Italy-Tuscany-7days loop
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Tuscany–Umbria Grand Arc (7 days · Full Loop from Florence)
Chianti hills, Val d’Orcia, Trasimeno and the Umbrian ridges in a 7-day rider’s loop from Florence, 180–230 km per day.
Nearest Airport(s)
Florence · FLR — Amerigo Vespucci (≈ 20–30 min taxi to city centre)
Pisa · PSA — Galileo Galilei (≈ 1 h 15 min by motorway to Florence)
Both airports are well connected to the city by shuttle bus, train and motorway. FLR is the natural gateway; PSA can work if flights are more convenient.
Tech overview · km & pacing
A 7-day loop designed for 180–230 km per day, balancing classic Tuscan passes, lakeside roads and Umbrian ridges.
Distances are estimated using real road connections between the named waypoints (no motorways required, occasional short dual carriageway to bypass traffic).
Route intro · Florence ⇄ Chianti ⇄ Val d’Orcia ⇄ Umbria
This loop stitches together many of central Italy’s dream roads into one coherent 7-day ride. From Florence you dive straight into the Chianti hills, linking stone villages, cypress-lined ridges and tight S-bends that warm up your tyres and shoulders. South of Siena the landscape opens into the rolling wheat fields and iconic clay ridges of the Val d’Orcia, where Montalcino, Pienza and Montepulciano punctuate the skyline with bell towers and fortress walls.
You then turn east, skirting the shores of Lake Trasimeno towards Perugia before climbing again to Gubbio and the high Apennine foothills. Classic balcony roads lead down towards Arezzo and the Valtiberina, then back up to the hill-towns of Assisi and Spello. From here the loop goes wilder: Norcia, Castelluccio and the Sibillini plateau deliver big-sky views and long, flowing curves that are still mostly quiet outside of peak weekends.
The last arc turns back towards Tuscany through Valnerina, the Piediluco lake basin and the tufa cliffs around Orvieto, then traces a final sequence of wine-country roads via Chiusi and Chianti to re-enter Florence. The riding remains fully tarmac yet varied, with a natural rhythm of one “hillier” day followed by something more open or lakeside.
Route map · Tuscany–Umbria Grand Arc
Stylised overview only. Use the GPX / turn-by-turn navigation on your device once you load the final file.
Day-by-day stages
Day 1 · Florence → Chianti ridge → Siena → Montalcino · ≈ 210 km
- Florence centre → Impruneta → Greve in Chianti (SR222 “Chiantigiana”) · ≈ 55 km
- Greve → Panzano → Castellina in Chianti · ≈ 35 km
- Castellina → Siena (via Quercegrossa secondary roads) · ≈ 40 km
- Siena → Buonconvento → Montalcino (via SR2 & SP14) · ≈ 80 km
Classic Chianti curves, vineyard viewpoints and a final run into the Val d’Orcia ridges around Montalcino.
Day 2 · Montalcino → Pienza → Montepulciano → Lake Trasimeno → Perugia · ≈ 205 km
- Montalcino → San Quirico d’Orcia → Pienza (SP146 scenic) · ≈ 40 km
- Pienza → Montepulciano via Monticchiello · ≈ 30 km
- Montepulciano → Castiglione del Lago (SR71 & lakeside roads) · ≈ 60 km
- Castiglione del Lago → Passignano sul Trasimeno → Perugia · ≈ 75 km
Iconic postcard viewpoints between Montalcino, Pienza and Montepulciano, then a relaxed sweep along the northern shore of Lake Trasimeno before climbing to Perugia’s historic centre.
Day 3 · Perugia → Gubbio → Apennine ridges → Città di Castello → Arezzo · ≈ 215 km
- Perugia → Gubbio (via SS298/SS219) · ≈ 45 km
- Gubbio → Scheggia pass area → Pietralunga loops (optional detour) · ≈ 70 km
- Pietralunga area → Città di Castello · ≈ 40 km
- Città di Castello → Arezzo (SS73 / backroads) · ≈ 60 km
This is the most “mountainous” day, with cool forested passes and sweeping ridge lines before dropping gently towards Arezzo’s medieval squares.
