Thomas Point Lighthouse
Waypoints Annapolis

Why Charter Local? Annapolis is the Sailing Capital of the U.S.!

AnnapolisAround AnnapolisCharter Tips

The Chesapeake Bay is the largest estuary in the U.S., offering so many options to the sailor and boater. From amazing sails under the magnificent Chesapeake Bay Bridge, exploring the many inlets, dropping anchor in a quiet cove, watching the stars at night, or sailing by the famous Thomas Point Lighthouse.

Not to mention, the many ports you can visit. Starting with Annapolis, you have the U.S. Sailboat Shows in the Spring and Fall, Blue Angels practice and main show during Commissioning week, and the historic treasures of downtown Annapolis to explore. Next is St.Michaels, a short day sail away with plenty to do, including a visit to the Chesapeake Maritime Museum, a tour of the local winery, and shopping. The local hotels on the water offer dockage and free use of the pool for those hot summer days. Oxford, Solomons, and Deale are other quaint little towns that offer a nostalgic feel and are known for their romantic destinations. If you are more into the big city life, Baltimore is close and easily reachable by boat.

  • Steamed crabs from the Chesapeake Bay
  • A woman relaxing on an inflatable raft

Want to have the Maryland Crab experience? Take a sail over to Cantler’s Riverside Inn for the riverfront experience of old school crab picking. It’s located on Mill Creek and a quick sail from our base.  

Want to enjoy a day in the water lounging on your water toys? Rent an NC33 powerboat and make your way over to Dobbins Island for a fun day anchored and enjoying all that the “Jewel of the Magothy” can offer you.

For music lovers, the Tides & Tunes Summer Concert Series offers 10 weeks of popular music ranging from rock to folk to jazz. It’s a great place on a Thursday night to drop your anchor, and enjoy the music.

You don’t have to leave— these are all great options just a short drive away or even in your backyard!