Welcome to Annapolis Carefree Boat Club! Thank you for visiting Carefree Boat Club – the best alternative to buying a boat!
About this club
Oak Grove Marina has offered great access to the Chesapeake Bay since 1954. Easily accessible by car, the Marina is just off Route 2 in Edgewater, Maryland. This marina is also a short drive from northern Virginia cities and Washington, DC.
Location and Access
Carefree Boat Club at the Oak Grove Marina is located on the South River near the middle of the Chesapeake Bay. Oak Grove is just five miles from the mouth of the Chesapeake Bay and one inlet south of the Severn River and downtown Annapolis.
At the Oak Grove Marina you will have everything you need! Carefree Boat Club maintains a spacious, beautifully decorated office and classroom at Oak Grove Marina, overlooking the South River. Carefree members have the opportunity to reserve the office for a special party or business meeting.
The Yellowfin Restaurant is on-site and is famous for their Sunday buffet, great seafood and steaks. Try happy hour at the bar where you can order sushi and other bar food at half price.
The marina offers fuel dock with both gas and diesel, pump-out services, and full restrooms with showers.
Things to Do Near the Marina
The Annapolis club is a perfect gateway to destination boating on the Bay!
As you cruise towards the mouth of the Bay, you will pass Harness Creek and beautiful Quiet Waters Park. The park offers one of the prettiest anchor spots on the Bay. A little further up the River on your starboard side is Almshouse Creek and Historic London Towne and Gardens. When you get to the beginning of the river look to your port side and you’ll see the Bay Bridge to the Eastern Shore.
Annapolis and the Naval Academy are just minutes away. You can dock at City Dock in downtown Annapolis, walk through the historic State Capitol and visit great restaurants and bars like Pusser’s Landing, the Chart House and Rams Head Tavern.
A little further up the Bay on the other side of the Bay Bridge is the entrance to the Magothy River. Once inside, the river widens and the water is smooth. The Magothy’s shoreline has numerous inlets and coves to explore. Dobbins Island, with its sandstone cliffs and sandy beach, is a favorite spot for boating families to meet up, drop anchor, picnic and splash in the shallows.
You may choose to cruise across the Bay and slightly south, around the tip of Kent Island and into St Michaels – a great day trip or overnight destination offering popular waterfront restaurants like the Crab Claw, as well as transient slips at Higgins and many bed and breakfast options. Follow sidewalks in the quaint town, along broad-shaded streets past specialty stores, art galleries and antique shops.
If you prefer to stay on the South River, you can head two miles upriver to the South River Water Ski Course. These calm waters are a designated ski and tubing spot and are buoyed off with a slalom course and ski ramp.
On the way back to the club, stop at Mike’s Crab House. Voted best Crabs and best Crab Cake, the restaurant offers outdoor seating right on the banks of the River.
Don’t forget fishing! Anglers will appreciate the many fishing options available in and along the shores of the Chesapeake Bay. The largest U.S. estuary, where freshwater meets saltwater that leads to the sea, the Chesapeake Bay starts in northeast Maryland and extends south about 200 miles to Norfolk, Virginia. Rockfish (striped bass), perch, flounder and croaker are all abundantly available.
At the Annapolis Carefree Boat Club you will always have the right boat for every activity. The Carefree fleet consists of luxury Sea Ray and other specialty boats. The fleet is reserved exclusively for our members. Click on the link for Our Boats for a complete list of the Annapolis fleet, but the boats include:
- Sea Ray Sundeck 220
- Sea Ray Sundeck 240
- Sea Ray Sundancer 260
- Sea Ray Amberjack 250
- Sea Ray Weekender 215
- Triumph Center Console
- Grady White
- 28’ Hunter Sailboat
- And more…
Learn how to become a member:
Contact our membership director (using the form to the right) to schedule a tour.