Julie Italy 16 Comments

Tuscany, with its hilltop towns, breathtaking landscapes, long list of vineyards, and famous cities such as Florence, Pisa, and Siena, is one of Italy’s most visited regions. But did you also know that you can go canyoneering, relax in a hot spring, or visit an island in Tuscany?

In this guide, we list 22 of the best things to do in Tuscany, ranging from day trips to charming medieval towns to some hidden gems you might not yet know about.

Tuscany is a joy to explore and we can’t wait to share this beautiful place with you.

What is Tuscany?

Tuscany (Toscana) is a region in central Italy. Florence is the capital of Tuscany and the largest city in the region.

Tuscany is famous for being the birthplace of the Italian Renaissance, for its wine, and for its long list of UNESCO World Heritage Sites.

Famous artists such as Michelangelo, Leonardo da Vinci, Donatello, Cimabue, Giotto, Brunelleschi, Ghiberti, and Andrea Pisano left their mark throughout Tuscany (and Italy), on the cathedrals, baptisteries, and palaces in the cities throughout Tuscany.

This one region is home to multiple wines, including Chianti, Brunello di Montalcino, Vernaccia di San Gimignano, and Vino Nobile di Montepulciano. Visiting the hilltop towns to go wine tasting is one of the best things to do in Tuscany.

And Tuscany is home to some of Italy’s most famous landmarks, including the Leaning Tower of Pisa, the Florence Cathedral, the towers of San Gimignano, and Piazza del Campo in Siena.

Tuscany Map

Map of Tuscany

Best Things to Do in Tuscany

1. Visit the Historic Center of Florence

Home to the Uffizi Gallery and Michelangelo’s David, famous piazzas and bridges, the amazing Duomo, as well as palaces, gardens, and spectacular viewpoints, Florence is not to be missed on a visit to Tuscany.

Most of Florence’s top sights are located within its small, compact city center. The historic center of Florence is listed as a UNESCO World Heritage Site.

For the best experience, plan on spending at least two days in Florence. This gives you just enough time to visit the highlights, climb a few towers for panoramic views over the city, visit a few photogenic viewpoints.

Top Experiences in Florence:

  • Visit the Florence Cathedral (the Duomo)
  • Tour the Uffizi Gallery
  • Stroll across Ponte Vecchio
  • See the statues in Piazza della Signoria
  • Watch the sunset from Piazzale Michelangelo
  • Climb the steps to the top of Giotto’s Bell Tower
  • See Michelangelo’s statue of David
  • Climb the tower at Palazzo Vecchio
  • San Lorenzo Market & Mercato Centrale
  • Visit the Boboli Gardens and/or the Bardini Gardens

Florence Italy | Best Things to Do in Tuscany

Sunset at Piazzale Michelangelo

 Florence Italy | Best Things to Do in Tuscany

The Florence Cathedral

Plan Your Visit: Get the full list in our article Best Things to Do in Florence. Learn how to plan your time with our One Day in Florence and Two Days in Florence itineraries.

2. Spend Some Time in Siena

Siena is one of our favorite cities in Tuscany. With its incredible Duomo, picturesque main square (Piazza del Campo), medieval streets to explore, wonderful collection of restaurants, and the views from the top of Torre del Mangia, there is plenty here to keep you busy all day.

Siena is a great town to use as your home base for exploring Tuscany. It is rather centrally located in Tuscany, and has a train station and bus station, so it is easy to get to many of the Tuscan hill towns from here. And Siena also has its own list of notable sites and great restaurants.

Top Experiences in Siena:

  • Visit the Siena Cathedral
  • Enjoy the view from Torre del Mangia
  • Spend some time in Piazza del Campo
  • Visit Santa Maria della Scala
  • Stroll through the historic heart of Siena

Siena Italy Photo | Best Things to Do in Tuscany

Siena | Best Things to Do in Tuscany

 Siena Cathedral | Best Things to Do in Tuscany

Siena Cathedral


Piazza del Campo Siena

Piazza del Campo

Plan Your Visit: Get the full list of things to do in our article Best Things to Do in Siena. Plan your time with our One Day in Siena Itinerary.

3. Road Trip through Val d’Orcia

Val d’Orcia is one of the prettiest areas in Tuscany. With its rolling hills and twisting lines of cypress trees, this is one of the most photographed landscapes in Tuscany and the inspiration for Renaissance painters.

Montalcino, Pienza, and San Quirico d’Orcia are located in Val d’Orcia and this is also where Brunello di Montalcino and Vino Nobile di Montepulciano wines are produced.