Day 4 · Arezzo → Anghiari → Sansepolcro → Umbertide → Assisi → Spello · ≈ 200 km
- Arezzo → Anghiari panoramic road · ≈ 35 km
- Anghiari → Sansepolcro → Umbertide · ≈ 60 km
- Umbertide → Assisi (via Gualdo Tadino / Valfabbrica options) · ≈ 60 km
- Assisi → Spello balcony road · ≈ 20–25 km
A day of postcard ridgelines and fortified villages, closing on the flower-strewn streets of Spello for a quieter overnight than neighbouring Assisi.
Day 5 · Spello → Valnerina balcony roads → Norcia & Castelluccio plateau · ≈ 190 km
- Spello → Foligno → Pale gorge access → road towards Norcia · ≈ 70 km
- Norcia → Castelluccio plateau loops · ≈ 60 km
- Castelluccio → Visso → return arc towards Norcia · ≈ 60 km
Shorter in kilometres but intense in scenery: long, empty curves above the plains of Castelluccio and the broken ridges of the Sibillini National Park. Ideal to ride at a relaxed pace with plenty of photo stops.
Day 6 · Norcia → Cascia → Leonessa → Piediluco → Orvieto → Chiusi · ≈ 220 km
- Norcia → Cascia → Leonessa (Apennine backroads) · ≈ 70 km
- Leonessa → Piediluco Lake → Terni bypass · ≈ 70 km
- Terni bypass → Orvieto (via SS205 / scenic connectors) · ≈ 50 km
- Orvieto → Chiusi · ≈ 30 km
A long transition day that swaps high ridges for lakeside curves and ends in classic Tuscan wine country around Chiusi.
Day 7 · Chiusi → Montepulciano → Pienza → Crete Senesi → Chianti → Florence · ≈ 200 km
- Chiusi → Montepulciano → Pienza (different approach from Day 2) · ≈ 50 km
- Pienza → Asciano via Crete Senesi backroads · ≈ 55 km
- Asciano → Gaiole in Chianti → Greve · ≈ 60 km
- Greve → Florence (SR222 northbound) · ≈ 35 km
Final montage of all the classic ingredients: clay ridges, vineyards, tight S-bends and a last run up the Chiantigiana back into Florence to close the loop.
Hotels · biker-friendly options along the loop
Three suggestions (Budget · Mid · Premium) around each overnight stop, all with secure or on-site parking. Links go directly to the property page on Booking.com.
Day 1 · Montalcino area
Small hilltop hotel right by Montalcino’s old walls, with panoramic pool and straightforward access from the Val d’Orcia roads. Secure on-site parking suitable for motorbikes.
Classic Montalcino property with terrace pool overlooking the vineyards; good balance of price, views and easy walk into the old town. Public but convenient parking, plus options for safer side-streets.
Restored castle above the Val d’Orcia with thermal pools and full resort services; a proper “treat” stay with private parking inside the estate for your bike.
Day 2 · Perugia
Historic-core hotel with rooftop terrace, simple but characterful rooms and good value for a night in the centro storico. Public parking nearby; ask reception for the easiest bike solution.
Design-driven boutique hotel just below Corso Vannucci, with rooftop spaces and modern rooms in a historic shell. Private parking options available by arrangement.
Classic grand hotel at the edge of the historic core, with indoor pool over Roman ruins and full 5-star service. Valet and private garage options make life easy with luggage.
Day 3 · Arezzo
Simple, rider-friendly base about ten minutes’ walk from the old town, with easy on-site parking and straightforward access from the ring road.
Modern 4-star property just outside the centre, popular with touring groups; large car park and easy bike access from the SS73 without wrestling city traffic.
Boutique option in the very heart of Arezzo, with individually decorated rooms and valet solutions to remove parking stress.
