• Updated with new information since originally published.
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  • Our editors recommend these diverse local experiences.

1. Academy Art Museum ⭐⭐⭐⭐⭐

Category: Museums & Culture for Couples
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2. Adkins Arboretum ⭐⭐⭐⭐⭐

Category: Weekend Activities & Fun Outdoors
© dwags/stock.adobe.com

3. American Cruise Lines

© Svetlana/stock.adobe.com

4. American Chestnut Land Trust

© hecke71/stock.adobe.com

5. Annapolis Yacht Club

© Darren Baker/stock.adobe.com

6. C&D Canal Museum

Category: Weekend Activities & Fun Outdoors
© indigolotos/stock.adobe.com

7. Calvert Cliffs State Park

Category: Weekend Activities & Fun Outdoors
© Navalaney/stock.adobe.com

8. Captain John Smith Chesapeake National Historic Trail

Category: Weekend Activities & Fun Outdoors
© ftlaudgirl/stock.adobe.com

9. Chesapeake Bay Maritime Museum

Category: Museums & Culture for Couples
© tamas/stock.adobe.com

10. Chesapeake Wine Trail

Category: Weekend Activities & Fun Outdoors
© russieseo/stock.adobe.com

11. Chester River Packet Company

Category: Weekend Activities & Fun Outdoors
© kite_rin/stock.adobe.com

12. Delmarva Balloon Rides

Category: Weekend Activities & Fun Outdoors
© Andy Dean/stock.adobe.com

13. Eastern Neck National Wildlife Refuge

Category: Weekend Activities & Fun Outdoors
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14. Harriet Tubman Underground Railroad State Park and Visitor Center

Category: Kids & Family Fun
© vulcanus/stock.adobe.com

15. Havre de Grace Decoy Museum

Category: Museums & Culture for Couples
© Jim Cox/stock.adobe.com

16. Historic St. Mary’s City

Category: Affordable Local Attractions
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17. Sandy Point State Park

Category: Weekend Activities & Fun Outdoors
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18. Smith Island

Romantic Islands
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19. St. Clement’s Island-Potomac River Museum

Category: Weekend Activities & Fun Outdoors
© nedomacki/stock.adobe.com

20. Tangier Island Cruise

Romantic Islands
© Svetlana/stock.adobe.com

21. Thomas Point Shoal Lighthouse

Category: Weekend Activities & Fun Outdoors
© eagan/stock.adobe.com

22. Tilghman Island

Romantic Islands
© EdNurg/stock.adobe.com

23. Virginia Barrier Island Center

Category: Affordable Local Attractions
© Virginia Barrier Island Center

24. Virginia Oyster Trail

Category: Weekend Activities & Fun Outdoors
© New Africa/stock.adobe.com

25. Watermen Heritage Tours

Tours in the Area
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Summary and Frequenly Asked Questions:

The City of Chesapeake and the Chesapeake Bay estuary are packed with things to see and do. Known for its beautiful natural scenery and rich cultural and historical significance, Chesapeake is home to over 20 miles of waterways, canals, lakes, and rivers, as well as several parks and outdoor recreation areas for mountain biking, horseback riding, and picnicking. There are also plenty of galleries, museums, and restaurants.

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