Photo by Martha Bakerjian

Tuscany Itineraries

Siena in a Day

Tuscany Hill Towns Road Trip

Florence, Pisa, hill towns, and wine

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Tuscany is one of Italy’s largest regions and most popular destinations for visitors. The Renaissance city of Florence is the heart of Tuscany. From Florence you can easily visit some Tuscany towns on day trips. Tuscany is also known for its wines and thermal spa towns such as Saturnia and Montecatini Terme.

Even though central Tuscany is very popular, it’s easy to get off the beaten track. Go to the far southern or northern parts of the region called Maremma (in the south) and Garfagnana and Lunigiana (in the north).

Tuscany Highlights:

  • Siena is probably the best-known and most popular hill town. Siena is famous for its big fan-shaped piazza, Piazza del Campo, and summer horse-race, il Palio di Siena. Many interesting monuments and museums are in its historic center. Discover the famous hill town in our Siena in one day itinerary.
  • San Gimignano, known for the medieval towers dominating its skyline, is another of the most popular hill towns. Use our Tuscany hill towns road trip itinerary to visit the top hill towns.
  • Pisa, on the Arno River, is famous for its leaning tower, in the stunning Piazza dei Miracoli. Other Romanesque monuments in the square include its beautiful cathedral and Baptistery.
  • Lucca, near Pisa, is one of the top Tuscan towns that’s not a hill town. Its historic center is completely enclosed by walls. On top of the walls is a park with a wide path for walking or biking around the perimeter of the city. Inside the walls are medieval towers, many churches, shops, restaurants, and even Roman ruins. Puccini was born in Lucca and there’s a small museum in his former house and festivals of his music.
  • Carrara is famous for the marble quarries, in use since Roman times, where Michelangelo and other Renaissance sculptors sourced their marble. Visit the quarries above the town of Carrara and take an interesting jeep tour.
  • Cortona is the hill town made famous by Frances Mayes’ book, Under the Tuscan Sun. Still enclosed by 3000 year-old Etruscan walls, its medieval center is charming and has great views.
  • The Chianti Wine Region, between Siena and Florence, is a pretty area of rolling hills, vineyards, wineries, and small wine towns. La Chiantigiana is the main road through the Chianti area, dotted with winery signs and good restaurants.
  • Montepulciano, a walled hill town built on a limestone ridge, has one of Tuscany’s nicest main squares. The area is famous for its wine. Another wine town to visit in southern Tuscany is Montalcino with a castle that has a wine cellar and tasting room. Nearby the pretty town of Pienza was designed to be a perfect Renaissance city. Montalcino and Pienza are in the beautiful Val d’Orcia, one of Tuscany’s UNESCO World Heritage sites.
  • Top places to go along the Tuscan coast include Monte Argentario, the resort town of Viareggio known for its Liberty style architecture, and the upscale beach town of Forte dei Marmi. Elba Island and the Tuscan archipelago are just off the coast, too.

For more about visiting Tuscany, click the categories on the yellow bar above.

Tuscany Guide Books:
Rick Steves Florence and Tuscany
DK Eyewitness Travel Guide: Florence and Tuscany
Tuscany for the Shameless Hedonist
Tuscany Memoirs

When To Go

Tuscany can be visited all year although parts of Tuscany get snow during winter. During late spring and summer there are many festivals, outdoor concerts, and food fairs and wildflowers and fields of sunflowers are in bloom. Fall brings truffles, mushrooms, wine, and chestnuts to many places in Tuscany, often with weekend festivals.

How Much Time To Spend

Tuscany is one of Italy’s largest regions and there’s a lot to see. At least one week is recommended but if you only have a few days, it’s best to choose one part of the region to explore rather than trying to fit in too much.

High and Low Season

Winter is low season in Tuscany. Summer is high season in most parts of the region, especially along the coast. Florence and popular hill towns see a lot of tourists from mid-spring through early fall.

Weather and Climate

Most of Tuscany has a Mediterranean climate. The mountains, and sometimes the hills, get snow in winter. Expect some rain in spring and fall and occasional thunder storms in summer. During summer, the hill towns are fairly hot but the temperatures cool off at night. Cities, especially Florence, are hot and humid in summer. Along the coast, temperatures are fairly mild.

See Pisa weather and climate and Siena weather and climate for average temperatures and more details.

Events and Holidays

Italy has 12 National holidays. Banks and most shops are closed on national holidays although in tourist areas many shops should be open. Most museums and sites are closed on Christmas and New Year’s Day and some are also closed on Easter and May 1. Public transportation runs on a Sunday and holiday schedule. You’re likely to find special events and festivals on most of these holidays.

