Vespa Countryside Tours in the USA: the 7 Best Rides

1.Scenic Sidecar Vineyard Tour Paso Robles

★★★★★★★★★★4.5 · 46 reviews · 1 hour (approx.) · from $65Our pick

Meet your guide at Cass Winery for a private, one-hour sidecar ride through Paso Robles wine country. Expect safety instructions, vineyard views, photo stops, and local wine talk. Guides such as Greg, Frank, JD, and Daniel have led past tours. A Wolff Winery tasting can be added.

“It was nice to get a tour of some of the vineyards. Our guide was knowledgeable. We ride motorcycles but it was still a cool experience to be in the side car. If you've never ride on a motorcycle before you will really enjoy this. Paso Robles gets hot in the summer. Choose the 10:00 slot if you can.”

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2.Scenic Sidecar Vineyard Adventure San Luis Obispo

★★★★★★★★★★4.5 · 15 reviews · 1 hour (approx.) · from $65

Meet your private guide at Wolff Vineyards for a safety briefing, then ride through San Luis Obispo wine country in a sidecar. Guides such as Jill, Steph, Isaac, and Francisco have shared vineyard knowledge, local history, and photo stops during this one-hour outing.

“Our tour guide Isaac was very friendly and informative! We thoroughly enjoyed our visit and the wine was delicious!”

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3.Sunset at the Vineyards Sidecar Wine Adventure Paso Robles

★★★★★★★★★★4.5 · 10 reviews · from $150

Meet your guide at Cass Winery for a safety briefing, then ride by sidecar through Paso Robles wine country as the sun drops. Stop for scenic photos and a private picnic with one bottle of wine and a cheese board. The 90-minute tour ends where it began.

“Loved our guides, amazing wine from Cass, beautiful scenery for our picnic. Couldn’t think of a better way to start our tour of Paso.”

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4.Santa Barbara: Private Scenic Tandem Sidecar Tour

★★★★★★★★★★3.9 · 9 reviews · from $99

Ride through Santa Barbara in a private tandem sidecar with an English-speaking driver-guide. From Fox Wine Co., you’ll see beaches, historic architecture, scenic viewpoints, and a wine room or brewery while learning about local culture. Steven is one guide named in guest feedback.

“Our guide, Steven, took us to some magnificent views.”

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5.Scenic Sidecar Vineyard Tour

★★★★★★★★★★5.0 · 3 reviews · from $65Top rated

Meet your English- or Spanish-speaking Third Wheel Tours guide at Cass Winery for a safety briefing, then ride a private sidecar through Paso Robles wine country. Your guide shares vineyard insight, stops for photos, and provides water and tour photos. Frank may be your driver.

“Frank the driver was awesome. Very knowledgeable and fun to be around. The ride was very nice around the vineyard relaxing and enjoyable.”

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6.Sunset at the Vineyards Sidecar Wine Adventure

★★★★★★★★★★5.0 · 3 reviews · from $150

You’ll ride in a private motorcycle sidecar from Cass Winery with an English-speaking operator and wine educator. Expect a safety briefing, vineyard stops, sunset photos, a guided look at vine-to-bottle work, wine tasting, a bottle of wine, and a cheese charcuterie board.

“This experience was an absolute treat. My girlfriend — who’s really into vine — loved it and couldn’t thank me enough; even though their team provided it all, incl a nice vibe. I strongly recommend doing it at night with the sunset. We also got lucky that it was just us. Really something to remember and next time we might even book a room at the vineyard’s hotel.”

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7.1-Hour Private Scenic Tandem Sidecar Tour in San Diego

★★★★★★★★★★5.0 · 3 reviews · 1 hour (approx.)

Ride beside a local guide in a private motorcycle sidecar, with stops around Old Town, Liberty Station, Little Italy, Balboa Park, and the harbor. Guides such as Jerry, Steve, and Cesar have tailored routes, shared local stories, and allowed time for photos.

“Steve was great!! I booked very last minute due to plans changing, and they got me scheduled and confirmed quickly. We hit some traditional tour landmarks but also some off the beaten path, which I never would have discovered on my own. The best part was the stories! He sprinkled fun anecdotes and history throughout our time, and made sure to take plenty of photos. The sidecar made this a great solo tour in SD. I had such a great time.”

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