Virginia Wine Country Day Trip from Washington DC: Private Mercedes Driver

Two winery tastings in Middleburg's vineyard country, no itinerary to plan.

A private, self-guided winery experience from Washington DC that puts you in a luxury Mercedes-Benz Sprinter with a professional driver for six hours while you pick which Middleburg-area wineries to visit and taste. The driver handles navigation, parking and timing; winery stops are confirmed before your tour date based on availability. Pickup is flexible across DC, Northern Virginia and Maryland.

Step-by-step itinerary

Explore Virginia Wine Country

• Travel from Washington DC
• Visit first Northern Virginia winery
• Enjoy wine tasting and vineyard views
• Visit second Middleburg winery
• Enjoy wine tasting and explore grounds

The Experience

Six hours gives you time to hit two winery tastings without rushing through the vineyard country. Your driver meets you at your chosen pickup location in the DC area, Northern Virginia or Maryland, and handles the drive to Middleburg while you settle into leather seating and climate control inside the Sprinter. The vehicle has room for your group and bottled water is included, so the logistics of getting there stay off your plate.

You're not following a fixed route — instead, you tell your driver which wineries appeal to you, and the stops get confirmed before the tour date to make sure they're open and ready. Your first tasting lands in Northern Virginia wine country, surrounded by the vineyards and countryside that make the region worth the drive. The second stop takes you into the heart of Middleburg, one of the East Coast's most recognized wine regions, where you can linger over tastings and walk the vineyard grounds at your own pace. Since availability shifts, the operator customizes the exact stops to fit what's actually open on your day.

The Sprinter's air conditioning and professional driver mean you're not navigating unfamiliar roads or hunting for parking between tastings — you arrive, taste, and move on. Parking fees are covered, so there's no surprise cost at each stop.

What’s included

• Private transportation in a luxury Mercedes-Benz Sprinter with leather seating and climate control.
• professional driver for the full six hours.
• bottled water.
• all parking fees at the wineries.

Good to know

Easy physical levelInfant seats availablePets welcomePublic transport nearbyInfants must sit on laps

Operated by RES-DMV.COM

Is this one for you?Choose this if you want to taste at your own pace without following a set itinerary — the driver handles the route and timing while you decide where to stop, making it ideal for groups who know what they're looking for or want to discover wineries as the day unfolds.

Top questions

How long does the Virginia wine country day trip from DC take?

The experience runs six hours total, which includes drive time to Middleburg, two winery tastings, and the return to your pickup location.

Can I choose which wineries to visit in Middleburg?

Yes — you tell your driver which wineries interest you, and the stops are confirmed before your tour date based on availability, so the experience stays flexible to your preferences.

What's included in the private wine country trip from Washington DC?

Private transportation in a luxury Mercedes-Benz Sprinter, a professional driver, bottled water, air conditioning, and all parking fees are included; gratuities and meals are not.

Where can I be picked up for this Middleburg wine tour?

Pickup is flexible across Washington DC, Northern Virginia and Maryland — your exact location is arranged when you book.

Is the Sprinter suitable for a large group?

The Sprinter option seats your group comfortably with leather seating and ample space; a Mini Bus for 36 passengers and a Business SUV are also available if your party is larger.