Annapolis, Maryland Walking Tours, Boat Cruises & Private Yacht Charters

Enjoy the Chesapeake Bay area by Land & Water!

Looking for things to do in Annapolis?

This is a great time of year for Walking Tours in Annapolis! You are shown the historic side of Annapolis from a period-dressed, knowledgeable and informative guide. Join us Saturdays in February!

Look no further! Watermark offers a stunning fleet of luxury yachts for private parties 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 in Maryland. Whether you are looking for Annapolis things to do on the water or on land, look to Watermark!

Journey into the history, culture and fun of Annapolis with Maryland's most skilled event planners and tour coordinators. On land, on water—private event or public outing—your unique Annapolis and Chesapeake Bay area experience awaits!

Celebrating 40 Years of Fun in 2012!

Four Centuries Walking Tour - Saturdays, 1:30pm from the information booth at Annapolis City Dock.

African American Walking Tour - Saturdays in February, 1pm from the information booth at City Dock.

Private Charters - Your private charter awaits! Charters for 2-200+ people ... let Watermark help you create your memorable event.

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 Private Boats—the perfect venue for boat charters, company outings, weddings and receptions or private parties.

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 Maryland's 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.

Cruises are pet-friendly. Dogs must be friendly and kept on a leash at all times.