A wine tasting tour with us is a chauffeured day through Virginia or Maryland wine country, with no designated driver. Everyone in the group tastes at every stop. Your chauffeur drives the whole route, parks at each winery, and gets you home safely. This page is the overview: how the day works, the two regions you can pick, and how to choose between them. When you know what you want, the specific tours below carry the named wineries and the exact timing.
The pull of the format is practical. Virginia and Maryland both have real wine country within an hour of DC, and once nobody has to stay sober to drive, the day changes. You can do a full tasting flight at each stop, talk to the people pouring, and carry a bottle out to the car. We handle the route, the parking, and the drive between vineyards.
How a chauffeured wine tour works
You pick a region and a length. This is a custom, self-paced private tour: we build the winery lineup around what your group drinks, then a chauffeur collects you at your door and drives the full loop. Want to set the wineries yourself? Build your own DC wine tour from a blank itinerary. Pickup is anywhere in DC, Maryland, or Northern Virginia. The vehicle stays with you all day, so coats, bags, and any bottles you buy ride along between stops.
Wine tours run a 6-hour minimum in every vehicle. The travel time alone makes a shorter day pointless: 45 to 60 minutes out, the same back, and real tastings in between. Two lengths cover most groups:
- The 6-hour day: roughly 3 wineries with a lunch stop built in. This is the standard wine outing and the one we book most on weekends.
- The 8-hour day: adds a fourth winery or a longer sit-down lunch in Leesburg or Middleburg. The better fit for a special occasion or a group making a full day of it.
Each tasting runs about 45 to 60 minutes. Drives between Loudoun wineries are short, usually 10 to 20 minutes. The drive out from DC to either wine region is about 45 to 60 minutes depending on your starting point and the day’s traffic.
Virginia or Maryland: choosing your region
Virginia wine country (most popular)
Loudoun County markets itself as DC’s Wine Country, and it earns the line. The trail runs west from Leesburg toward Purcellville and south toward Middleburg, with most of the well-known producers clustered along Route 7 and Route 50. Loudoun is closer to DC, most wineries open daily, and the trail is well marked. Middleburg sits on the Loudoun-Fauquier boundary and holds several of the most respected estates. First-time visitors almost always do Loudoun.
For a full Virginia day with named wineries and a built-in lunch, see the Virginia Wine Country Tour.
Maryland wine country
Maryland’s wine region is quieter, less crowded, and often a little cheaper on tasting fees. The producers cluster in Carroll County around Westminster and Mt. Airy, and in Baltimore County near Hydes, about 45 to 60 minutes north of DC by I-70. The estates tend to be smaller and more experimental, with several natural-wine and dry-farming producers. People who have already done Loudoun often cross over to Maryland for something different.
For the Maryland route and the wineries we recommend, see the Maryland Wine Tour.
Still deciding?
Pick Virginia for range and the classic Loudoun drive. Pick Maryland for a quieter day and smaller crowds. If your group has a specific winery in mind, that should settle it. Undecided groups should start with Virginia. The full lineup for either region lives on the wine country tours hub, which compares all the routes side by side.
Which vehicle fits your group
Vehicle choice comes down to headcount and how much room you want for the day.
- Town Car sedan, 1 to 3 guests: the entry price for a couple’s wine day.
- Executive SUV, 1 to 6 guests: the right size for a small group. We promise a full-size executive SUV, a Cadillac Escalade or Chevrolet Suburban class vehicle.
- Stretch Limousine, 1 to 10 guests: more of an occasion, with limo seating between stops.
- Mercedes Sprinter Van, up to 13 guests: the most practical pick for a larger group. High roof, open seating, easy to load and unload bottles at each winery. This is the workhorse for bachelorette parties and corporate outings.
For groups larger than 13, we run an Executive Mini Bus (22 to 32 passengers) or a Luxury Coach Bus. Tell us the headcount when you call and we will match the vehicle.
What is included
- A professional chauffeur for the full tour
- Door-to-door pickup from any DC, Maryland, or Virginia address
- Complimentary bottled water
- Bottle storage between stops
Tasting fees are paid at each winery directly. They typically run $15 to $30 per person per winery in Virginia, and a little less in Maryland. Many wineries credit the fee against a bottle purchase. Lunch and any food are also paid at the winery.
Common questions
How many wineries do you visit on a wine country tour?
The standard 6-hour day visits about 3 wineries with a lunch stop. An 8-hour day fits a fourth, or a longer sit-down lunch. Each tasting runs 45 to 60 minutes. Most groups find 3 relaxed tastings with food better than 5 rushed ones.
Do you provide a designated driver for wine tasting?
Yes, and that is the entire point. Your chauffeur drives the whole day, so everyone in the group tastes freely at every stop. Nobody has to sit out to stay sober for the drive home.
Are tasting fees included?
No. Tasting fees are paid directly at each winery, usually $15 to $30 per person per winery. The tour price covers the vehicle and the chauffeur.
Maryland vs Virginia wine country: which should we choose?
Virginia for quality range and the classic Loudoun drive. Maryland for a quieter, less crowded day and slightly lower tasting fees. If your group has strong feelings about a specific winery, let that decide. Undecided groups should start with Virginia.
What size group can do a wine country tour?
From 2 people in an Executive SUV up to 13 in a Mercedes Sprinter on the standard tours, and up to 55 in a coach bus for large groups. For 22 to 32, the Executive Mini Bus is the practical pick.
How far ahead should we book?
A week is comfortable for most dates. Spring and fall weekends, holiday weekends, and harvest season (September and October) fill faster, and some wineries require reservations for larger groups. Book 2 to 3 weeks out for those dates so we can confirm the winery lineup.
Pricing
Wine tours carry a 6-hour minimum in every vehicle. Starting at $660 for 6 hours for two guests in the Town Car sedan (up to 3 guests), $720 in an Executive SUV (up to 6 guests). Stretch Limousine from $810 (up to 10 guests). Mercedes Sprinter from $840 (up to 13 guests). Larger vehicles are priced on the regional tour pages. Tasting fees are paid at each winery.
Book a wine country tour from DC
Pick your region first: the Virginia Wine Country Tour or the Maryland Wine Tour. Both sit under the wine country tours hub. When you are ready, call (202) 609-9811 or book online. A dispatcher answers 24/7 and will help you match the region, the day length, and the vehicle to your group.
