Quick Details
Availability: Year round, Wed - Sun 
Pick Up Locations/Times:*
Duration: 7.5 hours
Ages: 21 & up
Food:
Unique Highlight: Vino Virginia Exclusive 5-star rated around the world wine cottage tasting experience
Upgrade Options:
Photos: We’ll send you pictures of the day
Private Middleburg Experience $243
more. Smaller parties may book privately at the
same 7-person rate for an exclusive experience.
Elegant Escape: Luxurious Wine, Cuisine, and Scenery
Elegant Escape: Luxurious Wine, Cuisine, and Scenery
Elegant Escape: Luxurious Wine, Cuisine, and Scenery
- Begin with a fun and engaging tasting at a storybook wine cottage - a stop you won't find on any other tour - sampling curated wines from around the world amidst locally made goods, all while entertained by the proprietor's enchanting stories.
- Continue your indulgence with a magical tasting at an ultra-modern winery, where Bordeaux-style Virginia wines are complemented by a decadent cheese & charcuterie board. Elevate your experience with exclusive customizations like a Cave or Estate tastings, or add a Celebration Gift Bag for those special moments.
- Savor a mouthwatering lunch on your own at one of Middleburg's spectacular restaurants - or, for private tours, enjoy reserved seating at select restaurants, where you can savor every bite at your own pace.
- The journey continues with artisanal ciders crafted from local apples, complemented by small-batch wines, pommeau, and kir. Paired with gourmet local popcorn, this tasting adds a memorable and distinctive highlight to your experience.**
Winery Upgrade Options
Winery Upgrade Options
Make your experience unforgettable with our exclusive upgrade options—add them at checkout to treat yourself or someone special.
**All prices include winery taxes and tip.
Add a festive touch to your winery visit with a Celebration Gift Bag package, perfect for birthdays, bridal showers, and other special occasions. Enjoy a selection of curated delights, including:
- Winemaker's Choice Half Bottle
- Wine Charm
- Chocolate
- Logo Wine Glass
- Price: $27 per person
- **Please note: wine and chocolate selections may vary based on availability to ensure the best experience.
A dream come true with this intimate Cave tasting. Sip five lush Bordeaux-style wines surrounded by French Oak barrels. Your dedicated server guides you through this exclusive tasting, complemented by a Deluxe Cheese & Charcuterie board. Conclude with a chocolate and wine pairing. You deserve it!
Price: $59 per person
Elevate your tasting adventure with The Estate Pairing – a journey inspired by French Bordeaux traditions. Step into the exclusive Cave for a private tasting of four high-end wines, each paired with delightful bites: Sample pairing includes Shrimp Tempura, Savory Mushroom Tart, Bacon-Wrapped Beef Tenderloin with Gorgonzola, and Espresso Tiramisu*. Culinary magic awaits!
**Food bites listed are samples and change seasonally.
Price: $95 per person
Guests who prefer a purely wine-focused experience may choose to replace the Mt. Defiance Cidery stop with a visit to one of Loudoun County’s acclaimed wineries. These optional upgrades provide a tailored way to enjoy Virginia’s wine country with experiences that highlight premium vineyards and elegant settings.
Nestled outside Middleburg, Greenhill Estate Winery pairs breathtaking scenery with handcrafted Virginia wines. Enjoy a guided casual bar tasting in the country charm tasting room, choose to purchase curated food pairings complementing your experience. (limited to 9 guests).
Greenhill Estate Winery Upgrade: $12/Guest
Perched on a bluff with sweeping views of the Bull Run Mountains, 50 West Winery, offers a refined yet relaxed seated tasting setting in a converted horse stable. Guests enjoy 100% Virginia-grown wines, with elegant Bordeaux-style blends that showcase the richness of the region.
50 West Winery Upgrade: $27/Guest
Enhance your private wine tour with a luxury vehicle upgrade to the Mercedes Sprinter — designed for guests who want to travel with extra space, elegance, and ease. While the Ford Transit (included with all private tours) offers clean, comfortable transport, the Sprinter provides a refined touch with upgraded interiors, high ceilings, and a sleek exterior that makes arriving at each winery feel like an event in itself.
