Portsmouth Winery Tour Charter Bus Rentals
Renting a bus for a wine tour out of Portsmouth, Virginia just got a whole lot easier! Portsmouthcharterbusrentals.com lets you fill out one quick form and instantly compare vehicles, packages, and pricing from a large network of independently owned transportation companies serving Portsmouth and all of Hampton Roads. Whether your group is heading to Williamsburg Winery up I-64, spending the afternoon at Holly Grove Vineyards in Chesapeake, or making a day of Virginia Beach's Pungo wine country, you'll see buses and pricing in under 30 seconds — no account needed. Call 948-220-0590 or use the online quote tool right now to get started!
Get Wine Tour & Brewery Transportation Pricing in Just 30 Seconds From a Network of Bus Companies
Portsmouthcharterbusrentals.com is not a bus company. It's a quote-comparison and referral website — which means you're never limited to whatever a single fleet happens to have parked on a Saturday. Fill out one form and you'll land on a results page showing vehicles, photos, amenities, and pricing from a large network of independently owned transportation companies serving Portsmouth, Norfolk, Chesapeake, Suffolk, Virginia Beach, and the rest of Hampton Roads.
Sprinter vans, 15- to 35-passenger minibuses, party buses, and full 56-passenger charter buses are all in the mix. Compare them side by side, pick the one that fits your group and your itinerary, and book right online — or call 948-220-0590 any time and a live agent will build a custom package around your wine tour stops.
Compare Vehicles and Online Rates for Wine Tour & Brewery Transportation in Seconds
Not every wine tour group looks the same, and on Portsmouthcharterbusrentals.com, you don't have to settle for a one-size-fits-all vehicle. A Sprinter van moves a tight group of eight to twelve friends between Chesapeake tasting rooms without the overhead of a full-size bus. A 15- to 35-passenger minibus handles a mid-size bachelorette group heading up to Williamsburg with room for everyone's bags and a smooth ride through the Downtown Tunnel.
Want the celebration to start before the first pour? A party bus comes loaded with a built-in bar, color-changing LED lighting, and Bluetooth sound, so the energy is already going when you roll out of Olde Towne. Whatever the size of your group and wherever your designated stops, you'll find what you need through this website!
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 948-220-0590 to view current vehicle options, photos, availability, and pricing. Confirm the exact vehicle details and amenities before booking.
Charter Buses to Williamsburg Winery and New Kent Tasting Rooms
The run from Portsmouth to Williamsburg Winery (5800 Wessex Hundred, Williamsburg, VA 23185) is about 45 miles northwest on I-64 — roughly 50 minutes off-peak, and closer to 75 minutes on a summer Friday afternoon when the Hampton Roads Bridge-Tunnel backs up westbound traffic past the Bowers Hill interchange. A charter bus handles all of it while your group settles into reclining seats instead of watching the VDOT travel time signs tick upward. Williamsburg Winery's tasting room is open daily 11:30am–7:30pm, with last call at 7pm, and offers estate tours and barrel tastings that pair well with a full-day itinerary.
The Williamsburg Winery tasting room hours give your bus a clear finish line for the afternoon. Add a stop at New Kent Winery (8400 Old Church Rd, New Kent, VA 23124) on the return leg — it's right off I-64 at Exit 214 — and you've turned a single-winery trip into a proper Virginia wine day, all without anyone touching a steering wheel. Call 948-220-0590 to build your Williamsburg wine run!
Buses to Holly Grove Vineyards and Chesapeake Wine Country
Not every wine tour out of Portsmouth needs to cross a tunnel or sit in Hampton Roads traffic. Holly Grove Vineyards (3440 Myrtle Beach Rd, Chesapeake, VA 23322) is roughly 20 miles south of Olde Towne — an easy shot down I-664 to US-17 through Great Bridge — and it's one of the closest full-service vineyards to Portsmouth. A 15-passenger minibus keeps the group together for the whole ride and parks cleanly in the vineyard's lot without the maneuvering headaches that come with a full-size coach on rural Chesapeake roads.
Pair it with a stop at one of the Pungo agricultural district's farm markets on the way back and you've got a genuinely local afternoon that doesn't require fighting the Downtown Tunnel at all. Portsmouthcharterbusrentals.com connects you to a network of bus companies so you can compare Chesapeake wine tour vehicles and pricing in seconds — no account, No waiting for callbacks to get pricing, just many options for your date!
