Let's Feel a Yacht Trip
Rent Chessie
About Us
Sail Annapolis in Style
Dine at waterfront restaurants and then step aboard our elegant Jeanneau Sun Odyssey and experience Annapolis like never before. Cruise past the historic Ego Alley, glide under the Naval Academy Bridge, circle Thomas Point Lighthouse and soak in sweeping views of the Chesapeake Bay. Perfect for proposals, sunset sails, or a relaxing day with friends — this is Maryland’s sailing charm at its finest.
Schedule your special event online or contact us for special events.
- Stunning Cruise
- Premium Yacht
- Quality Service Guaranteed
Our Services
What We Offer
Explore
Explore the Chesapeake
Book It
Booking coming soon
Enjoy
Enjoy the many add-ons and ammenities
Special Events
Host your special event
Testimonials
What Customer Say
Chessie was beautifully maintained, and Bryan take great care in patiently showing us all her ins and outs so that all parties felt comfortable. Bryan was very gracious with his time and conscientious about all aspects of the rental. We look forward to taking Chessie out on another adventure!
We loved sailing and having a comfortable place to sit.
Lisa