top of page
MD-Baltimore-Inner Harbor-13.jpg

Top Yacht Clubs in the Chesapeake Region: A Boater’s Paradise


Annapolis Yacht Club

The Chesapeake Bay is a haven for boating enthusiasts, offering unparalleled access to some of the most picturesque waterways in the country. Among the jewels of this region are its yacht clubs—exclusive hubs that combine community, camaraderie, and world-class facilities for boaters of all levels. Whether you’re an experienced sailor or just beginning your maritime adventures, the Chesapeake’s yacht clubs offer a rich blend of tradition, luxury, and recreation.


 

What Makes a Great Yacht Club?


Yacht clubs in the Chesapeake region are renowned for their:


  • Exceptional Facilities: Modern marinas, fuel docks, and well-maintained slips.

  • Amenities: Dining options, social events, and family-friendly activities.

  • Community: Networking with like-minded individuals who share a passion for boating.

  • Educational Opportunities: Sailing lessons, regattas, and workshops for boaters of all skill levels.


 

Top Yacht Clubs in the Chesapeake Region


Here’s a curated list of the top yacht clubs offering exclusive experiences for boaters:


Annapolis Yacht Club

1. Annapolis Yacht Club


Location: Annapolis, MD


Overview: As one of the most prestigious clubs in the region, the Annapolis Yacht Club is steeped in tradition and boasts a prime location near downtown Annapolis. It’s a hub for regattas, sailing lessons, and social events.


Amenities:

  • Full-service marina with 74 slips.

  • Waterfront dining with stunning views of the harbor.

  • Comprehensive youth and adult sailing programs.



 

Eastport Yacht Club

2. Eastport Yacht Club


Location: Annapolis, MD


Overview: Known for its welcoming atmosphere, Eastport Yacht Club offers a vibrant community for recreational and competitive sailors. The club actively promotes environmental stewardship on the Bay.


Amenities:

  • Social and racing events throughout the year.

  • Dockage facilities and transient slips.

  • Educational programs focused on sustainable boating.



 

Gibson Island Yacht Club

3. Gibson Island Yacht Club


Location: Gibson Island, MD


Overview: Nestled on exclusive Gibson Island, this private club combines scenic beauty with unmatched amenities. It’s a haven for both sailors and powerboaters.


Amenities:

  • Private marina with deep-water slips.

  • Access to the island’s golf course, tennis courts, and beach club.

  • Seasonal regattas and sailing camps.



 

Miles River Yacht Club

4. Miles River Yacht Club


Location: St. Michaels, MD


Overview: Situated in the charming town of St. Michaels, the Miles River Yacht Club is known for its family-friendly environment and commitment to water sports.


Amenities:

  • Full-service marina with 65 slips.

  • Sailing school for all ages.

  • Active social calendar, including the popular Governor’s Cup Race.



 

Herrington Harbour Yacht Club

5. Herrington Harbour Yacht Club


Location: North Beach, MD


Overview: Herrington Harbour Yacht Club offers a resort-like experience with a strong focus on environmental sustainability. Its marina is a popular stopover for Chesapeake Bay cruisers.


Amenities:

  • Award-winning marina with extensive dockage options.

  • Waterfront pool, fitness center, and private beach access.

  • Green initiatives, including native plant restoration and clean marina certifications.



 

Tred Avon Yacht Club

6. Tred Avon Yacht Club


Location: Oxford, MD


Overview: Founded in 1931, this historic club is a staple in the Eastern Shore’s maritime community. It’s renowned for its active racing schedule and strong emphasis on junior sailing.


Amenities:

  • Full-service marina with transient slips.

  • Regular regattas and cruising events.

  • Year-round social and educational programs.



 

Maryland Yacht Club

7. Maryland Yacht Club


Location: Pasadena, MD


Overview: Established in 1908, the Maryland Yacht Club is one of the oldest and most prestigious clubs on the Chesapeake Bay. It offers a perfect blend of tradition and modern amenities.


Amenities:

  • 100-slip marina with easy access to the Bay.

  • On-site restaurant and bar with panoramic water views.

  • Seasonal events, including fishing tournaments and fireworks displays.



 

Swan Point Yacht Club

8. Swan Point Yacht Club


Location: Swan Point, MD


Overview: Located on the Potomac River in Southern Maryland, Swan Point Yacht Club is a hidden gem offering breathtaking views, a welcoming community, and marina services for boating enthusiasts.


Amenities:

  • Marina with dockage for a variety of boat sizes.

  • Access to golf, dining, and social events at the neighboring Swan Point Yacht & Country Club.

  • Seasonal boating events and cruises.



 

Kent Island Yacht Club

9. Kent Island Yacht Club


Location: Chester, MD


Overview: Overlooking the Chester River, Kent Island Yacht Club provides a casual and inviting atmosphere with excellent marina facilities and social events. It’s a favorite among locals and visitors alike.


Amenities:

  • Spacious marina with slips for boats up to 80 feet.

  • On-site restaurant and Tiki bar with waterfront views.

  • Live music events, crab feasts, and holiday celebrations.



 

Cambridge Yacht Club

10. Cambridge Yacht Club


Location: Cambridge, MD


Overview: Established in 1912, Cambridge Yacht Club is one of the oldest yacht clubs on the Eastern Shore. It boasts a rich history and a beautiful location on the Choptank River.


Amenities:

  • Full-service marina with transient slips.

  • Elegant clubhouse for dining and events.

  • Hosting of regattas, fishing tournaments, and seasonal cruises.



 

Gibson Island Yacht Club

Why Join a Yacht Club?


Membership at a yacht club offers a wealth of benefits, including:


  • Exclusive Access: Priority docking and access to world-class facilities.

  • Community Building: Meet fellow boaters and participate in shared activities.

  • Educational Opportunities: Learn new skills, from sailing to navigation.

  • Prestige and Tradition: Be part of a legacy of maritime excellence.


Gibson Island Yacht Club
 

Plan Your Visit


Each yacht club in the Chesapeake region offers a unique experience. Whether you’re seeking competitive racing, family-friendly activities, or simply a picturesque setting to dock your boat, there’s a club to suit every preference. Visit their websites to learn more about membership options, upcoming events, and marina services.

bottom of page