Top 30 Best Sailing vacations in Maryland

Sail Alyosha is a premier travel agency located at 12817 Harbor Road in Ocean City, Maryland.

Sundance Sailing Charters is a premier travel agency located at 78 George Street in Georgetown, Maryland, United States.

Located at 951 Fell Street in Baltimore, Maryland, Bay Dream Sailing is a premier tourist attraction and travel agency that offers unforgettable boat tours along the stunning waters of the Chesapeake Bay.

Annapolis Sailing Adventures is a premier travel agency located in Annapolis, Maryland, United States. We offer a variety of sailing experiences, including private charters, sunset cruises, and sailing lessons.

Boat Baltimore offers exclusive private boat charters in the heart of Baltimore, Maryland. Located at 321 East Cromwell Street, our travel agency provides intimate sailing yacht cruises, large group charters, and fishing adventures.

Shardana Sailing Charters is a premier travel agency located at 20786 Rock Hall Avenue in Rock Hall, Maryland, United States. Specializing in sailing charters, they offer unforgettable experiences on the open water for individuals and groups alike.

Chesapeake Bay Charters offers an unforgettable family sailing adventure at their location in Solomons, Maryland.

BaySail School of Sailing, located at 100 Bourbon Street in Havre de Grace, Maryland, is an accredited American Sailing Association (ASA) school.

American Sailing Tours is a premier travel agency located at 400 Key Highway in Baltimore, Maryland. We offer unforgettable sailing experiences along the beautiful waters of the United States.

Cool Breeze Sailing Charters LLC is a premier travel agency located at 1900 Thames Street in Baltimore, Maryland. Specializing in sailing charters, they offer unforgettable experiences on the water for individuals, couples, and groups.

Blue Crab Chesapeake Sailing Charters is a premier travel agency located in Rock Hall, Maryland, United States.

The Sailing Academy is a premier institution located at 411 Deale Road in Tracys Landing, Maryland, United States.

Schooner Woodwind Sailing Cruises offers an unforgettable experience for visitors looking to explore the waters of Annapolis, Maryland.

Severn Sailing Association, located at 311 First Street in Annapolis, Maryland, is a premier sailing institution that hosts over a dozen fleets and a vibrant junior program.

2118 Sail Inn is a cozy bar located at 2118 Lincoln Avenue in Sparrows Point, Maryland. This waterfront establishment offers a relaxed and friendly atmosphere for patrons to enjoy a wide selection of drinks, including craft beers, cocktails, and wines.

Seas the Bay Private Sailing Charters is a premier travel agency located in Annapolis, Maryland, United States. Specializing in private sailing charters, they offer unforgettable experiences on the beautiful Chesapeake Bay.

Reflections DC - Private Sailing Cruises offers unforgettable experiences on the water, allowing guests to explore the stunning waters of the Chesapeake Bay.

Das Boot Sailing Charters is a premier travel agency located at 4883 Church Lane in Galesville, Maryland, United States.

Picture Perfect Sailing is a premier sailing institution located at 980 Awald Road in Annapolis, Maryland, United States. Escape the hustle and bustle of everyday life and enjoy quality time with family and friends on the beautiful Chesapeake Bay.

Classic Sail Charters is a premier sailing school located in Annapolis, Maryland, offering private sailing adventures for up to six passengers.

Chronic Sailing is a premier sailing school located at 7082 Bembe Beach Road in Annapolis, Maryland, United States. Our institution offers top-notch sailing instruction for all skill levels, from beginners to advanced sailors.

Deep Creek Sailing School is a premier institution located at 204 Yacht Club Road in Swanton, Maryland, United States. As a school specializing in sailing education, we offer a wide range of courses for all skill levels, from beginners to advanced sailors.

Experience Sail, LLC is a sailing charter institution located at 20786 Rock Hall Avenue in Rock Hall, Maryland, United States. The institution operates a 2011 Beneteau Oceanis 50 yacht that is well equipped and comfortable for sailing charters.

Blown Away Sailing LLC is a premier sailing institution located at 20880 Rock Hall Avenue in Rock Hall, Maryland, United States.

R&R Charters and Sail School, located in Chester, Maryland, United States, is a professional institution dedicated to sharing the joy of sailing with students.

Sail Solomons is a premier sailing school located at 245 C Street in Solomons, Maryland, United States. Our institution offers a range of sailing courses for all skill levels, from beginners to advanced sailors.

Sailing Center Chesapeake is a premier sailing institution located in Lexington Park, Maryland, United States.

Delmarva Sailing School, located at 21144 Green Lane in Rock Hall, Maryland, is a premier institution for those looking to learn the art of sailing.

Granmar Sailing is a premier travel agency located at #8 Randall Street in Annapolis, Maryland, United States. Specializing in sailing adventures, Granmar Sailing offers a variety of packages for individuals and groups looking to explore the open waters.

St. Michaels Sailing Charters is a premier tourist attraction located at 23672 Mount Pleasant Landing Circle in the picturesque town of Saint Michaels, Maryland, United States.