Tuscany 10-Day Itinerary

A comprehensive 10-day Tuscany road trip covering Florence, Siena, Chianti, the Val d'Orcia, Pienza, Lucca, and a day trip to Pisa. Built around a rental car, with wine tastings, medieval hill towns, Renaissance art, and Tuscan countryside—at a relaxed, immersive pace. For a shorter version, see the Tuscany 7-day itinerary, or for a broader Italy route, the Italy 10-day itinerary or the Italy 14-day itinerary.

Tuscany countryside
Photo by Rafael Peier on Unsplash

Route at a glance

This 10-day Tuscany route starts and ends in Florence, with a rental car loop through the whole region. Days 1–3 cover Florence in depth, then the route moves south to Siena for two nights, continues into the Val d'Orcia with a base in Pienza, and finishes north in Lucca with a day trip to Pisa before the final drive back to Florence Airport.

  • 1 Florence Days 1–3
  • 2 Siena Days 4–5
  • 3 Chianti Day 5 · Day trip
  • 4 Pienza Days 6–7
  • 5 Montepulciano Day 6 · En route
  • 6 Val d'Orcia Day 7 · Day trip
  • 7 Lucca Days 8–9
  • 8 Pisa Day 9 · Day trip

Where this trip comes to life

A quick visual preview of where this route settles in.

Day-by-day plan

Click a day to view the details

Planning tips for this Tuscany itinerary

Practical tips for Tuscany

Rent a car in Florence

A rental car is essential for this route. The Val d'Orcia villages, Chianti wineries, and countryside around Pienza have limited or no train connections. Pick up at Florence Airport on Day 1.

Book museums and key sights early

Reserve the Uffizi, Florence Cathedral dome, Siena Cathedral, and Pisa's Leaning Tower well in advance. These sell out quickly in summer.

Book wine tastings in advance

Chianti estates and wineries around Siena often require reservations. Booking ahead gives you access to cellar tours and a far richer tasting experience.

Watch out for ZTL zones

Most Tuscan historic centers are restricted traffic zones. Always park in designated areas outside the walls and walk in to avoid fines.

Travel in spring or autumn

May, June, September, and October offer the most comfortable conditions for driving and sightseeing. July and August are very hot and crowded.

Pick up local produce on the road

Pienza is famous for its pecorino cheese, Chianti for its wine, and Lucca for its olive oil. Bring a cool bag and stock up during your scenic drives.

Where to stay for this itinerary

  • Florence 2 areas
    Historic Center Best base for walking access to the Duomo, Uffizi, and Ponte Vecchio.
    Most practical
    Oltrarno Quieter and more local, with artisan shops and a relaxed atmosphere south of the Arno.
    Best atmosphere
  • Siena 2 options
    Historic Center Walk to Piazza del Campo, the Cathedral, and all main sights. The most immersive base in Siena.
    Best overall
    Agriturismo in Chianti Stay in the countryside between Siena and Florence for a more rural Tuscan experience.
    Best atmosphere
  • Pienza 2 options
    Pienza Town Center Small but perfectly located—everything is walkable and the views from the walls are stunning.
    Most practical
    Val d'Orcia agriturismo Farmhouse stays with vineyard views just outside Pienza—ideal for the Val d'Orcia experience.
    Best atmosphere
  • Lucca 1 area
    Inside the Walls Stay within Lucca's historic walls for the best access to the city's streets, piazzas, and restaurants.
    Best overall
Book agriturismo stays early

The best countryside farmhouses in Chianti and Val d'Orcia fill up fast, especially in May, June, and September. Book several months in advance.

Best time to visit Tuscany

A quick seasonal view for this route across Florence, Siena, the Val d'Orcia, and Lucca.

Jan
Cold · Quiet
Feb
Cold · Low season
Mar
Spring blooms
Apr
Best
May
Best
Jun
Warm · Long days
Jul
Hot · Busy
Aug
Very hot
Sep
Harvest · Best
Oct
Autumn colours
Nov
Cool · Rainier
Dec
Festive · Quiet

Spring (March to June) and autumn (September to October) are the best times for a Tuscany road trip, with mild temperatures, green rolling hills, and fewer crowds across Florence, Siena, and Lucca. September is particularly good for wine lovers, as the harvest is underway in Chianti and across the Val d'Orcia. July and August are hot and crowded in all major towns. Winter is quiet and affordable, with shorter days but excellent museum access in Florence and Siena.

Details

Tuscany 10-day itinerary overview

This itinerary covers three full days in Florence, two days in Siena with a Chianti wine tasting, two days based in Pienza exploring the Val d'Orcia, two nights in Lucca with a day trip to Pisa, and a final drive back to Florence Airport. Designed for a rental car with a relaxed, immersive pace and realistic driving times.

