America’s Sailing Capital: Annapolis, MD — Road Trip 2020

Boats in Annapolis Harbor

Who wouldn’t want to drive a little over 80 miles from Gettysburg to be in America’s Sailing CapitalAnnapolis — even if it’s just for a couple of days? After all, if you’re from East Tennessee as we are, the lure of the open sea, and the chance to see sailboats, historic 18th century buildings, and crab served in more ways than you can count was enough to put Annapolis, Maryland, on our Road Trip 2020 list.

To our good fortune, we had booked what unknowingly was a superb venue for two nights lodging — the Governor Calvert House, one of the Historic Inns of America. Tasteful furnishings and close proximity to the harbor make it a highly recommended stop if you’re going to be sightseeing Annapolis.

Governor Calvert House, Historic Inns of Annapolis

From the hotel, it was a quick stroll through a charming residential section to the waterfront, where makeshift open-air seating allowed social distancing and a view of the Chesapeake Bay while dining morning, noon, or night.

Street to Annapolis Harbor
Two-story homes pack the street from Governor Calvert House to Annapolis Harbor
Makeshift outdoor seating at Iron Rooster, Annapolis
Makeshift outdoor seating may not be glamorous, but it works at Iron Rooster (where they serve breakfast all day) in Annapolis.

Leading to the harbor, street shops put out their best Maryland and U. S. Naval Academy shirts and souvenirs.

Annapolis shirts and souvenirs

And not to miss: the Kunte Kinte – Alex Haley Memorial honoring a beloved Tennessee author. In a beautiful harbor setting, the memorial promotes strong family connections and mutual respect for all.

But Annapolis, for everyone who lives and visits there, is known for boating. That’s what we came to see. And we weren’t disappointed.

From sailboats on the open waters . . .

to boats big and small, tethered and moored. Boats were ever-present — and gorgeous. Yes, we had boat envy!

Boats lined up, Annapolis harbor
All lined up, ready for sailing!
Winning Drive, Annapolis Harbor
This fabulous boat, Winning Drive Yacht, is owned by Steve Biscotti, executive owner of the Baltimore Ravens.
Boats and masts, Annapolis Harbor
Typical view in Annapolis Harbor — masts filling the seascape.

An afternoon tour took us beyond the harbor and out to sea, moving past the U. S. Naval Academy where we watched the recruits going through their paces.

U. S. Naval Academy recruits, Annapolis, MD
Cadets in the U. S. Naval Academy get in shape at water’s edge.

If you’re headed to Annapolis, we have several recommendations to pass along:

  • Stay in or near downtown and the harbor for easy access to shops, restaurants, and views of some of the prettiest boats in the world.
  • Drive or Uber over to the Eastport section for great dining, especially if you have a hankering for local seafood. Boatyard Bar & Grill lived up to its pick by the Baltimore Sun for Best Crab Cake, but add a cup of Maryland Crab Soup to your order, and you’ll be smiling all night.
  • Make time for a boat tour — daily, sunset, any time. There’s nothing like seeing Annapolis from the water! (We like Watermark tours, but there are many to choose from.)
Sailboat at Annapolis, MD

While planning Road Trip 2020, we thought we’d focus on back roads, small towns, and historic sites. But we’re glad we added a visit to the big city of Annapolis in the middle of it. So much to enjoy!

Travel Annapolis,

Rusha & Bert

For more in our Road Trip 2020 series, check out these posts:

15 thoughts on “America’s Sailing Capital: Annapolis, MD — Road Trip 2020

    1. Oh, the Places We See

      Ah, boating in Maine. Much calmer waters and prettier scenery. But Annapolis is a pretty good place to visit for other reasons — the harbors, history, and food are all pretty good!!! (But I, too, like Maine better.)

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