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

Baltimore Inner Harbor Cruises & Private Charters

Enjoy the Chesapeake Bay Area by Land & Water!

Looking for things to do in Annapolis? It is always a great time to experience Watermark. We offer a full year of cruises, tours and special events. Our regular season of Annapolis Harbor cruises and daily Baltimore Inner Harbor Cruises are still in season. Special Event cruises are planned throughout the year.

Our historic Annapolis walking tours are offered every day. 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 from Spring to Fall. Our newest tour War of 1812 in Annapolis was developed with the United States Naval Academy.

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!

Watermark also offers a stunning fleet of luxury yachts for private parties, Annapolis wedding venues and group boat tours along the Chesapeake Bay and the Severn River.

View this week's schedule in Annapolis.
View this week's schedule in Baltimore.

Welcome to our 42nd Year of Fun!

Note: Many links on this website will take you to our newer websites for tours, charters and cruises info.

Annapolis Walking Tours
Daily Four Centuries Walking Tour. Historic Ghost Walk & War of 1812 on Weekends.

Annapolis Harbor Cruises and Inner Harbor Cruises
Daily Cruises from 40 minutes up to a full Day on the Bay.

Upcoming Special Events
Special Historic Hauntings, Battle of Baltimore, Chesapeake Schooner Race are here for Fall.

Field Trips in Annapolis & Baltimore
Student and Youth Travel tours with Destination Education by Watermark.

Yacht Charters on the Bay
Book your company outing or private event aboard our luxury vessels. Charters from Annapolis & Baltimore.

Wedding on the Bay
A refreshing alternative. Celebrate your big day on a private yacht charter on the Chesapeake Bay.

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 Chesapeake Bay Sightseeing Cruises

Annapolis by Water

Chesapeake Bay Sightseeing Cruises

During boating season, 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 run daily.

Pet Friendly Activities AnnapolisCruises are pet-friendly. Dogs must be friendly and kept on a leash at all times.