Ride a custom tandem sidecar through San Luis Obispo’s wine country, visiting two boutique wineries with guided tastings and scenic backroad views. This private three-hour tour pairs a motorized thrill with local history and tasting-room hospitality.
Ride a custom tandem sidecar through San Luis Obispo’s wine country, visiting two boutique wineries with guided tastings and scenic backroad views. This private three-hour tour pairs a motorized thrill with local history and tasting-room hospitality.
You meet at a low-slung garage on Monterey Street and the road greets you like an old friend: a narrow ribbon of pavement cutting through vineyards, the coastal air nudging at your jacket as you climb into a tandem sidecar built for two. Engines purr; the driver guides you past rolling rows of vines and ranch-style farmhouses while the countryside unfolds in clean lines of green and gold.
Verified experiences and guided adventures in the surrounding area.
Operated by Sidecar Tours Inc · San Luis Obispo, CA
You meet at a low-slung garage on Monterey Street and the road greets you like an old friend: a narrow ribbon of pavement cutting through vineyards, the coastal air nudging at your jacket as you climb into a tandem sidecar built for two. Engines purr; the driver guides you past rolling rows of vines and ranch-style farmhouses while the countryside unfolds in clean lines of green and gold.
San Luis Obispo County sits on the boundary between the Santa Lucia Range and the coastal plain. The soils here are a mix of alluvial loam and calcareous clay—ideal for chardonnay, pinot noir and syrah—shaped by uplift and the mild Pacific influence. Wine culture is rooted in 18th–20th century ranching and mission-era agriculture; tasting rooms today often pair modern winemaking with stories of land stewardship.
On this private, three-hour sidecar tour you visit two curated wineries. Drivers double as local narrators: expect history on the drive, short guided tastings at each stop, and time to linger in tasting rooms or on terraces. The experience blends motorized novelty with low-impact sipping—wineries provide seated tastings; admission and flights are included per stop.
Practical notes: wear a windproof layer and closed-toe shoes, bring ID and any required waiver information, and plan transport after the tour if you intend to buy bottles. Mid-morning or late-afternoon departures minimize midday heat and give better light for photos. The ride is easy physically but vivid in sensory detail—let the sidecar’s rhythm set your pace and the vineyards do the rest.
The standard tour visits two partner wineries with a tasting included at each stop, plus time to explore the tasting rooms.
Tastings at the two included wineries are provided as part of the tour; additional food or purchases are paid directly to the wineries.
Operators typically provide helmets or liners and require passengers to wear safety equipment; check specifics before riding.
Notify the operator when booking so they can confirm winery accessibility and accommodate basic needs; medical conditions affecting travel should be disclosed.
Sidecar Tours Inc operates guided outdoor trips and adventures with an emphasis on safety, stewardship, and memorable experiences.




You meet at a low-slung garage on Monterey Street and the road greets you like an old friend: a narrow ribbon of pavement cutting through vineyards, the coastal air nudging at your jacket as you climb into a tandem sidecar built for two. Engines purr; the driver guides you past rolling rows of vines and ranch-style farmhouses while the countryside unfolds in clean lines of green and gold.
You meet at a low-slung garage on Monterey Street and the road greets you like an old friend: a narrow ribbon of pavement cutting through vineyards, the coastal air nudging at your jacket as you climb into a tandem sidecar built for two. Engines purr; the driver guides you past rolling rows of vines and ranch-style farmhouses while the countryside unfolds in clean lines of green and gold.
San Luis Obispo County sits on the boundary between the Santa Lucia Range and the coastal plain. The soils here are a mix of alluvial loam and calcareous clay—ideal for chardonnay, pinot noir and syrah—shaped by uplift and the mild Pacific influence. Wine culture is rooted in 18th–20th century ranching and mission-era agriculture; tasting rooms today often pair modern winemaking with stories of land stewardship.
On this private, three-hour sidecar tour you visit two curated wineries. Drivers double as local narrators: expect history on the drive, short guided tastings at each stop, and time to linger in tasting rooms or on terraces. The experience blends motorized novelty with low-impact sipping—wineries provide seated tastings; admission and flights are included per stop.
Practical notes: wear a windproof layer and closed-toe shoes, bring ID and any required waiver information, and plan transport after the tour if you intend to buy bottles. Mid-morning or late-afternoon departures minimize midday heat and give better light for photos. The ride is easy physically but vivid in sensory detail—let the sidecar’s rhythm set your pace and the vineyards do the rest.