Chesapeake Winery Tour Charter Bus Rentals
A wine tour through Hampton Roads deserves a ride that keeps the celebration going from the first stop to the last! Chesapeakecoachbuscompany.com makes it incredibly easy for groups in Chesapeake, Virginia to find and compare wine tour transportation in seconds. Fill out one quick form and view vehicles, amenities, and online rates from a large network of independently owned transportation companies serving Chesapeake and all of Hampton Roads — no account required! Whether your group is heading to Elmo's Winery in Virginia Beach, crossing the 17.6-mile Chesapeake Bay Bridge-Tunnel for an Eastern Shore wine trail adventure, or making the run up I-64 to the Williamsburg Winery, Chesapeakecoachbuscompany.com connects you to sprinter vans, minibuses, and party buses ready for your itinerary.
Call 757-796-1250 or use our 30-second online quote tool right now!
Get Wine Tour & Brewery Transportation Pricing in Just 30 Seconds From a Network of Bus Companies
Don't limit your group to whatever one company happens to have available on your date! Chesapeakecoachbuscompany.com is not a bus company — it's a quote-comparison and referral website that brings together a large network of independently owned transportation companies serving Chesapeake and all of Hampton Roads. That means you're never stuck with a single fleet or a single price. Fill out one quick form and instantly compare vehicles, amenities, and rates side by side from multiple providers, all in one place.
From sprinter vans for an intimate group of eight heading to Mermaid Winery (3324 Virginia Beach Blvd, Norfolk, VA 23452) to a full party bus for a bachelorette group making a day of it across the region — you find what you need! Call 757-796-1250 or use the online quote tool to get started!
Every Bus You Can Book for Wine Tour & Brewery Transportation
It's never been easier to match the right vehicle to your group! Through a large network of transportation companies serving Chesapeake, you can compare sprinter vans for groups of 8–14, 15- to 35-passenger minibuses, and 15- to 50-passenger party buses — all with different amenities to fit exactly what your wine tour calls for. Want a party bus with a built-in bar, color-changing LED lighting, and a Bluetooth sound system to keep the energy high between wineries?
It's right there in the results. Need a sleek sprinter van for a smaller birthday group heading to Elmo's Winery (2500 Indian River Rd, Virginia Beach, VA 23456), just 15–20 minutes from the Great Bridge neighborhood? Done!
Just answer a few questions, compare your options, and choose the bus that works for you!
56 Passenger Charter Bus
35 Passenger Minibus
30 Passenger Minibus
28 Passenger Minibus
25 Passenger Minibus
20 Passenger Minibus
18 Passenger Minibus
15 Passenger Minibus
15-50 Passenger Party Buses
Sprinter Van with Driver
Sprinter Limo
School Bus
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 757-796-1250 to view current vehicle options, photos, availability, and pricing. Confirm the exact vehicle details and amenities before booking.
Cross the Chesapeake Bay Bridge-Tunnel to Virginia's Eastern Shore Wine Trail
Instead of splitting your group across multiple cars and paying separate tolls through the Chesapeake Bay Bridge-Tunnel — where charter buses are charged by axle count rather than the standard passenger-car rate of $16 off peak or $21 during peak season — one bus means one crossing, one toll, and everyone together for the full 17.6 miles across the mouth of the Chesapeake Bay. On the other side, Virginia's Eastern Shore is home to some of the most scenic wineries in the state. Chatham Vineyards (9232 Chatham Ln, Machipongo, VA 23405) requires advance reservations for group visits, so contact them ahead of your trip.
Bloxom Winery (26130 Mason Rd, Bloxom, VA 23308) sits along the Chesapeake Bay Wine Trail on Route 13 through the Eastern Shore. Rural winery roads mean rideshare availability is limited out here — a pre-arranged bus is the reliable option, and it's the one that gets your whole group back to Chesapeake together. Confirm current toll rates for your vehicle class at cbbt.com/tolls before your visit.
Chesapeakecoachbuscompany.com Is the Easy Way to Book a Bus to Williamsburg Winery and New Kent
Chesapeakecoachbuscompany.com is the easiest way to compare transportation for the longer wine country runs your group has been planning! The Williamsburg Winery (5800 Wessex Hundred, Williamsburg, VA 23185) sits about 60–75 miles up I-64 from Chesapeake — roughly an hour to an hour and fifteen minutes without traffic — and requires advance arrangements for buses, limos, or parties larger than 10 guests. Buses and parties larger than 10 can arrange their visit by calling the venue directly at (757) 229-0999 ext 132 through the Williamsburg Winery group reservation FAQ.
