I’ve been fortunate to spend time along Maryland’s Chesapeake Bay on a couple of trips over the past year, and there’s so much to enjoy in this part of the country.
Baltimore and Annapolis are only about 30 miles apart, but each has its own personality. If you enjoy history, good food, and exploring a city on foot, I highly recommend visiting both.
Let’s start with Baltimore.
There’s plenty to explore along the waterfront, but one of my favorite discoveries on this trip was Little Italy. Tucked into the city near the harbor, this historic neighborhood is filled with Italian restaurants, bakeries, and family-owned businesses. It’s a wonderful place to wander and enjoy a cold Yuengling or a leisurely dinner.
For literary history lovers, the Edgar Allan Poe House is another fascinating stop. Baltimore has a deep connection to Poe, and visiting his former home offers a glimpse into the life of one of America’s most famous writers.
You simply cannot visit Maryland without enjoying some Chesapeake Bay Blue Crabs.
During one trip, before sailing to Bermuda, we visited Harris Crab House on the Eastern Shore. It’s the best place, in my opinion, to experience Maryland’s famous steamed blue crabs. Roll up your sleeves, settle in, and take your time. Eating crab is as much an experience as it is a meal. Ironically two different friends were visiting Baltimore within days of my visit and both ate at Harris as well. This place earns it’s famous reputation.
Then there’s Annapolis.
I absolutely loved exploring this beautiful historic city, and one of my strongest recommendations is to book a guided walking tour. I was fortunate to have one booked for me by a local and it was a highlight of the trip.
Annapolis played an important role in the founding of our nation, and there’s nothing quite like walking through its old streets with someone who knows the stories behind the buildings.
The Maryland State House is remarkable and well worth visiting. You can also combine your historical explorations with a tour of the United States Naval Academy. Both offer fascinating perspectives on American history.
And here’s one of my favorite experiences from the trip.
We stopped at Middleton Tavern, which dates back to 1750 and once welcomed George Washington, Thomas Jefferson, Benjamin Franklin, and other prominent figures of the Revolutionary era.
We had oyster shooters in the very tavern where some of America’s early leaders once gathered. I love experiences like that. History isn’t just something you read about in a museum. Sometimes you can sit right in the middle of it, with an ale in your hand!
Of course, there’s also the harbor, the sailboats, the Chesapeake Bay cruises, and the pleasure of simply wandering through this beautiful town without being in a hurry.
Give yourself plenty of time for both cities. Take the walking tour, visit the historic sites, explore Little Italy, eat the seafood, or see a baseball game at Camden Yards.
Whatever you choose to explore, be sure to leave room for a few discoveries of your own. That’s the kind of travel I love most.