Optional add-on during checkout for private tour bookings
Whether you’re celebrating a milestone, traveling with a group of friends, or simply indulging in a more elevated experience, this upgrade ensures your journey through Virginia’s wine country is as memorable as the wine itself.
Upgrade available for all private tours.
Mercedes Sprinter Upgrade: $424
Ford Transit remains the standard vehicle for private tours and offers a clean, modern, and reliable ride.
Upgrade based on availability. Please book early to reserve your preferred vehicle.
Restaurant Options
Restaurant Options
Enhance your Middleburg private tour with a reserved table at one of our specially selected restaurants, each offering unique flavors and a touch of Middleburg’s charm. For private experiences, we’ll handle your reservation so you can relax and enjoy the day. For public experiences, most restaurants welcome drop-ins, so you can choose your spot on arrival.
How It Works:
- Select Your Preferred Dining: Explore our restaurant options below. Each listing includes a description and menu link, making it easy to find the perfect fit for your group.
- Private Reservations: During checkout, private groups will choose a restaurant option, and we’ll arrange your reservation. For public experience groups of 5 or more, leave us a note in your reservation, and we’ll secure a table for you.
- Enjoy & Pay Directly: On the day, order from the full menu and savor lunch at your leisure. Payment is made directly to the restaurant.
Imagine the joy of gathering with friends and loved ones, creating memories in a cozy setting that’s as unique as Middleburg itself!
Boxwood Estate Winery
It seems spontaneous and effortless. Extend your time at Boxwood Winery after your tasting with lunch in one of their beautiful settings. Indulge your senses surrounded by the winery environment. Delight in oven warmed baguette sandwiches piled high with imported French or Italian meats, artisanal cheeses, chips, dips and à la carte items. Fresh and flavorful. A true Middleburg wine country experience, blending modern Virginia winemaking with European-inspired fare.
Hunters Head Tavern
Step back in time at this historic and charming English style pub just outside Middleburg. Serving fine dining cuisine, pub fare, and mouthwatering homemade desserts you can't resist. Experience organic, local and humane friendly meats and produce that highlight Virginia's rich culinary heritage. Five different dining rooms and extensive outdoor patio garden seating making the perfect setting for your celebration. Endlessly fresh and inviting.
Red Horse Tavern
A Middleburg mainstay, Red Horse Tavern serves hearty American classics—burgers, sandwiches, and steaks—in a laid-back, welcoming setting. Guests can enjoy casual dining indoors or relax on the patio with views of town, making it a go-to lunch spot during wine country adventures.
Red Horse Tavern Menu
Thaiverse Restaurant
Dine in the heart of Middleburg at Thaiverse, set in a charming historic house with both cozy indoor tables and a welcoming patio for sunny afternoons. Celebrated for its authentic Thai flavors and warm hospitality, Thaiverse delights with vibrant dishes like Drunken Noodles and Beef with Rice — each crafted to transport you far beyond Virginia wine country while still rooted in Middleburg’s inviting charm.
Thaiverse Menu
Tremolo Wine Bar
Feel the difference at this modern wine bar located in historic downtown Middleburg. Savor a burst of flavor as they serve a delicious indulgence with elevated but unpretentious drinks, wine, and internationally inspired small plates. For small groups choose from the à la carte menu. Groups of 8 or more ask Vino Virginia to upgrade your experience to the 3-course food and wine pairing.
Savor a delicous indulgence lead by the Executive Chef as part of your all-inclusive winery experience. Tremolo is a favorite for those who appreciate contemporary style, artisanal flavors and intimate dining in wine country. Upgrade for $90pp. Includes 3 small plates, wine pairing, taxes and tip. Price is approximate and will be finalized upon registration.
King Street Oyster Bar (KSOB)
King Street Oyster Bar (KSOB)
A whole new freshness! Savor the rainbow of oysters at King St. Oyster Bar. This is true pleasure meant to be savored with the freshest and widest variety of oysters! Give in to the temptations with 10+ varieties of oysters on any given day. Indulge yourself with mouthwatering freshness with East Coast Oysters no more than 24 hours out of water and West Coast oysters less than 48 hours out of water. Freshness you can't hide.
If you prefer the excitement of seafood or even land food King St. Oyster Bar has a menu to please all palates. This restaurant is super popular and is booked far out. If this is your first choice, please select a second in case we can't get you a reservation.
