Chesapeake Winery Tour Charter Bus Rentals
Crossing the Hampton Roads region to reach your next tasting room is so much better when you're not the one navigating I-64 or hunting for parking on Pacific Avenue! Chesapeakecharterbuscompany.com makes finding wine tour transportation in Chesapeake, Virginia fast, easy, and completely stress-free. Fill out one quick form and instantly compare vehicles and rates from a large network of bus companies serving Chesapeake and the entire Hampton Roads area. Whether your group is heading south on US-168 toward Sanctuary Vineyards in Jarvisburg, northwest on I-64 to Williamsburg Winery, or cruising into Virginia Beach for a night at Mermaid Winery, Chesapeakecharterbuscompany.com has the bus for you.
Call 757-972-5040 or use the 30-second online quote tool right now!
Share Your Trip Details Once and Compare Wine Tour & Brewery Transportation Options Side by Side
Keep the whole group together from the first pour to the last stop — that is exactly what Chesapeakecharterbuscompany.com is built for! Chesapeakecharterbuscompany.com is not a local bus company and doesn't own any vehicles. Instead, it's a quote-comparison and referral website that connects you to a large network of independently owned transportation companies serving Chesapeake and the surrounding region. That means you're never stuck with whatever one fleet happens to have available on a Saturday in October.
You fill out one quick form, and you instantly see different buses, packages, and prices side by side from multiple providers — no account required, no callbacks to wait on. Compare your options, choose the bus that fits your group, and book it right online. Call 757-972-5040 any time for a free quote!
Pick From Every Bus Type for Wine Tour & Brewery Transportation
From a cozy sprinter van for six friends heading to Sanctuary Vineyards to a 56-passenger charter bus shuttling a corporate group out to Williamsburg Winery, the network has every size and style your group could need. Smaller 15- to 35-passenger minibuses are a great pick for the rural roads out toward Currituck County or the tight parking situation near Mermaid Winery on Shore Drive in Virginia Beach — nimble enough to get in and out clean without the headaches a full-size coach brings on narrow country lanes. Want the celebration to start the moment everyone boards?
Party buses come loaded with a full-length bar, color-changing LED lighting, Bluetooth sound, and wraparound perimeter seating, so the energy is high long before you reach the first vineyard. Whatever your group needs, you can compare it all in one place!
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 757-972-5040 to view current vehicle options, photos, availability, and pricing. Confirm the exact vehicle details and amenities before booking.
Head South to Sanctuary Vineyards and the Currituck Wine Trail
For easy access to one of the most popular winery destinations from Chesapeake, nothing beats a bus straight down US-168 and the Caratoke Highway into Currituck County, North Carolina. Sanctuary Vineyards (7005 Caratoke Hwy, Jarvisburg, NC 27947) sits about 45 to 60 minutes south of Chesapeake and draws Hampton Roads groups all season long — especially from Memorial Day through Labor Day when the outdoor event space and live music lineup are in full swing. Calling ahead to coordinate a group arrival is a good idea so the tasting room is ready for your bus.
Your group rides together, skips the US-168 weekend crawl, and walks straight into the tasting room. Compare minibuses, party buses, and charter buses for the Currituck run right now through the online quote tool!
Spend the Afternoon at Williamsburg Winery
Use I-64 west out of Chesapeake and you're pulling into one of Virginia's most celebrated wine estates in under an hour. Williamsburg Winery (5800 Wessex Hundred, Williamsburg, VA 23185) is a sprawling estate with a full restaurant and multiple tasting experiences — calling ahead to coordinate your arrival and group parking is recommended so the estate has your group on the schedule. A 56-passenger charter bus is a great choice for a larger group making the run from Chesapeake, with reclining seats, overhead storage, WiFi, and undercarriage luggage bays for anyone bringing home a case or two.
October is Virginia Wine Month and one of the busiest stretches of the year for Hampton Roads wine tour buses, so lock in your date early. Get your quote in seconds at 757-972-5040!
