At a glance
- If you add one more place in Tuscany, Lucca is our first pick. A walk along the city walls makes a nice break from the crowds in Florence and Pisa. If you’re renting a car, combine Montepulciano and Montalcino with Pienza. For another art city, choose Arezzo or Cortona.
- Many places in Florence require timed reservations, including the Uffizi and the Duomo complex. Instead of packing a museum and a cathedral viewpoint into the same day, pair one timed reservation with a walk through one part of the historic center.
- Don’t try to visit Pisa and San Gimignano on the same day. Take a round-trip train from Florence to Pisa, and visit San Gimignano separately by bus or tour while staying in Siena. This makes transfers and last-bus timing easier to manage.
- Plan Pienza for a day spent exploring the Val d’Orcia countryside. Instead of forcing a round trip by public transport from Siena, schedule it for a day when you can use a rental car or stay in Montepulciano or Pienza.
- Assisi is in Umbria, not Tuscany. Don’t squeeze it into a day trip from Florence; set aside an overnight stay or a separate day before or after traveling to Rome.
Group the cities, but travel in one direction each day
① Use Florence as a base for a round trip to Pisa, then ② move to Siena and visit San Gimignano. ③ Head south to Pienza and Val d’Orcia on a day when you can rent a car or arrange other transportation. Assisi is an extension into Umbria, outside the map.
See the travel guidance for each stop below.
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Florence 3 nights · Train base
Split museum reservations and walks through the historic center across two days.
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Pisa Day trip
Take the train there and back from Florence, and check the Leaning Tower reservation requirements.
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Siena 2 nights · Medieval city
Stay here for evenings in the historic center and a round trip to San Gimignano.
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San Gimignano Bus day trip
Check the round-trip bus schedule and last departure first.
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Pienza · Val d’Orcia 1 night · Rental car
Park outside the ZTL and choose just one scenic drive.
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Assisi Umbria extension
It’s outside Tuscany, so add a day to your trip toward Rome to visit.
Split the trip between northern trains and a southern rental car
5 Cities · 6 Nights, 7 Days
The order may change depending on train and bus schedules and museum reservation times on your travel dates. The key is not to cover two cities in one day. Stay in Florence and Siena without a car, and pick one up only when heading south to Pienza and Val d’Orcia.
Drop off your bags at accommodation near Firenze Santa Maria Novella station or in the historic center, then walk past the Duomo, Piazza della Signoria, and the Arno River. Don’t book the Uffizi or the dome viewpoint on your arrival day.
- Firenze S. M. Novella
- Piazza del Duomo
- Piazza della Signoria
Plan your morning around a reservation at either the Uffizi or the Accademia Gallery. In the afternoon, explore just one area, such as Santa Croce or Oltrarno, to keep the day manageable.
- Choose either the Uffizi or the Accademia Gallery
- Arrive at the entrance before your reserved time
Check trains for your travel date from Florence to Pisa Centrale, then walk from the station to Piazza dei Miracoli. Check the separate reservation requirements if you plan to climb the Leaning Tower, and return to Florence in the late afternoon.
- Round-trip train to Pisa Centrale
- Piazza dei Miracoli
- Check reservation requirements for climbing the Leaning Tower
Leave Florence in the morning or before lunch, and drop off your bags at your accommodation in Siena. Walk around Piazza del Campo and the Duomo, then spend the evening in the historic center. Don’t add Pisa or San Gimignano on a travel day.
- Piazza del Campo
- Siena Cathedral
- Check the distance between your accommodation and the bus stop
From Siena, first look for a round-trip Autolinee Toscane route 130 service that runs on your travel day. Choose the departure stop—Siena–Via Tozzi or Siena–Ferrovia—to match the specific service you select, and check whether your San Gimignano service stops at Porta San Giovanni or Piazzale Montemaggio. Some services require a transfer at Poggibonsi FS, so check for direct service and transfer wait times in both directions. After visiting Torre Grossa and the Civic Museum, return to Siena on a bus that leaves before the last one. If the connections don’t work, switch to a booked tour that includes round-trip transport.
- Round-trip Autolinee Toscane schedule
- Torre Grossa
- Choose a return trip earlier than the last bus
Pick up a rental car in Siena or travel to Pienza using transportation you’ve already booked. After exploring the historic center and Piazza Pio II, add just one scenic drive in Val d’Orcia. Stay in Pienza or near Montepulciano.
