Ages 21+ • Perfect for Couples and Small Groups • 4 Hour Tour • All-Inclusive! • Up to 10 People
Trade the tourist shuttle for a one-of-a-kind sidecar ride through San Luis Obispo wine country. Visit three boutique wineries, enjoy exclusive pours, and end with a signature tasting at Wolff Winery.
More ways to explore the area's outdoor wonders
Hang tight — photos are loading
This usually takes just a second.
Difficulty
easy
Duration
4 hours
Fitness Level
Basic mobility and comfort mounting a sidecar; sitting for four hours and short walks at tastings.
Wildlife
History
Wine growing in San Luis Obispo County expanded through the twentieth century as small producers multiplied; the region developed a reputation for varied terroirs and boutique estates.
Conservation
Small-group tours reduce traffic pressure on rural roads; support local producers and pack out trash—buying locally helps keep vineyards sustainable.
Third Wheel Tours
Ages 21+ • Perfect for Couples and Small Groups • 4 Hour Tour • All-Inclusive! • Up to 10 People
Third Wheel Tours operates curated sidecar wine tours across San Luis Obispo and Paso Robles, specializing in immersive vineyard adventures. The company offers guided sidecar rides that pair scenic motorcycle sidecar travel with expert narrative about vineyard practices, local varietals, and wine history. Guests visit multiple wineries, enjoy curated tastings, and often conclude with a memorable tasting at Cass Winery or other partner estates. Tours include daytime scenic rides, sunset excursions with a bottle of wine and a curated cheese board, and exclusive multi-winery itineraries in Paso Robles that last up to four hours. Each ride is led by an experienced guide who provides safety, regional context, and insider winemaking knowledge. Third Wheel Tours emphasizes small group sizes and intimate experiences, making tours suitable for couples, celebrations, and travelers seeking authentic wine-country exploration. Photogenic stops and dedicated photo opportunities are built into many routes to capture vineyard views and sunset moments. Add-on options such as private stops at Wolff Vineyard and special seasonal experiences are available through partner wineries. Third Wheel Tours coordinates logistics including winery reservations and tasting arrangements to create a seamless day in wine country. Safety gear and briefing are provided, and guides prioritize responsible enjoyment and local stewardship. The business partners with local wineries to highlight small-production producers and promote sustainable practices. Third Wheel Tours is a third-party operator featured on The Adventure Collective, trusted for delivering memorable, informative, and scenic sidecar wine adventures in California’s Central Coast wine regions.
Reservations recommended for peak season tours.
Regions Served
San Luis Obispo & Paso Robles
Scenic vineyard routes
Guided Rides
Expert Guide
Knowledgeable local narrators
Wine Experiences
Tastings & Bottles
Curated tastings and cheese
Typical Length
Up to 4 hours
Multi-stop immersive tours
Secure a curated vineyard ride through San Luis Obispo or Paso Robles — limited spots for sunset tours.
Bring government ID
This tour is 21+—bring a valid government ID to board and to taste at winery stops.
Layer clothing
Open sidecar rides amplify wind and temperature changes—bring a light jacket or layers.
Manage motion sickness
If you are prone to motion sickness, take preventative measures before the ride; the sidecar exposes you to wind and movement.
Plan purchases
If you fall for a wine, bring a card or plan space in your vehicle—many stops allow bottle purchases.
Valid government ID
Required for all guests to verify age for tastings.
Layered jacket or windbreaker
Keeps you comfortable in the open sidecar as temperatures and coastal breezes shift.
Sunglasses and hat
Protects eyes from glare during roadside stops and while riding.
summer
Closed-toe shoes
Useful for short vineyard walks and stable footing at tasting rooms.