Explore Mermaid Winery and Virginia Beach's Urban Wine Scene
Chesapeakecharterbuscompany.com can help you put together a Virginia Beach wine and nightlife crawl that your whole group will be talking about for months! Mermaid Winery (4401 Shore Drive, Virginia Beach, VA 23455) is the anchor of the Hampton Roads urban winery scene — a lively tasting room in the Chic's Beach area with live music events and a rotating wine list. Parking near Shore Drive is tight on a weekend evening, and rideshare surge pricing after a night of wine tasting adds up fast across a group.
A party bus or minibus drops everyone at the door, stages nearby, and is ready when your group is done — no hunting for parking, no splitting up the group, no surge pricing on the way home. It's only about 15 to 20 minutes from most Chesapeake neighborhoods, so the evening starts the moment you board!
Heading Outside Chesapeake? You Can Still Compare Wine Tour & Brewery Transportation Options
Choosing Chesapeakecharterbuscompany.com means you're never limited to Chesapeake city limits. The network of transportation providers reaches across all of Hampton Roads and beyond, so your wine tour can start wherever your group is gathering. Need a pickup in Virginia Beach before swinging through Chesapeake?
Done. Starting in Suffolk and heading south toward the Currituck County vineyards? Easy.
Coordinating a multi-city pickup across Norfolk, Portsmouth, and Chesapeake before the bus rolls northwest to Williamsburg? You can build that itinerary right into your quote request. Chesapeakecharterbuscompany.com helps you find bus rentals in Chesapeake and every nearby city — including Virginia Beach, Norfolk, Suffolk, and Portsmouth. Call 757-972-5040 to get your group moving today!
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 757-972-5040. | ||||
Frequently Asked Questions About Chesapeake Wine Tour & Brewery Transportation Services
Chesapeakecharterbuscompany.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.
Chesapeakecharterbuscompany.com is a quote-comparison and referral website. You fill out one quick form with your pickup location, date, group size, and destinations, and you instantly see vehicles and pricing from a large network of independently owned transportation companies serving Chesapeake and the Hampton Roads region. No account required, no waiting on callbacks — just compare your options and book the bus that fits your group.
Call 757-972-5040 any time for a free quote!
You share your trip details once through the 30-second online quote tool or by calling 757-972-5040. Those details go to a national booking platform that returns available vehicles and pricing from independent operators serving your route. You review the options side by side — bus type, amenities, price — and book the one that works for your group right online.
Transportation is provided by the independent operator; booking is completed through the national booking platform.
The most popular winery destinations from Chesapeake are Sanctuary Vineyards in Jarvisburg, NC (about 45–60 minutes south via US-168), Williamsburg Winery in Williamsburg, VA (about 45–60 minutes northwest via I-64), and Mermaid Winery in Virginia Beach (15–20 minutes). All are reachable in a single day from any Chesapeake neighborhood.
Book at least three to six months in advance for the best selection and pricing. October is Virginia Wine Month and one of the busiest stretches of the year for wine tour buses across Hampton Roads — availability tightens fast. Spring weekends in April and May are also busy because prom season across Chesapeake City Public Schools competes for the same vehicles.
Summer weekends fill quickly for Sanctuary Vineyards and Outer Banks-area trips. The earlier you book, the more options you'll have and the better your price.
Yes, and multi-stop pickup loops are one of the most common requests through the network. Chesapeake covers a large area — from Great Bridge to Greenbrier to Deep Creek — and your group may be gathering from several neighborhoods or even from neighboring Virginia Beach or Suffolk. List your pickup points in order when you fill out the quote form, or give them to a live agent at 757-972-5040.
Add about 10 minutes per additional stop to your departure window to keep the itinerary on schedule.
Yes! The network of transportation providers reaches across all of Hampton Roads. Chesapeakecharterbuscompany.com helps you find wine tour buses starting from Virginia Beach, Norfolk, Suffolk, Portsmouth, and every surrounding city — not just Chesapeake. Multi-city pickup routes are easy to build right into your quote request.
Wherever your group is starting, there's a bus in the network ready to make the wine tour happen. Call 757-972-5040 or use the online quote tool to get started!