Songwriters on the Severn
Celebrate the Annapolis Songwriters Festival with a 2.5 hour live music cruise on the Severn River! There will be performances by Lost Saints, TWINNIE, and Gowa Gibbs. Get your tickets …
The Hip Hop R&B Yacht Party
The Hip Hop R&B Yacht Party is the best party on the water! Join us in Annapolis on Sunday, April 26, 2026. Party on the 95-foot Catherine Marie Yacht, dancing …
Celebrate the Season in Annapolis with Watermark’s Holiday Experiences
There’s no place quite like Annapolis during the holiday season, when twinkling lights reflect off the water and history feels especially alive. This year, Watermark is offering a lineup of …
Christmas Express Cruise at Christmas Village
New this season, Watermark is bringing holiday magic to Baltimore’s Inner Harbor with the Christmas Express Cruise at the Baltimore Christmas Village. Step aboard our festively decorated vessel and set …
Kids Halloween Costume Cruises
Kids in costume cruise free! Join us on October 25-26 aboard Watermark’s Annapolis and Baltimore Harbor Cruises! Snap a photo in your costume, tag @Watermark + #HarborHaunts, and you could …
Wilma Lee Halloween Cruise
A Spooky Evening on the Chesapeake Bay Step aboard the historic Skipjack Wilma Lee for a special Halloween sunset cruise on the Chesapeake Bay. Enjoy a crisp autumn evening on …
New Year’s Eve Annapolis Yacht Party
Make your New Year’s Eve memorable with this special family-friendly celebration on the water in Annapolis. Cruise aboard a Watermark yacht and dance to DJ Lampdawg’s tunes. Enjoy a complimentary …
2025 Tour Guide Open House
Do you like history? Do you enjoy learning and interacting with people? Please join us for a reception to introduce you to the fun and enriching opportunities that are available …
Thomas Point Shoal Lighthouse Cruise
Sail to Thomas Point Shoal Lighthouse and learn about its history, importance, and present day condition by guest lecturer David Gendell, author of “Thomas Point Shoal Lighthouse: A Chesapeake Bay Icon” …
Annapolis Harbor & USNA Cruise
Step aboard the classic Harbor Queen for a narrated cruise of the Annapolis Harbor and the banks of the U.S. Naval Academy. Hear the history of the Naval Academy, Annapolis’ …