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? Spring is a wonderful time to experience Watermark. We have a full year of cruises, tours and special events planned. Choose from a variety of Annapolis Harbor cruises and Baltimore Inner Harbor Cruises every day.

Our historic Annapolis walking tours are currently offered daily. 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 our weekly schedule in Annapolis and Baltimore.

Visit Our New Website For All Walking Tour & Field Trip Information: AnnapolisTours.com

Annapolis Walking Tours
Four Centuries Walking Tour is offered twice daily.
Specialty tours including ghost tours on weekends.

Annapolis Harbor Cruises and Baltimore Inner Harbor Cruises
Daily Cruises are in Season

Fourth of July Fireworks Cruises -
Join us in Annapolis & Baltimore! New Dinner Cruise Added in Baltimore.

Dog Days of Summer Cruise-
To Benefit the Anne Arundel County SPCA on July 18th

War of 1812 in Annapolis -
Our newest tour! Celebrate the War of 1812 Bicentennial & explore Francis Scott Key's roots.

Yacht Charters on the Bay
Book your private event or wedding aboard our luxury vessels. Available year-round in Annapolis & Baltimore.

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

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.

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