At a glance
- 5 nights in Pistoia: Take day trips by train to Florence for 2 days, Lucca for 1 day, and Pisa for 1 day. Pistoia is a starting base for travelers looking to save on accommodation. If staying in Florence into the evening matters more, compare the Florence accommodation price and round-trip transportation costs for your dates and switch bases if you prefer.
- 4 nights in Siena: Explore Siena on arrival day and the following day, take a day trip to San Gimignano, and spend a day on a Chianti wine tour. Stay overnight so you can enjoy evenings in the old town and visit nearby towns.
- 3 nights in Montepulciano: Rent a car from this point on. Visit Montalcino, Pienza, and the Val d’Orcia countryside, and spend a day in Montepulciano walking the old town and tasting wine.
- 2 nights in Pitigliano: Add this section if you want to see the cliffside town and southern Tuscany. To shorten the trip, drop these 2 nights and drive directly from Montepulciano to Arezzo.
- 2 nights in Arezzo: Return the car and finish with art and walks through the old town. On the last day, visit Cortona if your departure time allows. This 17-day plan connects five bases; you can add rest days as needed.
Where to Stay and for How Many Nights
17 days, 5 accommodation stops
Split the trip between trains in the north and a car in the south. Go without a car while sightseeing in Florence and Siena, then use one for the six days heading down to Val d’Orcia, starting on Day 10 after you’ve finished sightseeing in Siena.
- 숙박
- 16 nights
- 거점
- 5 accommodation bases
- 숙박 총액
- Add up the room total for your actual dates, city tax, parking, breakfast, and rental car
- 평균 1박
- No fixed nightly rate provided
이동 경로
Pistoia → Siena → Montepulciano → Pitigliano → Arezzo
The accommodations below are options to search in each area. This does not mean they can all be booked for under €90. Check whether the room rate for two people fits your budget on your travel dates before choosing.
- 1Pistoia
- 2Siena
- 3Montepulciano
- 4Pitigliano
- 5Arezzo
- 6Cortona
-
Days 1–5 · 5 nights
Pistoia
Pistoia Inn Check room availability, taxes, parking, and cancellation terms for your dates on the official booking page
예약 보기 지도 -
Days 6–9 · 4 nights
Siena
Hotel Alma Domus Check room availability, taxes, and cancellation terms for your dates on the official booking page
예약 보기 지도 -
Days 10–12 · 3 nights
Montepulciano
Albergo Duomo Ask the accommodation about room availability and parking outside the ZTL for your dates
예약 보기 지도 -
Days 13–14 · 2 nights
Pitigliano
Km 0 dal Centro Check room availability, taxes, and parking location for your dates before booking
예약 보기 지도 -
Days 15–16 · 2 nights
Arezzo
Hotel Cecco Check room availability, taxes, and cancellation terms for your dates on the official booking page
예약 보기 지도
Where to Stay and What to See Each Day
17-Day Itinerary by Accommodation Base
The accommodation listed for each day is where you’ll sleep that night. On Day 17, check out and depart. Optional stops are just suggestions; skip the next place if you want to spend longer at a museum or town.
Drop your bags at the accommodation, then visit the Cathedral of San Zeno and the Baptistery of San Giovanni in Corte in Piazza del Duomo. Keep arrival day free of other cities and have dinner in Piazza della Sala. Check indoor visitor information and museum hours with Visit Pistoia for your travel date.
Walk from Pistoia station to the old town. Google Maps 길찾기
- Piazza del Duomo PistoiaGoogle MapsA good starting point for a walk, with the cathedral, baptistery, and town hall nearby.
- Cattedrale di San ZenoGoogle MapsPistoia Cathedral, on Piazza del Duomo. Check official information for visiting hours inside.
- Battistero di San Giovanni in CorteGoogle MapsThe baptistery in front of the cathedral. Easy to visit on a walk around Piazza del Duomo.
- Piazza della SalaGoogle MapsAn old-town square where you can find a market and dinner spots.
Visit the Duomo complex and Piazza della Signoria, cross Ponte Vecchio, then walk up to Piazzale Michelangelo. Return to Pistoia before dinner.
Take a regional train round trip between Pistoia and Firenze S. M. Novella. Google Maps 길찾기
- Cathedral of Santa Maria del FioreGoogle MapsEntry conditions differ between the free areas of the cathedral and the sites that require a paid complex pass.
- Piazza della SignoriaGoogle MapsA midway point on the walk from the Duomo down to Ponte Vecchio.
