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Customizable Services to Make Your Trip Special


Convenience and Comfort: Hiring transportation eliminates the need for individual cars or relying on public transportation. It provides a convenient and comfortable way for a small group to travel together without the hassle of navigating traffic, finding parking, or dealing with multiple vehicles.

Cost-Effective Solution: In certain situations, renting a vehicle or hiring a transportation service can be more cost-effective than each individual taking your own car or opting for ridesharing services. Splitting the cost of transportation among the passengers often proves to be a budget-friendly option.

Safety and Peace of Mind: Hiring professional transportation services ensures the safety of everyone in the group. Expert drivers who are well-versed in road regulations and safety measures handle the transportation, allowing passengers to relax, enjoy the ride, and focus on their destination.

Time Efficiency: Hiring transportation saves time by eliminating the need for everyone to coordinate their arrival and departure times or wait for each other at a designated meeting point. It streamlines the process and ensures that everyone arrives together and on time.


Special Occasions and Events: For special occasions like birthdays, anniversaries, or intimate group outings, hiring transportation adds a touch of luxury and elegance to the experience. It allows the group to enjoy the occasion fully while creating lasting memories.

Remember, even for small groups, choosing the right transportation provider is crucial. SSMG is a reputable company with a fleet of well-maintained vehicles, professional drivers, and a track record of excellent customer service.

Choose Your Own Adventure
Depending on the duration of your trip, choose 3-4 locations within a cluster.

Cluster 1 - Route 17

  • Barrel Oak

  • Blue Valley Vineyard

  • RDV 

  • 3 Fox Vineyard

  • Delaplane Cellars

  • Valley View Farm

  • Arterra 

  • Naked Mountain

  • Aspendel

  • Cobler Mountain Cellars

  • Maidstone Meadery

Cluster 4 - Bluemont

  • Veramar Vineyard

  • Twin Oaks Tavern Winery

  • Bluemont Vineyard

  • Bluemont Station Brewery & Winery

  • Bogati Winery

  • Williams Gap Vineyard

  • Otium Cellars

  • Stonehouse Meadery

  • Wild hare Cider Cabin

  • Bear Chase Brewing Company

  • Dirt Farm Brewing

Cluster 7 - Fauquier

  • Mediteranean Cellars Winery

  • Pearmund Cellars Winery

  • Winery of Sunshine Ridge

  • Vint Hill Craft Winery

  • Morais Vineyards

  • Molon Lave Vineyards

  • Granite Heights Winery

  • Winery at Lagrange

  • The Winery of Bull Run 

  • Paradise Springs Winery

  • Effingham Manor Winery

  • Two Silos

  • Murlarkey

Cluster 2 - Linden

  • Chateau O'brien

  • Crimson Lane

  • Capstone Vineyard

  • Fox Meadow

  • Philip Carter Winery

  • Linden Cellars

Cluster 5 - Little Washington 

  • Quieveremont

  • Little Washington Winery

  • Gadino Cellars

  • Magnolia Vineyard

  • Narada Winery

  • Gray Ghost Vineyards

  • Wisteria Winery

  • Copper Fox Distillery

  • Riverhill Distillery

  • Blue Shepherd Spirits

Cluster 8 - Winchester

  • Briede Family Vineyard

  • James Charles Winery

  • Old Town Cidery

  • Valerie Hill Winery

  • Star in the Valley Winery

  • Filibuster Distillery

  • Winchester Ciderworks

  • Vibissa Beer

  • Misty Mountain Meadeworks

Cluster 3 - Route 522

  • Rappahanock Cellars

  • Chester Gap Cellars

  • Chapelle Charlemagne

  • Glen Manor Vineyard

  • Honey & Hops Brewworks

  • Saga Meatery & Winery

  • On Cue Sports Bar & Grill

Cluster 6 - Route 50

  • Slater Run Vineyards

  • Boxwood Winery

  • Greenhill Winery

  • Chrysalias Vineyards

  • Cana Vineyards and Winery

  • 50 West Vineyards

  • Quattro Gumbas

  • Old Farm Winery at Hartland

  • Fleetwood Farms Winery

  • Mount Defiant Cider Barn

  • Lost Barrel Brewing

Cluster 9 - Shenandoah County

  • Wisteria Farm & Vineyard

  • Wolf Gap Vineyard

  • Muse Vineyard

  • North Mountain Vineyard

  • Shenendoah Vineyard

  • Cave Ridge Vineyard

  • Winery at Kindred Pointe

  • DeMello Vineyard

Exclusive Enhancements & Benefits

SSMG has tremendous knowledge about the region's wineries and breweries, providing insights on the best spots, unique offerings, and hidden gems.  We can help arranging VIP access or behind-the-scenes tours at select locations, providing customers with a more immersive and exclusive experience.  We can also assist with VIP tastings, private tours, room rentals, special events and more! 

Friends Drinking Beer



Whether you want to spend the day sipping on some of Virginia’s best wines, trying out a local craft beer at one of the many breweries, or finding out how whiskey is made at some of the state's most legendary distilleries, SSMG provides curated tours that best fit you and your needs. Allow us to transport you to some of Virginia’s most amazing wineries so your entire party can enjoy the experience! 

Wine and Cheese


Your Personal Travel Concierge

SSMG is your ultimate ally when embarking on a trip to an unfamiliar town. With our expertise and personalized services, we alleviate the stress of navigating the unknown. We can take care of every detail, from making reservations at the finest establishments to booking outings and experiences tailored to your preferences. We are very familiar with the town's areas of interest, uncovering hidden gems and must-visit attractions. Whether it's securing tickets to a popular show, arranging guided tours, or recommending local eateries, SSMG ensures that your trip is seamless and unforgettable. With our guidance and insider knowledge, you can confidently explore the town, knowing that every aspect of your journey has been thoughtfully curated. If you have any special needs or requests, SSMG has the connections and expertise to offer you and your loved ones an unforgettable time!

Check out the fleet below to determine the best vehicle for your event:

Wine and Cheese
Airplace flying by airport window


Airport, Train Station, Visits Through Town, Etc. 

Looking for reliable airport transportation services? Expecting friends or family flying in but unable to spare the time for pickups? Rest assured, SSMG is your trusted solution for all your travel requirements. 


If you are traveling to the Shenandoah Valley or surrounding areas, skip the rental car and schedule a private car service.  One of our experienced drivers will drop off or pick you up from Dulles international airport, Ronald Reagan Washington National Airport, and several other locations. Leave the driving to us as we get you safely to your destination! To learn more about our private car service, request a quote today!

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