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

Enjoy the Chesapeake Bay area by Land & Water!

Looking for things to do in Annapolis?

Share your story! It's Harbor Queen's 40th birthday and we want to hear your favorite memories of the Queen.

Spring is here and so are our daily Annapolis Harbor cruises and historic Annapolis walking tours. You are shown the historic side of Annapolis from a Colonial period-dressed, knowledgeable and informative guide. We offer a variety of walking tours including Annapolis ghost tours at dusk. Step aboard Annapolitan II for daily sightseeing Baltimore Inner Harbor Cruises.

Watermark also offers a stunning fleet of luxury yachts for private parties and boat tours 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 the region with Maryland's most skilled event planners and group tour coordinators. Private event or public outing—your unique Annapolis and Chesapeake Bay area experience awaits!

Check out our weekly schedule for Annapolis and our weekly schedule for Baltimore.

Check out our 2012 Brochure!

Celebrating 40 Years of Fun in 2012!

Day on the Bay to St. Michaels - Relaxing sightseeing cruise from Annapolis to beautiful St. Michaels. 3 hours of leisure time on land. May Dates: 19, 24, 26

Upcoming Special Events -
Blue Angels Cruises in Baltimore
Star-Spangleld Sailabration OpSail in Baltimore
Book a Private Charter during Sailabration
...and more!

Annapolis Walking Tours -
Our signature Four Centuries Walking Tour is offered twice daily. Specialty tours like our Historic Ghost Walk & more are offered on weekends.

Annapolis Cruises -
Daily 40 min. narrated cruises
Cruise for 90 min. on weekends on a Severn River Cruise, Bay Bridges Cruise & Thomas Point Lighthouse Cruise.

Baltimore Inner Harbor Cruises -
Daily 45 min. narrated cruises.
Speciality cruises on weekends.
The NEW National Anthem Tour by Sea is daily.

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).

Annapolis walking tours are offered daily! Specialty tours like our Civil War in Annapolis Tour are on weekends.

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.