Winery and Brewery Tour Buses Around Portsmouth's Olde Towne and Norfolk
You don't have to leave the city to make a day of it. Coelacanth Brewing (338 Elm Ave, Portsmouth, VA 23704) is right in Olde Towne, and a short hop through the Midtown Tunnel puts your group at Smartmouth Brewing (1309 Raleigh Ave, Norfolk, VA 23507) and O'Connor Brewing (211 W 24th St, Norfolk, VA 23517) for a craft beer crawl that covers two cities in one afternoon. The Midtown Tunnel (US-58) is a toll facility — expect $2.00 per axle eastbound — but a party bus or minibus handles the toll as one vehicle instead of six separate cars paying six separate fares and hunting for six separate parking spots in the Ghent neighborhood.
A party bus with Bluetooth sound and a built-in bar turns the ride between stops into part of the experience rather than dead time. Compare Portsmouth and Norfolk brewery tour buses through Portsmouthcharterbusrentals.com in under 30 seconds!
Virginia Beach Wine Festival Buses for Your Group
The Virginia Beach Wine Festival and the Boardwalk Art & Wine Festival along the Virginia Beach oceanfront draw big crowds to the resort strip each June, and getting there from Portsmouth means navigating the Downtown Tunnel, I-264, and the Virginia Beach–Norfolk Expressway (I-264 east) on one of the busiest travel weekends of the Hampton Roads calendar. Rideshare surge pricing kicks in hard on festival weekends, and parking near the boardwalk is expensive and fills early. A charter bus or minibus drops your group at the festival entrance and picks everyone up when the last glass is poured — no parking scramble, no surge pricing, no designated driver drawing straws.
According to Virginia Wine, Virginia is home to more than 300 wineries, and the festival circuit brings many of them to the coast in one place. Book your Virginia Beach wine festival bus through Portsmouthcharterbusrentals.com before the date fills!
Buses Across the Jamestown-Scotland Ferry to Surry County Wineries
Here's a Portsmouth wine tour route most groups never think of — and it's one of the best in the region. The Jamestown-Scotland Ferry runs free of charge between Surry County and Jamestown 24 hours a day, 365 days a year, and the crossing takes approximately 15–20 minutes. For GPS, use 2110 Jamestown Road, Williamsburg, VA 23185 on the Jamestown side and 16289 Rolfe Highway, Surry, VA 23883-3102 on the Surry side; the ferry can accommodate up to five large buses at a time.
VDOT's Jamestown-Scotland Ferry page also posts the current schedule and traffic queues. From Portsmouth, you reach the Surry landing via US-17 north through Smithfield — roughly 35 miles and 45 minutes before you even board. The ferry is free for passengers and vehicles, but wait times on busy summer weekends stretch to 30–45 minutes, so build that buffer into your departure window.
Once across, you're in Surry County's back roads, and the route connects easily to the Williamsburg area wine corridor from the north side of the James. A charter bus handles the ferry crossing as a single vehicle, keeps your group together for the full scenic crossing, and turns what would be a logistical puzzle into the most memorable part of the day. Call 948-220-0590 to plan your ferry wine tour!
Eastern Shore Winery Buses to Chatham Vineyards via the HRBT
Virginia's Eastern Shore is one of the state's most distinctive wine destinations, and Chatham Vineyards (9232 Chatham Rd, Machipongo, VA 23405) is a standout — a working farm winery on the seaside of the Delmarva Peninsula, about 85 miles from Portsmouth via the Hampton Roads Bridge-Tunnel (US-58 east) and US-13 north through Cape Charles. The HRBT toll runs $4.00 per axle for two-axle vehicles, so one charter bus pays one toll instead of ten cars paying ten. The drive up US-13 through the Eastern Shore's flat farmland and roadside produce stands is genuinely scenic, and the Chatham estate's waterfront setting makes the distance worth it for a group that wants something beyond the standard Hampton Roads wine circuit.
INRIX data shows I-64 eastbound near the HRBT runs at less than 30 mph on summer Saturday mornings — a charter bus turns that slowdown into a relaxed ride rather than a frustrating one. Compare Eastern Shore wine tour buses through Portsmouthcharterbusrentals.com today!
