Plan Your Trip to Annapolis with Watermark – Featured in The New York Times

Annapolis has long been known for its charm, history, and connection to the Chesapeake Bay — and recently, that magic caught national attention. Watermark was honored to be featured in The New York Times “36 Hours in Annapolis” (publication names in italics, story names in quotes) guide, highlighting the iconic Harbor Queen and her Annapolis Harbor and U.S. Naval Academy sightseeing cruise as a top experience for visitors.

For more than 50 years, Watermark has offered unforgettable experiences on land and water, helping guests explore the best of Annapolis and beyond. Whether you’re visiting for the first time or returning to dive deeper, here’s how to plan the perfect trip with Watermark.

Things to Do in Annapolis with Watermark Cruise the Chesapeake Bay

Watermark’s boat tours showcase the beauty of Annapolis from the water. Our fleet includes the famous Harbor Queen Sightseeing Cruise, offering narrated views of the U.S. Naval Academy, historic downtown, and the scenic waterfront.

Other popular cruises include:

• The intimate Spa Creek Tour
• Specialty cruises such as our live music cruises
• Seasonal and holiday cruises

Explore on Foot with a Guided Tour

Discover Annapolis on land with one of Watermark’s engaging walking tours. Each experience is led by passionate, trained, and certified guides who bring the city’s history to life.

Highlights include:

• Annapolis Historic District Tour
• African American Heritage Tour
• U.S. Naval Academy Tour

Ask us about creating a custom itinerary that pairs a walking tour with a cruise for the ultimate Annapolis experience.

Private Charters & Specialty Experiences

Planning a celebration or corporate event? Watermark offers a wide variety of private charters and cruises, perfect for weddings, birthdays, team-building events, and more.

We also provide private versions of our guided walking tours and boat cruises, allowing you to experience Annapolis your way.

Discover City Dock and Downtown

 Watermark tours depart from historic City Dock, the vibrant waterfront center of Annapolis. Before or after your tour, enjoy shopping, dining, and stunning views. Our team is always happy to recommend local favorites to round out your visit.

Plan Your Journey Today

 Watermark invites you to experience the best of Annapolis — trusted by locals, loved by visitors, and now featured in The New York Times.

👉 Explore our tours, cruises, and private charters and let us help you plan the perfect visit.