- Piazzale MichelangeloGoogle MapsAllow enough time for the climb and your return train.
Visit the Uffizi with a morning booking, then take a break after lunch in the lanes of Oltrarno and Piazza Santo Spirito. Don’t plan two museums back to back.
Take a regional train round trip between Pistoia and Florence. Google Maps 길찾기
- Uffizi GalleriesGoogle MapsBook a ticket for the correct name and time slot through the official seller.
- Piazza Santo SpiritoGoogle MapsA good square to relax in after the museum.
Start with a walk or bike ride on the walls, then wander the lanes between Piazza dell’Anfiteatro and Torre Guinigi. Don’t add Pisa to the same day.
Take a regional train round trip between Pistoia and Lucca. Google Maps 길찾기
- Lucca City WallsGoogle MapsAllow at least 1 hour 30 minutes to walk the entire wall, including breaks.
- Piazza dell’AnfiteatroGoogle MapsA square lined with houses following the oval footprint of a Roman amphitheater.
- Guinigi TowerGoogle MapsCheck the stair access and last admission time.
Visit the cathedral and baptistery in Piazza dei Miracoli, then walk along the Arno. If you booked entry to the Leaning Tower, plan around your time slot. Don’t add a beach town.
Compare connections on the same-day schedule from Pistoia to Pisa Centrale. Google Maps 길찾기
- Piazza dei MiracoliGoogle MapsSee the cathedral and baptistery too, rather than just stopping at the Leaning Tower.
- Ponte di Mezzo PisaGoogle MapsA stop connecting the two banks of the Arno for a walk before returning.
Take a morning train and drop off your bags. In the afternoon, see Piazza del Campo and the Contrada lanes, then return to the square at night.
Compare Pistoia-to-Siena routes with transfers in Florence or Empoli. Siena station is below the hill, so move large bags up to the historic center using the station access escalators, a local bus, or a taxi, depending on your accommodation's location. Allow separate time for the final walk through the lanes and for check-in. Google Maps 길찾기
- Piazza del CampoGoogle MapsA square that feels different by day and night, and a good reason to stay overnight.
- FontebrandaGoogle MapsA short walk to see traces of the medieval water system.
Visit the Duomo complex and Santa Maria della Scala, then choose between Torre del Mangia and an afternoon stroll through the lanes.
Get around the old town on foot.
- Siena CathedralGoogle MapsAllow extra time if the floor mosaics are on view.
- Santa Maria della ScalaGoogle MapsAn indoor option for a rainy or hot day.
- Torre del MangiaGoogle MapsChoose either the Duomo viewpoint or this stop.
Go by morning bus to see Piazza della Cisterna, views from the walls, and the Duomo. Return to Siena in the late afternoon.
For your visit date, search Autolinee Toscane route 130 and choose a boarding stop at Siena Ferrovia or Via Tozzi; confirm that you will get off at San Gimignano Porta San Giovanni. If there is no direct service, check the platform again for route 130 or a connecting service at Poggibonsi FS. For the return, save the schedules for the last two available services connecting Porta San Giovanni to Siena via Poggibonsi FS, and check which services run on school days. Google Maps 길찾기
- Piazza della CisternaGoogle MapsThe heart of San Gimignano’s old town.
- Rocca di MontestaffoliGoogle MapsA short scenic walk with views of vineyards and towers.
Book a wine tour with a driver departing from Siena to visit vineyards and wineries. The three towns below are options to consider when choosing a tour, not places to visit all in one day. If you can’t find a suitable tour, take a rest day in Siena.
It’s difficult to reach several towns and outlying wineries using local buses alone. Google Maps 길찾기
- Piazza Matteotti Greve in ChiantiGoogle MapsA market square to choose when the bus route works for your plans.
- Radda in ChiantiGoogle MapsA hill town option that’s easy to reach from Siena.
- Castellina in ChiantiGoogle MapsConfirm transportation before combining this with Radda.
Pick up the car outside Siena and photograph any existing damage and the fuel level. After seeing Montalcino, take a break in Bagno Vignoni and continue to Montepulciano.
Save public parking outside each town’s walls as your destination.
- Fortezza di MontalcinoGoogle MapsChoose your return driver before any Brunello tasting.
- Piazza delle Sorgenti Bagno VignoniGoogle MapsThe central basin in the square is not a bathing pool.
- Piazza Grande MontepulcianoGoogle MapsFollow the accommodation’s parking instructions, then walk uphill.
