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November 01, 2025

    4 Easy Day Trips from Chesapeake, Virginia

    A move to the Hampton Roads VA area means that you could find yourself at any number of bases: Norfolk Naval Shipyard, Portsmouth Naval Medical Center, or Naval Station Norfolk, to name a few, and the next thing you know, you’re signing a lease for one of the beautiful houses for rent in Chesapeake, VA.

    Who knows, its charm may even encourage you to make a larger commitment and search homes for sale in Chesapeake, VA. If you’re unfamiliar with the area, this city offers magic that reaches beyond the homestead.

    Within just a few hours’ drive, you can find so many things to do across Hampton Roads. Access a completely different culture, give yourself a mental break, and explore new scenery. And if you’re willing to drive a little further, say five or six hours, you can be in Philadelphia, PA, or Charlotte, NC.

    Wooden adirondack chairs facing rolling hills and winery in Charlottesville, NC among the Blue Ridge Mountains. Photo krblokhin from Getty Images via Canva.com

    1. Charlottesville, VA 

    Drive Time: About 2.5 hours  

    Where historical sites, outdoor adventures, and incredible food and wine meet, Charlottesville is the perfect place to unwind, unplug, and relax. Spend your mornings touring through history, then switch gears and go horseback riding, kayaking, or get an unforgettable view of the area from a hot-air balloon. However you choose to spend your day, don’t miss grabbing a seat at an elegant farm-to-table restaurant for a delicious meal. 

    Must-visit attractions in Charlottesville: 

    • Monticello
    • Carter Mountain Orchard 
    • Historic Downtown Mall 
    • Saunders-Monticello Trail
    • James Monroe’s Highland

    2. Colonial Williamsburg 

    Drive Time: 1 hour

    Only an hour from Chesapeake, Colonial Williamsburg might be considered more of a staycation. However you want to label it, this charming town is worth your time. Sure, you may have taken a day to visit a few of the historic sites, but have you settled in for a weekend?

    You’ll find a slower-paced culture and a quieter space to relax in Williamsburg. Travel back in time as you walk from site to site, observing life as it was in the 1800s. The Colonial Williamsburg Historic Area is home to a bindery, printing office, apothecary, brickyard, courthouse, garden, historical homes, and more.

    Must-visit attractions in Williamsburg:

    • Governor's Palace 
    • Great Hopes Plantation 
    • Anderson Blacksmith Shop and Public Armoury 
    • Merchant Square Shops 
    • Chowning’s Tavern

    Venture into town and you’ll find Busch Gardens Williamsburg to let the kids run around and explore. Don't forget to check for military discounts.

    Aerial view of the Governor's Palace in Williamsburg, VAPhoto by Backyard Productions via Canva.com

    3. Washington, DC

    Drive Time: About 3 hours  

    Washington, DC, is worth at least one visit during your time in Chesapeake. It doesn’t get more historic than standing in the nation’s capital surrounded by monuments that honor our past.

    Beyond the National Mall, Washington, DC, is full of things to do for the whole family, including over 70 museums (a large portion of them from the Smithsonian Institution) and the National Zoo. These attractions, coupled with tourists, amazing food, and festive events year-round, give this destination a unique culture.

    Must-visit attractions in Washington, DC: 

    • Lincoln Memorial 
    • Smithsonian National Air & Space Museum 
    • The United States Holocaust Memorial Museum
    • Arlington National Cemetery 
    • Tidal Basin (plan for the spring when the cherry blossoms are in bloom)

    4. Shenandoah National Park–Skyline Drive 

    Drive Time: About 3.5 hours 

    You can’t live in Virginia without setting your sights on the Blue Ridge Mountains. Shenandoah National Park is home to rushing waterfalls, blooming wildflowers, miles of hiking trails, exciting wildlife, and more. The easiest way to see it all is via Skyline Drive. This winding road is 105 miles long, allowing you to take in the gorgeous foliage and breathtaking views with ease. With lodging and camping options within the park, this destination is great for unplugging. (Note that military members get free park access.)

    Whether you’re exploring landmarks, indulging in local flavor, or breathing in Virginia’s natural beauty, living in Chesapeake has it all within easy reach. With so many exciting destinations just a short drive away, it’s no wonder families love calling this city home.

    If you’re just settling in, you’ll find plenty of houses for rent in Chesapeake, VA that offer comfort and convenience. And for those ready to plant deeper roots, there’s no shortage of beautiful homes for sale in Chesapeake, VA. It’s the perfect starting point for your next adventure.

    Are you moving to the Hampton Roads, VA, area? Download your free guide below. 

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    Woman with red hair holding camera leans toward open window in car to take photo with text, 4 Easy Day Trips from Chesapeake, VA

    Danielle Keech

    Author

    Danielle Keech

    Danielle Keech is a writer and content creator for MilitaryByOwner Advertising, where she illustrates aspects of military life in articles and video content. Whether she's diving into budgeting tips or featuring the next dream home, Danielle keeps it real for fellow military families navigating PCS chaos, tight budgets, and new beginnings. Married to her Marine for 14 years, she's mom to four spirited kiddos (and one loyal pup), and has called everywhere from Florida to Okinawa home, though Hawaii still holds the top spot. Danielle has PCS’d nine times in ten years and still sees each move as a new adventure. She thrives on creating content that supports the community she’s proud to be a part of.