THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
Dive into Santa Barbara’s wine country with tastings at film-famous wineries and a visit to the ostrich farm from *Sideways*. A private 8-hour tour blending wine, wildlife, and movie lore awaits.
Dive into Santa Barbara’s wine country with tastings at film-famous wineries and a visit to the ostrich farm from *Sideways*. A private 8-hour tour blending wine, wildlife, and movie lore awaits.
Book with Captain Jack's Santa Barbara Tours
Verified experiences and guided adventures in the surrounding area.
Operated by Captain Jack's Santa Barbara Tours · Santa Barbara, California
The Sideways Inspired Tour presents a distinctive way to experience Santa Barbara’s scenic wine country, combining immersive film history with outdoor discovery. This 8-hour private trip is tailor-made for fans of the cult classic Sideways and wine lovers seeking an engaging journey beyond ordinary tastings. Set in Santa Barbara, California, a renowned region known for its rolling vineyards and Mediterranean climate, this tour highlights the area's unique blend of natural beauty and cinematic heritage.
Participants are driven through iconic wineries featured in the movie, indulging in curated tastings at two beautiful estates. Along the way, the knowledgeable guide shares entertaining trivia and behind-the-scenes stories about Sideways, adding layers of context that enhance each stop. But this tour stands apart by offering a quirky wildlife experience—visiting the ostrich farm where a memorable chase scene was filmed. Here, guests can interact with and feed these large, fascinating birds, making it a rare encounter nestled within a wine region.
Santa Barbara’s wine country is defined by its cool coastal breezes and exceptional terroir, producing celebrated Pinot Noirs and Chardonnays. The valleys and rolling hills also make for a varied outdoor backdrop, perfect for a day of moderate walking between tasting rooms and farm attractions. The Sideways Inspired Tour gives visitors a well-rounded glimpse of the area’s charm, combining viticulture with cinematic allure and unexpected wildlife moments. It’s a standout choice for travelers wanting a private, personal plunge into one of California’s most beloved outdoor wine regions.
moderate.
8 hours.
Moderate fitness recommended to comfortably walk between winery stops and participate in farm activities.
Yes, it’s family-friendly, but children should be supervised around the animals for safety.
Yes, tastings at two wineries are part of the tour package.
Since it’s a private tour, some customization may be possible—contact the operator in advance.
Yes, private transportation is included to shuttle between stops comfortably.
Some tours may include light snacks or lunch—check with the operator for specifics.
Availability may depend on season and winery schedules, but it generally runs year-round.
Santa Barbara’s wine country gained international fame partly due to *Sideways*, boosting tourism since the film’s release in 2004.
Wineries in this region increasingly practice sustainable viticulture, balancing growth with environmental stewardship.
Captain Jack's Santa Barbara Tours operates guided outdoor and tasting experiences based in Santa Barbara, California. The company offers a diverse menu of private and shared tours, including stand up paddle boarding in Santa Barbara Harbor, multiple wine tasting options in the city and the Santa Ynez Valley, brewery tours, and coastal canyon horseback rides. Several experiences provide door-to-door or round-trip transportation, and private options are available for groups seeking customized itineraries. Guides and staff include experienced drivers, knowledgeable tour guides, and professional wranglers who lead horseback rides and document memorable moments. Tours vary in length from 1.5-hour paddle and horseback outings to multi-hour wine and film-themed excursions such as the Sideways-inspired tour. Tastings typically visit three wineries or tasting rooms, with some wine tours also including an olive oil farm and picnic elements for private bookings. Brewery tours feature visits to three local breweries with curated samplings and guided transportation. The platform emphasizes safety, local expertise, and seamless logistics—participants can expect provided transportation on many tours and guided interpretation of regional highlights like Stearns’ Wharf, the Santa Barbara Sea Center, and Santa Ynez wine country. Reservations accommodate varying group sizes, seasonal availability, and custom requests to create personalized Santa Barbara outings for celebrations, sightseeing, and memorable moments together.
Book with Captain Jack's Santa Barbara Tours