The Sideways Wine Trail GPS-guided Driving 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.

Note – TourFreely’s on‑demand tours are available 24/7, seven days a week.

Just download and go whenever it fits your schedule.

We recommend exploring during non-peak times for the best experience.

Find all nine tours at TourFreely.com.