Top Maryland Sailing Tours

Enjoy the views of Baltimore Harbor as dusk falls on an evening sail on your yacht, the Unforgettable. Bring your own bottle of wine to sip on board as you watch the colors of the sunset spread across the sky. This will be a peaceful experience as passenger numbers are capped at six, letting you enjoy the experience without large crowds.

Many sightseeing tours can feel exhausting, as you rush from one top sight to another. This sailing experience on Baltimore's Inner Harbor, on the other hand, offers the chance to soak up city views at a relaxed pace from the water. Sailing in a small group also means that the experience is amore personal one.

With your favorite bottle of wine in hand, step aboard a sailboat for a cruise from Baltimore's Inner Harbor Marina. Learn about the harbor and the Chesapeake Bay's history while taking in views of Fort McHenry, the USS Constellation, and the city's shimmering skyline from the boat's deck. Cheese is no longer provided, so please bring your own to enjoy on board.

Enjoy views out on the water of the Inner Harbor with this cruise that sets sail on authentic schooner with space for up to six passengers. Meet at the Oasis Marinas to board the sailboat, and sit back and relax as your captain and crew sail out to Fort McHenry. Enjoy the fresh air and views of Baltimore and the Inner Harbor.

Enjoy sunset out on the water of the Inner Harbor with this private sunset cruise on a sailboat, with space for up to six passengers. Meet at the Inner Harbor Marina to board the sailboat, then sit back and relax as your captain and crew sail out to Fort McHenry. Enjoy watching the sunset while savoring BYOB drinks.

Get views of a sunset over Baltimore's Inner Harbor on this evening sunset cruise. Snap photos of your loved ones against the backdrop of the sun sinking below the horizon and relax on board the boat. Listen to relaxing music and feel free to bring along your favorite bottle of wine, with corkscrew and glasses provided.

Hop aboard your private yacht and cruise through Chesapeake Bay for a special way to celebrate a special event, or just to make some lasting memories. Cake and party favors are served to help make this a memorable occasion. This cruise is just for you and your private group, without having to share with other tourists.

Find your own slice of paradise on this 1.5-hour moonlight sail around Baltimore Harbor. Listen to music inspired by the Caribbean as you enjoy the warm breeze and look at the moon and stars in the sky. Bring the tropics to Baltimore on this moonlight sailing experience. Both of our boats have seating on the cabin tops and allow people to spread out and have their own space.

Immerse yourself in the Chesapeake Bay's rich maritime history on a sailing tour of the Baltimore Harbor. Take in the sights of the Inner Harbor and listen to a guide detail Baltimore's and the Chesapeake's roles in the shaping of American history.

Cool off from Baltimore's hot summer nights with this moonlight sail around Baltimore Harbor. In a small group of no more than six passengers, you'll see historic sights such as the Fort McHenry National Monument and Historic Shrine under the light of the moon as you cruise around the harbor in an authentic schooner.