January 1, New Year’s Day or Capodanno
January 6, Epiphany, end of the Christmas season and also the day la Befana brings gifts
Easter Sunday, Pasqua, date varies
Easter Monday, La Pasquetta, the day after Easter
April 25, Liberation Day or Festa della Liberazione commemorating the end of WWII
May 1, Labor Day, the day of the worker
June 2, Republic Day, Festa della Repubblica
August 15, Ferragosto, also Assumption Day, is the traditional start of the August holidays
November 1, All Saint’s Day or Ognissanti
December 8, Immaculate Conception, traditional start of the Christmas season
December 25, Christmas or Natale
December 26, Saint Stephen’s Day or Santo Stefano

Time Zone

Tuscany, along with the rest of Italy, is in the central European time zone, or GMT 2 hours. Daylight savings usually begins the last Sunday in March and ends the last Sunday in October. For most of the year, the time in Italy is 6 hours ahead of the time in New York.

What it Costs

Tuscany is suitable for all budgets, from economical to luxurious.

Tuscany, and all of Italy, uses the euro. Euro coin denominations are 1, 5, 10, 20,and 50 euro cents and 1 and 2 euro. Paper currency is in denominations of 5, 10, 20, 50, 100, and 500 euro (and higher). The word euro is both singular and plural.

Abstract Pricing at a Glance

Prices often change or vary by season so we refrain from quoting exact prices that might be wrong. To give you a rough idea for planning purposes, we indicate general price ranges for points of interest.

Price ranges are quoted in €.

See & Do
N/A => Not applicable
€ => Tickets less than €15 per person
€€ => Tickets €15- €30 per person
€€€ => Tickets €30 or higher per person

Sleep — Out of town/rural

€ => Rooms less than €60 for a double
€€ => Rooms €60 – €100 for a double
€€€ => Rooms €100 or more for a double

Sleep — Large Cities
€ => Rooms less than €100 for a double
€€ => Rooms €100 – €150 for a double
€€€ => Rooms €150 or more for a double

€=> €5- €10 per person for a meal (without alcohol)
€€ => €10 – €25 per person for a meal (without alcohol)
€€€ => Above €25 per person for a meal (without alcohol)

€ => Tickets less than €25 per person
€€ => Tickets €25 – €50 per person
€€€ => Tickets more than €50 per person


Tuscany has 2 airports, Pisa and Florence, that serve mainly flights from other parts of Italy and Europe. It is possible to fly directly from New York to Pisa.

While you can reach the major cities of Tuscany by train, a rental car is recommended if you want to explore the countryside and smaller towns. Be sure to read these things to know about driving in Italy.

Florence is a major rail hub and can be reached by fast train from Rome or Venice. A regional train line runs between Florence and Viareggio on the coast with stops in towns such as Lucca, Montecatini Terme, Pistoia, and Prato and another regional line runs from Florence to Siena. A rail line runs along the Tuscan coast with stops in the cities of  Grosseto, Livorno, Pisa, Viareggio, Massa, and Carrara as well as some smaller towns between if you take a regional train.

Getting Around

Tuscany’s cities and bigger towns can be reached by train or bus. A major rail line runs along the coast and another connects Florence to Rome and Venice. Small towns and the countryside, including the Chianti wine region and most hill towns, are best explored by car.



Central Tuscany is known for the bistecca alla Fiorentina, a large steak like a T-bone that comes from Tuscany’s Chianina breed of cattle. For special pork, look for Cinta Senese, an heirloom pig from Tuscany. If you’re adventurous you can try the typical street food of Florence, Lampredotto, made from the fourth stomach of the cow.  Other dishes to try are crostini (bread) topped with chicken liver, ribolitta (Tuscan bread soup), panzanella (bread salad),  and cinghiale (wild boar). In southern Tuscany, the special pasta is pici, a kind of fat spaghetti often served with a garlicy sauce. Of course by the coast, seafood is the star and many towns make their own special version of seafood stew.

Since Tuscany is such a large region, food varies in different parts of the region so be sure to ask about local specialties wherever you go. Top wines include Chianti, Brunello di Montalcino, and Vino Nobile di Montepulciano and the dessert wine, Vin Santo, often served with cantucci, also called biscotti. Tuscany also produces very good olive oil and pecorino (sheep’s milk) cheese.


The Italian spoken in Tuscany is said to be the purest or most correct form of Italian. In tourist areas many people speak good English but if you go off the beaten track you often won’t find much English spoken.

Websites and Maps

Tuscany Maps on Wandering Italy


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