Annapolis Walking Tours, Boat Cruises & Private Yacht Charters

Enjoy the Chesapeake Bay area by Land & Water!

Looking for the perfect Annapolis activity? Look no further! Watermark offers a stunning fleet of luxury yachts for private events and public boat cruises along the Chesapeake Bay and the Severn River. Watermark's experienced guides provide walking tours through historic downtown Annapolis, the U.S. Naval Academy and nearby destinations. There’s never been more to do and see!

Journey into the history, culture and fun of one of America’s most eventful destinations with the areas most skilled event planners and tour coordinators. Go for less than an hour or as long as you like. On land, on water—private event or public outing—your unique Annapolis and Chesapeake Bay area experience awaits!

African-American Heritage Tour Black History Month Thurgood Marshall Memorial Black History Month

African-American Heritage Tour

Annapolis Guided Walking Tours

Annapolis by Land

Guided Walking Tours

Walk side-by-side with colonial-attired guides through historic Annapolis and the U.S. Naval Academy’s famous landmarks (and some hidden gems).

Trace the steps of African-American history or enjoy a Haunted Ghost Tour.

Watermark Private Yacht Charters Annapolis, Baltimore Maryland's Eastern Shore

Wedding, Corporate, Social Private Boat Charters

Luxury Yachts—the perfect venue for boat charters, corporate outings, weddings and receptions or social gatherings

Yacht charters serving the Annapolis, Baltimore, and Maryland's Eastern Shore. Providing Annapolis Boat Charters, Baltimore Boat Charters, and Chesapeake Bay Boat Charters.

Annapolis by Water

Chesapeake Bay Sightseeing Cruises

Explore the local waterways aboard the Chesapeake’s largest fleet. Cruise for as little
as 40-minutes up to a complete
Day on the Bay to St. Michaels.

Baltimore by Water

See Federal Hill, Fells Point, the USS Constellation and Ft. McHenry on our 45-minute Baltimore Inner Harbor Cruise.