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Wineries and Tasting Rooms Offering Wine Tasting Flights in Virginia

16 of the 495 wineries we track in Virginia have wine tasting flights available. Full listings for every city are on the Virginia page.

16wineries
15cities
495wineries statewide

This directory lists urban tasting rooms and estate wineries offering structured wine tasting flights and guided pours. Featured venues provide curations of current vintages, single-varietal pours, or regional blends accompanied by tasting notes from staff. Before visiting, verify whether reservations are mandatory for weekend visits or if counter walk-ins are permitted.

Haymarket 2

  1. LaGrange Winery

    Haymarket, VA

    Mon-Thu 12-6pm, Fri-Sat 12-8pm, Sun 12-6pm

    TastingsOutdoor seatingPrivate events
    All Haymarket

  2. The Winery at La Grange

    4950 Antioch Rd, Haymarket, VA 20169-2259

    Mon-Thu 12-6pm, Fri-Sat 12-8pm, Sun 12-6pm

    TastingsOutdoor seatingPrivate events
    Call Website All Haymarket

Bedford 1

  1. Peaks of Otter Winery

    1218 Elmos Rd, Bedford, VA 24523-1911

    Mon-Fri 12-5pm, Sat 10-5pm, Sun 11-5pm

    TastingsFood servedOutdoor seatingPrivate eventsDog friendly
    Call Website All Bedford

Bluemont 1

  1. Bluemont Vineyard

    18755 Foggy Bottom Rd, Bluemont, VA 20135-1858

    Sun-Thu 11am-7pm, Fri-Sat 11am-8pm

    TastingsToursFood servedOutdoor seatingPrivate eventsDog friendly
    Call Website All Bluemont

Charlottesville 1

  1. Oakencroft Farm & Winery

    1455 Oakencroft Cir, Charlottesville, VA 22901-5452

    Thu 1-8pm, Fri-Sun 11-5pm

    TastingsToursFood servedPrivate events
    Call Website All Charlottesville

Etlan 1

  1. DuCard Vineyards

    40 Gibson Hollow Ln, Etlan, VA 22719-1956

    Mon-Thu 12-5pm, Sat-Sun 12-6pm

    TastingsToursOutdoor seatingPrivate eventsDog friendly
    Call Website All Etlan

Fincastle 1

  1. Virginia Mountain Vineyards

    4204 Old Fincastle Rd, Fincastle, VA 24090-3559

    TastingsPrivate events
    Call Website

Glen Allen 1

  1. James River Cellars Winery

    11008 Washington Hwy, Glen Allen, VA 23059-1904

    Mon-Thu 11am-7pm, Fri 11am-9pm

    TastingsOutdoor seatingPrivate eventsDog friendly
    Call Website All Glen Allen

Louisa 1

  1. Fifty-Third Winery and Vineyard

    13372 Shannon Hill Rd, Louisa, VA 23093-3929

    Mon-Sun 11am-5pm

    TastingsFood servedOutdoor seatingPrivate eventsDog friendly
    Call Website All Louisa

Luray 1

  1. House Strunk Winemaking

    925 Boston Rd, Luray, VA 22835-6308

    TastingsToursPrivate events
    Call Website All Luray

Machipongo 1

  1. Chatham Vineyards

    9232 Chatham Rd, Machipongo, VA 23405-2727

    Daily 10am-5pm

    TastingsFood servedOutdoor seatingPrivate eventsDog friendly
    Call Website

Markham 1

  1. Chateau O'Brien at North Point

    3238 Railstop Rd, Markham, VA 22643-1841

    Thu-Mon 11am-5pm

    TastingsOutdoor seatingPrivate events
    Call Website All Markham

Round Hill 1

  1. Williams Gap Vineyard

    35521 Sexton Farm Lane, Round Hill, VA 20141

    Thu-Mon 12pm-7pm

    TastingsFood servedOutdoor seatingPrivate eventsDog friendly
    Call Website All Round Hill

Smithfield 1

  1. SummerWind Vineyard

    71 Eagle Nest Ln, Smithfield, VA 23430-2573

    Thu-Sun 12pm-9pm (varies)

    TastingsFood servedOutdoor seatingPrivate events
    Call Website All Smithfield

Upperville 1

  1. Slater Run Vineyards

    1500 Crenshaw Rd, Upperville, VA 20184-1802

    TastingsFood servedPrivate events
    Call Website All Upperville

Waterford 1

  1. 8 Chains North Winery

    38593 Daymont Ln, Waterford, VA 20197-1038

    Mon, Tue, Thu 12pm-6pm, Wed, Fri 12pm-9pm, Sat-Sun 11am-6pm

    TastingsFood servedOutdoor seatingPrivate eventsDog friendly
    Call Website All Waterford
Check group reservation policies as most tasting rooms require advance booking for parties of 6 or more and automatically add an 18-20% gratuity to the bill.

Also in Virginia

Good to know

How much does a standard wine tasting cost?

Standard wine tasting flights typically cost between $15 and $35 per person for 4 to 6 pours of 1-ounce to 2-ounce samples. Reserve or estate flights featuring small-lot or library vintages range from $40 to $85 per guest. Many wineries waive the tasting fee if you purchase 2 or more bottles or join their wine club.

Do I need a reservation for a wine tasting?

Walk-ins are frequently accepted at urban tasting bars during weekday hours, but weekend visits usually require reservations. Groups larger than 6 guests almost always need advance bookings and a designated seating slot. Reservation windows typically open 30 to 60 days in advance via platforms like Tock or OpenTable.

How long does a typical wine tasting session last?

A standard counter or self-guided tasting takes approximately 45 to 60 minutes. Seated, educational tastings led by a sommelier or winemaker usually last 75 to 90 minutes. Arriving 10 to 15 minutes before your scheduled slot is required so check-in does not reduce your allotted table time.

Is Napa or Sonoma better?

Napa Valley is generally known for luxury estate experiences and Cabernet Sauvignon, while Sonoma County offers a more relaxed, rustic atmosphere with diverse microclimates. Choosing between them depends on whether you prefer high-end luxury or informal country vineyards. You can explore 16 top wine destinations across Virginia on WineryAtlas.

How to find cheap weekend getaways?

Look for tasting rooms and boutique vineyard stays in emerging wine regions rather than major tourist centers, and book mid-week or off-peak seasons. Visiting local tasting rooms offers affordable entertainment and regional culture. Discover budget-friendly wine getaways across 16 locations in Virginia.