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Sideways Movie Wine Trail: A Self-Guided Driving Tour

5 Reviews 4.60 out of 5 stars Based on 5 reviews collected by Key West Private Charters and TripAdvisor | Santa Barbara, USA
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from $19.99 per group (up to 15)

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Sideways Movie Wine Trail: A Self-Guided Driving Tour Image 1
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Don't miss out!
On average, this is booked 26 (0) days in advance.
90 to 120 minutes (approx.)
Mobile ticket
Offered in: English
Instant confirmation

Overview

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.

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
  • Smartphone and headphones
  • Personal expenses for admission fees not included during the tour
  • Food and drink
See 3 moreSee 4 more

Meeting Location

Meeting point

Alisal Commons Park
Alisal Road, Solvang, CA 93463, USA

Show on Google Maps

Detailed check-in instructions, including the exact address, are provided with your booking confirmation.

End point

610 East Highway 246
Solvang, CA 93463, USA

The tour ends at the Ostrichland USA, East Highway 246, Solvang, CA, USA.

What To Expect

Book Online

Our secure website provides real-time availability, instant confirmation, and free, no-hassle cancellations up to 24 hours before your tour begins.
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Safe & secure Easy breezy Hassle‑free

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.
Read more

Santa Ynez Valley (pass by)

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.
Read more

Brave & Maiden Estate (pass by)

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.
Read more

Kalyra Winery (pass by)

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.
Read more

Beckmen Vineyards (pass by)

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.
Read more

Roblar Winery & Vineyards (pass by)

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.
Read more

Los Olivos Wine Merchant & Cafe (pass by)

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.
Read more

Fess Parker Winery & Vineyard (pass by)

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.
Read more

Andrew Murray Vineyards (pass by)

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.
Read more

Firestone Vineyard (pass by)

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.
Read more

Sideways Inn (pass by)

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.
Read more

Hitching Post 2 (pass by)

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.
Read more
Show 11 more stops

Additional Info

  • Confirmation is instant and will be received at time of booking
  • Suitable for all physical fitness levels
  • The total tour time includes walking the route and passing by the attractions

Frequently Asked Questions (7)

Q: What is the cancellation policy for the Sideways Movie Wine Trail: A Self-Guided Driving Tour?

A: You can cancel up to 24 hours in advance of the tour for a full refund. For a full refund, you must cancel at least 24 hours before the tour start time.If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.Any changes made less than 24 hours before the tour start time will not be accepted.Cut-off times are based on the tour local time (PST). Read more Apr 2025

Cancellation Policy

You can cancel up to 24 hours in advance of the tour for a full refund.

Still have questions?

We're here to help.
Activity code: C-110804P1086

Traveler Photos

Reviews

4.60
5 reviews

Average 4.60 out of 5 stars based on 5 traveler reviews collected by Key West Private Charters and partner sites such as Cool Destinations and TripAdvisor

5 stars
4
4 stars
0
3 stars
1
2 stars
0
1 star
0
Don't miss out!
On average, this is booked 26 (0) days in advance.
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Frequently Asked Questions (7)

Activity name

The answers provided below were previously given in response to questions from Key West Private Charters customers.

Filter by:

Q: What is the cancellation policy for the Sideways Movie Wine Trail: A Self-Guided Driving Tour?
A:
You can cancel up to 24 hours in advance of the tour for a full refund.
  • For a full refund, you must cancel at least 24 hours before the tour start time.
  • If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.
  • Any changes made less than 24 hours before the tour start time will not be accepted.
  • Cut-off times are based on the tour local time (PST).
Apr 2025
Q: What's included in the price?
A:
The following is 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.
  • Directions to the starting point so that when you’re in the right place, the tour will start.
  • Flexibility to explore at your own pace with a self-guided GPS tour.
The following is NOT included:
  • Smartphone and headphones.
  • Personal expenses for admission fees not included during the tour.
  • Food and drink.
  • Transportation.
Apr 2025
Q: What is the minimum age for this tour?
A:

There is no minimum age for this tour, so bring your wee one along for an adventure..

Apr 2025
Q: My date is not available in the calendar, I am just checking to see if it is available?
A:

If a date or time is not listed on the calendar, it’s sold out or unavailable for another reason. Support cannot assist further if a date or time is not on the calendar.

If you find a date and time that works for you, book it NOW because things always sell out at this time of year.

Apr 2025
Q: Is this an accessible tour?
A:

Accessibility information for the Sideways Movie Wine Trail: A Self-Guided Driving Tour is as follows:

  • Suitable for all physical fitness levels
Apr 2025
Q: Where is the meeting point for this activity?
A:

Detailed check-in instructions – including meeting point address, Google map, and parking information – for Sideways Movie Wine Trail: A Self-Guided Driving Tour will be included in your confirmation email from Key West Private Charters. Please be sure to double and triple check your email address is correct at checkout so this important email makes its way to you!

 

 

Mar 2024
Q: How long does a refund take to reach my card, and can I get it faster?
A:

Once your refund is processed, it usually shows on your card statement within 5–10 business days. The exact timing depends on your bank or card issuer.

Want it sooner? When you cancel, choose Receive a refund to my wallet instead. The credit is in your Wallet straight away and is applied automatically at checkout on your next booking when you’re signed in with the same email. You can see your balance any time in My Wallet.

If you paid part of your booking with Wallet credit, that part always goes back to your Wallet. Trip protection isn’t refundable.

Oct 2026

What's Included

Activity name

  • 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
  • Directions to the starting point so that when you’re in the right place, the tour will start
  • Flexibility to explore at your own pace with a self-guided GPS tour
  • Smartphone and headphones
  • Personal expenses for admission fees not included during the tour
  • Food and drink
  • Transportation

Additional Info

Activity name

  • Confirmation is instant and will be received at time of booking
  • Suitable for all physical fitness levels
  • The total tour time includes walking the route and passing by the attractions

Report Product Issue

Activity name