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Chesapeake Wine Tour & Brewery Transportation

Chesapeake Winery Tour Charter Bus Rentals

Just planning a wine tour out of Chesapeake is exciting enough — figuring out how everyone gets there and back shouldn't be the hard part! Chesapeakecharterbusservices.com makes it incredibly easy to find and compare wine tour transportation in Chesapeake, Virginia. Fill out one quick form and instantly see vehicles and pricing from a large network of bus companies serving the Hampton Roads region. Whether you're heading up I-64 to the Williamsburg Winery, rolling south on VA-168 toward Sanctuary Vineyards in Currituck County, or making a short run west to Smithfield, Chesapeakecharterbusservices.com helps you find the right bus fast.

Call 757-290-3430 or use the 30-second online quote tool to get started today!


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The Easiest Way to Find and Book Chesapeake Wine Tour & Brewery Transportation

Moving your whole group from a Great Bridge neighborhood to a winery tasting room — and back, safely, with everyone together — is exactly what this website was built to help you arrange. Chesapeakecharterbusservices.com is not a local bus company. It's a quote-comparison and referral website that connects you to a large network of independently owned transportation companies serving Chesapeake and all of Hampton Roads. You fill out one quick form, and a results page shows you vehicles, photos, and pricing from providers serving your route.

No account required. No calling five companies. No waiting on callbacks.

Whether you need a sprinter van for a small group of friends or a full-size motorcoach for a corporate wine retreat, the network has options ready for your date. Call 757-290-3430 or get your free online quote in under 30 seconds!

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Find What You Need Through a Network of Independent Transportation Providers Serving Chesapeake

Compare Buses, Packages, and Prices for Wine Tour & Brewery Transportation All in One Place!

Why settle for whatever one company happens to have available when you can compare buses from an entire network? Through Chesapeakecharterbusservices.com, you'll find sprinter vans for intimate groups of six to fourteen, 15- to 35-passenger minibuses that are nimble enough to navigate downtown Smithfield's historic Main Street or the urban parking around Mermaid Winery in Virginia Beach, and full-size 56-passenger charter buses with undercarriage luggage bays for big groups making the run up I-64 to Williamsburg. Party buses with built-in bars and LED lighting are available for bachelorette wine tours that want the celebration to start before the first pour.

You get TONS of different bus types, amenities, and price points — all from one form, in seconds. Find the bus that fits YOUR group!

Vehicles shown above are NOT the exact makes and models available for every trip. We are NOT a transportation company and do not own or operate vehicles. Photos are examples only and may show stock or typical vehicles, not the exact vehicle offered for your reservation. Fill out the online quote form or call 757-290-3430 to view current vehicle options, photos, availability, and pricing. Confirm the exact vehicle details and amenities before booking.

Wine Tour Buses to the Williamsburg Winery and the I-64 Corridor

It's easier than ever to plan a full-day wine tour up I-64 West to the Williamsburg area — and a charter bus makes the whole trip smoother for everyone in your group. The Williamsburg Winery (5800 Wessex Hundred, Williamsburg, VA 23185) is one of Virginia's oldest and most celebrated wineries, with a large parking lot that accommodates charter buses and motorcoaches comfortably. Groups of ten or more should call ahead at (757) 229-0999.

Buses and parties larger than 10 guests must arrange their visit in advance through the winery's event team at (757) 229-0999 ext. 132; the Williamsburg Winery group-visit information covers the reservation path. The drive from Chesapeake runs roughly 60 to 75 minutes via I-64 West — and on a Friday afternoon, I-64 through the Norfolk corridor can add 20 to 40 minutes, which is exactly why one bus beats a caravan of cars where nobody wants to be the designated driver. Compare 35- to 56-passenger buses for this run through Chesapeakecharterbusservices.com!

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wine tour buses to the williamsburg winery and the i 64 corridor

Sprinter Vans and Minibuses for Smithfield Winery and the Isle of Wight Run

sprinter vans and minibuses for smithfield winery and the isle of wight run

Browse a curated selection of sprinter vans and compact minibuses — the right vehicles for a wine tour through historic Smithfield, Virginia. Smithfield Winery (117 North Church St, Smithfield, VA 23430) sits right on Main Street in Smithfield's narrow historic district, about 45 minutes from Chesapeake via US-17 North and VA-10. Large motorcoaches cannot easily navigate those historic downtown streets, so a 15- to 25-passenger minibus or a sprinter van is the smart pick for this run — nimble enough to drop your group at the tasting room door and stage nearby while you enjoy the pour.

Through Chesapeakecharterbusservices.com, you can compare available minibuses and sprinter vans from a network of providers serving Chesapeake and Isle of Wight County. Call 757-290-3430 for help picking the right size!

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Wine Tour Transportation South on VA-168 to Sanctuary Vineyards and Currituck County

Browse a large selection of buses for one of the most scenic wine tour routes out of Chesapeake — south on VA-168 through the Chesapeake Expressway corridor into Currituck County, North Carolina. Sanctuary Vineyards (7005 Caratoke Hwy, Jarvisburg, NC 27947) is about 75 minutes south of Chesapeake and sits right on US-158 with a large rural parking area that handles charter buses and motorcoaches with no trouble — call ahead at (252) 491-2387 for group visits. Just keep in mind that VA-168 south gets heavy Outer Banks tourist traffic on summer Saturdays; an early departure or a Friday run keeps the drive smooth.

