Italy-Tuscany-2legs
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Overview
Starting and ending in Florence, this compact Tuscan loop combines the classic ridge roads of Greve in Chianti and Radda in Chianti with the stronger medieval weight of Siena, Montalcino, Pienza and Montepulciano. The return leg shifts east through Cortona, Arezzo, Loro Ciuffenna and Reggello, giving the loop a cleaner riding rhythm and avoiding a simple out-and-back.
This is not a high-speed route and it is not built around passes. Its appeal comes from linked hill towns, measured curves, vineyard scenery and steady secondary roads where the riding remains engaging without becoming technical. Stage 1 is the emotional high point, with the strongest postcard-Tuscany atmosphere. Stage 2 is slightly leaner and more rider-focused, connecting eastern Tuscany back to Florence through a sequence of historic towns and quieter roads.
Distances below are indicative only. Use the final GPX trace for effective riding distance.
Interactive map
Legend: black = waypoint, red = POI, blue = hotel, green = restaurant. The route polyline closes the loop only at the end.
Technical overview
Approx. 305 km
2
Approx. 155 km
Approx. 150 km
Provincial roads, hill-town access roads, scenic ridges
Late spring and early autumn
Seasonality
Late April to June, and September to October. These months usually give the best balance between scenery, light, temperature and manageable traffic.
Possible, but expect more heat and slower movement near Siena, Pienza, Montepulciano and Florence. Start early and avoid long midday stops in exposed squares.
Excellent for vineyards, colour and food stops. Harvest-time traffic can still affect Chianti and Val d’Orcia, especially on weekends.
Practical riding notes
Mostly smooth provincial roads with occasional patched surfaces near villages, agricultural accesses and scenic lay-bys. Grip is generally predictable but can vary after farm traffic.
The route is simple to ride, but tourist traffic, buses and town-centre congestion can interrupt rhythm near Siena, Montepulciano, Cortona and Florence.
There is little real altitude exposure, though ridgeline sections around Chianti and Val d’Orcia can feel breezier on open viewpoints.
Safety and effort level
Easy / Moderate
Moderate
Tourist traffic, buses, narrow urban accesses, farm vehicles
Start early, keep town stops short at peak hours, and ride the scenic sections before lunch
The route is suitable for riders wanting a strong visual experience without technical mountain riding. It demands attention in and around historic centres more than it demands advanced cornering skills.
Stage 1 – Florence to Montepulciano – approx. 155 km
Main WP: Florence – Greve in Chianti – Radda in Chianti – Siena – Montalcino – Pienza – Montepulciano
The opening stage delivers the most recognisable Tuscan atmosphere of the whole loop. You leave Florence and settle quickly into the vineyard roads of Greve in Chianti and Radda in Chianti, before the route grows more monumental around Siena. South of Siena, the scenery opens into the broader shapes of Montalcino, Pienza and finally Montepulciano. Indicative km only; use the final GPX trace for effective distance.
La Vineria Di Montepulciano – Via di Gracciano nel Corso 72
A strong stage-finish choice in the historic centre, well placed for a relaxed evening stop with local cuisine and wine focus.
Meuble Evoe
Central, compact and practical for an old-town stop, with nearby parking repeatedly mentioned in guest feedback. A smart low-key base for a one-night motorcycle stage.
La Terrazza Di Montepulciano
A dependable middle option right along the main approach to the centre, appreciated for position, comfortable rooms and convenient parking access.
Terra Antica – Resort, Winery & SPA
The most indulgent finish for the day: valley views, winery setting and a calmer edge-of-town position. Best suited if you want the overnight stop to feel like part of the experience.
Stage 2 – Montepulciano to Florence – approx. 150 km
Main WP: Montepulciano – Cortona – Arezzo – Loro Ciuffenna – Reggello – Florence
The second stage feels cleaner and slightly more road-focused. From Montepulciano the route turns towards the hillside elegance of Cortona, then drops into the broader urban texture of Arezzo. The run through Loro Ciuffenna and Reggello gives the return leg a quieter closing rhythm before the final re-entry into Florence. Indicative km only; use the final GPX trace for effective distance.
Osteria Vespucci
A practical finish for the loop in central Florence, with live TheFork booking availability and a solid all-round rating for food and atmosphere.
Hotel David
A very strong motorcycle-friendly city base thanks to free parking, easy access compared with tighter historic-core options, and consistently warm guest feedback.
The Social Hub Florence Belfiore
A more contemporary Florence stop with on-site parking and a newer, design-led feel. Useful if you want a city finish without the tightest historic-centre logistics.
Hotel La Gemma
A polished premium finish in the city centre with private parking / valet-style support. Best for riders who want a luxury close to Florence’s main historic landmarks.
The loop closes back in Florence with a complete two-stage experience: classic wine-country ridges on day one, then a more road-led return through eastern Tuscany on day two.
POI Photo Gallery
Photo credits: images from Wikimedia Commons (see captions for authors and licenses). Used under CC BY-SA / public domain terms where applicable.