Top Experiences in Val d’Orcia:

  • Visit Montalcino, Pienza & San Quirico d’Orcia
  • Go wine tasting
  • Take a photography tour
  • Visit the famous Val d’Orcia viewpoints

Montalcino Wine Tasting Photo | Best Things to Do in Tuscany

Wine tasting in Montalcino

4. Go Wine Tasting in Montalcino

Perched on a hilltop, overlooking the Sangiovese vineyards and stunning landscape of Val d’Orcia, a visit to this small town is a must for wine lovers.

The to do list in Montalcino is short and sweet. Climb the fortress walls for views of the town, stroll the city streets, and taste Brunello di Montalcino wine.

Montalcino | Best Things to Do in Tuscany


5. Visit the Wine Cellars in Montepulciano

This is another hilltop town where wine tasting is the #1 thing to do.

Underground wine cellars are found throughout Montepulciano, and wine tasting in one (or more) of these cellars is a must do for wine aficionados. But you can also stroll the picturesque streets, climb a tower for a view over Montepulciano, and get a history lesson in a museum.

Top Experiences in Montepulciano:

  • Visit Piazza Grande
  • Stroll the city streets
  • Taste Vino Nobile di Montepulciano wine
  • Visit an underground wine cellar
  • Climb the Clock Tower
  • Visit Temple of San Biagio

Palazzo Comunale Montepulciano | Best Things to Do in Tuscany

Montepulciano | Best Things to Do in Tuscany

6. Explore Lovely Pienza

Like Montalcino, this small town in Val d’Orcia has a very short to do list. The best thing about Pienza is strolling its very pretty streets and sampling pecorino cheese.

PRO TRAVEL TIP: Pienza, Montepulciano, and Montalcino are all located near each other, so these three towns can be visited in one busy day.

Top Experiences in Pienza:

  • Tour Palazzo Piccolomini
  • Try Pecorino di Pienza cheese
  • Visit Piazza Pio II
  • Walk the city walls
  • Stroll the side streets
  • Visit the Pienza Cathedral and its crypt

Pienza Photo | Best Things to Do in Tuscany



Where to Eat in Pienza

7. Spend a Few Hours in San Quirico d’Orcia

San Quirico d’Orcia is a lesser known town in Tuscany but it is a great place to have lunch or dinner and to stroll through another picturesque Tuscan town.

This very small town is located in Val d’Orcia, not far from Montalcino and Pienza. The list of sights is small. Stroll along Via Dante Alighieri, the main street through town, visit the Collegiate Church of San Quirico d’Orcia, and visit Horti Leonini. For a small town, San Quirico is also home to a surprisingly long list of highly rated restaurants, including a few with Michelin stars.

Two to three hours is all the time you need to spend here, and most of that time will be spent at lunch or dinner.

San Quirico Lunch

Lunch in San Quirico d’Orcia


San Quirico dOrcia | Best Things to Do in Tuscany

San Quirico d’Orcia

8. Take a Cooking Class

One of the best things to do in Tuscany is to take a cooking class. Cooking classes are located in many towns and villas, where you learn to make homemade pasta, pizza, or even gelato.

Here a few of the highest rated cooking classes in Tuscany:



9. Relax in a Hot Spring

Tuscany is filled with beautiful sites but this one just may be one of the most unique. Cascate del Mulino, also called the Thermal Baths of Saturnia, is a hot spring that is located in southern Tuscany.

This cascading thermal spring is open all year and is free to visit. During peak tourist season, it can be a crowded spot, so plan your visit early or late in the day for the best experience, if you will be in Tuscany from June through September.

Cascate del Mulino | Best Things to Do in Tuscany

Cascate del Mulino | shutterstock.com/travelwild

10. Go Wine Tasting in the Chianti Wine Region

Chianti is a wine region that sits to the south of Florence. This wine region, also called Monti del Chianti, includes the provinces of Florence and Siena and extends towards Arezzo, Val d’Orcia, and Pisa.

This wine region is further divided into smaller appellations, including Chianti Classico, Chianti Montalbano, Colli Senesi, and Chianti Rufina, just to name a few.

You can day trip into the Chianti wine region by visiting the towns in this area (such as Siena, Arezzo, Volterra, and San Gimignano) or join a tour that has wine tastings in the vineyards in this area.

One of the best ways to visit the Chianti wine region is on a tour.

This highly rated tour includes a visit to two wineries in the Chianti Classico region with food and wine pairings.

On this half day tour from Florence, visit two wineries in the Chianti wine region. And this tour from Florence includes lunch at a winery plus visits to Siena, Pisa, and San Gimignano.