From 15-passenger minibuses to full-size 56-passenger coaches, Chesapeakecharterbusservices.com helps you find and compare the right bus for your group size and your itinerary!

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wine tour transportation south on va 168 to sanctuary vineyards and currituck county

Mermaid Winery and Urban Tasting Room Tours Around Virginia Beach and Chesapeake

mermaid winery and urban tasting room tours around virginia beach and chesapeake

Let your group explore the growing urban wine and tasting room scene between Chesapeake and Virginia Beach without anyone worrying about parking or a designated driver. Mermaid Winery (4401 Shore Drive, Virginia Beach, VA 23455) is about 30 minutes from South Chesapeake — an urban winery in a residential commercial area where a sprinter van or 15-passenger minibus is the right call over a full-size coach, given the street parking situation. The Virginia Beach location is open Tuesday through Thursday from 12 PM to 9 PM, Friday and Saturday from 12 PM to 10 PM, Sunday from 12 PM to 9 PM, and closed Monday; your bus can build the stop around that published window using Mermaid Winery's visit hours.

Through Chesapeakecharterbusservices.com, you can compare sprinter vans and compact minibuses from a network of providers serving Virginia Beach and Chesapeake, mix in additional tasting room stops on your custom itinerary, and find the bus that fits your group's size and plans. Call the venue directly at (757) 460-0075 to confirm group visit details with Mermaid Winery directly, then lock in your bus through Chesapeakecharterbusservices.com!

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Bachelorette Wine Tours and Party Buses Out of Chesapeake

Whatever your bachelorette wine tour itinerary looks like — a morning sprinter van pickup in Great Bridge, a stop at Nansemond Ridge Winery in Suffolk, then a full afternoon at the Williamsburg Winery before dinner back in Chesapeake — Chesapeakecharterbusservices.com makes it easy to find a bus that matches the energy of the whole day. Party buses with built-in bars, color-changing LED lighting, Bluetooth sound systems, and wraparound perimeter seating are available through the network for groups that want the celebration rolling from the very first pickup. Or compare a sleek sprinter limo for a smaller, more intimate group of eight to twelve.

You set the itinerary, you choose the stops, and you pick the bus that fits your group. Fill out one form to compare party buses and sprinter vans from a network of companies serving Chesapeake, Virginia Beach, Suffolk, and all of Hampton Roads!

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bachelorette wine tours and party buses out of chesapeake

You Can Find and Book Wine Tour & Brewery Transportation in Chesapeake and Any Nearby City!

Coordinating a wine tour that starts in one Hampton Roads city and picks up guests in another? No problem at all! Chesapeakecharterbusservices.com helps you find wine tour transportation in Chesapeake and every nearby city — Virginia Beach, Norfolk, Suffolk, Portsmouth, Hampton, and Newport News are all within easy reach of the network. Whether your group is gathering from across the region or you need a single pickup at one address in South Chesapeake before heading south on the Chesapeake Expressway toward Currituck County, the network of bus companies serving this region can handle it.

Fill out one form with your pickup city, date, and passenger count, and compare your options side by side — no account needed, and a live agent is always available at 757-290-3430 to help you build a custom itinerary!

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chesapeake wine tour brewery transportation onboard seating
2026 Wine Tour & Brewery Transportation Rates

How Much Does Wine Tour & Brewery Transportation in Chesapeake Cost?

Typical Chesapeake Bus Rental Prices
Type of Vehicle Cost Per Hour Weekdays Cost Per Hour Weekends Cost Per Day Cost Per Mile
56 Passenger Charter Bus $215 – $400+ $235 – $425+ $1,720 – $3,040+ $6.40 – $9.15+
35 Passenger Minibus $235 – $385+ $265 – $400+ $1,890 – $2,495+ $6.40 – $9.15+
30 Passenger Minibus $215 – $380+ $250 – $395+ $1,740 – $2,415+ $6.10 – $8.80+
28 Passenger Minibus $200 – $370+ $230 – $385+ $1,605 – $2,335+ $5.85 – $8.45+
25 Passenger Minibus $200 – $365+ $205 – $380+ $1,480 – $2,260+ $5.60 – $8.10+
20 Passenger Minibus $200 – $355+ $200 – $370+ $1,355 – $2,155+ $5.35 – $7.70+
18 Passenger Minibus $200 – $345+ $200 – $365+ $1,260 – $2,065+ $5.20 – $7.45+
15 Passenger Minibus $190 – $325+ $190 – $345+ $1,200 – $1,950+ $4.95 – $7.15+
15-50 Passenger Party Bus $260 – $445+ $280 – $480+ $1,905 – $3,065+ $6.95 – $10.20+
Sprinter Van with Driver $200 – $390+ $230 – $485+ $1,455 – $2,950+ $5.20 – $7.15+
Sprinter Limo $200 – $355+ $200 – $370+ $1,355 – $2,155+ $5.35 – $7.70+
ABOVE PRICES ARE JUST EXAMPLES. Your final price and vehicle options depend entirely on your specific trip details. To get an instant price quote for your trip, request an online quote or call 757-290-3430.
Have Questions? We're Here to Help You!

Frequently Asked Questions About Chesapeake Wine Tour & Brewery Transportation Services

Call 757-290-3430
Call 757-290-3430