Chesapeake Winery Tour Sprinter Van Rentals

Planning a day out at the vineyards or a night hopping through the best breweries in Tidewater? Chesapeake Sprinter Van Rental is your local expert for group travel. Whether you are aiming for a relaxed afternoon in the countryside or a high-energy crawl through the city, we have the right ride to keep your group together. Skip the stress of multiple rideshares and the headache of finding parking in crowded nightlife districts. Call us at 948-356-5700 or use our online quote tool to get custom pricing for your trip in seconds. We handle the logistics so you can focus on the fun.

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A few of the thousands of companies that trust Chesapeake Sprinter Van Rental

General Dynamics Information Technology Chesapeake Regional Medical Center Tidewater Community College Greenbrier Farms Dollar Tree

Providing Chesapeake Winery Tour Transportation Since 2011

Since 2011, we have been the go-to choice for groups exploring the hidden gems of Chesapeake and the surrounding Coastal Virginia region. We know the local roads better than anyone—from the winding backways of Hickory and Great Bridge to the busy stretches of I-64 and the Chesapeake Expressway. Over the last decade, we have helped thousands of passengers celebrate birthdays, bachelorette parties, and corporate outings with zero stress. We understand that a winery tour isn't just about the destination; it’s about the time spent together between stops. That is why we provide sleek, modern sprinter vans equipped with the amenities you actually want, like climate control to beat the Virginia humidity and sound systems to keep the energy up. Our deep roots in the community mean we know exactly where to stage for quick pickups at local favorites and how to avoid the weekend congestion near Greenbrier Mall or the Battlefield Boulevard corridor. When you book with us, you are choosing a team that has spent years perfecting the art of group travel in Chesapeake. We make sure your itinerary runs like clockwork so you never have to worry about the clock.

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Sprinter Vans Perfect For Any Winery Tour Transportation Need in Chesapeake, Virginia

No two group outings are exactly the same, which is why our fleet is designed for total flexibility. Whether you have an intimate group of 8 or a full party of 20, we have a sprinter van that fits your headcount and your style perfectly. For smaller groups looking for a more high-end feel, our sprinter limousines feature perimeter wrap-around seating, fiber optic lighting, and integrated bar areas—ideal for a celebratory toast between vineyards. If you are moving a larger crew for a company retreat or a massive family reunion, our 15, 18, and 20-passenger sprinter vans provide massive headroom and ample space for everyone to stretch out. Virginia’s weather can be unpredictable, but our vans stay crisp and cool with heavy-duty air conditioning units that handle the 90°F summer days with ease. Many of our models also include WiFi and power outlets, so you can share photos of the day in real-time or keep your devices charged for the next stop. We also offer plenty of storage for any bottles you pick up along the way, ensuring your wine hauls stay safe and secure in the back. From the sleek exterior to the plush leather interiors, our vehicles are built to impress. You get the VIP treatment from the moment we pull up to your curb until the final drop-off of the night.

Enjoy Modern, Premium
Sprinter Van Amenities

  • Fiber-Optic/LED lighting
  • Bluetooth/AUX sound connectivity
  • Wraparound or premium comfortable seating
  • On-board entertainment system
  • Climate control (air conditioning/heat)
  • Tinted windows for privacy and style
  • Dropdown cooler/bar area
  • Privacy divider
  • WiFi connectivity

What Groups Say About Our Chesapeake Wine Tour Transportation

Rented a 12-passenger Sprinter for a family beach trip to Sandbridge and it was a lifesaver. The van was spotless and had way more legroom than I expected. Pickup was quick, which I appreciated with three kids in tow. Highly recommend if you’re doing a group trip!
Madison P.
Best rental experience I've had in a while. I needed a large van last minute for a move and they were way more accommodating than the big chain companies. The van drove like a dream and was surprisingly good on gas for its size. Fair pricing and honest people.
Bryce C.
Best way to get a big group to the airport! We had a ton of luggage for our cruise and everything fit with room to spare. Much better than trying to coordinate three different Ubers. The van felt brand new and the ride was very smooth.
Ethan W.

Custom Rides to the Best Vineyards and Winery Day Trips

Getting out to the country should be the most relaxing part of your day. When you rent a sprinter van for a winery tour, you skip the frustration of navigating the narrow, two-lane roads in Pungo or the heavy traffic backing up on Route 168. We take your group straight to the front doors of local staples like Mermaid Winery (330 W 22nd St, Norfolk, VA 23517) or help you venture further out to the scenic estates in Virginia Beach and beyond. Your van will drop you off right at the tasting room entrance before staging nearby, so you never have to hike through gravel parking lots in your best outfit. Whether you are planning a single-stop afternoon or a full-day coastal vineyard hop, we keep your schedule on track while you enjoy the scenery.

