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Annapolis – Gateway To The Chesapeake

Annapolis – Gateway to the Chesapeake

The Chesapeake Bay is one of nature’s greatest wonders. My heart skips a beat every time I drive over the Bay Bridge towards Annapolis. Not just because the bridge is scary (it is) but because of spectacular Chesapeake Bay below. The Bay is huge with navigable water from just south of Wilmington DE down to the Atlantic Ocean at Norfolk Virginia, about 165 miles. But the Bay is also so much more than just the area we see. The Chesapeake Bay watershed (drainage basin) extends south from the headwaters of Otsego Lake, near Cooperstown, New York and east from Blacksburg, Virginia. It is essentially a giant, sprawling system of rivers that all drain into one shallow tidal basin, the Chesapeake Bay and its tidal tributaries (average depth, only 21 feet).


Fish, crabs, sailboats, cruise ships, yachts, container ships and oil tankers all share this beautiful body of water and Annapolis is your gateway to the entire Chesapeake Bay. As a visitor (or resident) you have lots of ways to get out on the water. Here are just a few of the ways to do so, all within an hour from downtown.

Out and About in Annapolis Harbor

In the harbor itself you can rent kayaks and paddle boards in Eastport and explore the basin, ego alley and Spa Creek. Or you can leave the work to others and just hop on the Harbor Taxi. This is one of my favorite ways to see Annapolis by water. No reservation required. Pick up the taxi at Ego Alley and get dropped off in Eastport. Walk over to Bach Creek and get a water taxi out Back Creek, into the Severn River and back to Ego Alley. The Water Taxi Captains know the city well and if you give them a good tip, will tell you great stories about Annapolis. Some might even be true.

Go Sailing – take a lesson.

In Eastport there are boats for rent and classes for sailors of all levels. From instruction on the basics of sailing to coaching for experienced teams, you don’t need a boat of your own to get out and sail.

Go Sailing – and crew.

For readers who know how to sail already, just head to the Annapolis Yacht Club, or the Severn Sailing Association, or Eastport Yacht Club on a Wednesday, Thursday or Saturday afternoon and ask if anyone needs a crew. If you look and act like a sailor, someone will grab you to go sailing with them. If you actually know what your doing, they might ask you back next week!

Be a tourist.

Several tour boats take day trips from downtown. There are pirate boats, sailing schooners, and cruise boats with a variety of tours available.

Go to the Beach

To see the Bay in all its glory, I recommend several places in particular: Sandy Point State Park at the Western end of the Bay Bridge and The Chesapeake Bay Foundation located between Annapolis Cove and Highland Beach and Thomas Point Park.

Sandy Point State Park is a big public beach and small boat launching facility. The views of the Northern Bay and the Bay Bridge are terrific. Bring a chair and watch the boats go by. You’ll see everything from 14’ fishing boats to 900’ massive cargo ships.

The Chesapeake Bay Foundation is a non-profit organization dedicated to protecting the Chesapeake Bay. The have a beautiful museum right on the Bay with spectacular views of the Bay south of the Bay Bridge. If you visit on the weekends, you will see hundreds of sailboats racing just off Tolly Point.

Between the South River and the Severn River is Thomas Point with the iconic light house another half mile out in the bay. At the end of Thomas Point itself is a beautiful county park with unsurpassed views of the bay in all directions. Bring a lunch, grab a picnic table and enjoy.

Take a drive

As much as we like Annapolis, no vacation would be complete without a day trip to the Eastern Shore. Across the Bay from Annapolis are several charming towns build on fish, oysters and crabs. You can expect quaint shops, spectacular vistas, and awesome restaurants.

Head over the Bay Bridge and take Route 50 South to Easton Md. From there go west to St. Michaels, MD. This seaport has a bustling inner harbor that may remind you of Annapolis, only smaller and cuter.  Grab lunch at any place that catches your eye. You can’t go wrong.

From St. Michaels head towards the Oxford – Bellevue Ferry. The ferry is the oldest, continuously operated ferry in the United States and it holds about 20 cars for the 10-minute trip across the Tred Avon River to Oxford, MD. The oldest Port in the United States and home to Robert Morris who is one of the signers of the Declaration Of Independence. Grab an iced tea on the porch of the Robert Morris Inn. On your way out of town stop in to the Oxford Market for a home-made sandwich and some ice cream. Oxford is a tiny town with a deep sailing history. Drive around and look at all the marinas and boats. I’m pretty sure there are more boats in Oxford than people.

From Oxford head back to Annapolis and a well-deserved dinner back on the waterfront.

What have we missed? Tell us what your favorite way is to be out on the Bay.

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