Planning a getaway? Check out Annapolis, MD — home to the US Naval Academy and a coastal destination with a vibrant downtown. A summer trip to Annapolis almost guarantees beautiful sunsets over the Bay + the best crabcakes you’ll ever try.
Why go?
- Once the capital of the US and now the capital of Maryland, it’s hard to walk down the brick streets of Annapolis without running into a historically significant (and beautiful) building.
- It’s easy to board a boat from downtown’s Ego Alley to explore local waterways.
- During the Chesapeake Bay Paddle (Fri., Aug. 27 + Sat., Aug. 28), local and national paddlers will embark on an endurance challenge to protect the Bay.
- Every summer, countless sailboats whir around downtown during the Annapolis Yacht Club’s Wednesday Night Race Series .
- Check out the 2022 Annapolis Travel Guide for help planning your trip.
Act like a local:
- Coffee: Don’t miss the seasonal Coconut Iced Latte at Rise Up Coffee Co.
- Sweets: Order the almond croissant at Bakers & Co. , any flavor cruffin at Black Market Bakers + two scoops from Annapolis Ice Cream Company .
- Outdoors: Sail the Chesapeake Bay on a 74-foot wooden schooner.
- Shop: Browse new and used titles at Old Fox Books + bring home a handmade treasure from The Annapolis Pottery .
- Listen: Refresh your vinyl collection at KA-CHUNK!! Records .
- Explore: Paddle around Eastport in a kayak or canoe.
- Dinner: Savor seasonally-inspired pizza at Vin 909 Winecafé , lump crabcakes at Boatyard Bar & Grill + high-end small plates at Level .
- Watch: Enjoy a performance under the stars at the Annapolis Summer Garden Theatre .
You can’t beat pizza from Vin909.
Photo by RALtoday
Where to stay:
- Local hotel: Historic Maryland Inn in the heart of Annapolis (~$159/night)
- Vrbo: Mid-1800s, renovated downtown home within walking distance from Spa Creek (~$324/night)*
- Splurge: 134 Prince blends rich history with modern luxury (~$499/night)
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