Jolly Express is Canceled for Sunday, December 8th due to Weather. Book a Seat for Next Weekend.
Wondering what to do in Annapolis? Annapolis is a beautiful historic seaport that’s wonderfully explored by water! Get out on the water with Watermark on a sightseeing Annapolis boat tour. Relax, enjoy the sea breezes – it can be up to 10 degrees cooler on the water in the summer! – and learn about Annapolis history, the United States Naval Academy and the people that live here. We offer a variety of narrated Annapolis cruises and each one is different. Our boats have plenty of capacity so come on down and find us at Annapolis City Dock under the red umbrella.
Annapolis boat tours have been a Watermark specialty for 40 years. Chesapeake Bay Cruises are a wonderful way to experience the beautiful region of Annapolis and the Eastern Shore. We have the largest private fleet in the area so when it comes to boat rides in Annapolis, we’ve got you covered. Cruise for as little as 40 minutes on a Harbor Queen and Miss Anne Annapolis cruise or up to a full day to St. Michaels and back. Marvel at the engineering feat of the Chesapeake Bay Bridge on a 90 minute Chesapeake Bay Bridges Cruise. Lighthouse enthusiasts will love our lighthouse cruises. Browse our calendar and types of Annapolis boat rides to find your perfect match. We have a lot of fun things to do in Maryland!
Our boats have full cash bar service with light snacks available for purchase and restrooms on board. Your own sandwiches and snacks are welcome but please, no drinks. Most of our vessels are handicapped accessible (learn more). Our cruises are dog friendly and as long as Fido is leashed and friendly, he cruises free. All of our vessels are available for private charter. Learn more at Yacht Charters on the Bay. Ask us about group bookings and field trips too!
Any cruise may be cancelled due to severe weather, mechanical breakdown or lack of participation.