We recently shook up our usual wine country routine with an unforgettable Sidecar Tours experience in San Luis Obispo! This was one of those “let’s do something different” ideas that turned out to be an absolute blast. Sidecar Tours operates in several iconic California wine destinations—including Temecula, Paso Robles, Napa, Sonoma, Santa Barbara, and more—but since we’re locals in the Napa/Sonoma area, we decided to venture a little farther and explore somewhere new.
San Luis Obispo was the perfect pick. Matt had visited once before and loved it, and Kyle had always heard amazing things. Spoiler alert: SLO totally lived up to the hype. The town is charming, the wines are flowing, and riding around in a sidecar? Total core memory.
Our tour was about four hours long, and while the wine tasting fees aren’t included in the Sidecar price, the convenience and experience more than make up for it. Bonus: the meeting point was just steps from our hotel. We were greeted by our driver David, who immediately felt like a friend. Turns out, he’s a former nurse—instant connection with Kyle!
Now let’s talk about that sidecar. Neither of us had ever ridden in one before, and it was wild in the best way. It’s a little surreal to be zooming around in the open air, helmet and goggles on, just taking in the scenery. Think: California breeze in your hair, vineyards rolling past, and zero stress about who’s driving.
Our first stop was Baileyana Winery, where we were treated to a generous tasting lineup. We sat outside with sweeping views of vineyards that Baileyana once owned—1400 acres, sold in 2020, but still used for many of their wines. Along with their signature Baileyana label, we also tasted wines from their Tangent and True Myth lines. They specialize in Chardonnay and Pinot Noir, and yes, we snagged a bottle of Pinot to savor later.
Next up: Claiborne & Churchill Winery. We played it smart here and ordered different tasting flights so we could sample even more varietals—Travel Daddyz pro tip: always diversify your tastings and revisit your faves at the end. This spot also had delicious charcuterie boards with some standout cheeses, which is basically our love language.
David took us on one last scenic ride through downtown SLO before wrapping up the tour back at our starting point. Throughout the afternoon, he was a stellar guide—friendly, informative, and full of great local recs. We felt totally taken care of and had such a great time chatting with him.
If you’re looking to shake up your next wine tasting outing, Sidecar Tours is a unique, fun, and photo-worthy way to do it. Whether it’s just the two of you or you’re rolling deep with friends and multiple bikes, we totally recommend adding this to your California wine country bucket list.
