Top Maryland Sailing Tours

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

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.

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.

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.

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.