- Pienza historic centre
- Park outside the ZTL
- Return to your accommodation before sunset
In the morning, visit just one place you missed in Montepulciano or Pienza. If you plan to taste wine, decide in advance who will drive without drinking. Book the car from Siena for return to the same Siena office. First allow time for the return deadline, refueling, and travel from the rental office to the station or bus stop; then decide how long to spend sightseeing. Afterward, continue to Florence or your next city. If you want to return the car in a different city, check during booking whether one-way returns are allowed and whether there is an extra fee. If you’re continuing toward Rome, don’t add Assisi to this day; allow an extra day for it.
- Montepulciano
- Don’t drive after wine tasting
- Check your car return time
Places and meals
Choose places that require timed reservations, such as the Uffizi or the Duomo, first.
Google MapsThis square is home to the Leaning Tower of Pisa and the cathedral. Check the reservation requirements for climbing the tower on your travel date.
Google MapsA day trip from the Siena area to see towers and medieval lanes.
Google MapsExplore the historic center around Piazza del Campo and the Duomo.
Google MapsA good town for a walk through a Renaissance-era historic center before entering Val d’Orcia.
Google MapsA hill town in Umbria. Keep it outside your Tuscany itinerary and set aside a separate day.
Google MapsWhy this itinerary works for first-time travelers
This itinerary suits travelers who want to combine museums, medieval squares, hill towns, and countryside in one trip. If you don’t want to rent a car, follow only Days 1–5 and skip Pienza or choose a local tour.
Reality check
For Florence to Pisa, check Trenitalia. For Florence to Siena, compare trains and buses for your travel date. Check the Autolinee Toscane timetable for buses from Siena to San Gimignano. Public transport to Pienza and Val d’Orcia is infrequent, so a rental car or pre-booked tour can make it easier to manage your schedule.
Allow at least two days for Florence, half a day to a full day for Pisa, one day for Siena, half a day to a full day for San Gimignano, and one day for Pienza and Val d’Orcia. If you add Lucca, swap it for Pisa or add another day. Don’t squeeze Assisi into your 7 days in Tuscany; add a day before or after traveling to Rome.
The Uffizi, Accademia, Duomo, and Leaning Tower of Pisa each have different reservation and admission requirements. Recheck train and bus fares, as well as rental car, fuel, parking, and ZTL conditions, for your travel dates.
Keep your bag in front of you at busy stations and squares in Florence and Pisa. Don’t drive a rental car into a ZTL; check with your accommodation about parking and whether you need to register your license plate. Don’t drive after wine tasting.
If plans change
Skip the one-night stay in Pienza and Val d’Orcia, and add a day in Florence or Siena. If you really want to see Pienza, check that the buses and return service work for your travel date, or compare small-group tours.
Instead of rushing through Pisa and Lucca in one day, swap Lucca for Pisa or add a day. If walking along the city walls is your priority, take an early train from Florence and allow at least half a day.
After your final day in Tuscany, add one night in Umbria or a day trip from a base in Rome. Check the visiting hours for the Basilica of Saint Francis and the bus from the station to the old town.
Small tip
If you have more time in Florence, consider adding Lucca instead of Pisa. If you prefer historic towns, choose Arezzo or Cortona; if wine is your priority, add Montepulciano or Montalcino to your one-night stay in Pienza. If you’re interested in the coast and islands, plan Elba Island separately from this itinerary.
Final check before departure
- First decide which places in Florence to reserve—the Uffizi, Accademia, or Duomo—and choose the times.
- If you want to climb the Leaning Tower of Pisa, check the separate reservation requirements.
- Save the round-trip bus schedule from Siena to San Gimignano, including the last bus.
- If you’re staying in Pienza and using a rental car, check parking outside the ZTL and parking at your accommodation.
- Remember in your itinerary and accommodation bookings that Assisi is in Umbria, not Tuscany.
Reservation requirements and opening hours for museums, churches, and towers, as well as train and bus schedules and rental car ZTL and parking rules, vary by season and date. If the itinerary doesn’t fit, you can swap Pisa and Lucca or postpone Val d’Orcia or Assisi until the next day. Recheck the official operators’ information and schedules for your travel dates before departure.
Information checked: 2026-10-02