You Can Find and Book Wine Tour & Brewery Transportation in Portsmouth and Any Nearby City!
Portsmouthcharterbusrentals.com helps you find wine tour buses in Portsmouth and the entire surrounding region, so you can find the right vehicle no matter where your group is starting from. Whether you need a Norfolk wine tour bus, a Chesapeake party bus, a Virginia Beach wine tour rental, or transportation out of Suffolk heading toward Surry County's back roads — Portsmouthcharterbusrentals.com can match you with the perfect bus. Spend 30 seconds on one form to browse minibuses, party buses, and charter buses from different local providers across Hampton Roads, all in one place.
Call 948-220-0590 to get a custom quote built around your exact route and group size!
How Much Does Wine Tour & Brewery Transportation in Portsmouth 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 948-220-0590. | ||||
Frequently Asked Questions About Portsmouth Wine Tour & Brewery Transportation Services
Portsmouthcharterbusrentals.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.
Portsmouthcharterbusrentals.com is a quote-comparison and referral website — not a bus company. You fill out one quick form with your date, group size, pickup location, and wine tour stops, and you land on a results page showing vehicles, photos, and pricing from a large network of independently owned transportation companies serving Portsmouth and Hampton Roads. No account required, and a free quote is always available online or by phone at 948-220-0590.
Enter your trip details into the 30-second online quote tool — pickup address, destination wineries, date, and passenger count. You'll be taken to a national booking platform's results page showing available buses and pricing from independent operators serving your route. Review the options side by side, pick the vehicle that fits your group and your itinerary, and book right online.
Rather talk it through? Call 948-220-0590 any time and a live agent will build a custom package for you.
Williamsburg Winery is about 45 miles northwest of Portsmouth via I-64 — roughly 50 minutes off-peak. On a summer Friday afternoon or a busy Saturday, westbound I-64 near the Hampton Roads Bridge-Tunnel corridor can add 20 to 30 minutes to that drive. Build at least a 30-minute buffer into your departure if you're traveling on a weekend, and your charter bus driver handles all of it while your group relaxes on board.
Yes. The Jamestown-Scotland Ferry accommodates tour-size buses, with up to five large buses at a time, and the crossing is free. The ferry operates 24 hours a day, 365 days a year, and takes approximately 15–20 minutes to cross.
On busy summer weekends, wait times for vehicle loading can reach 30–45 minutes, so plan your Portsmouth departure window accordingly and build that buffer into your wine tour schedule.
Yes — Holly Grove Vineyards in Chesapeake (3440 Myrtle Beach Rd, Chesapeake, VA 23322) is about 20 miles south of Olde Towne Portsmouth via I-664 and US-17 through Great Bridge, with no tunnel crossings required. It's one of the most accessible full-service vineyards from Portsmouth and makes a great half-day option for groups that want to skip the Downtown Tunnel and I-264 congestion entirely.
Absolutely. The Downtown Tunnel (I-264) and the Midtown Tunnel (US-58) are both toll facilities — the Midtown Tunnel runs $2.00 per axle for two-axle vehicles. A bus pays one toll as a single vehicle instead of your group splitting across multiple cars and paying multiple fares.
Your driver handles the toll lane, and everyone stays together in one comfortable cabin rather than coordinating a multi-car caravan through Hampton Roads traffic.
Book at least two to four months out for most wine tour dates, and stretch that to six months for busy weekends. Summer Saturdays from June through August are the tightest stretch in the Hampton Roads market — Virginia Beach wine festivals, Williamsburg winery events, and general peak-season demand all compete for the same vehicles. Bachelorette groups booking a Saturday party bus should lock in early; waiting until the last minute means higher rates and limited options.
Yes. Multi-stop itineraries are one of the most common wine and brewery tour setups booked through the network. A typical Hampton Roads crawl might start at Coelacanth Brewing in Olde Towne Portsmouth, cross the Midtown Tunnel to Smartmouth or O'Connor in Norfolk, and finish with dinner in Ghent — all in one vehicle, on one flat rate.
List your stops when you fill out the quote form, or call 948-220-0590 and an agent will build the route around your itinerary.