Sideways Movie Wine Trail: A Self-Guided Driving Tour

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.

1. 1

   Old Mission Santa Ines

   Pass by

   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.

2. 2

   Santa Ynez Valley

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   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.

3. 3

   Brave & Maiden Estate

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   Pass by what was famously spotted in the Sideways film as “like something out of a wine country daydream.” Appointment-only tastings offer visitors acclaimed Cabernet and Syrah, sustainable practices, and a scenic, intimate estate experience. Personal expenses for admission fees not included during the tour.

4. 4

   Kalyra Winery

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   Catch a glimpse of Kalyra Winery, featured in the film Sideways, in the playful Jack-and-Stephanie flirtation scene, nestled among grapevines in the Santa Ynez Valley. The original tasting room is closed, but visitors can enjoy wine at their Buellton location. Personal expenses for admission fees not included during the tour.

5. 5

   Stop 5

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   Drive by a standout in the Santa Ynez Valley, celebrated for its biodynamic vineyards and bold Syrah and Grenache. Visitors can savor tastings amid rolling hills and breathtaking vineyard vistas. Personal expenses for admission fees not included during the tour.

6. 6

   Roblar Winery & Vineyards

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   Pass by forty acres of oak-studded splendor, producing Cabernet, Merlot, and a full Bordeaux chorus. Visitors can enjoy tastings, farm-to-table dining, and panoramic vineyard views daily. Personal expenses for admission fees not included during the tour.

7. 7

   Stop 7

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   Drive by what became legendary thanks to the film "Sideways", where Miles’ “I am NOT drinking any f**ing Merlot!” made Pinot Noir famous. Visitors can stroll this charming strip, enjoy award-winning tasting rooms like Brewer-Clifton and Stolpman Vineyards, and savor curated wine flights in a walkable, wine-loving destination. Personal expenses for admission fees not included during the tour.

8. 8

   Fess Parker Winery & Vineyard

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   Founded in 1989 by the actor famed for Daniel Boone and Davey Crockett, pass by and learn how it gained Sideways fame as “Frass Canyon.” Known for estate-grown Rhône and Burgundian varietals, it offers daily tastings, scenic verandas, picnic spots, and authentic Santa Barbara hospitality, making it a must-visit wine-country destination. Personal expenses for admission fees not included during the tour.

9. 9

   Andrew Murray Vineyards

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   Drive by a standout on the Foxen Wine Trail, celebrated for Rhône varietals like Syrah and Grenache. Known for hands-on, sustainable winemaking and expressive, high-scoring wines, it welcomes walk-ins and appointments, offering visitors a vibrant Santa Ynez experience and a taste of innovative California wine craftsmanship. Personal expenses for admission fees not included during the tour.

10. 10

    Firestone Vineyard

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    Drive by another winery featured in Sideways, where Miles, Jack, Maya, and Stephanie sneak out of a dull lecture for a romantic, candlelit barrel-room stroll. Visitors can enjoy daily tastings of estate-grown Cabernet, Merlot, and Chardonnay, plus private tours, barrel sneak peeks, and food pairings in a stunning Santa Ynez setting. Personal expenses for admission fees not included during the tour.

11. 11

    Stop 11

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    Pass by The Sideways Inn, Buellton’s Days Inn reborn, a cinematic shrine where Miles and Jack checked in during "Sideways". Room 234 and the windmill are iconic, drawing fans eager to relive Pinot-soaked moments, just steps from the legendary Hitching Post II, where Merlot disdain became wine-country legend. Personal expenses for admission fees not included during the tour.

12. 12

    Stop 12

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    Pass by one of the twin temples of Sideways debauchery and charm, a wood-paneled paradise of oak-grilled meats and Pinot-fueled revelations, capturing both the humor and heart of Sideways. Personal expenses for admission fees not included during the tour.

• Suitable for all physical fitness levels
• The total tour time includes walking the route and passing by the attractions

For a full refund, cancel at least 24 hours before the scheduled departure time.