Florence Sidecar Tour: Oltrarno, Piazzale Michelangelo & Hills

Summary

Vintage Motorcycle Sidecar Ride: Florence’s Hidden Gems & Views

If you want to see Florence from a totally new angle—literally—this vintage sidecar tour is for you. You’ll zip through lively neighborhoods, catch sweeping views from Piazzale Michelangelo and San Miniato al Monte, and even cruise out into the hills where vineyards meet olive groves. It’s fun, personal, and gives you stories (and photos) no regular tour can match.

What’s the experience like?

The first thing I noticed was the hum of the old engine as we met outside Caffè Pasticceria Gamberini. The smell of fresh pastries drifted out onto via del Curtatone—tempting, but our ride was waiting. Helmets on, we squeezed into the sidecar (surprisingly comfy) and rolled off toward San Frediano’s ancient gate. The city felt different from this low vantage point—closer, more alive.

Crossing into Oltrarno, our guide started pointing out little things I’d never have caught on my own: laundry flapping above narrow streets, a guy selling tiny bunches of violets near a corner bar. We wound up to Piazzale Michelangelo just as the sun started to dip, and honestly, the view over Florence is something else—domes and rooftops glowing in that soft Tuscan light. There’s always a crowd here snapping photos, but from the sidecar you get a bit of distance from the bustle.

Next stop was San Miniato al Monte—the church where our guide quietly mentioned he got married (you could see he meant it). Inside, it’s cool and smells faintly of old stone and candle wax. The mosaics catch the late afternoon light in a way that makes you want to linger. Afterward, we zipped out past Arcetri and into those winding Chianti roads—vineyards on one side, olive trees on the other. You catch little bursts of wild herbs in the air if you’re paying attention.

The ride back into Florence hugged the river. We passed joggers and couples out for an evening stroll; someone was playing guitar near Ponte alle Grazie. Back in the city center, it felt like we’d seen both sides of Florence—the busy heart and its quiet green edges—all in just a couple hours.

Step-by-step itinerary

Day 1 — Vintage Sidecar Tour of Florence

• Meet at Caffè Pasticceria Gamberini
• Ride to Oltrarno district
• Visit Piazzale Michelangelo terrace
• Stop at San Miniato al Monte church
• Ride through Chianti vineyards and olive trees
• Drive along river and city center

Top questions

Is this sidecar tour safe for kids?

Yes! Kids can join as long as they’re with an adult. Just let us know their ages when booking so we can plan seating safely.

What should I wear for the ride?

Smart casual is best—layers help since it can get breezy in the hills. Helmets are provided for everyone.

Can I bring my camera or phone?

Absolutely! The sidecar is perfect for snapping photos or videos along the way—just keep your gear secure during the ride.

Are there weight or health restrictions?

We use vintage motorcycles with sidecars, so there’s a weight limit for safety reasons. Also not recommended for pregnant travelers or those with spinal injuries.

What’s included

Your ride includes a friendly local driver-guide who knows Florence inside out, helmets for everyone, live commentary during the journey, all local taxes and fuel costs covered. Just bring your sense of adventure—and maybe sunglasses!