The draw of the exotic usually has me chasing down adventures in far-flung places across the globe that require a passport and possibly a few vaccinations. But I also love to explore locally, because my country has so much to offer. And yours does too! Adventures don’t need to include a plane ride. So in that spirit, I headed down to Maryland for a weekend in Annapolis. It’s such a cute town and I definitely recommend paying it a visit! Let me show you how to spend an awesome weekend in Annapolis.
How to Spend a Weekend in Annapolis
After you arrive in town and get settled in, it’s time to start exploring. Take a walk around the docks at the marina downtown, and then head over to the Dock Street Bar and Grill for some of that famous Maryland crab. I went for the crabcakes and they were delicious! The whole place smells of fresh fish, so you know you’re getting the fresh stuff, straight off the boats. Afterwards, if you’re ready to do some dancing, head over to the Castlebay Irish Pub or Middleton Tavern for some late night fun!
Start your Saturday off with a hearty breakfast at Cafe Normandie, a great little French cafe that’s right downtown. From there you have easy access to all the shops along the quaint brick-laid Main Street where you can do some shopping or just browsing. I loved the selection at Lilac Bijoux, Local By Design, and Nautical North (just to name a few!). Then head over to the Naval Academy Visitor Center to learn more about the school that’s at the center of all the action in Annapolis. You’ll see ‘Go Navy!’ flags everywhere in town, so you might as well join the fun! If you have time still, try to also visit the Sailing Hall of Fame and the Maryland State House. The State House is right in the middle of town, with the traffic circle surrounding the grand building. Some of the nation’s most significant historical events took place here, and for a history nerd from Boston it was really cool! Then finish off the day with dinner and drinks at Galway Bay, the coolest little Irish bar. You’re likely to run into some Navy folks there, since it seems to be their watering hole of choice. Now that’s an essential Annapolis experience!
For your last day in Annapolis I’m actually sending you out of town! Don’t worry, it’s for a good reason (wine!). But first, fuel up with a quick breakfast at 49 West Coffeehouse. It’s a cool eclectic cafe that doubles as a gallery and serves up a unique experience. Then head out to The Vineyards at Dodon for a wine tour and tasting. You know how much I love a wine tour, and I’ve been to some great ones in Chile and Sonoma and the Finger Lakes. So I was excited to learn about the wine industry in Maryland because it’s a young market and they’ve only recently discovered that it’s a great area for growing grapes. Don’t let the age of the industry fool you though, there are some really impressive wines to be had here in Maryland. Call ahead to schedule your tour and tasting, and you may even be able to meet the head winemaker! If you still have time when you’re back in Annapolis, I would suggest seeking out the antique shops in town which are chock full of old gems to be discovered, and the Hammond-Harwood House where you can tour 18th century art and architecture!
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