Free Concierge Service
    Text or call 1-877-GREET-WELL
    Ask AIAI
    Ask AIAI
    1. Local experiences
    2. /Things to do in Arlington…
    3. /Wine and Spirits
    4. /Wine Tours
    5. /Sunday Wine Tasting Tour in Middleburg
    Why travelers choose Greetwell

    Curated by our team

    Every experience is hand selected and approved by Greetwell.

    Personal concierge

    Real humans available to help before, during, and after your booking.

    Intimate & authentic

    Including unique in-home experiences you won't find anywhere else.

    Easy booking & cancellation

    Reserve in minutes with free cancellation on most experiences.

    Greetwell

    Experiences that stay with you long after the trip

    Greetwell curates authentic local experiences and provides personal concierge support in over 500 destinations, helping you explore confidently wherever you go.

    About

    • Our Story
    • For Experience Providers
    • For Hospitality Partners
    • For Developers

    Resources

    • Travel Guides
    • Help Center
    [email protected]1-877-GREET-WELL

    Safe & Secure Payments

    © 2026 Greetwell, Inc. All rights reserved.
    Privacy PolicyTerms
    Product image 1
    Product image 2
    Product image 3
    Product image 4
    Product image 5
    Gallery image
    Gallery image 1
    Gallery image 2
    Gallery image 3
    Gallery image 5

    Sunday Wine Tasting Tour in Middleburg

    Wine tastings, brunch and guided travel through Virginia’s countryside

    5.0 stars• 210 reviews
    From$221/ personincl. taxes and fees

    Includes

    Wine tastings, brunch, transport

    Highlights

    Explore Northern Virginia wine country on a Sunday outing to Middleburg. Sample curated wines with a chef-selected brunch board as your guide shares local history, culture and landscapes.
    • Travel through rural wine country, past scenic vineyards and countryside
    • Sample curated wines at the winery
    • Relax in the tasting room, on the deck or beside the creek
    • Learn about Virginia wine and winery traditions from your guide
    • Capture moments from the day with included photos

    What's Included

    • Curated wine tasting fees, taxes and winery tip
    • Chef-selected brunch board
    • Transportation
    • Guide and wine education
    • Customized music playlist
    • Day-of photos
    • Bottled water

    Know before you go

    • Ages 21+ only
    • Bring a valid government-issued photo ID for alcohol service
    • Arrive at your pickup location 10–15 minutes early
    • Complete the required waiver before the tour
    • Do not bring food or consume alcohol on the vehicle
    • At the winery, only alcohol purchased there may be consumed on the property
    • Private pickups outside the standard service area may incur an additional charge

    Cancellation Policy

    Full refund for cancellations 5 or more days before the tour. Cancellations less than 5 days before receive a 50% refund; no refunds within 48 hours. Full refund if the operator cancels due to weather or other unforeseen circumstances.

    FAQs

    Dress for the weather and bring a light jacket for the vehicle. Wear comfortable shoes or flats for getting in and out of the vehicle and walking on grass or soft ground.

    Eat a hearty breakfast before your Middleburg wine tour, as you’ll sample a considerable amount of wine.

    Avoid perfume and cologne, as strong aromas can interfere with wine tasting.

    Experience provided by Vino Virginia
    Experience provided by Vino Virginia

    How can we help?

    We are here to assist with special requests, large groups, last minute needs, and any questions you may have.

    Call or text 1-877-GREET-WELL

    Report an issue

    Reference #2ZQGFT

    Public Middleburg Experience

    $221.54

    0

    Why book through Greetwell?

    • No Added Fees

      No booking or service fees, ever

    • Concierge Support Included

      Real humans ready to help with timing, questions, or special requests

    • Free Cancellation Available

      Most experiences can be cancelled for a full refund

    Discover what we've curated for you

    Review summary

    5.0
    Excellent
    210 reviews•Google Maps
    197
    6
    0
    1
    0

    Paul is clearly the heart of this operation, and reviewers can't stop talking about him. He handles everything from winery selection to lunch reservations and even curates a playlist for the ride, leaving guests free to simply enjoy the day. First-timers and seasoned wine tour veterans alike consistently describe the experience as the best they've had, with several mentioning they've already booked a return trip. The tours typically visit four to five wineries across Northern Virginia and Loudoun County, with each stop chosen to offer something distinct. Paul's local knowledge adds real depth to the experience, weaving in regional history and wine country context between tastings. Pickup from area hotels is available, which reviewers appreciated. The overall vibe is relaxed and fun, with a social atmosphere that tends to bring groups together naturally over the course of the day.

    What people are saying

    Review 1 of 5
    5/5

    AMAZING experience!! Loved it! Lived in VA for about 7 years and this is one of the coolest things I’ve done! Paul is a wonderful guide and knew so much information! Letting us stay late at the last stop and taking us to the pie place was so special and made it feel personal! Would recommend and come again!

    Photo of yvette rigdon

    yvette rigdon

    June 26, 2026

    Review 1 of 1
    5/5

    AMAZING experience!! Loved it! Lived in VA for about 7 years and this is one of the coolest things I’ve done! Paul is a wonderful guide and knew so much information! Letting us stay late at the last stop and taking us to the pie place was so special and made it feel personal! Would recommend and come again!

    Photo of yvette rigdon

    yvette rigdon

    June 26, 2026

    Nearby activities

    Thumbnail
    Wine Tours

    Explore Virginia Wine Country Guided Tasting Tour

    $189.74/ person
    Thumbnail
    Wine Tours

    Sunday Brunch & Wine Tasting Tour in Arlington

    From$169/ person
    Thumbnail
    Kayaking Tours

    Single Kayak Rental At Columbia Island Marina

    From$26/ kayak
    Thumbnail
    Food Tours

    Explore Old Town Alexandria Walking Food Tour

    $92.22/ person
    Thumbnail
    Food Tours

    Georgetown Guided Food Tour in Washington, DC

    $94.34/ person
    Thumbnail
    Food Tours

    Taste Ethiopian Cuisine on a Washington, DC Guided Tour

    $80.56/ person