Sideways Movie Wine Trail: A Self-Guided Driving Tour
Pick your date
Highlighted days have spots open. Grey days are sold out or not running.
September 2026
Loading live availability
Who is going?
Adults
Age 13 and over
Children
Age 12 and under
Select a highlighted day to see live departure times and the exact price for your group.
Free cancellation up to 24 hours before. Same price on Viator, Outty earns a commission.
Traveler rating
4.6/5
Based on 5 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Sideways Movie Wine Trail: A Self-Guided Driving Tour worth booking?
Sideways Movie Wine Trail: A Self-Guided Driving Tour is a 1.5-hour experience in Santa Barbara, United States, from $20 per person. It scores 65 out of 100 on the Outty Ranking, which we label “Solid Choice”, based on a 4.6/5 rating across 5 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 65 / 100
- Rating
- 4.6/5 (5)
- Duration
- 1.5 hours
- From
- $20 per person
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 vineyar
What you get
About this experience
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
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
Not included
- Smartphone and headphones
- Personal expenses for admission fees not included during the tour
- Food and drink
- Transportation
What you'll see and do
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.
Pass by without stopping
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.
Pass by without stopping
Brave & Maiden Estate
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.
Pass by without stopping
Kalyra Winery
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.
Pass by without stopping
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.
Pass by without stopping
Roblar Winery & Vineyards
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.
Pass by without stopping
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.
Pass by without stopping
Fess Parker Winery & Vineyard
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.
Pass by without stopping
Andrew Murray Vineyards
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.
Pass by without stopping
Firestone Vineyard
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.
Pass by without stopping
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.
Pass by without stopping
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.
Pass by without stopping
Where it starts and ends
Meeting point
Santa Barbara
The tour starts by the River Course at Alisal, on the corner of Juniper Drive and Alisal Road, under the California pepper tree. Before arrival, please install the mobile app and use the code provided on your confirmation ticket. Detailed starting point instructions are available after downloading
Hotel pickup
No pickup: everyone meets at the start point.
Ends at
The tour ends at the Ostrichland USA, East Highway 246, Solvang, CA, USA.
Before you book
- Cancellation
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Languages
- en
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 15 travelers per booking
- Operated by
- VoiceMap Audio Tours
Know before you go
- Suitable for all physical fitness levels
- The total tour time includes walking the route and passing by the attractions
Photos
What travelers are saying
Outty’s summary of the themes that recur across 5 traveler reviews. Written by us, not quoted from reviewers.
Knowledge and storytelling
3 mentionsReviewers describe the commentary as informative rather than scripted.
Food and drink
3 mentionsThe tastings and food stops are a highlight for most reviewers.
The guide
1 mentionTravelers single out the guide as the reason the experience works.
Traveler reviews
5 verified traveler reviews for Sideways Movie Wine Trail: A Self-Guided Driving Tour. Ratings and reviews provided by Viator and Tripadvisor.
Sideways??
Well you’re in wine country so that’s a real plus. But this should not have been called Sideways the wine tour, should’ve been called a the great wine trail with a few spots from Sideways the movie. Had rewatched the movie recently and they could’ve put additional places on the tour. We love wine but we are big fans of the movie and thought this tour should be called something else.
Response from the operator: Hi there, I'm sorry that the content wasn't as informative as you hoped. We will review the tour content and see where updates and improvements may be needed. Thank you for your honest feedback, as this helps us ensure that tour content remains valuable and that improvements can be made over time. Best, Helene
via Viator
Sideways tour was totally satisfying, interesting and informational!
I 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.
via Tripadvisor
A highly recommended tour!
This 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
via Tripadvisor
Santa Ynez Sideways Experience!
What 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!
via Tripadvisor
No Fing Merlot!
As 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.
via Tripadvisor
Good to know
- Duration
- 1.5 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Every day
- Hotel pickup
- No pickup, meet at start point
- Booked in 30 days
- 2
- Verdict
- Solid Choice
Why this scores 65
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Sideways Movie Wine Trail: A Self-Guided Driving Tour: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Santa Barbara.
How much does Sideways Movie Wine Trail: A Self-Guided Driving Tour cost?
+
Prices start at $20 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Santa Barbara usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.
How long does Sideways Movie Wine Trail: A Self-Guided Driving Tour take?
+
Plan for about 1.5 hours from start to finish, not counting travel to the meeting point. Most travelers leave another 30 minutes on either side so the rest of the day in Santa Barbara is not rushed.
Is Sideways Movie Wine Trail: A Self-Guided Driving Tour worth it?
+
It holds an Outty Ranking of 65 out of 100, which we label "Solid Choice". That score blends traveler sentiment (4.6/5 across 5 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in Santa Barbara, and how flexible the cancellation terms are.
Can I cancel or reschedule Sideways Movie Wine Trail: A Self-Guided Driving Tour?
+
Yes. Cancel free up to 24 hours before the start time for a full refund. Inside that window the booking is non-refundable, and no-shows are not refunded.
Is Sideways Movie Wine Trail: A Self-Guided Driving Tour suitable for kids and families?
+
Yes, all ages are welcome. Families should still weigh the 1.5-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book Sideways Movie Wine Trail: A Self-Guided Driving Tour?
+
Around 2 people booked this in the last 30 days, so popular slots go early. Two to three weeks ahead is comfortable in shoulder season, while summer weekends and holidays in Santa Barbara can sell out a month out. Same-day spots do open up when other travelers cancel, so it is worth checking if you are already in town.
What should I bring or wear?
+
Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in Santa Barbara and add a light layer if any part of the 1.5-hour experience runs outdoors or after sunset.
Where does Sideways Movie Wine Trail: A Self-Guided Driving Tour start and how do I get there?
+
The exact meeting point and directions are on your voucher once you book, and they sit in central Santa Barbara within reach of public transport. Arrive 15 minutes early: late arrivals are treated as no-shows by most operators.
What are the best things to do in Santa Barbara?
+
Santa Barbara runs wine tours into the Santa Ynez Valley, harbour sailing and whale watching, Channel Islands day trips, and Spanish colonial walking tours through the Presidio and Mission. Tasting-room access and group size make the biggest difference in wine tours here. On Outty we rank every Santa Barbara experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include Santa Barbara Electric Bike Tour, Kayak Tour of Santa Barbara with Experienced Guide, Small-Group Wine Tour in Santa Barbara to Exclusive Vineyards. The city page groups everything into most popular, highest reviewed, last minute and family-friendly so you can build a day around what actually delivers.
When is the best time to visit Santa Barbara?
+
March to June and September to November, dodging the May and June marine layer. Booking patterns follow the same curve: prices and queues climb in peak weeks, while shoulder season gives you better availability on the top-ranked experiences and more room to change plans.
How many days do you need in Santa Barbara?
+
Three full days covers the headline sights without sprinting. A workable rhythm is one anchor experience each morning, such as this one, an unhurried afternoon in a single neighborhood, then a food or nightlife booking in the evening. Five days lets you add a day trip outside the city.
Do I book through Outty or through the operator?
+
Outty ranks and explains the experiences, then hands you to Viator to complete the booking with the operator directly. The price is the same as booking on Viator yourself, and Outty earns an affiliate commission on the referral, which is how the rankings stay free to read.
Ready to lock in your spot?
Pick a date, choose your group, and see the exact price for Sideways Movie Wine Trail: A Self-Guided Driving Tour.
Pick your date
