Top 20 Best Sailing charters in Annapolis, Maryland

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.

Watermark Tours, Charters, Cruises is a premier tourist attraction and travel agency located at 1 Dock Street in the charming city of Annapolis, Maryland, United States.

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

The Annapolis Yacht Club is a prestigious and historic institution located at 2 Compromise Street in 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.

Darling Charters is a premier travel agency located at 1 Dock Street in Annapolis, Maryland.

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.

Tour Boat Annapolis is a premier travel agency located at 710 Americana Drive in Annapolis, Maryland. We specialize in providing unique and unforgettable boat tours of the beautiful Annapolis area.

Ohana Charters is a travel agency located at 500 Piney Narrows Road in Chester, 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.

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.

J World Annapolis is a premier sailing school located in the heart of Annapolis, Maryland. Our experienced instructors offer a wide range of sailing courses for all skill levels, from beginners to advanced sailors.

Chesapeake Sailing Tours is a premier travel agency located in Annapolis, Maryland.

Island Chill Yacht Charters (ICYC) is a travel agency located at 1444 Shore Drive in Edgewater, Maryland, United States.

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.

Jobson Sailing Associates is a renowned sailing school located at 3 Church Circle in Annapolis, Maryland, United States.

Annapolis Yacht Sales and Services is a premier marine dealership located at 216 Old Love Point Road in Stevensville, Maryland.

Z Flight Parasail and Watersports is a premier travel agency located at 300 Second Street in Annapolis, Maryland, United States.

Eastport Yacht Club is a premier sailing and social club located at 317 First Street in Annapolis, Maryland, United States. With a rich history dating back to 1982, the club offers a vibrant community of boating enthusiasts, sailors, and social members.

Knapp’s Narrows Marina & Inn is a waterfront lodging institution located on Maryland’s Eastern Shore in Tilghman Island.

The Captain's Cottage is a charming lodging located at 985 Awald Road in Annapolis, Maryland, United States. This cozy retreat offers a unique and inviting atmosphere for guests looking for a relaxing getaway.

Liberte, The Schooner is a renowned travel agency located at 222 Severn Avenue in Annapolis, Maryland, United States.

Chesapeake Boating Club, located at 213 Eastern Avenue in Annapolis, Maryland, is a unique institution that offers sail and power boat charters and rentals.

The International Star Class Yacht is a prestigious institution located at 914 Bay Ridge Road in Annapolis, Maryland, United States.

Schooner Woodwind Offsite Business Office is a travel agency located at 1930 Lincoln Drive in Annapolis, Maryland.