New Kent Winery (8400 Old Church Rd, New Kent, VA 23124) is another award-winning stop along the same I-64 corridor, also recommending advance reservations for groups. Groups of 8 or more can reserve a table at New Kent Winery by emailing [email protected] or calling the venue directly at (804) 922-7414; the New Kent Winery tasting and group reservation page has the current booking details. On a full-size 56-passenger charter bus, your group gets reclining seats, climate control, WiFi, power outlets, and undercarriage luggage bays — everything you need to arrive relaxed and ready to taste.
Fill out one form, compare charter buses and minibuses from a network of providers serving Chesapeake, and book the vehicle that fits your headcount!
Book a Party Bus for Your Chesapeake Wine Tour Bachelorette or Birthday
Book your party bus early — especially if your wine tour falls during Virginia Wine Month in October or the busy spring weekends in April and May, when Hampton Roads bus availability tightens fast! Virginia Wine Month brings special tastings and events to Hampton Roads wineries every October, and it's one of the most popular times of year to plan a group wine tour from Chesapeake. A 15- to 50-passenger party bus comes with a full-length bar, color-changing LED lighting, wraparound perimeter seating, flat-panel TVs, and a premium Bluetooth sound system — so the celebration starts the moment your group boards, not when you arrive at the first winery.
Whether you're starting in Great Bridge, Greenbrier, or anywhere else in Chesapeake, the party bus picks everyone up together and keeps the group together all day. Call 757-796-1250 to lock in your date before it fills!
Check Out Surry Cellars With a Bus That Handles the Route
Check out Surry Cellars in Surry, Virginia — about 60–70 miles from Chesapeake via I-664 and Route 10, roughly an hour to an hour and twenty minutes — without turning the drive into a group coordination headache. One of the most scenic ways to reach Surry County is via the Jamestown-Scotland Ferry, a free VDOT-operated ferry between Jamestown and Scotland Wharf that accommodates buses and operates 24 hours a day, 365 days a year. The crossing takes approximately 15–20 minutes, and the posted limits are 12'6" in height and 16 tons for large trucks; your bus skips the bridge detour when it fits those limits.
Your bus handles the route, the navigation, and the timing while your group enjoys the views across the James River. Because Chesapeakecoachbuscompany.com connects you to a network of transportation companies serving Chesapeake and the surrounding region, you can compare minibuses and charter buses for this kind of day-trip run and find the vehicle that fits your headcount and your itinerary. Use the online quote tool or call 757-796-1250 to see what's available for your date!
If Your Group Is Heading to Mermaid Winery in Norfolk, Skip the Parking Search
If your wine tour night includes a stop at Mermaid Winery , you already know that parking in Norfolk can be its own challenge — especially on a weekend evening when the whole group is trying to arrive at the same time. A sprinter van or minibus drops everyone off together, stages nearby while you're inside, and picks the group up when you're ready for the next stop. No one circles the block.
No one misses the first pour waiting for a parking spot. And because the Hampton Roads Bridge-Tunnel sees its worst delays between 4 and 7 p.m. on weekday evenings, a pre-arranged bus lets your group plan the departure time around the traffic window instead of guessing. Chesapeakecoachbuscompany.com makes it easy to compare sprinter vans, minibuses, and party buses from a network of providers serving Chesapeake and Norfolk — fill out one form and see your options in seconds!
Not in Chesapeake? You Can Still Find Wine Tour & Brewery Transportation Nearby
Make your wine tour pickup as easy as the tasting itself! Chesapeakecoachbuscompany.com helps you find wine tour transportation starting from anywhere in the Hampton Roads region — not just Chesapeake. Whether your group is gathering in Suffolk, Portsmouth, Norfolk, or Virginia Beach before heading out to the wineries, the network of transportation companies on this site has you covered. You share your pickup location once, compare available vehicles, and book the bus that works for your group and your itinerary.
No calling five companies. No waiting on callbacks. Just one quick form and instant results showing vehicles, photos, and pricing.
Call 757-796-1250 any time or use the online tool to see what's available for your date!
