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.

Sail the serene waters of the Chesapeake Bay aboard the historic Lady Patty. This two-hour cruise offers a unique opportunity to unwind while taking in the picturesque views of St. Michaels, MD. Your journey includes gliding through the harbor and possibly spotting wildlife like osprey and dolphins. Enjoy a friendly crew that shares captivating stories about the area and sailing. Whether you’re looking for a fun family outing or a peaceful escape, this sailing experience is perfect for all ages. - Duration: 2 hours, with daily availability - Max capacity of 13 guests, ensuring a personalized experience - Beer and wine tasting available for adults, with complimentary water - Departing from Harbour Inn, 101 N Harbor Road, St. Michaels, MD

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.

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.

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.

We depart right from downtown Annapolis, putting you immediately in the heart of the waterfront, Spa Creek, Ego Alley, and the harbor scene without needing to travel to an outlying marina. Enjoy a customized experience tailored to your group with a USCG-licensed captain. Whether you want to cruise Spa Creek, sail the Bay, anchor for a swim, stop at a waterfront restaurant, or enjoy a sunset picnic, the classic teak-appointed Nauticat offers a refined and relaxed way to enjoy the water. Bring your own food and drinks or opt for catering to make your outing extra special. Enjoy a private boat experience with just your group and no crowds. Depart from downtown Annapolis, right in the heart of the waterfront. Choose from two vessels: the classic Nauticat 331 or the nimble AB Oceanus RIB. Suitable for family outings, casual celebrations, or intimate getaways. Flexible trip lengths and itineraries to match your preferences.

Set sail on a 2-hour adventure aboard the modern catamaran, Epiphany, in the tranquil waters of St. Michaels, MD. Designed for comfort, this spacious vessel offers cushioned seating and panoramic views of the Chesapeake Bay. Glide through scenic vistas and spot local wildlife while enjoying a brief harbor tour, including the historic Hooper Strait Lighthouse. Whether you choose to relax or learn a bit about sailing, the friendly crew ensures an enjoyable experience for everyone on board.

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.

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.

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.