Route at a glance

  • Florence (Days 1–3)
  • Siena (Days 4–5) · Chianti wine tasting Day 5
  • Pienza (Days 6–7) · Montepulciano en route Day 6 · Val d'Orcia walk Day 7
  • Lucca (Days 8–9) · Pisa day trip Day 9
  • Departure from Florence Airport (Day 10)

Day-by-day highlights

  1. Day 1 (Florence): Arrival, Ponte Vecchio, Piazzale Michelangelo, Oltrarno dinner
  2. Day 2 (Florence): Uffizi, Duomo climb, gelato, Piazza della Repubblica
  3. Day 3 (Florence): Boboli Gardens, Santo Spirito artisans, sunset Arno walk
  4. Day 4 (Siena): Drive south, Piazza del Campo, Siena Cathedral, dinner in Etruscan caves
  5. Day 5 (Siena): Sunday market, Museo Civico, Chianti wine tasting tour
  6. Day 6 (Pienza): Montepulciano en route, Pienza Cathedral, pecorino cheese tasting
  7. Day 7 (Pienza): Val d'Orcia hike near Bagno Vignoni, Montefollonico village
  8. Day 8 (Lucca): Drive north, walk on city walls, Piazza dell'Anfiteatro
  9. Day 9 (Lucca + Pisa): Day trip to Pisa's Leaning Tower, return for dinner in Lucca
  10. Day 10 (Florence): Torre Guinigi, pastries, drive to Florence Airport

Customize this itinerary in minutes

Generate an editable plan with maps, photos, and day-by-day views.

Create your own plan See the interactive planner

Other Italy itineraries

Country routes

TCity routes

Complete 10-day Tuscany itinerary (day-by-day plan)

Full written version of this 10-day Tuscany itinerary, including the main stops, transfers, and highlights for each day.

For a shorter trip, see the Tuscany 7-day itinerary. Travelers looking for a broader Italy trip can see the Italy 10-day itinerary.

Day 1: Florence (arrival, Ponte Vecchio, and Piazzale Michelangelo)

Arrival at Florence Airport, rental car pick-up, and a relaxed afternoon introduction to the city with a walk along the Arno and dinner in the Oltrarno.

  • 12:00 — Arrival at Florence Airport, rental car pick-up
  • 13:00 — Check-in in historic center
  • 14:00 — Lunch at Trattoria Mario
  • 15:30 — Walk along Ponte Vecchio and explore Oltrarno
  • 17:00 — Visit Piazzale Michelangelo viewpoint
  • 20:00 — Dinner at Osteria Vini e Vecchi Sapori

Transport: Rental car pickup at Florence Airport, short drive to historic center, walking in central Florence.

Day 2: Florence (Uffizi, Duomo, and gelato)

Full day exploring Florence's Renaissance masterpieces and its most iconic landmarks, with time for gelato and an evening stroll.

  • 09:30 — Visit Uffizi Gallery
  • 12:30 — Lunch at La Prosciutteria Firenze
  • 14:00 — Visit Florence Cathedral and climb Brunelleschi's Dome
  • 16:30 — Gelato at Gelateria La Carraia
  • 18:00 — Stroll through Piazza della Repubblica
  • 20:00 — Dinner at Trattoria 4 Leoni

Transport: Walking and local transfers within Florence. No intercity travel.

Note: For a more immersive experience in Florence, see the Florence 3-day itinerary or Florence 4-day itinerary.

Day 3: Florence (Boboli Gardens, Santo Spirito, and sunset Arno walk)

A quieter Florence day exploring the gardens, artisan workshops, and the riverside at golden hour.

  • 09:30 — Visit Boboli Gardens
  • 12:30 — Lunch at Trattoria Cammillo
  • 14:30 — Visit artisan workshops in Santo Spirito
  • 17:00 — Coffee at Ditta Artigianale
  • 19:00 — Sunset walk along the Arno River
  • 20:30 — Dinner at Il Santo Bevitore

Transport: Walking and local transfers within Florence.

Day 4: Siena (drive south, Piazza del Campo, and cathedral)

Morning drive to Siena for a full afternoon in the medieval city center, finishing with dinner inside Etruscan caves.

  • 09:00 — Drive Florence → Siena (Car, ~1h15, 75 km)
  • 10:30 — Check-in in Siena city center
  • 11:30 — Visit Piazza del Campo and Torre del Mangia
  • 13:00 — Lunch at Osteria La Sosta di Violante
  • 14:30 — Visit Siena Cathedral (Duomo di Siena)
  • 16:30 — Walk through Contrada districts and Piazza Salimbeni
  • 20:00 — Dinner at Antica Osteria da Divo

Transport: Car Florence → Siena, local walking in Siena city center.

Day 5: Siena (Museo Civico and Chianti wine tasting)

Morning at Siena's civic museum, followed by an afternoon wine tasting tour in the Chianti countryside.