See Pienza’s Renaissance square and viewpoints, then have lunch in Monticchiello. In the afternoon, walk through the gardens and lanes of San Quirico.
Save parking outside the walls of all three towns before setting out.
- Piazza Pio II PienzaGoogle MapsThe central square for seeing Pienza’s urban design.
- MonticchielloGoogle MapsCheck parking location before driving into town.
- Horti LeoniniGoogle MapsA garden where you can relax out of the afternoon heat.
Walk uphill from Porta al Prato to Piazza Grande. Book just one Vino Nobile cellar visit and spend the afternoon resting at your accommodation.
Leave the car at the accommodation’s parking area. Don’t drive after tasting wine.
- Porta al PratoGoogle MapsA gateway to start walking uphill from the lower part of the old town.
- Piazza Grande MontepulcianoGoogle MapsThe upper part of town, with the cathedral and historic wine cellars.
- Tempio di San BiagioGoogle MapsFactor in the long downhill and uphill walks.
Spend the morning driving and park outside the walls. In the afternoon, walk through the Jewish Quarter and old town, then take in the cliffside panorama from a viewpoint.
Check in before sunset to avoid driving mountain roads at night.
- Pitigliano Historic CenterGoogle MapsExplore the steep, narrow old town on foot, without a car.
- Madonna delle Grazie ViewpointGoogle MapsA roadside viewpoint over the cliffside town.
Take your time exploring Sovana’s square and Sorano’s fortress. If you’d rather visit hot springs, skip Sorano and go to Saturnia. Visiting both towns and the springs makes for a tight day of driving and parking.
Avoid driving country roads after dark.
- Piazza del Pretorio SovanaGoogle MapsSovana’s small historic center.
- Fortezza Orsini SoranoGoogle MapsCheck opening days and exhibition hours.
- Cascate del Mulino SaturniaGoogle MapsA natural hot spring where you should be prepared for crowds, the need to keep your belongings secure, and slippery surfaces.
Refuel, photograph the car’s condition, and return it. In the afternoon, walk around Piazza Grande and the old town.
If dropping off the car in Arezzo one-way is impossible or expensive, compare it with returning the car in Siena and taking the train. In that case, first check the rental company's Siena drop-off location and hours, and transit from the drop-off location to Siena station. Then check Trenitalia for connections and arrival times from Siena to Arezzo on your travel date. The drive from Pitigliano to Siena, car return, transfer to the station, and time waiting for a connection make this a long-distance travel day, so skip afternoon sightseeing in Arezzo and plan only to check in to your accommodation.
- Piazza Grande ArezzoGoogle MapsSee Arezzo’s sloping Piazza Grande and the Loggia designed by Vasari.
- Arezzo Railway StationGoogle MapsA landmark for getting around after returning the car.
Plan around your reserved visit to the frescoes in the Basilica of San Francesco, then walk to the Basilica of San Domenico and the Medici Fortress.
Get around the old town on foot.
- Basilica di San Francesco ArezzoGoogle MapsThe highlight is the Legend of the True Cross fresco cycle.
- Basilica di San Domenico ArezzoGoogle MapsSee Cimabue’s Crucifix.
- Fortezza Medicea ArezzoGoogle MapsA final walk with views of the old town and the surrounding valley.
If you have a morning flight or long-distance train, head straight to your departure point. If you leave in the late afternoon or are continuing your trip, leave your bags in Arezzo and visit Cortona. Take a bus from Camucia-Cortona station up to town to see the square and a museum, leaving enough time to return for your bags.
After the regional train from Arezzo to Camucia-Cortona, take a bus to the old town. Google Maps 길찾기
- Piazza della Repubblica CortonaGoogle MapsA square where you can start exploring the old town after getting off the bus.
- MAEC CortonaGoogle MapsAn indoor visit to see Etruscan artifacts.
- Basilica di Santa Margherita CortonaGoogle MapsThe uphill walk is long, so skip this depending on your departure time and energy.
숙박비는 2인 1실 검색 범위입니다. 16 nights 평균은 No fixed nightly rate provided이며, 실제 결제 전에는 총액, 도시세, 조식, 욕실 형태와 무료 취소 마감을 같은 조건으로 비교하세요.
일정 옆에 두는 여행 노트
보고, 이해하고, 쉬는 법
날짜별 일정에 이미 나온 내용을 다시 나열하지 않고, 여행 중 여러 번 꺼내 볼 기준만 모았습니다.