You can also go truffle hunting or tour the Chianti wine region on a Vespa.

11. Stay in a Villa

One of the best experiences in Tuscany is to stay in a villa.

Staying in a villa has perks that you don’t typically get when staying in a hilltop town (although that can be a memorable experience as well). From your room, gaze across the vineyard, have a sunset dinner surrounded by vines, and have a private wine tasting. Some villas provide gourmet dinners, private tours, and some even have a pool and/or a spa.

We spent three nights at Villa le Prata, which is a short drive from Montalcino and a great home base for exploring Val d’Orcia. At the villa, we had dinner each night, plus sunset wine tastings and tours of the vineyard. In 2024, Villa le Prata received one Michelin key, a new award for extraordinary hotels.

Villa le Prata | Best Things to Do in Tuscany

Villa le Prata

12. See the Leaning Tower of Pisa

The Leaning Tower of Pisa is one of Italy’s most famous landmarks. The city of Pisa is located in western Tuscany, not far from the Cinque Terre and the Ligurian Sea.

Pisa is easy to get to using public transportation and a visit here lasts just a few hours, so it makes a great day trip option from other towns in Tuscany. It can also be combined with Lucca, mentioned next.

Leaning Tower of Pisa

Leaning Tower of Pisa

13. Walk the Lucca City Walls

Lucca is a small town that is located near Pisa. Walking the Renaissance-era walls, climbing the numerous towers for a view over the city, and having lunch in Piazza dell’Anfiteatro all top the list of the best things to do in Lucca.

Top Experiences in Lucca:

  • Visit the Lucca Cathedral
  • Walk or bike the city walls
  • Climb Torre Guinigi and Torre dell Ore for views over Lucca
  • Have lunch in Piazza dell’Anfiteatro

Where to Eat in Lucca | Best Things to Do in Tuscany

Lunch in Lucca | Best Things to Do in Tuscany


Lucca in September


Plan Your Visit: Get the full list in our article Best Things to Do in Lucca and plan your day trip in our article How to Day Trip to Pisa and Lucca.

14. Montecatini Terme

Montecatini Terme recently made it onto the list of “Great Spa Towns of Europe” UNESCO World Heritage Site. There are eleven mineral springs in Montecatini Terme and on a visit here, you can relax in a sauna and the healing thermal waters, and have a mud bath or beauty treatment.

On a visit here, you can also ride the funicular to Montecatini Alto, a small hilltop town that overlooks Montecatini Terme.

Montecatini Terme

Montecatini Terme | shutterstock.com/Hibiscus81

15. Climb the Towers in San Gimignano

San Gimignano is one of the most accessible towns in Tuscany. It is also one of the most touristy, but it is a delight to explore.

San Gimignano has more towers than any other hill town in Tuscany. Climbing these towers for a view over the town and the Tuscan hillside is one of the best things to do in San Gimignano. It’s also a wonderful place to go shopping and dine on local foods.

Top Experiences in San Gimignano:

  • Climb to the top of Torre Grossa
  • Stroll through the historic center of San Gimignano
  • Visit the Duomo di San Gimignano
  • Torri Salvucci Maggiore
  • Go shopping

San Gimignano Italy | Best Things to Do in Tuscany

San Gimignano


San Gimigano Tuscany

San Gimignano

16. Visit Cortona

Cortona is located in the southeastern corner of Tuscany. Due to its location (it takes longer to get to Cortona from Siena and Florence than many other Tuscan towns), Cortona doesn’t get quite as many visitors as the other hill towns. But don’t be expecting a ghost town. Quite a few people travel here to see Villa Bramasole, the villa made famous by the movie Under the Tuscan Sun.

Top Experiences in Cortona:

  • Visit Piazza della Repubblica
  • Stroll along Via Nazionale
  • Explore the side streets
  • Visit the Cortona Cathedral
  • Enjoy the view from Piazza Garibaldi
  • Visit the Girifalco Fortress
  • Visit Convent Le Celle

Cortona Italy | Best Things to Do in Tuscany

Cortona | Best Things to Do in Tuscany


Cortona Shopping

Shopping in Cortona

Italy Travel Guide Rome

17. Spend Some Time in Arezzo

Arezzo is located near the southeast corner of Tuscany, not far from Cortona.

With its grand piazzas, hilltop views, and medieval buildings and streets, Arezzo is one of the prettiest towns in Tuscany. On a visit here, you can fill your time by visiting the churches and art museums, enjoying the views from the fortress, shopping for antiques, and learning about jousting.