  • 09:00 — Browse Mercato di Piazza Matteotti
  • 11:00 — Visit Museo Civico di Siena
  • 13:00 — Lunch at La Taverna di San Giuseppe
  • 15:00 — Chianti wine tasting tour at a family-run vineyard
  • 19:30 — Dinner at Ristorante Il Bandierino

Transport: Local walking in Siena, short car drives to Chianti countryside and back.

Day 6: Pienza (Montepulciano en route, cathedral, and cheese tasting)

Drive south via Montepulciano to Pienza, with afternoon exploration of the Renaissance town and local pecorino tasting.

  • 09:00 — Drive Siena → Montepulciano (Car, ~1h)
  • 10:15 — Walk Montepulciano historic center
  • 12:00 — Lunch at Osteria Acquacheta
  • 13:30 — Drive Montepulciano → Pienza (Car, ~30 min)
  • 14:15 — Check-in in Pienza town center
  • 15:00 — Visit Pienza Cathedral and Palazzo Piccolomini
  • 16:30 — Pecorino cheese tasting at La Buca delle Fate
  • 20:00 — Dinner at La Porta in Monticchiello

Transport: Car Siena → Montepulciano → Pienza, local walking in both towns.

Day 7: Pienza (Val d'Orcia hike, Bagno Vignoni, and Montefollonico)

Full day exploring the Val d'Orcia countryside with a scenic hike, a visit to the thermal village of Bagno Vignoni, and a detour to Montefollonico.

  • 09:00 — Morning hike in Val d'Orcia near Bagno Vignoni
  • 12:00 — Lunch at Trattoria La Chiocciola
  • 14:00 — Visit Montefollonico village
  • 16:00 — Gelato and afternoon walk in Pienza
  • 20:00 — Dinner at La Terrazza della Val d'Orcia

Transport: Short car drives between villages, local walking throughout.

Day 8: Lucca (drive north, city walls, and Piazza dell'Anfiteatro)

Morning drive north to Lucca, with an afternoon walk on the Renaissance walls and an evening stroll through the historic center.

  • 09:00 — Drive Pienza → Lucca (Car, ~2h30, 150 km)
  • 11:30 — Check-in inside Lucca's walls
  • 12:30 — Lunch at Trattoria da Leo
  • 14:00 — Walk and bike ride on Lucca's Renaissance walls
  • 16:30 — Explore Piazza dell'Anfiteatro
  • 20:00 — Dinner at Ristorante Giglio

Transport: Car Pienza → Lucca, local walking and optional bike rental in Lucca.

Day 9: Lucca and Pisa (day trip to the Leaning Tower)

Day trip to Pisa to visit the Leaning Tower and Piazza dei Miracoli, returning to Lucca for a final evening dinner.

  • 09:00 — Drive Lucca → Pisa (Car, ~30 min)
  • 09:45 — Visit Piazza dei Miracoli: Leaning Tower and Pisa Cathedral
  • 12:30 — Lunch at Ristorante La Buca, Pisa
  • 14:00 — Walk along Arno River and visit Piazza dei Cavalieri
  • 16:00 — Drive Pisa → Lucca (Car, ~30 min)
  • 18:00 — Evening walk in Lucca historic center
  • 20:00 — Dinner at Buca di Sant'Antonio

Transport: Car day trip Lucca ↔ Pisa, local walking in both cities.

Note: Book the Leaning Tower climb in advance—slots sell out quickly in peak season.

Day 10: Lucca and Florence (Torre Guinigi and departure)

Final morning in Lucca with a climb up the Torre Guinigi and pastries before the drive to Florence Airport.

  • 09:00 — Visit Torre Guinigi
  • 10:30 — Coffee and pastries at Pasticceria Taddeucci
  • 11:15 — Walk around Piazza Napoleone
  • 13:00 — Light lunch at Ristorante Da Pasquale
  • 14:30 — Hotel checkout and luggage collection
  • 15:00 — Drive Lucca → Florence Airport (Car, ~1h15, 80 km), rental car return

Transport: Local walking in Lucca, car transfer to Florence Airport with rental car drop-off.

FAQ

Is this itinerary customizable?

Yes—MyTripBlueprint generates editable plans. You can change pace, interests, and transport preferences.

Does the full plan include maps and photos?

Yes—generated plans include an interactive day view with maps, routing, and place photos.

Is 10 days enough for Tuscany?

Yes—10 days allows a well-paced exploration of Tuscany's highlights, from Florence's Renaissance art to the medieval streets of Siena, the Val d'Orcia countryside around Pienza, and the walled city of Lucca with a day trip to Pisa.

Do I need a car for this Tuscany itinerary?

Yes—a rental car is essential for this route. The Val d'Orcia villages, Chianti wineries, and countryside around Pienza have no direct train connections. Pick up at Florence Airport on Day 1 and drop off there on Day 10.

Can I use this Tuscany itinerary as a starting point?

Yes—this sample plan is meant to help you start with a realistic route. In MyTripBlueprint, you can create your own editable version and adapt the stops, pace, and transport style.