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chesapeake 15 passenger sprinter van

Chesapeake Brewery Tours, Bar Hops, and Pub Crawls

Chesapeake’s craft beer scene is booming, but finding parking near the best spots can be a nightmare. Avoid the chaos of the Greenbrier business district and let us handle the ride to Big Ugly Brewing (1296 S Battlefield Blvd, Chesapeake, VA 23322) or The Garage Brewery. If your crawl takes you toward the Elizabeth River, we provide seamless door-to-door service to Studly Brewing Company or the many taprooms in the neighboring Chelsea district. Roll straight in, grab a flight, and ride out to the next spot without ever waiting for a rideshare to find your location. With a private sprinter van, the party stays together and the energy never drops between rounds.

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chesapeake 8 passenger sprinter van interior

Serving Every Major Local Winery, Brewery, and Nightlife District

We know every corner of Chesapeake’s social scene, from the bustling heart of Greenbrier to the laid-back vibes of Western Branch and Deep Creek. Our vans are a common sight at the Power Plant at Hampton Roads and the downtown Norfolk waterfront, where we frequently drop groups for evenings at Grain or The Main. If your night involves the bars along Monticello Avenue or a trip to the Cavalier Hotel’s Tarnished Truth Distilling Co. (4200 Atlantic Ave, Virginia Beach, VA 23451), we’ve got the route covered. We also provide regular service to the many distilleries and tasting rooms in the Suffolk and Portsmouth areas, ensuring your group has total coverage across the Tidewater region. Navigating the Hampton Roads Bridge-Tunnel (HRBT) or the Midtown Tunnel is a non-issue for us—we monitor live traffic patterns on I-264 and I-64 to ensure you spend less time in the tunnel and more time at the bar. Whether you are heading to a local neighborhood pub or a high-end distillery tour, our vans provide the ultimate bridge between destinations. You never have to worry about road closures during local festivals or the typical evening rush hour congestion on Military Highway; we use the best secondary routes to keep your group moving.

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chesapeake employee shuttle van service

Sprinter Van Sizes for Any Winery or Pub Crawl Group

Whether it’s a tight-knit group of friends or a massive corporate department, we have the capacity to handle your crew. Our 10 and 12-passenger vans are favorites for bachelorette parties, offering enough room for everyone to sit comfortably without feeling like they are in a massive bus. For larger events, our 18 and 20-passenger models are the gold standard, providing the space needed for a full pub crawl roster. Every van is designed for social interaction, with seating layouts that make it easy to talk and laugh as you travel. We match the vehicle to your specific headcount so you never overpay for unused space.

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chesapeake 12 passenger sprinter van

Transportation Across the Entire Tidewater Region and Beyond

Our service area doesn't stop at the Chesapeake city limits. We provide group travel solutions throughout Virginia Beach, Norfolk, Portsmouth, Suffolk, and Newport News. Planning a longer excursion to the historic wineries in Williamsburg or a weekend trip up to the Blue Ridge mountains? We handle long-distance winery tours across the entire state. We frequently pick up groups in suburbs like Grassfield, South Norfolk, and Western Branch for day trips to the Eastern Shore or Richmond’s brewery districts. No matter where your starting point is in the 757 area code, we provide consistent, reliable service that takes you exactly where you need to be.

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chesapeake 10 passenger sprinter van interior

Great Prices and Packages for Group Outings

We believe that high-end group travel should be accessible and transparent. That is why we offer straightforward pricing based on your vehicle choice and the time of day. Weekday daytime rates for an 8-passenger van start between $130–$230 per hour, while our larger 20-passenger models range from $220–$320 during the same window. For those looking for a full-day experience, we offer 10-hour day packages that provide significant savings compared to hourly booking. A 10-hour weekday rental for a 12-passenger van runs between $1,800–$1,900, ensuring you have the vehicle at your disposal for the entire tour. Weekend evening rates (after 6 pm) are slightly higher due to peak demand, but they offer the best value for groups wanting a dedicated ride for a night on the town. We provide a full cost breakdown with every quote, so you aren't hit with surprise fees at the end of the night. Whether you need a quick 5-hour shuttle or an all-day vineyard expedition, we work with your budget to find the best package. Investing in a private van is often more cost-effective than multiple premium rideshares, and it offers a much higher level of service and comfort.

