Sunset Cruises

Sunset Cruise @ Leonardtown Wharf

Come along with Captain Phil for a scenic cruise through St. Mary's waterways under the delightful glow of the sunset.

You'll board the Lisa S., a 48-foot vintage Chesapeake Bay charter boat, at Leonardtown Wharf before experiencing the natural beauty of Breton Bay and discovering a stunning view of St. Clement's Island you can only get from the water. Relax and unwind as you breathe in the fresh air and take in the unforgettable sights and sounds of St. Mary's.

This two-hour cruise departs from Leonardtown Wharf Park, located at 22510 Washington Street, Leonardtown, MD 20650. Bring your favorite snacks, drinks, and adult beverages aboard. Check out our Leonardtown suggestions for places to pickup food or drinks for the cruise, and to see what other activities you can add to your trip! Guests 12 years old and up are welcome aboard this evening cruise.

Sunset Cruise @ Point Lookout Marina

Join Captain Phil for a cruise “down county” and experience the natural beauty of the St. Mary’s River in the golden glow of a summertime sunset.

After boarding the Lisa S., a 48-foot vintage Chesapeake Bay charter boat, at Point Lookout Marina, Captain Phil will take you out on the water to delight in the rural landscape and spot wildlife along the river. You'll continue up the waterway to discover unbelievable views of Historic St. Mary's City and the Maryland Dove, a working replica of one of the first boats to sail to what later became the Maryland colony.

This two-hour cruise departs from Point Lookout Marina, located at 16244 Millers Wharf Rd, Ridge, MD 20680. Bring your favorite snacks, drinks, and adult beverages aboard. Guests 12 years old and up are welcome aboard this evening cruise.

Want more fun, on-the-water activities from Fish the Bay Charters and Captain Phil? Find opportunities for charter fishing, watermen heritage tours, and more sunset cruises here.

We look forward to seeing you on board!