Day Trips from Chesapeake
← All Chesapeake day tripsDay Trips from Chesapeake: Wineries & Vineyards
Discover the best wineries and vineyards within driving distance of Chesapeake, VA. From intimate tasting rooms to sprawling estate vineyards, these destinations make for a perfect day trip or weekend wine getaway. Real drive times, ratings, and booking links included.
12 wineries near Chesapeake
Blue Ridge Wine Excursions
Charlottesville, VA 22911
Just 2 hrs 36 min from Chesapeake, rated 5.0 stars by 554 visitors, a popular destination with plenty to see and do.
Best time to visit: Spring and fall offer mild weather and smaller crowds at most attractions.
Virginia Beach Winery
Virginia Beach, VA 23452
Just 25 min from Chesapeake, rated 4.9 stars by 348 visitors, known for excellent food, drink, and local flavor.
Best time to visit: Year-round, but harvest season (Sep-Oct) is peak for wineries and farm-to-table.
A Secret Garden Winery
Pikeville, NC 27863
Just 2 hrs 47 min from Chesapeake, rated 4.9 stars, known for excellent food, drink, and local flavor.
Best time to visit: Year-round, but harvest season (Sep-Oct) is peak for wineries and farm-to-table.
Saudé Creek Vineyards
Lanexa, VA 23089
Just 1 hr 16 min from Chesapeake, rated 4.7 stars by 494 visitors, known for excellent food, drink, and local flavor.
Best time to visit: Year-round, but harvest season (Sep-Oct) is peak for wineries and farm-to-table.
Summerwind Vineyard
Smithfield, VA 23430
Just 53 min from Chesapeake, rated 4.7 stars by 182 visitors, known for excellent food, drink, and local flavor.
Best time to visit: Year-round, but harvest season (Sep-Oct) is peak for wineries and farm-to-table.
James River Cellars Winery
Glen Allen, VA 23059
Just 1 hr 45 min from Chesapeake, rated 4.6 stars by 380 visitors, known for excellent food, drink, and local flavor.
Best time to visit: Year-round, but harvest season (Sep-Oct) is peak for wineries and farm-to-table.
Sanctuary Vineyards Outer Banks Winery
Jarvisburg, NC 27947
Just 58 min from Chesapeake, rated 4.6 stars by 505 visitors, known for excellent food, drink, and local flavor.
Best time to visit: Year-round, but harvest season (Sep-Oct) is peak for wineries and farm-to-table.
Windmill Creek Winery & Farm Kitchen
Berlin, MD 21811
Just 2 hrs 38 min from Chesapeake, rated 4.6 stars by 338 visitors, known for excellent food, drink, and local flavor.
Best time to visit: Year-round, but harvest season (Sep-Oct) is peak for wineries and farm-to-table.
Hazy Mountain Vineyards & Brewery
Afton, VA 22920
Just 2 hrs 57 min from Chesapeake, rated 4.5 stars by 901 visitors, known for excellent food, drink, and local flavor.
Best time to visit: Year-round, but harvest season (Sep-Oct) is peak for wineries and farm-to-table.
Williamsburg Winery
Williamsburg, VA 23185
Just 1 hr 2 min from Chesapeake, rated 4.5 stars by 925 visitors, known for excellent food, drink, and local flavor.
Best time to visit: Year-round, but harvest season (Sep-Oct) is peak for wineries and farm-to-table.
Potomac Point Winery & Vineyard
Stafford, VA 22554
Just 2 hrs 43 min from Chesapeake, rated 4.4 stars, known for excellent food, drink, and local flavor.
Best time to visit: Year-round, but harvest season (Sep-Oct) is peak for wineries and farm-to-table.
Smithfield Winery
Smithfield, VA 23430
Just 45 min from Chesapeake, rated 4.4 stars, known for excellent food, drink, and local flavor.
Best time to visit: Year-round, but harvest season (Sep-Oct) is peak for wineries and farm-to-table.
Frequently Asked Questions About Wineries Day Trips from Chesapeake
What are the best wineries near Chesapeake, VA?
The best wineries near Chesapeake include award-winning vineyards, tasting rooms, and estate wineries all within a few hours' drive. Check the destination cards above for ratings, drive times, and direct booking links.
Are there wine tours near Chesapeake?
Yes. Many wineries near Chesapeake offer guided tastings and tours. Use the "Book Activities" button on any card to find wine tour packages through Viator and GetYourGuide, which often include transportation and multi-winery stops.
How far are the closest wineries from Chesapeake?
The closest wineries to Chesapeake are typically 45 minutes to 2 hours away, making them ideal for a day trip. Some regions farther out (2-3 hours) are worth an overnight stay for a full wine weekend.
What is the best time to visit wineries near Chesapeake?
Fall harvest season (September-October) is peak time for wineries, with grape picking and crush events. Spring and summer offer beautiful vineyard scenery. Most tasting rooms are open year-round, and winter visits mean smaller crowds and more personal attention.
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