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chesapeake 20 passenger sprinter van

Book Your Chesapeake Winery Tour Van Today

Don't leave your group's night to chance with unpredictable apps and long wait times. Secure your private sprinter van with Chesapeake’s most trusted transportation company. Our team is ready to help you map out the perfect itinerary through Virginia’s best vineyards and breweries. Whether you are ready to book right now or just have a few questions about the best local spots, we are here for you. Call 948-356-5700 to talk to a local expert or use our 30-second online quote tool to see pricing and availability for your dates. Let’s get your trip started!

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chesapeake corporate sprinter van service

Book your Wine Tour Transportation Today!

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Chesapeake Wine Tour Transportation Pricing & Packages

Sprinter van rental prices in Chesapeake cost between $150 and $320+ per hour, or roughly $880 to $2,560+ per day. Exact rates will vary, and to get the best deals and exact rates for your trip, just call or use our online quote form!
Vehicle Type Per Hour Weekday Per Hour Weekend Per Day Weekday Per Day Weekend
8 Passenger Sprinter Van $110 - $130 $130 - $155 $880 - $1040 $1040 - $1240
10 Passenger Sprinter Van $130 - $155 $150 - $175 $1040 - $1240 $1200 - $1400
12 Passenger Sprinter Van $140 - $165 $160 - $190 $1120 - $1320 $1280 - $1520
15 Passenger Sprinter Van $150 - $175 $170 - $200 $1200 - $1400 $1360 - $1600
18 Passenger Sprinter Van $165 - $195 $185 - $220 $1320 - $1560 $1480 - $1760
20 Passenger Sprinter Van $180 - $210 $200 - $240 $1440 - $1680 $1600 - $1920
Sprinter Limousine $220 - $260 $260 - $320 $1760 - $2080 $2080 - $2560

* The prices above are current as of 2026. Your final rate will depend on your specific itinerary, passenger count, and any seasonal demand surcharges. Contact the Chesapeake Sprinter Van Rental team at 948-356-5700 for sprinter van pricing in Chesapeake for your exact trip.

Frequently Asked Questions About Our Wine Tour Transportation Services in Chesapeake

How much does winery tour transportation cost in Chesapeake?

Pricing depends on the van size and how long you need it. Hourly rates for a 12-passenger sprinter range from $175 to $275 during the day. For groups looking for a full-day experience, 10-hour packages provide a fixed rate that often saves money. Use our online tool for a custom quote tailored to your specific date and group size.

How many wineries can we visit in one day?

Most groups find that three to four wineries is the sweet spot for an enjoyable day. This allows you about 60 to 90 minutes at each location to enjoy a tasting without feeling rushed. Since your van stays with you, we can easily adjust the schedule if you decide to linger longer at a favorite vineyard or skip a stop.

How many passengers can your Sprinter Vans accommodate for a winery tour?

We offer a variety of sizes to fit your crew perfectly. Our fleet includes 8, 10, 12, 15, 18, and 20-passenger sprinter vans. If you want a more festive atmosphere, our sprinter limousines are great for groups of 10 to 14. We will help you choose the model that gives everyone enough room to relax with their purchases.

Can we create our own custom winery tour itinerary?

Absolutely. You are in total control of where we go. You can provide a list of your favorite Chesapeake and Coastal Virginia spots, or we can suggest a route based on local favorites. Your van will follow your lead, making as many stops as you like within your booked time frame. The schedule is built entirely around your group.

How long should we book transportation for a winery tour?

A typical winery tour usually lasts between six and eight hours, especially if you are traveling between Chesapeake and neighboring cities. This gives you time for travel, multiple tastings, and a lunch break. If you are planning a more extensive trip across the state, our 10-hour day packages are the most popular and cost-effective choice for long-distance vineyard visits.

Can we play our own music during the winery tour?

Yes! Our sprinter vans come equipped with integrated sound systems that feature Bluetooth and AUX connectivity. You can sync your phone and play your curated playlist for the day to keep the vibes exactly where you want them. Whether it’s chill acoustic for the vineyards or upbeat tracks for the pub crawl, you have full control over the audio experience.

Do you provide round-trip pickup from our home, hotel, or Airbnb?

We provide door-to-door service for every trip. We can pick up your entire group at a single residence, a local hotel like the Delta Hotels by Marriott Chesapeake, or any Airbnb in the region. We can also coordinate multiple pickups if your group is scattered, ensuring everyone is on board and ready to go before we head to the first winery.

How far in advance should we book winery tour transportation in Chesapeake?

We recommend booking at least three to six months in advance, especially for Saturday trips during the spring and fall. These are the peak seasons for winery tours in Virginia, and our fleet fills up quickly. Booking early ensures you get your preferred van size and the best possible rate for your group’s big day out.

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948-356-5700