Explore Virginia Wine Country In Style
"Visited 4 wineries without worrying about driving. Best deci..."
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(301) 531-5737"Visited 4 wineries without worrying about driving. Best decision we made for our..." — Sarah M., Arlington
Explore Virginia Wine Country In Style
Need help booking?
(301) 531-5737Fortune 500Trusted by
Companies
8+Years
Excellence
20,000+
Successful Rides
99%
On-Time Performance
Why Choose DMBJ for Virginia Winery Tour Transportation
Premium transportation tailored specifically for your experience
Curated Winery Routes
Not sure which vineyards to visit? Our chauffeurs know the best tasting rooms, hidden gems, and scenic routes through Loudoun County, Fauquier, and the Shenandoah Valley.
Multi-Stop Flexibility
Visit 3, 4, or 5 wineries in a single day. We handle all the driving and logistics so you can linger at the vineyards you love without watching the clock.
Your Schedule, Your Pace
No rigid tour bus itinerary. Stay an extra 30 minutes at a winery you love or skip one that doesn't speak to you. Your chauffeur adapts to your group in real time.
Luxury Between Pours
Travel between vineyards in a climate-controlled SUV or sedan with complimentary water, phone chargers, and cooler space for your wine purchases.
What to Expect (After Booking)
A seamless, premium experience from the moment you book until you reach your destination.
Instant Confirmation
Receipt and trip details sent immediately.
Pre-Trip Reminders
Automatic reminders before your scheduled pickup.
Driver Connection
Your chauffeur texts/calls before pickup day-of.
Premium Pickup
On-time arrival, luggage help, smooth transfer.
Featured Virginia Wineries & Vineyards
From the rolling hills of Loudoun County to the Blue Ridge foothills, we serve every top vineyard in Virginia wine country.
Stone Tower Winery
Leesburg, VA
Breaux Vineyards
Purcellville, VA
Bluemont Vineyard
Bluemont, VA
Sunset Hills Vineyard
Purcellville, VA
Hillsborough Vineyards
Purcellville, VA
Casanel Vineyards & Winery
Leesburg, VA
8 Chains North Winery
Waterford, VA
Fabbioli Cellars
Leesburg, VA
RdV Vineyards
Delaplane, VA
Chrysalis Vineyards
Middleburg, VA
Boxwood Winery
Middleburg, VA
Linden Vineyards
Linden, VA
Greenhill Winery & Vineyards
Middleburg, VA
Early Mountain Vineyards
Madison, VA
Barboursville Vineyards
Barboursville, VA
King Family Vineyards
Crozet, VA
Ready to Elevate Your Experience?
Skip the parking hassle and arrive in style. Our professional chauffeurs ensure you enjoy every moment — on-time guarantee or your trip is free.
Virginia Winery Tour Transportation Packages
All-inclusive packages with gratuity included
Select your vehicle to see package pricing
Half-Day Wine Tour
Perfect for a morning or afternoon escape. Visit 2-3 wineries in Loudoun County with a dedicated chauffeur at the wheel.
4 Hours · Gratuity included
Full-Day Wine Country
The ultimate Virginia wine experience. Visit 4-5 wineries, enjoy a vineyard lunch, and explore the best of Loudoun or Fauquier County.
8 Hours · Gratuity included
Sunset Wine Experience
Start mid-afternoon and end with a sunset tasting at one of Virginia's most scenic hilltop vineyards. Ideal for date nights and celebrations.
5 Hours · Gratuity included
Our Premium Fleet
Executive sedans, luxury SUVs, and premium vehicles from BMW, Mercedes, Tesla, and Cadillac
Each vehicle represents its class — you reserve a class, not a specific car.
Executive Van
Mercedes Sprinter
Premium SUV
Cadillac Escalade Premium Luxury
Executive Sedan
BMW X3
Executive Sedan
Tesla Model Y
Executive Sedan
Mercedes E-Class
Executive Sedan
BMW 5 Series
First Class
Mercedes-Benz S-Class
Exact Price Upfront
Your total is shown after vehicle selection. No surprises at the end.
No Surge Pricing
Unlike rideshares, our rates stay consistent regardless of demand or time of day.
Gratuity Included
All package prices include gratuity. The price you see is the price you pay.
