Private Sidecar Winery Tour through San Luis Obispo - Exploring Claiborne & Churchill Winery

Private Sidecar Winery Tour through San Luis Obispo

Experience San Luis Obispo’s vineyards on a private tandem sidecar tour for $215, including wine tastings, stunning views, and personalized service in just 3 hours.

Discover the Unique Private Sidecar Winery Tour in San Luis Obispo

Private Sidecar Winery Tour through San Luis Obispo - Discover the Unique Private Sidecar Winery Tour in San Luis Obispo

The Private Sidecar Winery Tour through San Luis Obispo offers a fresh way to explore California’s famous wine country. Priced at $215 per person, this 3-hour adventure takes you on a ride in one-of-a-kind tandem sidecars modified for comfort and fun. Departing from Pismo Beach, it’s a private experience led by knowledgeable drivers eager to share the region’s culture, scenery, and wines.

What makes this tour stand out is the combination of adventure and intimacy. You get to feel the thrill of riding in a motorcycle sidecar while enjoying visits to two celebrated wineries. Perfect for those seeking a more personal, engaging wine tour, this experience promises beautiful views, delicious tastings, and a touch of excitement on the backroads.

While the tour does not include snacks or alcohol, it offers a stunning route, exclusive access, and the chance to relax between stops. The private nature of this adventure ensures a tailored experience, making it ideal for couples or small groups wanting something different from traditional wine tours.

Key Points

  • Private, personalized experience in a tandem sidecar with knowledgeable drivers
  • Two winery stops: Claiborne & Churchill Winery and Saucelito Canyon
  • Includes wine tastings at both wineries, with plenty of time to relax or explore
  • Stunning views of San Luis Obispo’s backroads and landmarks
  • Duration of 3 hours, starting from 1947 See Canyon Rd in San Luis Obispo
  • No meals or alcohol included, but food and drinks can be purchased at stops

The Charm of Riding in a Tandem Sidecar Through San Luis Obispo

Private Sidecar Winery Tour through San Luis Obispo - The Charm of Riding in a Tandem Sidecar Through San Luis Obispo

This tour features the world’s first and only tandem sidecars, specially modified to carry two passengers comfortably. The drive is led by skilled drivers who prioritize safety while making the ride a fun and memorable experience. The patience and enthusiasm of the driver are often highlighted as major positives, ensuring a smooth ride through scenic areas.

The ride itself offers beautiful views of the countryside and landmarks, combining the thrill of a motorcycle with a relaxed sightseeing experience. The tandem configuration allows both passengers to enjoy the scenery and the driver’s commentary, making it an engaging way to see San Luis Obispo.

Exploring Claiborne & Churchill Winery

Private Sidecar Winery Tour through San Luis Obispo - Exploring Claiborne & Churchill Winery

The first stop on this tour is Claiborne & Churchill Winery, a well-known spot where guests are taken to a dedicated tasting room. Here, multiple tastings of the winery’s notable wines are served, with ample time to savor the flavors and enjoy the relaxed atmosphere. This winery is appreciated for its well-curated selection and the chance to explore well-known and hidden landmarks en route.

Guests have the opportunity to purchase additional food or drinks if desired, allowing for a flexible experience. The 45-minute duration at this stop provides enough time to soak in the surroundings and get a feel for the local wine scene.

Discovering Saucelito Canyon and Its Signature Wines

Private Sidecar Winery Tour through San Luis Obispo - Discovering Saucelito Canyon and Its Signature Wines

The second stop is Saucelito Canyon, another standout winery with a reputation for its signature wine selection. The scenic drive between the two wineries adds to the overall enjoyment, offering more breathtaking views and the excitement of riding in the tandem sidecar.

At Saucelito Canyon, visitors are shown around by the winery staff and enjoy an additional tasting session. The 30-minute visit is designed to allow guests to relax, sample more wines, and take in the peaceful vineyard environment. This stop complements the first by offering a different style of wine and a chance to unwind.

