwind and Woodwind II offer a real Ches...

Boating

Cap’n Mike’s Full Moon Adventures

Offering boutique charters for up to six passengers, rates begin at $500 and range up depending up the type and venue of the adventure you select: sightseeing, biking, paddleboarding, kayaking, sailb...

Boating

Cruises on the Bay by Watermark

Cruises on the Bay by Watermark has been offering sightseeing cruises to visitors and residents of Annapolis for over 45 years! Cruises run daily through early Spring until early Fall with Special Eve...

Boating

Foxglove Charters

Charter this classic Motor Yacht. Cruise Annapolis and the Chesapeake Bay in Style. Annapolis Yacht Charter. One way to describe this fine 1926 classic motor yacht is simply... Grand. FOXGLOVE ha...

Boating

Liberte, The Schooner

Plan a Special Event on the Water! The Schooner Liberté is a 49-passenger sailboat offering private, personalized charters out of Annapolis from late April through June, then September through Octob...

Boating

South River Boat Rentals

Powerboat and sailboat rentals and charters on the Chesapeake Bay. We offer bareboat or captained charters by the half day, full day and weekly. Team building and corporate charters....

Boating

Yacht Charters on the Bay by Watermark

Chartering a beautiful yacht for a corporate or social event is easy at Yacht Charters on the Bay by Watermark. With a fleet of 13 yachts from 24' to 99’, our boats are elegant, luxurious and unique...