If you’re searching for a distinctive way to savor the sights, tastes, and stories of San Luis Obispo’s wine region, this private sidecar winery tour offers a memorable twist. Unlike standard wine tastings or cycling adventures, this experience combines the thrill of riding in a tandem sidecar with the sophisticated pleasure of tasting local wines, all amidst stunning scenery. It’s a rare mix of fun, elegance, and adventure that appeals to those eager for something beyond the usual.
What we particularly like about this tour is its personalized nature and the way it elevates the wine tasting experience with a dash of excitement. The customized tandem sidecar—the world’s first of its kind—bridges the gap between adventure-seeking and wine lover. Plus, the knowledgeable drivers are passionate about sharing the region’s culture and stories, making each stop more meaningful.
However, a potential consideration is the weather dependency—since the experience is outdoors and relies on good weather, your plans could be affected by rain or wind. That said, the tour provider offers options for rescheduling or full refunds if weather conditions turn unfriendly.
This tour is perfect for adventurous couples on a date night, wine enthusiasts seeking a different tasting experience, or anyone wanting to combine scenic views with a touch of thrill. If you’re up for something memorable, fun, and intimate, this tour might just be your ideal San Luis Obispo outing.
Key Points

- Unique Transportation: First and only tandem sidecars in the world, providing a memorable riding experience.
- Personalized & Private: Only your group participates, ensuring an intimate adventure.
- Scenic & Educational: Enjoy beautiful views and learn about San Luis Obispo’s culture and wine region.
- Two Quality Stops: Visits to Claiborne & Churchill and Saucelito Canyon wineries, with tastings included.
- Flexible & Refundable: Free cancellation up to 24 hours in advance.
- Value for Money: At $215 per person, it offers a distinctive experience blending adventure with wine tasting.
The Experience: A Closer Look
You can also read our reviews of more private tours in Pismo Beach
Starting Point and Duration
The tour begins at 1947 See Canyon Rd, San Luis Obispo, where your private group will meet the driver. The whole adventure lasts roughly 3 hours, making it an ideal half-day activity. Since it is a private tour, only your group will be on board, allowing for a tailored experience and the opportunity to ask questions or customize the stop time if needed.
The Ride in the Tandem Sidecar
What sets this tour apart is the tandem sidecar, a modified motorcycle seat built for two. Riding behind the driver, you’ll experience a sense of freedom and connection that’s hard to replicate in a car or bus. The driver’s patience and skill are often praised—one reviewer called the driver “interesting and fun,” emphasizing safety and enjoyment.
The views from the sidecar are another highlight. You’ll pass through well-known landmarks and hidden gems of San Luis Obispo, making the journey as scenic as the stops. The open air and panoramic vistas make each turn and stretch of road more exciting.
Winery Stop 1: Claiborne & Churchill
The first winery, Claiborne & Churchill, offers a relaxed environment perfect for tasting their notable wines. The tour includes multiple tastings within the winery’s tasting room, giving you a chance to compare and enjoy different varietals. The hosts are knowledgeable, and the tasting is designed to showcase the winery’s best.
The included admission ticket means you won’t have to pay extra for tasting fees, and you’re free to linger or explore the area—perhaps grab a snack or a glass of wine outside, if you choose.
Winery Stop 2: Saucelito Canyon
Next, the tour takes you to Saucelito Canyon, another highly regarded winery. Here, you’ll be shown around by staff and offered more signature wines to sample. This stop is slightly longer—around 30 minutes—giving you a good amount of time to relax, enjoy the setting, and perhaps buy a bottle or two to take home.
The breath-taking views between stops are a true highlight, providing perfect photo opportunities and a chance to appreciate the landscape’s natural beauty. One reviewer noted that the ride itself was “FUN,” adding a memorable layer to the tasting experience.
You can also read our reviews of more wine tours in Pismo Beach
Additional Considerations
While snacks are not included, the tour allows you to bring your own food or purchase snacks at the winery. Since alcoholic beverages are not included in the price, you’ll want to plan accordingly if you wish to indulge more extensively.
Weather can impact the experience, so checking the forecast is wise. The provider offers full refunds or rescheduling if poor weather forces cancellations, which is reassuring given the outdoor nature of the tour.
Value and Practicality

At $215 per person, this tour offers a combination of adventure, culture, and wine that’s hard to find elsewhere in the region. When you consider the private transportation, guided stops, and the novelty of the tandem sidecar ride, the price is quite reasonable. It’s an experience that’s more than just a wine tour—it’s a story you’ll tell afterward.
For wine lovers, it’s a chance to taste some excellent wines in a setting that elevates the usual tasting room visit. The scenic rides add an element of excitement and allow for a different perspective on the vineyards and countryside.
Authentic Experience
The fact that this is a private tour enhances the feeling of exclusivity and comfort. You won’t be part of a large group, and your driver can tailor the experience slightly if desired. Plus, the local guides are passionate about San Luis Obispo, making their commentary engaging and informative.
Who Might Not Love It
If you’re not comfortable outdoors or dislike riding in open air, this might not be your best choice. Also, if you’re hoping for a full meal or extensive wine tasting, you’ll need to plan on supplementing this tour with your own snacks or additional wine stops.
The Sum Up: Who Will Love This Tour?

This private sidecar winery tour is perfect for those who want to combine a sense of adventure with sophisticated wine tasting. It’s especially suited for couples looking for a fun date night, small groups eager to experience something new, or anyone craving a scenic, active way to explore San Luis Obispo’s wine country.
The stunning views, excellent wine selection, and personalized experience make it a compelling choice for travelers wanting more than just a typical wine tasting. If you’re up for a bit of adrenaline and a lot of flavor, this tour delivers on both fronts.
The value lies in its uniqueness—this isn’t just a ride or a tasting, but a memorable story to share and a new way to see California’s Central Coast. Just remember to check the weather forecast, arrive ready for fun, and prepare to leave with stories and perhaps a few bottles of local wine.
FAQ

Is this tour suitable for all ages?
While most travelers can participate, it’s designed for those comfortable with outdoor riding, and children might need to be older depending on height and safety considerations.
How long is the entire experience?
The tour lasts about 3 hours, which includes transportation, winery visits, and tasting time.
Are the winery visits included in the price?
Yes, the admission tickets and tastings at both wineries are included in the price.
What should I wear?
Dress comfortably for outdoor riding. Layers are recommended, especially if the weather is cooler or windier.
Can I bring snacks or food?
Snacks are not provided, but you’re welcome to bring your own or purchase food at the wineries.
Is alcohol included in the tour?
No, alcohol is not included—tastings are paid for separately at the wineries.
What if the weather turns bad?
The tour provider offers full refunds or rescheduling if canceled due to poor weather.
How many people can join?
This is a private tour, so only your group will participate, typically accommodating 2-4 people comfortably.
Can I customize the stops or experience?
Since it’s a private tour, you may be able to discuss preferred timing or additional stops with your driver.
This innovative tour blends scenic beauty, wine tasting, and a dash of adrenaline—perfect for travelers seeking a more lively, engaging way to explore San Luis Obispo’s wine country.
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