먼저 알고 가면 좋은 맥락
Compare the Medici patronage and Renaissance art of Florence with Siena’s Piazza del Campo and Contrada traditions. It’s an easy way to see how the rivalry between the cities shaped their architecture and layout.
The Val d’Orcia cultural landscape is a UNESCO World Heritage Site. Instead of treating Pienza, San Quirico, and Montalcino as isolated stops, leave time for the drive through farmland and along cypress-lined roads.
Around Pitigliano and Sovana, tuff cliffs and Etruscan sites remain. Pitigliano’s Jewish Quarter and synagogue help explain why the town is known as Little Jerusalem.
놓치지 말아야 할 장면
- Pistoia Piazza del Duomo지도
A starting base for northern train trips, and a square worth visiting in its own right on your first day.
- Florence Duomo지도
A key reservation to make for your first day in Florence.
- Lucca City Walls지도
Set aside a full day for Lucca instead of combining it with another city.
- Piazza del Campo Siena지도
The heart of the day and evening, and a reason to stay overnight in Siena.
- Piazza della Cisterna San Gimignano지도
A day trip from Siena by bus.
- Fortezza di Montalcino지도
See a town in Brunello country and its surrounding views.
- Piazza Pio II Pienza지도
A square that captures the idea of a Renaissance ideal city.
- Piazza Grande Montepulciano지도
The upper part of the old town in the Vino Nobile area.
- Pitigliano Viewpoint지도
A viewpoint over the entire town perched on tuff cliffs.
- Cascate del Mulino Saturnia지도
Know that the free natural hot springs can be crowded and have limited facilities before you decide to visit.
- Piazza Grande Arezzo지도
The center of a walk through Arezzo’s old town.
- Piazza della Repubblica Cortona지도
A hilltop old town reached by bus from Camucia station.
먹고 쉬는 법
In Pistoia and Florence, try everyday dishes that make use of bread, vegetables, and offal, such as ribollita, pappa al pomodoro, and lampredotto. You don’t need to order bistecca at every meal.
Chianti Classico centers on Sangiovese; Montalcino is known for Brunello, Montepulciano for Vino Nobile, and San Gimignano for Vernaccia white wine. These distinctions make the regions easier to tell apart. Bolgheri is on the western coast, so don’t force it into this itinerary.
In Pienza, look for pecorino cheese; in Siena, try pici and panforte; in Pitigliano, look for local Jewish dishes and tortelli. Small-town restaurants may close for an afternoon break and have limited kitchen hours, so check opening times on the day.
Don’t drive after a wine tasting. On tasting days, have a driver who doesn’t drink or book transportation with a driver.
작은 팁Set aside a full day each for Florence, Lucca, Siena, and Val d’Orcia. Don’t add Pescia, Empoli, or Poggibonsi except as transfer points. If 17 days feels too long, dropping the 2 nights in Pitigliano shortens the trip to 15 days while preserving the main route.
When to Rent a Car
For the first 9 days, stay several nights in Pistoia and Siena without a car. After sightseeing in Siena, pick up a car on Day 10 to visit Montepulciano, Pitigliano, and Arezzo, then return it on Day 15. On wine-tasting days, choose a designated driver or book a tour with a driver.
Transportation, Budget, and Parking
Montecatini Terme, Lucca, and Florence are easy to reach by regional train from Pistoia, but whether a specific train is direct and how long it takes vary by train and track work. On days that involve a transfer or bus for places like Pisa, Siena, San Gimignano, or Cortona, do not add more towns. Eurail can be used on Trenitalia Regionale, and regional trains usually do not require reservations, but compare the cost of using a pass travel day with individual tickets for each date. According to Trenitalia's official guidance, paper regional train tickets must be validated at a machine in the departure station before boarding. Digital regional tickets are validated automatically at the scheduled departure time of the selected train, so no separate check-in is needed; to change trains, make the change in the app before the original scheduled departure. Check the validity conditions on the purchase screen for other ticket types, including electronic tickets. Cars may appear in searches for your reservation date in Pistoia, but do not assume a rental is available until the location and automatic transmission inventory are confirmed. This itinerary recommends picking up the car after sightseeing in Siena so you do not have days when the car sits unused in the north.
The itinerary gives separate days to Florence (2), Lucca (1), Pisa (1), Siena (2), San Gimignano (1), and Chianti (1). For a round trip near Pistoia, add the outbound and return train times shown in the Trenitalia search for your visit date, then add time separately for walking to and from the station and waiting for connections. On the day you drive from Siena to your accommodation in the south, add at least 60–90 minutes to the map's driving time for pickup, parking, and moving luggage, and limit paid attractions to one or fewer. Keep rental car days to no more than three towns each.
