Private Sidecar Winery Tour San Luis Obispo: Tandem Sidecars

Taste two wineries without driving or planning the route yourself.

A private sidecar winery tour in San Luis Obispo pairs you and a companion in a tandem sidecar, the world's only two-passenger motorcycle sidecar, for a three-hour ride through wine country with stops at two partner wineries for tastings. A live English-speaking guide drives and narrates the region's history and landmarks along the way. Minimum age is 21. Service animals are welcome.

Step-by-step itinerary

Sidecar winery tour and tastings

• Pick up from starting location
• Drive sidecar to first winery
• Enjoy wine tasting at first winery
• Explore winery area and optional food/drinks
• Drive sidecar to second winery
• Tour second winery with staff
• Wine tasting at second winery
• Relax with snack or additional wine
• Return to sidecars for departure

The experience

The tour starts from a set location and picks up your group in a tandem sidecar: a modified motorcycle sidecar built to hold two passengers side by side. You ride through San Luis Obispo's backroads, passing well-known and hidden landmarks while your driver points out the region's history and culture. The sidecar itself is the draw here: it's not a standard shuttle between tasting rooms, but a hands-on way to move through the wine country instead of sitting in a car.

At the first winery, you're taken to the tasting room and given multiple pours of the house's notable wines, with time to linger, order food or drinks if you want, and soak in the grounds. Then you load back into the sidecar for the ride to the second stop, passing more views along the way. At the second winery, the staff shows you around and you taste their signature selection. You'll have roughly 30 minutes there to relax, snack, and enjoy the space before heading back. The whole experience runs three hours from pickup to drop-off.

The tour operates at set times (10:00am, 10:30am, or 1:30pm departures available), and it's a private booking for your group only. Your guide speaks English and knows the region's wineries and backroads. Rides are not recommended for pregnant travelers or those with cardiovascular concerns, but the pace suits all fitness levels otherwise.

What’s included

• Private transportation in a tandem sidecar for two passengers.
• wine tastings at two partner wineries.
• a live English-speaking guide who narrates San Luis Obispo's history and landmarks.

Options for this experience

4 options

Private sidecar winery tour in San Luis ObispoGuide in English · 10:00, 10:30 and 13:30

Wine tour at 10:00amGuide in English · 10:0010:00am time slot

Wine tour at 10:30amGuide in English · 10:30Time slot at 10:30am

Wine tour at 1:30pmGuide in English · 13:301:30pm time slot

You see the exact price of each option when you check availability.See dates & prices

Before you book

Days and timesThursday to SundayDepartures at 10:00, 10:30 and 13:30

Book up to4h before

AgesAdult (21 and older) · Under 21: can't be included in the booking

GroupPrivate

Live guideEnglish

Meeting point and pickupNo hotel pickup: you go to the meeting point. Ends back at the starting point.

Cancellation and refundsFree cancellation up to 24 h before the start. After that, no refund.It may be canceled due to bad weather. If that happens, you're offered another date or a refund.

Prices and times updated yesterday

Good to know

Easy physical levelPets welcomePublic transport nearbyNot for pregnant travelersNot for heart conditions

Operated by Sidecar Tours Inc

Is this one for you?Book the morning departure if you want to start early and have the afternoon free afterward. The 1:30pm option works better if you're sleeping in or arriving later in the day. Either way, the private sidecar means you're not sharing the ride or the guide's attention with other groups.

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Top questions

What happens if it rains?

It may be canceled due to bad weather. If that happens, you're offered another date or a refund. Free cancellation up to 24 h before the start.

What exactly is a tandem sidecar and how does it work on this tour?

A tandem sidecar is a modified motorcycle sidecar built to seat two passengers side by side instead of one behind the driver. You and your companion sit together in the sidecar while the guide operates the motorcycle, taking you between the two wineries and through San Luis Obispo's wine country roads. It's the operator's own design: the world's only two-passenger sidecar setup.

How much wine tasting is included, and what if I don't want to drink?

You receive multiple pours at each of the two partner wineries, tasting their notable or signature selections. Food and additional drinks are available for purchase at both stops if you'd like them. You're welcome to skip tastings or order non-alcoholic options instead.

What time should I plan to be picked up, and where does the tour start?

The tour offers three departure times: 10:00am, 10:30am, or 1:30pm. You'll be picked up from a set starting location. Confirm the exact address when you book. The full experience takes three hours from pickup to return.

Is this tour suitable if I've never ridden in a sidecar before?

Yes, the sidecar is designed for two passengers and requires no experience. Your guide handles all the riding. The tour suits all fitness levels, though it's not recommended for pregnant travelers or those with cardiovascular health concerns. You must be at least 21 years old to participate.