Savanna and Charleston instantly come to mind when you think of U.S. cities oozing European vibes.
With cobbled roadways, village-like boulevards, and centuries-old architecture, these cities are a unicorn.
Obviously, venturing off to Europe has no true comparison but the vibes are immaculate nonetheless.
If you thought these were the only cities that truly do exude European flair, a record number of tourists will tell you that you’re overlooking one of America’s most underrated waterfront getaways — and no, it’s not St. Augustine either.
Dating back to 1649, a time when horses caused traffic jams and curly white wigs were still considered fashion goals, Maryland’s picturesque capital stands the test of time with brick row-homes with colonial charm and a harbor so full of sailboats it looks like a postcard come to life.
Drawing in a record 7.2 million tourists last year was no small task for a city of roughly 41,000 residents, but the truth is it delivers.
Expect to be wowed with unexpected delights like classic taverns in buildings older than the country itself and the town’s deeply ingrained boating culture, where it’s said there are more boats than parking spaces.
A City Older Than America Itself
Quite possibly the most bizarre thing I’ve seen in my travels is George Washington’s “teeth” on display down the road at the National Museum of Dentistry in Baltimore.
Is that really a time capsule anyone wants to unpack?
On the other hand, a place like Annapolis, still illuminated with timeless character through storybook streets and classic taverns, is exactly the type of place you’ll want to turn back the clock…right?
Annapolis is a couple of decades shy of its 400th birthday, while America is set to celebrate the big 250 next year.
As we all know, much of America simply doesn’t look like quintessential Europe — you know, immacutely-preserved marvels and endless mazes of stone-worn walkways.
Truth be told, we’re a country of contrasts with shimmering modern skylines that oftentimes tower over the poorest neighborhoods in the city.
But that’s where Annapolis comes into play. If urban playgrounds that resemble human ant farms are more your style, head over to Baltimore or numerous other Northeastern cities.
If European flair packed with captivating history is more up your alley, Annapolis is just the place.
Grab a brewskie at Reynolds Tavern & Middleton Tavern, both 1700s watering holes where, legend has it, our first president’s aforementioned chompers may have sipped a pint or two…or three or four.
Swap high-rises for the unmissable 1600s St. Anne’s Church backdropping the picturesque townscape.
Stop by the 1800s William Paca House & Garden, home to one of the originators of the Declaration of Independence.
And, of course, there’s the Maryland State House, America’s oldest continuously used state capitol.
America’s ‘Sailing Capital’: How Is There Not A Margaritaville Here?
If Jimmy Buffett were still around, I gotta believe Annapolis would be next on the docket for a Margaritaville hotel or resort.
Though settling for a historic inn with rave reviews isn’t a bad alternative.
It’s just too obvious. Factoring in Maryland’s world-famous seafood along with Annapolis’s scenic waterfront and not being able to turn your head without seeing a boat, it’s the perfect spot for a ‘cheeseburger in paradise’…or out-of-this-world crab concoctions.
Annapolis is known as America’s ‘sailing capital’, a moniker overshadowed by the U.S. Naval Academy, which is anchored here today.
Not everyone can sail — I certainly can’t. One option is to book a boat tour on the stunning Chesapeake Bay.
Popular sunset cruises are a great alternative to witness fiery skies if you can’t score a table at a bayside restaurant.
There are also harbor tours that narrate the town’s history and highlight the current significance of the Naval Academy.
For the more adventurous, kayaking and paddle-boarding are popular activities, or you can take a nice stroll on the waterfront City Dock.
Fall Splendor In Annapolis
Annapolis boasts mild weather from now into November. In fact, it’s still quite summery right now.
As Visit Annapolis puts it, “fall is for festivals”.
This capital city is loaded with fun events this fall, starting this month.
Whether it be the Maryland Seafood Festival that just passed or the Annapolis Boat Shows and Maryland Corn Mazes to look forward to, there’s something for everyone in the coming months.
Though Annapolis is more known for its bayside bliss and epic eats, leaf peepers won’t be disappointed.
Check out the sprawling Quiet Waters Park for autumn’s rush of colors.
Sam Sears
Sam, our Lead Writer & Journalist based in San Diego has visited 36 countries and written over 1000 articles with a focus on sharing his own travel experiences and shining a light on lesser-known gems.
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