Virginia

7 Best Places for One Day Trips from Chesapeake, VA

11 Jun 2026Updated last time

Best One Day Trips from Chesapeake, VA

Chesapeake, Virginia, is an ideal starting point for a variety of enriching and exciting day trips. Whether you're a local looking to explore your own backyard or a visitor eager to discover the region's most compelling destinations, Chesapeake offers convenient access to stunning natural landscapes, historical sites, and vibrant cultural attractions. From the sun-soaked shores of Virginia Beach to the immersive historical experiences at Colonial Williamsburg, and from the botanical wonders of Norfolk Botanical Garden to the serene trails of First Landing State Park, there is something for everyone. Each location promises unique experiences, ensuring your one-day adventure will be memorable and fulfilling. Dive into the details of these must-visit spots, and start planning your perfect day trip!

Recommended Activities

  • 1

    Virginia Beach

    Virginia Beach offers a beautiful coastline, a vibrant boardwalk, and various outdoor activities such as surfing, fishing, and biking. It's a perfect spot for relaxation and enjoying the ocean.
    Virginia Beach
    Virginia Beach
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    Virginia Beach
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    Virginia Beach
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    Virginia Beach
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  • 2

    Colonial Williamsburg

    Colonial Williamsburg is a living-history museum that provides an immersive experience of America's colonial past. Visitors can explore historic buildings, interact with costumed interpreters, and watch demonstrations of 18th-century crafts and trades.
    Colonial Williamsburg
    Colonial Williamsburg
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    Colonial Williamsburg
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    Colonial Williamsburg
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    Colonial Williamsburg
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  • 3

    Norfolk Botanical Garden

    Norfolk Botanical Garden boasts over 60 themed gardens and miles of walking paths. It's a serene place to explore a vast diversity of plants, enjoy scenic views, and participate in educational programs and seasonal events.
    Norfolk Botanical Garden
    Norfolk Botanical Garden
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    Norfolk Botanical Garden
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    Norfolk Botanical Garden
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    Norfolk Botanical Garden
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  • 4

    First Landing State Park

    First Landing State Park is rich in history and natural beauty. It offers hiking and biking trails, opportunities for kayaking, and a beautiful beach. It's a great spot for outdoor enthusiasts and history buffs alike.
    First Landing State Park
    First Landing State Park
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    First Landing State Park
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    First Landing State Park
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    First Landing State Park
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    First Landing State Park
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    First Landing State Park
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  • 5

    Jamestown Settlement

    Jamestown Settlement offers a fascinating look into the first permanent English colony in America with interactive exhibits, re-creations of colonial structures, and the chance to board replicas of the three ships that brought settlers to Virginia.
    Jamestown Settlement
    Jamestown Settlement
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    Jamestown Settlement
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    Jamestown Settlement
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  • 6

    Chesapeake Arboretum

    Chesapeake Arboretum is known as a natural classroom showcasing diverse plant life. It provides picturesque walking trails, gardens, and educational programs, making it a peaceful retreat for nature lovers and garden enthusiasts.
    Chesapeake Arboretum
    Chesapeake Arboretum
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    Chesapeake Arboretum
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    Chesapeake Arboretum
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    Chesapeake Arboretum
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  • 7

    Great Dismal Swamp National Wildlife Refuge

    Great Dismal Swamp National Wildlife Refuge is a unique and ecologically significant area offering visitors the chance to explore diverse habitats, extensive trails, and Lake Drummond. It's an ideal destination for wildlife observation, bird watching, hiking, and experiencing pristine natural beauty.
    Great Dismal Swamp National Wildlife Refuge
    Great Dismal Swamp National Wildlife Refuge
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    Great Dismal Swamp National Wildlife Refuge
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    Great Dismal Swamp National Wildlife Refuge
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    Great Dismal Swamp National Wildlife Refuge
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Restaurants

  • Picture for Freemason Abbey Restaurant

    Freemason Abbey Restaurant

    209 W Freemason St, Norfolk, VA 23510, USA
    Housed in a 19th-century church, this unique dining venue offers a charming atmosphere and an extensive menu of American cuisine.
    4.6
    $$$$
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  • Picture for Grain Rooftop Beer Garden

    Grain Rooftop Beer Garden

    100 E Main St, Norfolk, VA 23510, United States
    Situated atop Hilton Norfolk The Main, this rooftop restaurant offers stunning views of the city along with a wide selection of craft beers and delicious pub fare.
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    • Picture for The Birch Bar

      The Birch Bar

      1231 W Olney Rd, Norfolk, VA 23507, United States
      Known for its vast selection of rare and unusual craft beers, this cozy bar is a haven for beer enthusiasts looking to try something new.
      4.7
      $$$$
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      • Picture for Doumar's Cones & Barbecue

        Doumar's Cones & Barbecue

        1919 Monticello Ave, Norfolk, VA 23517, USA
        A historic eatery famous for inventing the ice cream cone. Enjoy classic BBQ and old-fashioned ice cream treats in a retro setting.
        4.5
        $$$$
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      • Picture for The Hunt Room

        The Hunt Room

        4200 Atlantic Ave, Virginia Beach, VA 23451, USA
        Located in the historic Cavalier Hotel, this speakeasy-style bar offers handcrafted cocktails and gourmet small plates in a vintage setting.
        4.6
        $$$$
        Google Maps

      Hotels

      • The Cavalier Hotel - Virginia Beach, Virginia

        4200 Atlantic Ave, Virginia Beach, VA 23451, United States

        A luxurious historic hotel with stunning architecture, beautifully restored rooms, and exquisite amenities, making it a landmark destination in Virginia Beach.

        • Wedmore Place

          5810 Wessex Hundred, Williamsburg, VA 23185, United States

          4.6
          A boutique European-style hotel located in the heart of a picturesque vineyard, offering an old-world charm and an immersive wine country experience.

        • The Historic Powhatan Resort

          3601 Ironbound Rd, Williamsburg, VA 23188, United States

          4.3
          Set on a former colonial plantation, this resort offers a unique historical setting with spacious accommodations and a variety of recreational facilities.

        • The Mariners' Museum Park

          Boundary Rd, Newport News, VA 23601, United States

          4.8
          While not a traditional hotel, this site offers a unique camping experience with scenic views, providing an unconventional and adventurous lodging option within a historical park.

          • Hilton Norfolk The Main

            100 E Main St, Norfolk, VA 23510, United States

            4.4
            A contemporary hotel known for its upscale amenities, stylish decor, and the rooftop Grain Beer Garden, offering panoramic views of Norfolk's skyline.

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