Weekend Winery Tour in Charlottesville, VA

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Curated By

Oluwaseyi Aladeselu

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  • USA

  • Virginia

  • Domestic Travel

  • Food & Wine

  • Countryside

  • Wineries

  • Outdoors

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Curator’s statement

Head to Charlottesville and enjoy gradually sipping your way around town with incredible food, wine and views. Looking for a sign to escape to Virginia Wine Country? This is your sign! Here's the perfect guide to Virginia for the ultimate wine lover. Hop on a horse for a unique winery tour or in a hot air balloon for endless views or winery hop. Either way, grab your partner or friends and make it an experience to remember.

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Insider knowledge

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Where to stay

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Keswick Hall

Keswick Hall is a luxurious historic hotel and golf resort nestled in the picturesque countryside of Charlottesville, Virginia.

Fora Perks
  • $100 hotel / resort credit.

  • Breakfast daily.

  • Upgrade & extended check-in/out whenever possible.

Oakhurst Inn

Nestled in one of Charlottesville’s most prestigious neighborhoods next to the University grounds, the Oakhurst Inn brings charming accommodations, creative cuisine, and a place to connect to visitors and locals alike.

The Clifton

Charming boutique hotel set on 100 acres of Virginia countryside located only minutes from downtown Charlottesville and the surrounding historic sites and award-winning wineries.

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Unlock perks by contacting Oluwaseyi to book your trip.

Day 1: Check in to your Charlottesville hotel

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Start your weekend staycation with exploring the grounds of your hotel. 

Relax and unwind with tennis, golf or a dip in the pool with drinks and apps.

Grab dinner on site at Marigold with a nightcap at Crawford's.

Day 2: Enjoy a day of winery hopping

green grass field under a blue sky during daytime

Start your morning off right with a heavy breakfast before exploring the Wine Trail.

First stop on our winery hop tour? Keswick Vineyard, take a short drive up to the vineyard for a horseback ride & tasting tour. 

Follow with stops at both Barboursville & Honah Lee Vineyards.

Ending with dinner at Well Hung.

Head back to relax after a nice day of winery hopping.

Recommended Tour Companies: Monticello Wine Tour, Norm’s Transportation, C’Ville Hop On Tours and Blue Ridge Wine Tours.

Prefer a self-guided tour of vineyards/wineries? I recommend: Stinson, King Family, Reynard Florence, Veritas, Barboursville, Hill Top Berry, Pippin, Glass House and more.

I recommend 3 maybe 4 winery stops a day plus a DD if opting for self-guided.

A note from Oluwaseyi

Check out Pippin Hill's cooking classes and other events and stop by the tasting room! Also a great winery for full day experiences.

Day 3: Visit UVA and explore Charlottesville

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Add a little adventure into your weekend staycation by exploring Virginia from above...sunrise air-balloon anyone? (not your thing, opt for rafting, tubing, hiking, etc).

After catching a firsthand glimpse of the sunrise head to brunch at the Clifton.

Stroll around The Rotunda at UVA (UNESCO Site) and tour Jefferson's Monticello.

Wander Charlottesville Downtown Mall visiting local boutiques and restaurants along your stroll (especially Albemarle Baking Company).

Ending your weekend escape with a toast at Quirk's rooftop bar before heading back home!

Need to Know

Ready to explore the nation's capitol? Check out my guide to D.C.: Local's Guide to Hotels & Activities in Washington, DC.

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Travel Advisor

Oluwaseyi Aladeselu

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