Logistics of the San Luis Obispo Sidecar Tour

Private Sidecar Winery Tour through San Luis Obispo - Logistics of the San Luis Obispo Sidecar Tour

The tour starts at 1947 See Canyon Rd in San Luis Obispo, with private transportation guiding the entire experience. The group size is limited to your private booking, ensuring a more personal atmosphere. The tour ends back at the starting point, making planning straightforward.

Participants should note that service animals are allowed, and the tour is accessible to most travelers, provided weather conditions are suitable. Since the experience relies on good weather, cancellations due to poor weather are fully refundable or can be rescheduled.

The Experience of the Driver and Guide

Private Sidecar Winery Tour through San Luis Obispo - The Experience of the Driver and Guide

The driver plays a key role in making this tour special. With a focus on safety, patience, and fun, the driver maintains a skillful ride that balances excitement and comfort. The interesting and friendly attitude of the guide enhances the journey, making it feel more like a personal adventure than just transportation.

Many reviews praise the driver’s professionalism and the enjoyable nature of the ride, with some noting it as well worth the adventure. The excitement of riding in a sidecar is a highlight, especially for first-timers or those seeking a different perspective on wine country.

Booking, Duration, and Cost Considerations

Private Sidecar Winery Tour through San Luis Obispo - Booking, Duration, and Cost Considerations

This private tour is typically booked 24 days in advance, reflecting its popularity. The cost of $215 per person covers all transportation and tastings at two wineries, making it a good value for the unique experience offered.

The duration of approximately 3 hours fits well into a day of sightseeing or relaxation, with enough time allocated for each stop and the ride itself. Since no meals or alcohol are included, visitors might want to plan to purchase additional food or drinks at the winery stops.

Weather Policies and Cancellation Options

Private Sidecar Winery Tour through San Luis Obispo - Weather Policies and Cancellation Options

The tour requires good weather for the ride, which is essential for safety and enjoyment. If canceled due to weather, full refunds are available, or rescheduling is possible. Cancellation must be made at least 24 hours in advance to qualify for a full refund, emphasizing flexibility and customer service.

Who Will Appreciate This Tour Most?

This experience appeals to wine lovers seeking something different, adventure enthusiasts, and those who value privacy and personalized service. It’s especially suited for small groups or couples who want a romantic or fun outing with a touch of adrenaline.

The scenic views, delicious wines, and friendly driver create a relaxed yet exciting atmosphere. It’s perfect for those who appreciate stunning landscapes, good wine, and a unique travel experience.

Private Sidecar Winery Tour in San Luis Obispo: Worth It?

The combination of scenic rides, exclusive winery access, and private transportation makes this tour a standout option. The custom tandem sidecars add a sense of novelty, and the wine tastings at Claiborne & Churchill and Saucelito Canyon are high-quality and thoughtfully arranged.

The 3-hour duration strikes a good balance between adventure and relaxation, and the private setting ensures a tailored experience. While it does not include food or alcohol, the flexibility to purchase at stops complements the overall experience.

This tour offers a fun, intimate way to explore San Luis Obispo’s wine country, ideal for small groups, couples, or anyone looking to combine scenic riding with wine tasting.

Ready to Book?

Private Sidecar Winery Tour through San Luis Obispo



5.0

100% 5-star

“Well worth the adventure. My first ride in a side car. One could see the same property in a car but I wanted the experience in a side car. FUN! Dri…”

— A Tripadvisor Reviewer, Oct 2025

Frequently Asked Questions

Is this tour suitable for people who don’t ride motorcycles?
Yes, as the experience involves riding in a tandem sidecar, it’s accessible for those comfortable with motorcycle rides, but no special riding skills are required.

How many wineries are visited during the tour?
The tour visits two wineries: Claiborne & Churchill Winery and Saucelito Canyon.

Are meals provided during the tour?
No, the tour does not include meals or snacks, but guests can buy food or additional drinks at the winery stops.

What is the cancellation policy?
Cancellations made at least 24 hours in advance are fully refunded. Cancellations less than 24 hours before the start are non-refundable.

Is the tour accessible for most travelers?
Yes, it’s suitable for most travelers, and service animals are allowed. The experience depends on good weather conditions.

How far in advance should I book?
The tour is typically booked about 24 days in advance, due to its popularity and limited availability.