Leave the driving to someone else
The safest (and most fun) way to taste your way through the County. These local operators handle the route, the reservations, and, most importantly, the driving.
Hop-on group tours and private charters with knowledgeable local guides. Most run 4–6 hours and visit 3–4 wineries.
The County's longest-running tour operator. Guided wine, brewery, cider, and distillery tours by shuttle bus, plus private car-and-guide options. They'll even pick you up from the Belleville train station.
Guided tasting tours across the County's wine regions with door-to-door service. A well-established choice for first-timers who want the classics covered in a single afternoon.
Sommelier-guided wine tours with shuttle pickup at your accommodation, in the County or as far away as Kingston. Great if you want deeper wine knowledge along with your pours.
Five-hour custom guided wine and brewery tours with free door-to-door pickup from across the County plus Belleville, Trenton, Brighton, and Carrying Place. You pick the stops; they build the day.
Private tours for two to four in a BMW X3, with every winery visit and tasting fee bundled into the price. The operator puts that at $75–$100 a head. Wineries and cideries only.
Picton-based private tours for two to seven guests, five hours door to door, plus an hourly driver service if you just need the wheels. Ask about tasting fees when you book.
Family-run tours in two electric VW ID. Buzz vans, in five, six or seven-hour lengths. They plan and drive but stay out of your tastings, which keeps the price down. Tastings and tax are extra.
Five-hour tours to three or four wineries, cideries, or breweries. Aboard a vintage 1970s Volkswagen Westfalia. Easily the most photogenic ride in the County.
Custom private tours with complimentary pickup and drop-off anywhere in the County. Build your day across wineries, breweries, cideries, and even distilleries. A consistent Tripadvisor favourite.
A small, family-run operation offering flexible private tours, typically four wineries with tastings, picked up right at your accommodation. Groups of two to seven, fully licensed and insured.
Private, build-your-own tours across wineries, breweries, cideries and distilleries, with the guide alongside you the whole way to answer questions and carry the bottles. The four-hour half-day is the usual pick; pickups from outside the County carry a small upcharge.
Private and small-group wine, beer, and cider tours mixing scenic vineyard drives with craft tasting stops, plus dedicated County shuttle service for groups who already know where they're going.
The biggest difference between these companies isn't the price on the tin. It's whether tasting fees are included. A $140 tour with tastings extra can cost more than a $210 tour with twelve pours covered. Tick the ones you like and send them the tour you've planned.
| Pick | Operator | From | Tastings | Style | Group | Visits | Length | Pickup |
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Prices are the lowest each operator publishes, usually for their largest group size, and were checked in September 2026. Tap a column heading to sort. Always confirm the price for your own group and date.
The Hillier wineries cluster within a few flat kilometres of each other, perfect cycling country, with the Millennium Trail running the length of the County.
Long-standing local shop renting bikes, e-bikes, and trailers, right in the middle of wine country. Ask for their route advice. They know every back road.
A 46 km rail-trail crossing the entire County from Carrying Place to Picton, passing close to many Hillier and Wellington wineries. Flat, car-free, and gorgeous in fall.
Use our interactive planner to build a custom tasting itinerary with drive times between wineries.
Open the tour planner