Pub Crawl & Winery Tour Transportation Chesapeake, Virginia

With us on your side, you’ll never have to worry about how you’ll get to the next tasting or who will be your designated driver. Perfect for large groups, bachelorette parties, birthday celebrations, corporate outings, or a weekend getaway with friends, we’ll make sure everyone travels together, arrives on time, and stays comfortable throughout the entire trip. Call our team anytime at 948-203-2230 to learn more about our services or get an instant quote on your next wine tour or pub crawl bus rental in Chesapeake!

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Why Choose Chesapeake Party Bus Company for Your Winery or Brewery Tour?

When you book with Chesapeake Party Bus Company, you’re getting a company that puts you first. We operate 24/7/365 because we know group travel doesn’t stick to regular business hours—if your brewery crawl runs past midnight or your wine tour starts at sunrise, we’ll be there. Need something special? Just ask—we can arrange custom amenities like coolers, WiFi, or even a “party bus” setup with Bluetooth sound systems and LED lighting. And if you’re planning a multi-day trip to explore Virginia’s best craft beverage destinations, we’ll handle all the logistics so you don’t have to worry about a thing.




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Types of Buses We Offer for Winery Tours & Bar Crawls in Chesapeake

$185–$300+ per hour Exterior of Chesapeake Party Bus Company's 14 Passenger Sprinter Limousine in Chesapeake Interior of Chesapeake Party Bus Company's 14 Passenger Sprinter Limousine in Chesapeake

14 Passenger Sprinter Limousine

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$240–$300+ per hour Exterior of Chesapeake Party Bus Company's 15 Passenger Party Bus in Chesapeake Interior of Chesapeake Party Bus Company's 15 Passenger Party Bus in Chesapeake

15 Passenger Party Bus

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$240–$300+ per hour Exterior of Chesapeake Party Bus Company's 18 Passenger Party Bus in Chesapeake Interior of Chesapeake Party Bus Company's 18 Passenger Party Bus in Chesapeake

18 Passenger Party Bus

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$235–$310+ per hour Exterior of Chesapeake Party Bus Company's 20 Passenger Party Bus in Chesapeake Interior of Chesapeake Party Bus Company's 20 Passenger Party Bus in Chesapeake

20 Passenger Party Bus

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$250–$320+ per hour Exterior of Chesapeake Party Bus Company's 25 Passenger Party Bus in Chesapeake Interior of Chesapeake Party Bus Company's 25 Passenger Party Bus in Chesapeake

25 Passenger Party Bus

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$260–$330+ per hour Exterior of Chesapeake Party Bus Company's 28 Passenger Party Bus in Chesapeake Interior of Chesapeake Party Bus Company's 28 Passenger Party Bus in Chesapeake

28 Passenger Party Bus

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$280–$360+ per hour Exterior of Chesapeake Party Bus Company's 30 Passenger Party Bus in Chesapeake Interior of Chesapeake Party Bus Company's 30 Passenger Party Bus in Chesapeake

30 Passenger Party Bus

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$280–$360+ per hour Exterior of Chesapeake Party Bus Company's 40 Passenger Party Bus in Chesapeake Interior of Chesapeake Party Bus Company's 40 Passenger Party Bus in Chesapeake

40 Passenger Party Bus

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$300–$420+ per hour Exterior of Chesapeake Party Bus Company's 50 Passenger Party Bus in Chesapeake Interior of Chesapeake Party Bus Company's 50 Passenger Party Bus in Chesapeake

50 Passenger Party Bus

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$114 – $244+ per hour 20 Passenger Minibus 20 Passenger Minibus Interior

15-35 Passenger Minibus

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$159 – $359+ per hour 50 Passenger Charter Bus 50 Passenger Charter Bus Interior

40-56 Passenger Charter Bus

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Custom Itineraries Built Around You

Tired of rigid schedules and cookie-cutter tours? With Chesapeake Party Bus Company, you set the agenda. Tell us which breweries, wineries, cideries, or distilleries you want to visit, and we’ll create a custom itinerary that hits every stop on your list. Planning a special event like a birthday party, bachelor/bachelorette weekend, or corporate outing? We can add restaurant reservations, hotel drop-offs, or even airport transfers to make sure your trip goes smoothly from start to finish. This is group travel done your way—on your schedule, at your pace, with zero compromises.

chesapeake wine tour and pub crawl bus rentals
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Chesapeake Brewery Bus Rentals

Craft beer lovers will feel right at home in Chesapeake. The city and its surrounding areas are home to several breweries and taprooms that showcase the region’s talent for brewing. Plan a brewery tour with your friends and rent a party bus to easily hop between local favorites like Big Ugly Brewing, The Garage Brewery, and Wasserhund Brewing Company. With a private bus and designated driver, everyone can enjoy sampling flights and pints without worrying about how they’ll get home.

Chesapeake Winery Bus Rentals

Did you know that Virginia is one of the top wine-producing states in the country? Chesapeake is conveniently located near several beautiful wineries and vineyards that are perfect for a day trip or weekend getaway. Gather your fellow wine enthusiasts and book a party bus rental to visit nearby spots like Greenbrier Farms, Williamsburg Winery, or even venture out to the wineries along the Eastern Shore. Your bus will provide comfortable seating, storage space for purchased bottles, and a relaxing ride through scenic countryside.

Group Transportation to Chesapeake Wine & Food Festivals

Chesapeake hosts a variety of food and drink festivals throughout the year that attract visitors from all over the region. From wine tastings and craft beer events to seafood festivals and barbecue competitions, there’s always something delicious happening in town. Skip the hassle of parking and traffic by arranging group transportation with Chesapeake Party Bus Company. We’ll drop you off close to the action and pick you up when you’re ready to head home, making it easy for everyone to enjoy the festivities together.

