Maryland Sailing

Set sail on Maryland’s beautiful waters with our Maryland sailing experiences. This gift offers a peaceful yet exhilarating day on the Chesapeake Bay, perfect for novices and seasoned...Read more

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Half Day Private Sail

Half Day Private Sail

Saint Michaels, Maryland

Half Day Private Sail

From $1235
Beer Tasting Sail on a Historic Yacht

Beer Tasting Sail on a Historic Yacht

Saint Michaels, Maryland

Beer Tasting Sail on a Historic Yacht

From $149
Wine Tasting Sail on a Historic Yacht

Wine Tasting Sail on a Historic Yacht

Saint Michaels, Maryland

Wine Tasting Sail on a Historic Yacht

From $149
Sunset Sailing Cruise

Sunset Sailing Cruise

Rock Hall, Maryland

Sunset Sailing Cruise

From $45
Sail the Chesapeake on a Historic Yacht

Sail the Chesapeake on a Historic Yacht

Saint Michaels, Maryland

Sail the Chesapeake on a Historic Yacht

From $123
History Sail on Summer Wind

History Sail on Summer Wind

Baltimore, Maryland

History Sail on Summer Wind

From $63
Chesapeake Bay Sailing Cruise

Chesapeake Bay Sailing Cruise

Rock Hall, Maryland

Chesapeake Bay Sailing Cruise

From $44
Weekday Harbor Sail on Unforgettable

Weekday Harbor Sail on Unforgettable

Baltimore, Maryland

Weekday Harbor Sail on Unforgettable

From $63
Weekday Moonlight Sail on Summer Wind

Weekday Moonlight Sail on Summer Wind

Baltimore, Maryland

Weekday Moonlight Sail on Summer Wind

From $75
Weekday Sunset Sail on Summer Wind

Weekday Sunset Sail on Summer Wind

Baltimore, Maryland

Weekday Sunset Sail on Summer Wind

From $75
Weekday Evening Sail on Unforgettable

Weekday Evening Sail on Unforgettable

Baltimore, Maryland

Weekday Evening Sail on Unforgettable

From $75
Weekday BYOB Sunset Sail on Unforgettable

Weekday BYOB Sunset Sail on Unforgettable

Baltimore, Maryland

Weekday BYOB Sunset Sail on Unforgettable

From $75
Weekend Harbor Sail on Summer Wind

Weekend Harbor Sail on Summer Wind

Baltimore, Maryland

Weekend Harbor Sail on Summer Wind

From $75
History Sail on Summer Wind - Weekend

History Sail on Summer Wind - Weekend

Baltimore, Maryland

History Sail on Summer Wind - Weekend

From $75
Weekend Sunset Sail on Summer Wind

Weekend Sunset Sail on Summer Wind

Baltimore, Maryland

Weekend Sunset Sail on Summer Wind

From $87
Weekend Moonlight Sail on Unforgettable

Weekend Moonlight Sail on Unforgettable

Baltimore, Maryland

Weekend Moonlight Sail on Unforgettable

From $87
Weekend Evening BYOB Sail on Summer Wind

Weekend Evening BYOB Sail on Summer Wind

Baltimore, Maryland

Weekend Evening BYOB Sail on Summer Wind

From $87
Weekend BYOB Sunset Sail on Unforgettable

Weekend BYOB Sunset Sail on Unforgettable

Baltimore, Maryland

Weekend BYOB Sunset Sail on Unforgettable

From $87
Chesapeake Bay Private Sailing Cruise for 6

Chesapeake Bay Private Sailing Cruise for 6

Rock Hall, Maryland

Chesapeake Bay Private Sailing Cruise for 6

From $252
Private Sailing Charter on the Chesapeake for 6

Private Sailing Charter on the Chesapeake for 6

Saint Michaels, Maryland

Private Sailing Charter on the Chesapeake for 6

From $715
4 Hour Private Yacht Charter

4 Hour Private Yacht Charter

Baltimore, Maryland

4 Hour Private Yacht Charter

From $2552

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