Cruise Annapolis is Now Waypoints Annapolis®
Established yacht charter company Cruise Annapolis has announced its corporate name change to Waypoints Annapolis®, effective September 22, 2020.
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Why Charter Local? Annapolis is the Sailing Capital of the U.S.!
The Chesapeake Bay is the largest estuary in the U.S., offering so many options to the sailor and boater.
Meet Captain Chris Munson: ASA Sailing Instructor
Meet ASA Sailing Instructor, Captain Chris Munson! Captain Chris joins us with expertise in the Chesapeake Bay area and a wealth of knowledge from his illustrious sailing career.
Meet Captain Molly Winkelman: ASA Sailing Instructor
Captain Molly joins us with a wealth of knowledge and experience in her 30-year international sailing career.
Choosing a Powerboat for Your Chesapeake Charter
Experience the thrill of a powerboat charter trip on the Bay
Sample Itinerary: U.S. Virgin Islands
Thinking of chartering the U.S. Virgin Islands? Look no further than Waypoints. Our charter concierge can work with you to develop a custom itinerary based on your goals and desires.