Things to Do Boating

Cruises on the Bay by Watermark

1 Dock St., Annapolis, MD 21401
(410) 268-7601

About 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 Event cruises all year long. A narrated 40-minute cruise on Harbor Queen is a must-do Annapolis activity. Cozy Miss Anne takes guests on a relaxing 40-minute cruise of Spa Creek. Other cruises include 90-minute cruises for a longer tour to see the Severn River, Chesapeake Bay or Thomas Point Lighthouse. Explore treasures of the Chesapeake Bay on a 3-hour Bay Lighthouses Cruise or the new Time & Tide: Tales of Annapolis & the Chesapeake Bay. Or spend a full "Day on the Bay" and journey to St. Michaels and back for a fun day trip. View the full schedule on Watermark's website.



- Family Friendly

- Pet Friendly



- Outdoor Seating

- Waterside Seating



- Wheelchair

Group Size

- 0-10

- 101-500

- 11-100


- Monday

8:30 a.m.-5 p.m.

- Tuesday

8:30 a.m.-5 p.m.

- Wednesday

8:30 a.m.-5 p.m.

- Thursday

8:30 a.m.-5 p.m.

- Friday

8:30 a.m.-5 p.m.

Cruise to the WineFest at St. Michaels
1 Dock St, Annapolis MD.

Cruise to the WineFest at St. Michaels

April 25, 2020

Travel across the Chesapeake Bay to the St. Michaels Wine Festival. Take a round trip cruise on a Watermark Yacht from Annapolis to St. Michaels. The St. Michales Wine Festival features hundreds of wines from around the world, artisan crafts, and gourmet food.  Wine tasting venues will be setup around the town. Cruise to St Michaels and avoid the Bay Bridge Traffic.  You will receive complimentary morning donuts and a non-alcoholic beverage on your trip over.  Ticket prices INCLUDE admission to the Wine Festival and the Chesapeake Bay Maritime Museum.  A complimentary small sandwich snack will be provided for the return trip.  All vessels have a full bar on board, accepting cash and credit cards.   This event will sell out. Tickets available on a first come, first serve basis.