Explore Virginia Wineries With a Private Bus

Did you know that Virginia is home to over 300 wineries across 10 distinct wine regions? While Chesapeake itself isn’t located within one of these regions, it’s still a great starting point for exploring nearby wine trails. Gather your friends, family, or coworkers and book a private bus to visit popular destinations like the Williamsburg Winery, New Kent Winery, or even venture further out to the Monticello Wine Trail near Charlottesville. With a private bus rental from Chesapeake Party Bus Company, you can customize your itinerary and visit as many wineries as you’d like without worrying about transportation.

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Book Your Chesapeake Brewery & Winery Tour Bus Rental Today!

Ready to hit the road? Contact Chesapeake Party Bus Company today to get a free, no-obligation quote on your next brewery or winery tour bus rental in Chesapeake. Our team is available 24/7 to answer questions, check availability, and help you choose the perfect vehicle for your group. Once you see how easy and affordable it is to travel with us, you’ll never want to go back to carpooling or rideshares again. Call 948-203-2230 now and let’s get this party started!

What Wineries and Breweries Do You Serve in Chesapeake?

We provide transportation to any winery or brewery in Chesapeake and the surrounding areas—including all of Hampton Roads, Virginia Beach, Norfolk, Suffolk, Portsmouth, and beyond. Popular local destinations include Big Ugly Brewing, The Garage Brewery, Wasserhund Brewing Company, and Hickory Ridge Farm Winery. Want to go farther? We also serve regional favorites like Williamsburg Winery, New Kent Winery, Back Bay’s Farmhouse Brewing Co., and even custom routes to Richmond, Charlottesville, or Northern Virginia wine country. If it pours drinks, we’ll get you there.

What Types of Vehicles Do You Offer for Wine Tours and Pub Crawls in Chesapeake?

Our fleet includes party buses (10–50 passengers), minibuses (15–35 passengers), and full-size charter buses (40–56 passengers). Party buses are perfect for small to medium-sized groups who want a fun, social atmosphere with wraparound seating and optional LED lighting. Minibuses offer a comfortable, budget-friendly option for mid-sized groups, while charter buses provide the most space and amenities for large parties or longer trips. Not sure what you need? Tell us your group size and itinerary, and we’ll recommend the best vehicle for your tour.

How Much Does Winery Transportation Cost in Chesapeake?

The cost of renting a bus for a wine tour or pub crawl in Chesapeake depends on several factors: the type of vehicle, the length of your trip, the number of stops, and the time of year. Hourly rates typically range from $150 to $450+ on weekdays and $150 to $500+ on weekends, with daily rates between $1,000 and $2,800. For example, a four-hour wine tour might cost around $1,200–$2,000 total. The best way to get an accurate price is to call us with your exact itinerary—we’ll give you a free, personalized quote with no extra fees.

How Far in Advance Should I Book Wine Tour Transportation in Chesapeake?

We recommend booking your wine tour or pub crawl transportation at least four to six weeks in advance—especially if your trip falls on a weekend or during peak season (spring and fall are busiest for winery tours). Buses tend to sell out quickly for popular dates, and reserving early gives you the best selection of vehicles and the lowest rates. Last-minute bookings are possible if we have availability, but planning ahead ensures everything goes smoothly. Once you have a tentative date and headcount, contact us to lock in your reservation.

How Do I Book With You?

Booking a wine tour or pub crawl bus rental in Chesapeake is easy! Just give us a call at 948-203-2230 or fill out the online quote form on our website. We’ll ask for a few details about your trip—including the date, pickup location, destination(s), and number of passengers—and then provide you with a free, personalized quote. Once you’re ready to reserve, you can complete the booking process online or over the phone. Our team is available 24/7 to answer questions, check availability, and help you plan the perfect outing.

Client Reviews of Our Brewery & Winery Tour Transportation in Chesapeake

maria m

Maria M.

I have used Chesapeake Party Bus Company twice now once for a wedding shuttle and once for a birthday party and both times were perfect. Their team is really responsive, the driver showed up early, and the bus itself was super clean and comfortable. We had so much fun using the Bluetooth sound system. Definitely recommend these guys if you need a party bus in Chesapeake!

john a

John A.

Great communication all around from Chesapeake Party Bus Company! We booked a 40-passenger party bus for my daughter’s wedding at The Greenbrier and they handled everything perfectly. The driver was professional, showed up early, and made sure everyone got to the venue and back to their hotel comfortably even with multiple stops for photos along the way. The bus itself was spotless, comfortable, and had plenty of room for dresses and coolers. I would definitely recommend these guys if you need reliable wedding transportation!

sarah c

Sarah C.

Brandon was very helpful today while booking a wedding shuttle for my daughter’s big day at the Historic Greenbrier Farms. We had guests staying in different hotels around Chesapeake and Norfolk, so he suggested a 28-passenger minibus that could run back-and-forth all night long. The bus arrived early, was spotless inside, and had plenty of room for everyone’s dresses and suits. The driver was super friendly and even helped elderly relatives get on and off comfortably. After the reception, they made sure every guest got dropped off at the right hotel even waited until everyone was inside before leaving. Excellent service from start to finish! This company really takes care of their customers.

david w

David W.

Very responsive, on time and professional! We used Chesapeake Party Bus Company for a corporate outing to Topgolf in Virginia Beach and the whole experience was smooth from start to finish. The 28-passenger minibus was spotless, comfortable, and had plenty of storage for everyone’s bags and clubs. The driver was punctual, friendly, and made sure we got to our dinner reservation afterward right on schedule. I would definitely use them again for any group transportation needs!

Winery Tour Transportation Available In Chesapeake & Nearby Cities