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When planning a trip to Washington D.C. and nearby National Harbor (we stayed at the Gaylord and loved it!), there are plenty of opportunities for memorable family outings just outside the city. One of my favorite discoveries was a day trip to Annapolis, Maryland, where we enjoyed the Annapolis Harbor & USNA Cruise with Watermark.
It was the perfect way to get out on the water, soak in some sun, and learn something new along the way.
Watermark offers a variety of cruises around Annapolis and the Chesapeake Bay, including day trips to St. Michaels, Chesapeake Bay lighthouse cruises, and special themed cruises—perfect for families, history lovers, or anyone who just wants to enjoy time on the water. We went on the Annapolis Harbor & USNA Cruise. My friend, Candy, who lives in Washington D.C., joined me for the day with her guide dog (who loved the fresh breezes just as much as we did!).
The 40-minute narrated cruise was both relaxing and surprisingly educational. We learned about the United States Naval Academy, Annapolis’ important role as a historic seaport, and the region’s waterways.
Seeing the Chesapeake Bay Bridge from the water was an unforgettable highlight. It felt less like a sightseeing trip and more like a floating museum experience—fun, engaging, and filled with fascinating history.
The atmosphere on board was laid-back and welcoming. Families, couples, and friends of all ages were enjoying the ride, and the staff went above and beyond to make everyone comfortable.
The cruise offers two levels of seating—choose the shaded lower deck (with open seating at the bow) or head upstairs for panoramic views and plenty of sunshine.
There’s a bar onboard with both alcoholic and non-alcoholic drinks, which made it even more enjoyable.
One staff member even stopped by to ask if we needed anything and kindly offered to take our photo—such a thoughtful touch that made the day even more memorable.
For anyone visiting Washington D.C. or National Harbor, I highly recommend adding a cruise in Annapolis to your itinerary. It’s an easy drive, a refreshing change of pace, and a wonderful way to experience the beauty and history of the Chesapeake Bay region.
👉 Check out more details about the cruise here: Annapolis Harbor & USNA Cruise