Day 4 · Spello / Foligno area
Family-run hotel perched above the valley with terrace views and a welcoming, low-key feel. Public parking and nearby spots that work well for bikes.
Characterful hotel built into the medieval fabric of Spello, with panoramic pool and restaurant. Parking around the structure; check in advance for motorbike-friendly arrangements.
Elegant villa-style hotel near Foligno station, convenient if you prefer a slightly larger town stay while still being minutes from Spello and Assisi. Private parking in the grounds.
Day 5 · Norcia
For a basic, good-value stay in the wider Valnerina/Norcia area, look at Bianconi group properties which are used to hikers and touring guests; many offer practical parking and on-site restaurants.
(Use Norcia as your keyword on Booking and cross-check for parking notes; availability is still evolving after the earthquakes.)
Traditional Norcia properties under the same ownership, right in the historic centre with classic interiors and a strong food focus. Good walkable base for an evening passeggiata after riding Castelluccio.
(Check current Booking listings for up-to-date opening status and parking details.)
Refined Relais & Châteaux townhouse a few steps from Norcia’s main square, with small wellness area and fine dining. Ideal if you want a high-end “basecamp” for exploring the Sibillini.
Day 6 · Chiusi / Val di Chiana
Roadside-style hotel with restaurant and easy access from the main road, ideal for a quick in-and-out after a long riding day. Large car park with plenty of space for bikes.
Countryside villa overlooking the valley, with pool and gardens. Good compromise between comfort, atmosphere and cost, with on-site parking for your bike.
(Search “Villa Hotel Del Sole, Chiusi” directly on Booking; ratings around 8.5 / 10.)
19th-century noble villa with pool, park and well-regarded restaurant, set in the countryside between Chiusi and Chianciano. Large private grounds and gates make parking secure for motorbikes.
Day 7 · Florence (final night)
Compact central hotel a short walk from Santa Maria Novella, often used as a simple overnight base with practical access and nearby garages.
(Search “Hotel Dedo, Florence” on Booking; check current name/branding and parking options.)
Design hotel with inner garden, spa and pool a few minutes’ walk from the station, offering a quiet retreat once you are off the bike. Nearby garages cater well to motorbikes.
Landmark 19th-century villa above the Arno, set in a private park with pool. A refined end to the trip, with private parking and concierge support to store the bike safely.
Restaurants · bookable via Google Maps
All suggestions are mid-range trattorie or osterie that typically support online booking via Google Maps (“Reserve a table” / “Prenota un tavolo”). Ratings are approximate Google scores.
Day 1 · Around Montalcino
Day 2 · Lake Trasimeno & Perugia
Day 3 · Gubbio & Arezzo
Day 4 · Assisi & Spello
Day 5 · Norcia & Castelluccio
Day 6 · Orvieto & Chiusi
Day 7 · Florence finale
Activities · bookable on GetYourGuide
Optional rest-day or off-bike experiences that match the spirit of this loop. All links use Epic Moto Journey’s partner code.
Chianti Wineries Tour from Florence
Half-day coach-supported wine tour into the Chianti hills, ideal if you want a tasting day without riding.
Val d’Orcia: Montepulciano, Pienza & Montalcino with winery
Full-day minibus tour through the same villages you ride, but with structured tastings and hosted cellar visits.
From Rome: Assisi & Orvieto Day Tour
For companions arriving or departing via Rome, this day trip mirrors part of your loop with guided visits to Orvieto and Assisi.
Seasonality & safety
Best months for this loop are April–June and September–October. July and August can be very hot in the valleys and busy around the major towns, while winter brings ice risk on the Sibillini and Apennine passes. Always check local forecasts for Castelluccio, Norcia and Valnerina before committing to higher roads, and have a lower-altitude alternative ready if conditions turn.
Fuel is generally easy to find along the route, but some stations in rural areas are unmanned outside peak hours: carry a card that works at Italian self-service pumps and avoid arriving in Norcia or Castelluccio on reserve.
