Sideways Movie Wine Trail: A Self-Guided Driving Tour

Highlights

Inclusions

Itinerary

1. 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.

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2. 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.

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3. 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.

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4. 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.

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5. 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.

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6. 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.

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7. 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.

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8. 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.

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9. 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.

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10. 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.

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11. 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.

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12. 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.

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Cancellation

Free cancellation up to 24 hours before the experience starts, for a full refund.

Reviews

Ratings come from 5 reviews collected by our booking partner. They are travellers' own words, in the order they were written — never reordered to flatter the experience.

Know before you go

How it compares in Santa Barbara

• Its from-price is 84% below the median of the 153 experiences we list in Santa Barbara.
• It is shorter than most of them.
• By number of reviews it ranks 86 of 153.
• The operator lists free cancellation on it.

About Santa Barbara

Santa Barbara is a Spanish-style city on California's central coast, set between the Pacific and the Santa Ynez Mountains.

Santa Barbara sits on a south-facing shore with the Santa Ynez Mountains rising right behind it. After an earthquake in 1925, the city rebuilt in a uniform Spanish Colonial Revival style, with white walls, red tile roofs and arches, and the County Courthouse, with its clock tower and mural room, is a showpiece of the style. Old Mission Santa Barbara, founded in 1786 and known as the Queen of the Missions, stands on a hillside above town.

Top-ranked sights in Santa Barbara: Santa Barbara Waterfront, Santa Barbara County Courthouse, Stearns Wharf.

See all 153 experiences in Santa Barbara