The Sideways Wine Trail Tour: Uncork the Movie, Sip the Magic

(5 reviews)

Santa Barbara, California audio tour: The Sideways Wine Trail Tour: Uncork the Movie, Sip the Magic

This is a 30.5mi driving tour

It takes an average of 90 mins to complete.

Santa Barbara, California

The United States

$19.99

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About the Tour

California’s Santa Ynez Valley is more than just beautiful scenery. It’s the bucolic wine region that was catapulted to fame after the 2004 film Sideways made it a pilgrimage site for wine enthusiasts. On this self-guided driving tour, you’ll journey through the valley’s diverse microclimates and distinctive wine trails to visit iconic movie locations that made Pinot Noir sexy and Merlot infamous.

The tour starts near the Santa Ynez River at the bridge by the River Course at Alisal – the site of the golf ball battle where Miles and Jack’s tempers flared in the film. You’ll wind through quaint towns and along scenic routes, passing Mission Santa Ynez and the Chumash Reservation before. You’ll have a chance to explore Los Olivos, with its charming Victorian storefronts and range of tasting rooms. Along the way, you’ll discover how the valley’s unique east-west orientation creates perfect conditions for a remarkable variety of wine grapes.

You’ll visit renowned vineyards including Fess Parker (which appeared as “Frass Canyon” in the movie), where Miles famously downed the spit bucket in one cringe-worthy gulp. The tour showcases both award-winning estate wineries and hidden gems, culminating at the Sideways Inn (formerly Days Inn) and the legendary Hitching Post II restaurant where Miles pined for Maya. The tour ends at Ostrich Land, another memorable film location where Jack’s adventures took a chaotic turn.

On this 90-minute tour, you’ll have a chance to:

Learn about the “Sideways Effect” that doubled Pinot Noir sales while devastating Merlot’s popularity
Discover the unique characteristics of five distinct wine trails including Foxen Canyon and Los Olivos Promenade
Visit the Los Olivos Wine Merchant & Café where Miles declared “I am NOT drinking any f***ing Merlot!”
Explore biodynamic and sustainable vineyards producing award-winning estate wines and understand how the Santa Ynez Valley creates perfect conditions for diverse wine varieties
See the barrel room at Firestone Vineyard where the film’s pivotal romantic scene unfolded
Learn which wineries earned gold and platinum medals based on quality, sustainability, and accessibility
Discover the valley’s rich history, from Spanish missions to celebrity residents like Ronald Reagan and Michael Jackson

Whether you’re a serious wine enthusiast or a fan of the film, this tour offers the perfect blend of cinematic nostalgia and viticultural discovery through one of California’s most charming wine regions.

Tour Producer

TourFreely

9 tours

TourFreely: Discover More. Wander Freely

TourFreely was founded by Southern California natives Mindy and Jerry Flanagan. As a GPS‑guided tour company, TourFreely transforms local history and culture into immersive storytelling adventures. With nine curated SoCal tours—spanning both walking and driving experiences—they offer travelers a dynamic way to explore the region. From sun‑drenched vineyards to storied city streets, TourFreely invites curious explorers to discover the vibrant spirit and natural beauty of Southern California.

At our core, we’re fueled by freedom, curiosity, and connection. We want locals to fall in love with their hometowns all over again—and visitors to feel like insiders the moment they hit play. Our tours are flexible, affordable, and delightfully stress‑free: no crowds, no schedules, just you - exploring at your own pace.

TourFreely’s growing catalog includes:
• Six immersive walking tours: La Jolla, Carlsbad, Beverly Hills/Rodeo Drive, the Sunset Strip, UC San Diego, and Santa Barbara
• Three unforgettable driving tours: San Diego, Temecula Wine Country, and Santa Barbara Wine Country/Sideways Wine Trail

And for even more adventure, we’ve joined forces with Adventure Inc. and created three self‑guided Orange County drives, complete with their signature jeeps, e‑bikes, and open‑air mokes.

Whether you’re strolling Hollywood’s storied sidewalks or cruising past rolling vineyards, TourFreely invites you to slow down, stay curious, and see Southern California through a new lens—your own.

Preview Location

Location 6

Santa Ynéz Valley AVA

Mindy: Turn right on Mission Drive and keep going straight for while. We'll tell you when to turn again.

As we make our way to Sideways film locations and notable wineries and vineyards, we wanted to give you some history about the American Viticulture Areas or AVAs here an... Mindy: Turn right on Mission Drive and keep going straight for while. We'll tell you when to turn again.

As we make our way to Sideways film locations and notable wineries and vineyards, we wanted to give you some history about the American Viticulture Areas or AVAs here and the wine trails within them.

