Sideways Movie Wine Trail: A Self-Guided Driving Tour
Overview
Available languages
Mobile ticket
California’s Santa Ynez Valley, made famous by the film Sideways (2004), is a scenic wine region and film pilgrimage site. On this 90-minute self-guided driving tour, explore iconic movie locations, award-winning vineyards, and charming towns. Highlights include:
• Learn about the “Sideways Effect” on Pinot Noir and Merlot
• Discover five distinct wine trails, including Foxen Canyon and Los Olivos Promenade
• Visit Los Olivos Wine Merchant & Café and the Firestone Vineyard barrel room
• Explore biodynamic, sustainable wineries producing estate wines
• See which wineries earned gold and platinum medals for quality and accessibility
• Discover rich local history, from Spanish missions to celebrity residents
A perfect mix of cinematic nostalgia and wine-country discovery.
Additional Info
Suitable for all physical fitness levels
The total tour time includes walking the route and passing by the attractions
What To Expect
Old Mission Santa Ines
Founded in 1804, pass by one of California’s 21 Spanish missions, showcasing colonial architecture, Franciscan heritage, and Chumash culture amid the scenic Santa Ynez Valley.
Santa Ynez Valley
Drive along the pristine Santa Ynez Valley AVA, famed for its rolling vineyards, Pinot Noir and the 2004 film Sideways, which boosted the region’s global wine reputation.
Options
Sideways Movie Wine Trail: A Self-Guided Driving Tour
What‘s Included
Lifetime access to this tour in English before your booking date and after it
Offline access to audio, maps, and geodata
App for Android and iOS
Flexibility to explore at your own pace with a self-guided GPS tour
Directions to the starting point so that when you’re in the right place, the tour will start
Smartphone and headphones
Personal expenses for admission fees not included during the tour
Food and drink
Transportation
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
Reviews
4 reviews
Total reviews and rating from Viator & Tripadvisor
Sideways tour was totally satisfying, interesting and informational!
I2415RTmaureenm,May 8, 2026
- Review from Tripadvisor
5.00I recently went on the Sideways tour with Tour Freely to the Santa Ynez Valley. It was truly an experience. We visited and or drove by the key filming locations of the Sideways movie, including Buellton, Solvang and Los Olivos. We learned about the history of entire area including the Mission of Santa Ynez, the history of the Chumash and their rich relationship to the area. We drove through the unique town of Los Olivos, where there are numerous shops and wonderful restaurants. We discovered that many well-known actors live in the Santa Ynez Valley. The guide was very well moderated giving superb information about the wineries of the area. We learned quite a lot about choosing a superb wine. I would highly recommend this tour.
A highly recommended tour!
richardlX9233LU,May 1, 2026
- Review from Tripadvisor
5.00This Sideways movie tour is a unique experience because it lets you relive the movie nostalgia while giving the listener thoughtful insider guidance along the way. It feels like a choose-your-own adventure through the bucolic vineyards. I especially liked learning about the wineries as they were being rated by the narrators. It made the day more fun and "intentional." The GPS storytelling, the stops, the pacing was thoughtfully arranged. If you seek a way to explore Santa Barbara wine country- This is it! Rick
Santa Ynez Sideways Experience!
B9025BDgeorgek,Apr 14, 2026
- Review from Tripadvisor
5.00What a great way to relive and experience the destinations from the movie Sideways! We had a beautiful day for our Santa Ynez trip and made several stops to explore the sites as well as sample some exquisite wines. It was fun to see the sites where the movie was filmed as well as other points of interest such as the beautiful Mission Santa Ines. Mindy and Jerry did a fantastic job of giving us background information and insights along the route. Such a pleasurable trip and Tour Freely made it a great day for us! Thank you Mindy and Jerry!
No Fing Merlot!
gustavooS3585BU,Jan 3, 2026
- Review from Tripadvisor
5.00As a Sideways fan, I had high expectations, and this tour honestly exceeded them. It captures the vibe of the movie really well but also goes much deeper into the Santa Ynez Valley, the wineries, and what makes the region special. It felt like having a knowledgeable friend riding along, pointing things out and sharing context as we went. The winery ratings were on point and made choosing stops easy. Fun, informative, and a great way to experience the area.
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Operated by VoiceMap Audio Tours