If you live in Southern Maryland and are looking to explore a bit further, there are plenty of great destinations just a couple hours away. Annapolis is a top destination with many activities and attractions to explore. This scenic city is often called the sailing capital of the nation, with many land and water adventures to choose from as well as delicious restaurants to explore. Annapolis is also famed for its historic charm, with plenty of 18th-century attractions to peruse. If you’re making the trip north, here’s the best way to get there and a few recommendations for when you arrive:

Getting there:

Depending on where you’re coming from, Annapolis is under an hour or two from any point in Southern Maryland, making it an easy day trip. It’s located in the northwest of the state, so you’ll likely take either 301N to 50E or follow 2N all the way there.

Tour: United States Naval Academy

One major attraction you won’t want to miss is the United States Naval Academy. At their free museum, you can take a self-guided tour, or you can upgrade to a guided walking tour of the beautiful campus, which delves further into the academy’s Beaux-Arts architecture and landscaping. In the museum, be sure to check out their current exhibit “Over There: the Navy and Marine Corps in World War I”, in the Cheevers Gallery. Don’t miss the Noon Meal Formation when midshipmen march in formation on the grounds when weather permits.

Stroll: Historic Annapolis / Ego Alley

Depending on your budget and your level of interest, there are plenty of ways to explore the history of Annapolis. “Historic Annapolis” typically refers to the converted row houses on Main Street which now house shops, restaurants, and galleries. This makes for a nice stroll, and you can continue your wanderings into downtown and the harbor, with more historic spots like the Banneker-Douglass Museum and the Hammond-Harwood House. Be sure to check out Ego Alley, which isn’t actually an alley but a narrow waterway at City Dock which connects with the Chesapeake Bay. On a balmy summer evening, it’s common for visitors to watch yachts and boats of all kinds parade through.

Eat: Dine on the water at Carrol’s Creek Cafe

Speaking of looking out over the water, there are plenty of great places to grab a bite with a view in this scenic city. The spot with perhaps the best view is Carrol’s Creek Cafe. They’re one of the most popular seafood spots in Annapolis, so be sure to come hungry. If you can time your visit right, come on a warm day and sit outside on their patio where you’re likely to catch a sunset over the marina.

 

Sip: Great Frogs Winery

For a relaxing outing, visit Great Frogs Winery on Harness Creek Vineyards. They’ve been around since 1999, but their tasting room has only just opened in the last few years. Tastings are available on Fridays and Saturdays by reservation only, so make sure to schedule ahead. Most people tend to stay for an hour or two at this leisurely tasting which includes a snack plate charcuterie board as well. This dog-friendly winery also hosts occasional events and live music every Saturday afternoon.

 

Explore: Boating and Sailing adventures

If you’re the adventurous type or the water is calling you, make sure you catch a  sightseeing or sailing cruise around the harbor during your visit. Schooner Woodwind sailing cruises offer you the chance to sail around for a relaxing afternoon experience, an overnight “boat and breakfast” stay, or even a multi-day long-distance adventure. Of course, a more budget-friendly way to get on the water is to take the Water Taxi around the harbor, where you can still catch some picturesque views. If you want to leave Annapolis with some new skills under your belt, sign up for sailing lessons (or rentals) through Annapolis Sailing School.

 

 

 

Whether you’re looking for the best steamed crabs around, or you’re seeking a new waterside adventure, consider a visit to Annapolis for your next road trip. In under a couple hours’ drive from Southern Maryland, it’s a convenient and close option for a nice change of scenery and a bit of history, too. Have you explored Annapolis for yourself? What are some of your top recommendations?