The Santa Ynéz Valley AVA is a significant wine-producing region situated between the Santa Ynéz and San Rafael Mountains; its unique east-west orientation allows cool air and fog from the Pacific Ocean to funnel inland, creating a diverse range of microclimates. Established as an AVA in 1983, it is the largest in the county, spanning over 30 miles east to west. This results in a cool, foggy western end at Vandenberg Air Base that is ideal for cool-climate varieties like Pinot Noir and Chardonnay and a warmer, sunnier eastern end suited for Rhone and Bordeaux grapes. The unique growing conditions within the Santa Ynez Valley naturally led to the official recognition of several smaller AVAs, often referred to as sub-AVAs that we'll describe a little later

Jerry: The Santa Ynéz Valley AVA is a patchwork of vines, barrels, and bliss! Not one road, not one trail, no —this isn’t Napa’s prim cousin—this is a full-blown wine safari, Mindy! A labyrinth of routes, trails, twists, and turns, each one corkscrewing through a new varietal, a new view, and a new pour of liquid gold.

Distinct from an AVA is a wine trail, which is a designated route or collection of wineries and related attractions that visitors can explore to experience a wine region's unique offerings. And on this tour? We hit five trails:

• Buellton Wine Trail—rustic, rowdy, bold.
• Foxen Canyon—the long, winding ribbon of tasting-room ecstasy.
• Los Olivos Promenade—a wine-walk fantasy down Main Street charm.
• Santa Ynéz Valley Trail—classic, pastoral, sunlit serenity.
• Santa Rita Hills—cool-climate, Pinot-perfect, fog-kissed majesty!

Five trails...one glass at a time. So, let’s swirl.

Mindy: The Los Olivos Promenade is centered in the village of Los Olivos and located within the Los Olivos District AVA and the Promenade is a wine trail described as a "hub for tasting rooms" where visitors can easily park and stroll between numerous tasting rooms of producers from all Santa Ynez AVAs. This trail offers a more concentrated, walkable experience of the valley's wine scene, and we will spend some time there soon, as it's also an important Sideways film location.

Keep driving until you hear from me again. Read More

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Major Landmarks

River Course At Alisal
Solvang Restaurant
Mission Santa Inés
Santa Ynez Valley AVA
Brave & Maiden Estate
McKinney Family Vineyards
Roblar Winery and Vineyards - Santa Ynez Estate Tasting Room
Beckmen Vineyards
Los Olivos Wine Merchant & Cafe
Petros Winery
Fess Parker Winery & Vineyard
Koehler Winery
Andrew Murray Vineyards
Firestone Farming
Sideways Inn
Sideways Lounge
A J Spurs Saloon & Dining Hall
Hitching Post Wines

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Getting There

Route Overview

VoiceMap tours follow a route from a set starting point. It’s how we give turn-by-turn directions and tell a story greater than the sum of its parts.

Start location
Alisal Rd, Solvang, CA 93463, USA
Total distance

49km
Final location
610 E Hwy 246, Solvang, CA 93463, USA
Distance back to start location

4km

Directions to Starting Point

We begin our tour near the bridge for the Santa Ynez River and beside the River Course at Alisal, on the corner of Juniper Drive and Alisal Road, beneath the California pepper tree. With the golf course on your right, Juniper Drive on your left and the bridge behind you, you will be ready to start the tour after a brief introduction.

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Tips

Places to stop along the way

Tour Tips & Local Favorites
Public restroom available at 1630 Mission Drive, Solvang.
Some of our favorite eats along or near the route:
• Mattei’s Tavern – Don’t miss the hot fried chicken sandwich!
• Los Olivos Wine Merchant & Café – Cozy, curated, and delicious. Try the steak cobb salad.
• Dos Carlitos Restaurant & Tequila Bar, Santa Ynez – Flavor-packed Mexican fare.
• The Lucky Hen, Santa Ynez – Fresh, seasonal, and charming.
• Maverick Saloon, Santa Ynez – Classic country vibes and casual bites.
• Brothers Restaurant at the Red Barn, Santa Ynez – Elevated comfort food in a rustic setting.
• Whiskey N Rye, Solvang – Sweet tooth alert: the skillet chocolate chip cookie is a must.
• Nella Kitchen & Bar, Los Olivos – Stylish spot with Italian-inspired plates.
🛏️ Where to stay- some of many great spots:
• Wine Valley Inn & Cottages, Solvang – Quaint and cozy.
• The Inn at Mattei’s Tavern, Los Olivos – Luxe, historic, and fabulous.
🛍️ Where to shop - some of the many delightful options:
• Olive + Lavender Farms, Los Olivos – Local charm and artisan goods.
• Solvang Olive Press – Tasty tastings and gourmet gifts.
• Future Perfect, Los Olivos – Artsy finds, friendly staff, and wine tasting too.
• The Right Gift, Solvang – Under the windmill and packed with treasures.
• Valley Hardware and Garden Center, Solvang - Yep - the local hardware store! Way more than just hardware.
• Jule Hus- Solvang's Christmas Store

Best time of day

Best time of day
The tour is available from dawn till dusk. On weekdays, we recommend enjoying the tour between 10- 3PM. On the weekends to minimize traffic, we recommend starting the tour in the morning.

Precautions

Two of the towns, you will pass through, Solvang and Los Olivos can be bustling towns during the busy season - be on the lookout for pedestrians, riders on bikes and scooters. You'll want to go the speed limit or slightly slower to abide by the law and to not miss any stories or directions. By accessing our GPS tour, you are agreeing to release all liability. Tour at your own risk.

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