Ride a Two-Seat Sidecar Between San Luis Obispo Wineries
Your own driver handles the motorcycle while you ride in the sidecar between wineries around San Luis Obispo.
A chauffeur rides the motorcycle, and you sit in the sidecar. Sidecar Tours redesigned its sidecars to carry two guests each, and with very large groups it can seat a third rider behind the driver. This listing is private, so the bikes carry only your group, up to eight travelers on one booking. Expect wine country backroads between stops, with the driver handling every mile.
Booking is per person at USD 215, adults 21 and over only. Departures run Thursday to Sunday at 10:30 AM and 1:30 PM, plus 10:00 AM on Thursdays. Cancel at least 24 hours ahead for a full refund.
Private Sidecar Winery Tour through San Luis ObispoPrivate sidecar tour by Sidecar Tours Inc: a chauffeured motorcycle, two guests per sidecar, booked as three hours, ages 21 and over.www.viator.comThe Address on the Listing, and the Call After Booking
The booking page puts both the start and the finish at 1947 See Canyon Road in San Luis Obispo. That is the address of the Kelsey See Canyon Vineyards tasting room, according to the winery's own site, and the same site points visitors to Sidecar Tours. The operator's San Luis Obispo page handles pickup differently. Its team reaches out after you book to coordinate a pickup and drop-off location. Reply to that message to set your pickup, and until you hear back, plan around 1947 See Canyon Road, the address on the booking page.
Which Wineries Depends on the Day
The itinerary on the booking page lists two winery stops of about 45 minutes each, with several of each winery's wines poured in the tasting room. The operator's own San Luis Obispo page says three wineries and calls the outing a two-and-a-half-hour ride, while the booking is sold as three hours. The operator's FAQ says it works with five to eight wineries in the area and visits different ones depending on the day of the week and the time of day. A rider in a February 2026 review found the winery they were sent to closed, "but we were flexible and it was mostly about the ride anyway." Book it for the sidecar and the backroads, and let the tasting list surprise you.
What the Price Leaves Out
The itinerary describes pours at each winery, yet the same listing puts alcoholic beverages under what is not included. The operator's FAQ adds that tastings are covered only on tours whose page says so, and its San Luis Obispo page does not. Plan to pay for tastings at each stop. Meals are not provided either, though the itinerary leaves time at the wineries to pick up food or another glass. The operator's terms also say spills or getting sick in the sidecar can bring a cleaning charge, so pace the pours.
Who Fits, and What Rain Changes
Every traveler must be 21 or older, and the listing sells only an adult ticket for ages 21 to 99. For two guests sharing a sidecar, the operator sets a combined weight limit of 650 pounds and a maximum height of 6 feet 8 inches to fit comfortably. Its helmets are DOT certified. The listing marks the tour suitable for all fitness levels but not recommended for pregnant travelers or anyone with poor cardiovascular health. If the forecast shows a 50 percent chance of rain or worse, the operator reschedules, and in wet conditions it may swap the sidecar for other transport. Pets stay home under the operator's FAQ and terms. The listing also ticks service animals allowed and public transportation nearby, and neither appears on the operator's pages.
Sign the waiver before you ride, since the listing says it serves as your ticket. Arrive 10 to 15 minutes early, and pack a jacket if the day looks less than sunny. Then sit back while someone else takes the curves between the vineyards.