How Much Does Wine Tour & Brewery Transportation in Chesapeake Cost?
| Type of Vehicle | Cost Per Hour Weekdays | Cost Per Hour Weekends | Cost Per Day | Cost Per Mile |
|---|---|---|---|---|
| 56 Passenger Charter Bus | $205 – $385+ | $225 – $410+ | $1,650 – $2,950+ | $6.20 – $8.95+ |
| 35 Passenger Minibus | $225 – $370+ | $255 – $385+ | $1,815 – $2,415+ | $6.20 – $8.95+ |
| 30 Passenger Minibus | $205 – $365+ | $240 – $380+ | $1,670 – $2,335+ | $5.90 – $8.60+ |
| 28 Passenger Minibus | $190 – $355+ | $220 – $370+ | $1,540 – $2,255+ | $5.65 – $8.25+ |
| 25 Passenger Minibus | $190 – $350+ | $195 – $365+ | $1,420 – $2,180+ | $5.40 – $7.90+ |
| 20 Passenger Minibus | $190 – $340+ | $190 – $355+ | $1,300 – $2,080+ | $5.15 – $7.50+ |
| 18 Passenger Minibus | $190 – $330+ | $190 – $350+ | $1,210 – $1,990+ | $5.00 – $7.25+ |
| 15 Passenger Minibus | $180 – $310+ | $180 – $330+ | $1,150 – $1,880+ | $4.75 – $6.95+ |
| 15-50 Passenger Party Bus | $248 – $426+ | $265 – $460+ | $1,827 – $2,954+ | $6.75 – $9.95+ |
| Sprinter Van with Driver | $190 – $373+ | $218 – $466+ | $1,395 – $2,848+ | $5.00 – $6.95+ |
| Sprinter Limo | $190 – $340+ | $190 – $355+ | $1,300 – $2,080+ | $5.15 – $7.50+ |
| School Bus | $205 – $365+ | $240 – $380+ | $1,670 – $2,335+ | $5.00 – $7.60+ |
| 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 757-796-1250. | ||||
Frequently Asked Questions About Chesapeake Wine Tour & Brewery Transportation Services
Chesapeakecoachbuscompany.com helps you compare buses rental options; it is not a transportation company and does not rent, own, or operate vehicles. When you submit the quote form, your trip details go through a booking company so you can review pricing and available vehicles for your date. You compare the options and book through the process shown with your quote.
Chesapeakecoachbuscompany.com is a quote-comparison and referral website, not a bus company. You fill out one quick form with your pickup location, date, group size, and winery stops, and you're taken to a results page showing vehicles, photos, and pricing from a network of independently owned transportation companies serving Chesapeake and Hampton Roads. No account required, and a free quote is always available online or by phone at 757-796-1250.
You share your trip details once using the online quote tool — pickup location, date, passenger count, and any winery stops on your itinerary. Once submitted, you land on a results page through a national booking platform showing available vehicles and pricing from a network of independent transportation companies serving your route. Review your options side by side, pick the bus that fits your group, and book right online in minutes.
Or call 757-796-1250 and a live agent will help you put together a custom package!
It depends on the winery. Williamsburg Winery requires advance arrangements for buses, limos, or parties larger than 10 guests — contact them directly before your trip. Chatham Vineyards on the Eastern Shore is open for tastings by appointment, and group visits require advance reservation.
Elmo's Winery and Mermaid Winery are more walk-in friendly, but calling ahead for larger groups is always recommended. Confirm directly with each winery when you finalize your itinerary.
Yes — charter buses and motorcoaches are permitted to cross the Chesapeake Bay Bridge-Tunnel. Tolls are charged by vehicle class and axle count rather than the standard passenger-car rate of $16 off peak or $21 during peak season, so the bus toll will be higher per vehicle — though one bus still means one toll instead of multiple cars paying separately. Confirm the current toll rate for your vehicle class at cbbt.com/tolls before booking your Eastern Shore wine tour.
Book as early as possible — ideally 4 to 6 weeks out for standard dates, and 2 to 3 months out for October weekends and spring Saturdays in April and May. Virginia Wine Month in October is the single busiest stretch of the year for wine tour bus rentals in Hampton Roads, and availability across the network tightens fast. Waiting until the last minute almost always means higher prices and fewer vehicle options to choose from.
Through the network of transportation companies serving Chesapeake, you can compare sprinter vans (8–14 passengers), 15- to 35-passenger minibuses, and 15- to 50-passenger party buses. Party buses come with a built-in bar, LED lighting, and Bluetooth sound — great for bachelorette parties and birthday wine tours. Minibuses and sprinter vans are a better fit for smaller groups or longer runs up I-64 to Williamsburg.
Just enter your group size and date to see what's available!