Sailing Annapolis and the Chesapeake Bay

27th Jun 2018

What better way to mark Independence Day than taking a look at our awesome coastline and exploring the diversity of our own cruising grounds. When it comes to our precious vacations, we often want to experience other cultures and ‘get away from it all’. This often means a long haul flight, so let’s take a look at the jewels that lie a little closer to home on the east coast…

The gateway to Chesapeake Bay
Sail the United States’ largest estuary from Annapolis and explore the wonder of the Chesapeake Bay with its 200 miles of shoreline, protected waters, exciting anchorages and natural beauty. Originally named Anne Arundel’s Towne in the 1600s after the UK’s Princess Anne, Annapolis was the former capital of the US and now it’s popular with sailors from all over the world.

If you love your food, then the bay provides a feast and you can literally dine your way around the coast. It’s known for menus brimming with delicious crabs and did you know that “Chesapeake Bay” is Powhatan for “Great Shellfish Bay”?

The region’s sailing season runs from mid-May all the way through to mid-October. Whether you go north or south from our base at Back Creek in Port Annapolis Marina, there’s plenty to see and do for all the family.

Recommended stop offs, north to south

  • Rock Hall – A waterfront fishing town with wonderful fresh oysters and crabs plus a farmer/artisan market on weekends
  • Baltimore Inner Harbor – Listen to live music, visit the aquarium, try Maryland blue crabs and experience the lively nightlife
  • Chester River – At Eastern Neck National Wildlife Refuge you can enjoy nature walks and the butterfly garden, as well as a great view of the bay across to Baltimore
  • Whitehall Bay – Enter the bay and pick up the flashing channel marker 320 NW to find the famous Cantler’s Restaurant, a traditional Maryland crab house and Chesapeake tradition
  • St. Michael’s  – This popular yachting centre is home to the Chesapeake Bay Maritime Museum, which is so large that the entry price includes a two-day pass
  • Wye Island – A protected island that focuses on preserving wintering waterfowl and native wildlife. Hike the six miles of trails and find the holly tree that is nearly 300 years old
  • Herrington Harbour  – A popular location on the west of Chesapeake Bay with two marinas – you’ll need to make a reservation
  • Oxford – One of Maryland’s oldest towns and former international shipping center, this waterfront town is known for its boater-friendly atmosphere
  • Cambridge – Browse the shops and restaurants in the downtown area, which is now a heritage district
  • St Leonard Creek – Famed as one of the most beautiful areas on Patuxent River with peaceful anchorages
  • Solomon’s Island – Walk around the sculpture park, hunt for fossils or trawl the waterfront for restaurants, such as Zahniser’s Dry Dock and the Lighthouse Restaurant and Dock Bar

4th of July celebrations
Booking a charter in Annapolis during 4th of July will make your vacation extra special with live music, parades and several large firework displays that can be enjoyed from the water. One is held at Sherwood Forest and the fireworks on Independence Day are set off from Annapolis harbor. Our Annapolis fleet gets booked up quickly so plan now for 2019.

Learn more
For more information on sailing Annapolis, get in touch with our team. Email us at or give us a call at 855.650.8902.