Calculate accommodation, city tax, parking, breakfast, and rental car costs together based on your dates and booking terms. Check regional train prices for the same date and train on Trenitalia, then compare with Eurail travel days. Listed prices and parking fees for specific accommodations may change with availability and terms, so don’t treat them as fixed budget figures.
For safety, do not decide whether parking is permitted based only on the color of the parking lines. For white spaces, check the signs for eligible users, time limits, and resident-only restrictions; follow the posted signs for blue paid spaces and yellow permit-only spaces as well. Check for the white circle with a red border at ZTL entrances, and do not enter the historic center. If your accommodation is inside a ZTL, confirm in writing before arrival whether they can register your vehicle's license plate. Bring your original Korean driver's license and an International Driving Permit recognized in Italy or an official translation, along with your passport and a payment card in the main driver's name. Check the rental company's requirements for additional documents.
Adjust the Plan to Your Trip Length and Transportation
If you skip the two nights in Pitigliano and Saturnia, travel to Arezzo on Day 13 after Montepulciano on Days 10–12, return the car, spend all of Day 14 in Arezzo, and depart on Day 15. Don’t keep the original car-return plan for Day 15. This makes it easier to preserve your time in the key cities than to cut Florence or Siena.
After five nights in Pistoia and four in Siena, finish with three nights in Arezzo. Choose a Val d'Orcia day tour with a driver instead of the Chianti tour on day 9 in Siena. If you want both, add one night in Siena. Save Pitigliano, Sovana, and Saturnia for another trip.
Expand your search to Porta Camollia in Siena, Chianciano Terme near Montepulciano, and south of Arezzo station. Compare the final total including city tax, parking, and breakfast, along with cancellation terms, before considering a nonrefundable deal.
Take a local bus to one town or spend another day in Siena. Don’t set off on foot to an outlying winery on a whim or drive after a tasting.
Only change the order of outdoor walks and indoor museums within the same accommodation base. If heavy rain is forecast on a Val d'Orcia driving day, shorten it to one nearby town reachable by safe paved roads, or rest at your accommodation. Change it with a museum day at another accommodation base only if you can change all the accommodation, rental car, and timed-entry bookings.
Final check before departure
- Search for all 16 nights using the same dates and one room for two people, then record the final total: a €1,440 room-cost cap plus city tax, parking, and breakfast.
- For accommodations in Pistoia, Siena, and Arezzo, check the actual walking route and slope to the station or bus stop, as well as late check-in terms.
- For accommodations in Montepulciano and Pitigliano, get written confirmation of parking location outside the ZTL, whether it’s free or paid, and whether they can register your license plate.
- Save the Trenitalia schedules for your travel dates: Pistoia to Florence, Lucca, and Pisa; Pistoia to Siena; and Arezzo to Camucia-Cortona.
- Check weekday and weekend service with Autolinee Toscane for Siena–San Gimignano buses and buses from Camucia-Cortona station to Cortona’s old town.
- If you are buying a Eurail pass, compare its price with the total cost of individual regional train tickets. After activating a travel day on a mobile pass, add each train to your pass in Rail Planner before boarding, and check that the train appears on that day's QR ticket for inspection. With a paper pass, follow the official procedure of writing the travel date and each leg in the pass's travel record before boarding. This record is required even for regional trains that do not require reservations.
- Compare the total cost of picking up a rental car in Siena and returning it in Arezzo with a round trip return in Siena. Check the one-way fee, automatic transmission availability, insurance excess, deposit, and requirements and fees for adding another driver.
- Bring your original Korean driver’s license, an international driving permit recognized in Italy or an official translation, your passport, and a payment card in the main driver’s name.
- Check the official websites for timed entry requirements at the Uffizi, Florence Duomo, Siena Duomo, and Basilica of San Francesco in Arezzo.
- For winery tasting days, arrange for a driver who won’t drink or book transportation with a driver.
Official information was checked on October 1, 2026. Regional train times and fares, bus routes, accommodation availability, and prices vary by travel date. Check monument and museum hours in Pistoia again with Visit Pistoia for your travel dates. Travel times and accommodation prices in this guide are planning estimates; recheck the Trenitalia and Autolinee Toscane schedules and the accommodations’ official booking pages for your departure dates.
Information checked: 2026-10-01