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Discover the Santa Ynez Valley on a 5-star Sideways movie-inspired wine tour, visiting 4 wineries, filming locations, and the Ostrich Farm with tastings and lunch.

This 8-hour guided tour offers a chance to follow the famous Sideways wine trail through the Santa Ynez Valley. Priced at $295 per person, it is perfect for those interested in wine, film history, and scenic vineyard views. The tour is led by a small group of up to 8 participants, ensuring a personalized experience with a knowledgeable live guide in English.
Starting from Santa Barbara, the tour takes you through the landscapes and locations that made the movie Sideways memorable. You visit 4 wineries featured in the film, enjoy tastings at 2 of these sites, and stop at notable filming locations. A highlight is the lunch break at the Wine Merchant, where the characters’ first double date took place. An added fun stop is the Ostrich Farm, where Jack was famously chased in the movie.
This tour is a well-rounded mix of wine tasting, movie trivia, and scenic beauty. It’s an ideal choice for fans of the film, wine enthusiasts, or those seeking a relaxed, informative day in a beautiful vineyard setting. The full refund policy if you cancel 24 hours in advance and the option to reserve now and pay later make planning flexible.
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The core of this tour is tracing the famous wine trail from the film Sideways. Travelers explore the scenic vineyards and learn how the movie’s locations influenced real-world tourism in the Santa Ynez Valley. With visits to 4 specific wineries, the tour offers wine tastings at 2 of them, giving a taste of the region’s renowned wines.
The guide shares insights and trivia about the film’s production and scenery, enriching the experience with behind-the-scenes stories. The film locations are carefully selected, allowing a visual connection to the movie’s narrative. The tour’s pacing keeps it engaging without feeling rushed, making it ideal for a leisurely day out.

The four wineries on this tour are integral to the movie’s storyline. While the specific names aren’t provided, the guided visits focus on the vineyards and tasting rooms that appeared on screen. Expect to sample local wines and hear about the region’s winemaking traditions from knowledgeable staff.
The tastings at 2 wineries give a good sense of the varieties and quality of Santa Ynez wines. These stops are well-paced, allowing ample time to enjoy the views, ask questions, and understand the winemaking process. The tour emphasizes learning about the wine trail’s significance in the film’s plot.

Beyond wine tasting, the tour stops at key filming sites from the movie. These include locations where memorable scenes were shot, providing a visual link to the story of Miles, Jack, and the others. The guide explains the film’s connection to each site, bringing the scenes to life.
One notable stop is the Ostrich Farm, where Jack was chased in a comedic scene. Visitors get to see the farm up close, adding a playful element to the day. These locations offer great photo opportunities and deepen the connection between the film and the landscape.
More Great Tours NearbyA highlight of this tour is the lunch stop at the Wine Merchant. This historic spot is where Jack, Stephanie, Miles, and Maya shared their first double date in the movie. The setting is casual and charming, allowing participants to enjoy a meal of their choice (lunch is not included in the tour price).
This break offers a relaxed atmosphere to discuss the film, reflect on the morning’s visits, and savor local food and wine. It’s a perfect midday pause amid vineyards, adding a personal touch to the overall experience.

The tour’s unique stop at the Ostrich Farm is a fun highlight. Visitors see first-hand where Jack was chased by ostriches in the movie, adding a humorous twist to the day. This stop offers a lighthearted contrast to the wine tastings and scenic vineyard views.
The farm visit is brief but memorable, and provides additional photo opportunities and insights into the movie’s playful side. It’s suitable for anyone interested in quirky attractions and film-related fun.
The tour starts with a hotel pickup in Santa Barbara, making it accessible for visitors staying in that area. The small group size of up to 8 participants ensures a more intimate experience, with flexible interaction and personalized attention from the guide.
Participants should bring comfortable shoes, a sun hat, camera, sunscreen, and water for the day. Drinks are not allowed in the vehicle, so plan accordingly. The tour operates with a live English-speaking guide and offers full flexibility with reserve & pay later options.

This experience is best suited for film fans, especially those who love Sideways, as well as wine enthusiasts eager to explore Santa Ynez’s vineyards. It suits travelers seeking a relaxed, educational, and scenic day out with plenty of photo ops and fun trivia.
The 8-hour duration balances sightseeing, tastings, and stops comfortably. The capped group size enhances the experience, making it ideal for small groups or couples. It’s less suitable for children under 18 due to the focus on wineries and adult tastings.

The Santa Ynez Valley: Sideways Movie Inspired Wine Tour offers a rich blend of cinema history, vineyard visits, and scenic beauty. For $295, it provides tastings at two wineries, visits to film locations, and a chance to see the Ostrich Farm, all led by a knowledgeable guide in a small-group setting.
While lunch is not included, the opportunity to choose your own meal at the Wine Merchant adds flexibility. The tour’s focus on film fans and wine lovers makes it a distinctive experience that combines pop culture with regional viticulture.
This tour is a great pick for those wanting a personalized, fun, and scenic day exploring the famous wine trail from the movie Sideways. Its small group format and flexible cancellation policy make it a practical option for planning a memorable outing in Santa Ynez.
How long is the Sideways wine tour?
The tour lasts 8 hours, providing ample time for visits, tastings, and sightseeing.
What is the price of the tour?
It costs $295 per person, including tastings at 2 wineries and the Ostrich Farm visit.
Are lunch or drinks included?
Lunch is not included, giving you the freedom to dine at the Wine Merchant. Drinks in the vehicle are not allowed.
How many wineries will I visit?
You will visit 4 wineries, with tastings at 2 of them.
Is this tour suitable for children?
No, children under 18 are not recommended, as the focus is on wine tastings and adult activities.
What makes this tour unique?
The tour’s focus on film locations from Sideways, combined with visits to famous vineyards and a quirky Ostrich Farm, creates a memorable themed experience.
Is there a cancellation policy?
Yes, you can cancel up to 24 hours in advance for a full refund.
Do I need to prepare anything for the tour?
Bring comfortable shoes, a sun hat, camera, sunscreen, and water for comfort and safety during the day.
What language is the tour conducted in?
The tour is conducted in English.