Why Wine Lovers Choose DMBJ
We've driven thousands of wine tours through Virginia wine country. Our chauffeurs don't just drive — they help you plan the perfect day.
Local Wine Country Knowledge
Our chauffeurs know which wineries have the shortest waits, the best food pairings, and the most scenic patios. Ask for recommendations — they're happy to help.
Safe Tasting, Zero Worry
Enjoy every pour without a second thought. Your designated driver is a licensed professional who ensures everyone gets home safely, no matter how many wineries you visit.
Optimized Routes
We plan efficient routes between wineries so you spend more time tasting and less time on the road. Our drivers know every back road in Loudoun and Fauquier County.
Room for Your Haul
Our SUVs have ample cargo space for cases of wine. We provide a cooler to keep your whites and rosés chilled on warm days.
Safety & Trust
On-Time Guarantee
We arrive on time, every time — or your trip is free. We've kept this promise for over 8 years and 20,000+ rides.
What Our Clients Say
"We booked the full-day tour for my wife's birthday and it was the best decision. Our driver suggested we start at Stone Tower Winery for the views and end at Bluemont for sunset — it was absolutely perfect. We bought three cases and he loaded everything carefully."
David R.
Ashburn, VA
"Four couples, one Escalade, five wineries, zero stress. Our chauffeur had a cooler ready for our purchases and knew exactly which back roads to take between stops. We've done bus tours before and this was in a completely different league."
Samantha K.
Bethesda, MD
Frequently Asked Questions
Are tasting fees included in the tour price?
No. Tasting fees are paid directly at each winery and typically run $15-$30 per person, per vineyard. Some wineries waive the fee with a bottle purchase. Your DMBJ package covers transportation, chauffeur, vehicle, water, and cooler — not the pours themselves.
How many wineries can we visit in one day?
Most groups visit 2-3 wineries on a half-day (4-hour) tour and 4-5 on a full-day (8-hour) tour. We recommend 60-75 minutes per tasting room — enough time for a flight, the vineyard view, and a relaxed exit. Your chauffeur paces the day so you're never rushed and never stranded.
Which vehicle should we book — sedan, SUV, or Sprinter?
Couples and pairs usually take a sedan. Groups of 3-6 fit comfortably in our Cadillac Escalade or Lincoln Navigator (with room for wine cases). Bachelorette parties and groups of 8-14 take a Mercedes-Benz Sprinter or a two-SUV convoy. Picking the right size up front saves money — overpacking a sedan with wine purchases is a common rookie mistake.
Loudoun County vs. Shenandoah Valley vs. Charlottesville — which should we pick?
Loudoun County is closest to DC (45-60 min drive) and home to 40+ wineries — best for a half-day or first-time tour. The Middleburg corridor and Fauquier County add horse-country scenery and higher-end estates like RdV and Boxwood. Charlottesville is a full-day commitment (2.5 hours each way) but worth it for Barboursville, King Family, and Early Mountain. Tell us your priorities and we'll match the region.
Is there room in the vehicle for wine purchases?
Yes. Our SUVs have generous cargo space for multiple cases. We also provide a complimentary cooler to keep whites and rosés at proper temperature on warm-weather drives. Most groups buy 1-3 cases per tour — plan to leave room in the back row if you intend to stock up.
What if we want to linger at one winery and skip another?
That's the advantage of a private car service over a bus tour. Your chauffeur adjusts the day in real time. If you're loving a vineyard, stay as long as you like — we'll trim the remaining stops or extend your booking on the spot. No fixed itinerary, no group of strangers waiting on you.
When is the best time of year for a Virginia wine tour?
May through October is peak season — vines are full, patios are open, and harvest tastings happen September through early November. Winter tours have shorter taproom hours but smaller crowds and cozier indoor experiences. Spring brings bloom and rosé releases. We run tours year-round and will steer you toward the wineries open on your date.
Do you offer transportation for bachelorette winery tours?
Yes — winery tours are one of our most popular bachelorette bookings. We accommodate groups up to 14 in a Sprinter or a multi-vehicle convoy and can coordinate custom decorations, signage, and a champagne stop on the way home. Book 4-6 weeks ahead for peak spring and fall weekends.
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Book Your Virginia Winery Tour Transportation Transportation
Professional chauffeurs, premium vehicles, and an on-time guarantee. Let us handle the driving so you can enjoy the experience.
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