Take a stroll along the harbor and watch the boats glide by. Great for people-watching, grabbing a scoop of ice cream, or just enjoying the waterfront vibe.
Great Frogs Winery
3218 Harness Creek Road, Annapolis, MD 21403
Nestled just outside Annapolis, this rustic winery offers tastings of handcrafted wines in a serene setting.
Forward Brewing
418 Fourth Street, Annapolis, MD 21403
A cozy microbrewery in Eastport serving small-batch beers with a local twist. Enjoy a laid-back atmosphere and delicious bites.
Naval Academy
121 Blake Road US Naval Academy, Annapolis, MD 21402
Even if you're not into military history, the campus is beautiful and full of fascinating stories. Be sure to bring ID to enter.
Chick & Ruth's Delly
165 Main Street, Annapolis, MD 21401
A quirky Annapolis staple serving up giant sandwiches and all-day breakfast. Don’t miss the milkshakes.
Sandy Point State Park
1100 East College Parkway, Annapolis, MD 21409
If you're craving beach time, head here for swimming, picnic spots, and stunning views of the Chesapeake Bay Bridge.
Jug Bay Wetlands Sanctuary
1361 Wrighton Road, Lothian, MD 20711
Explore over 1,700 acres of tidal freshwater wetlands, forests, and meadows. Perfect for hiking, birdwatching, and immersing yourself in nature.