Head east, less than 40 miles from DC, and you will find the charming town of Annapolis, Maryland. On warm, sunny days, locals and tourists alike fill the streets of this capital city, relaxing by City Dock and enjoying the small town ambiance. Filled with history, boats of every shape and size, and some of the best seafood in the area, there are plenty of things to do during a visit to Annapolis. But there is no easier way to get to know the city than to take a tour with a local guide. Keep reading to learn more about the Original Annapolis Seafood Crawl before you plan a visit to Annapolis.
*The Original Annapolis Seafood Crawl is no longer affiliated with Urban Adventures. It is still run by the same Annapolis locals who we toured with, now under the name Annapolis Eventours.
To begin your visit, you should know that the town known as America’s Sailing Capital is a popular weekend destination. It’s home to the United States Naval Academy, and locals and tourists arrive in town by both car and boat. Parking can be a bit of a challenge, but our friends at the tour office had a great tip about using the Calvert Street garage, which offers free parking on the weekends. We didn’t mind the short walk, especially since our tour was departing from the nearby Visitor’s Center. Traffic can get very hectic downtown with all the pedestrians, so walking into the main waterfront area is always a good idea. 
The tour began at 1:30 p.m., so we had plenty of time to wander around a bit both before and after. Our local guide Craig promptly arrived to pick us up at the Visitor Center in a sporty eCruiser. I have to say that riding in a small electric vehicle for our tour was cool for many reasons; it gave us the ability to travel farther than a regular walking tour, it made it much easier for the driver to maneuver around the busy streets of Annapolis and nearby Eastport, and the small size allowed us to carry on a conversation within our small group of 5.
The itinerary for the next two hours would include a fun mix of history and food, including visits to several of the beautiful, historical churches in Annapolis. We learned tidbits of history during each stop about the young leaders of America in the early days. I loved stepping back in time at St. Anne’s Church, uniquely located in the middle of Church Circle, with a history that began in 1692. We were surprised to learn that the current building, completed around 1859 after the 2nd church burned down, houses two beautiful Tiffany glass windows. Our driver also stopped for us to admire the beautiful St. Mary’s Church, pictured below, which dates back to the 1820’s. Fun fact: the land that the church and rectory sits on was given by 4 granddaughters of Charles Carroll of Carrollton, the only Catholic signer of the Declaration of Independence. 
As we crossed the bridge into Eastport, Craig shared stories of some of the local traditions, including the Annapolis Oyster Roast and Sock Burning Party, along with the annual “Maritime Republic of Eastport” vs. Annapolis Tug of War across the water—both sound like Annapolis Bucket List items for sure! Once in Eastport, he stopped to pick up our first seafood sample, a decadent Crab Pretzel, from Davis’ Pub, which we ate picnic style inside the nearby Annapolis Maritime Museum. While there, we explored the local history around oyster harvesting and packing, and learned how the cannon pictured here was used to battle oyster pirates during the Oyster Wars on the Chesapeake Bay! Outside we found one of the best views of the Chesapeake Bay in town!
Jumping back in our eCruiser, Craig took us back over the bridge to downtown Annapolis, where the Sunday afternoon traffic was a bit heavier as we made our way to our next stop, the BAROAK in the Hotel Annapolis. It’s a casual spot and was perfect for us to relax and enjoy a bowl of their signature mussels in a garlic, white wine, and butter sauce! Located not far from the United States Naval Academy, the restaurant is known for its locally sourced food and Maryland inspired dishes.
From there, we headed to Harry Browne’s, a local dining institution, for our third seafood stop. The restaurant has served local politicians and governors for over 34 years with its prime location just across the street from the historic Maryland State House. For this round of food, we were treated to a steaming bowl of the popular cream of crab soup in the upstairs dining area. I have to say that by the end of the tour, I felt like the food samples were just enough to give us a true local flavor, without feeling totally stuffed. Keep in mind that the tasting menu changes from day to day. Harry Browne’s was just around the corner from the Visitor’s Center, where we ended our adventure for the day. While at the Visitor's Center, I would suggest you pop in to learn more about the history of Annapolis and find out what's happening around town. 
Taking the Original Annapolis Seafood Crawl is one of many fun ways to spend the day in Annapolis, which is why it’s one of our 5 favorite day trips from DC. I still have plenty to do on my Annapolis bucket list, like catching a sunset aboard a 74-foot wooden schooner (the Woodwind and Woodwind II set sail in May), or enjoying a bushel of crabs outside with friends at nearby Cantler’s Riverside Inn. And don’t forget to top off any warm-weather visit to Annapolis with dessert at the Annapolis Ice Cream Company.
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