Arezzo is famous for its monthly antique market and its historical reenactments of the Saracen Joust which is held twice a year.

Top Experiences in Arezzo:

  • Visit Piazza Grande
  • Enjoy the view from the Clock Tower
  • Visit the Church of Santa Maria della Pieve
  • Stroll along Corso Italia
  • Vasari’s House
  • Fortezza Medicea
  • Visit Arezzo’s churches and cathedrals
  • Visit the Archaeological Museum and Roman Amphitheater

Piazza Grande Arezzo Italy

Piazza Grande, Arezzo


Arezzo Antique Market Photo

Arezzo antique market


Corso Italia Arezzo Italy

Corso Italia

18. The Mascagni Terrace in Livorno

The Mascagni Terrace, with its black and white checkered floor and views of sea, is one of the most photogenic places to visit in Tuscany.

This terrace is enormous…8,700 square meters with a balustrade of 4,000 columns. It was built between 1927 and 1951 and named after composer Pietro Mascagni.

The Mascagni Terrace is located in Livorno, a seaside town in western Tuscany.

Terrazza Mascagni

Terrazza Mascagni | shutterstock.com/Sean Pavone

19. Visit Elba

Elba, also called Isola d’Elba, is a small Mediterranean island in Tuscany. It is part of Arcipelago Toscano National Park, a series of several Tuscan islands. Elba is the largest island in this archipelago.

Napolean was exiled to Elba in 1814. He lived on the island for ten months, escaping to France in 1815.

Elba is home to beautiful beaches, crystal clear water, and small colorful towns along its coastline. You can get to Elba by ferry from the mainland and from Sardinia.


Elba | shutterstock.com/essevu

20. Walk the Walls at Monteriggioni

Monteriggioni is a small, walled town in Tuscany, Italy. It is just 30 minutes from Siena by car and bus.

A visit here is quick, with a stroll through town and a walk on the walls topping the list of things to do.



21. Go Canyoneering

In northern Tuscany, rivers have worked their magic, carving out gorges and canyons in the mountainous landscape. If you are looking for adventure on your visit to Tuscany, look no farther.

With an experienced guide, you can go canyoneering and river walking through these gorges.

On this tour, you will walk, swim, climb and float in the Canyon of Cocciglia. 

On this tour in Garfagnana Valley, you will go canyoning and slide down waterfalls and natural slides.


22. Visit Volterra

Volterra is one of the larger towns in Tuscany. It was first inhabited by the Etruscans and later by the Romans. One of the best things to do in Volterra is to visit the museums, to learn about the Etruscan civilization, and to visit one of the best preserved Roman theaters in Italy.

Like the other Tuscan hill towns, strolling the medieval streets, trying local foods, shopping, and climbing a tower or two are more ways to spend your time in Volterra.

Plan on spending at least a half of a day here, because there is quite a long list of sights to see.

Top Experiences in Volterra:

  • Visit Piazza dei Priori
  • Climb the tower of Palazzo dei Priori
  • Visit the Roman Theater
  • Guarnacci Etruscan Museum
  • Visit an Alabaster shop
  • Visit Fortezza Medicea
  • Visit the Ecomuseo dell’Alabastro

Volterra Tuscany Italy Photo

Volterra | Best Things to Do in Tuscany


Roman Theater Volterra

Roman theater in Volterra


Street in Volterra

Best Things to Do in Tuscany: On a Map

How to Use This Map: Click the icons on the map to get more information about each point of interest. Click the star next to the title of the map to add this map to your Google Maps account. To view it on your phone or computer, open Google Maps, click the menu button, go to “Your Places,” click Maps, and you will see this map on your list.

How to Get Around Tuscany

The best way to get around Tuscany is by car. The smaller towns are not easily accessible by public transportation, so if you want to visit places like Volterra, Pienza, Montalcino, and the viewpoints in Val d’Orcia, the best way to do it is to rent a car for a few days.

If you plan to stay in a villa, you will also need to rent a car.

Some Tuscan towns are reachable by train. On this list are Pisa, Lucca, Florence, Siena, and Arezzo.

San Gimignano and Siena are easy to get to by bus.

How Much Time Do You Need in Tuscany?

At a minimum, plan on spending three days in Tuscany. This gives you two days in Florence plus a day for a day trip to another town or two in Tuscany. Each additional day that you can add to your trip allows you to visit more hill towns in Tuscany, go wine tasting in Chianti, relax in the hot springs, and day trip to Elba.

To do everything we listed above, you will need a minimum of ten days.

In our Tuscany Itinerary, we give suggestions on how to plan your time, whether you have 3 days, 5 days, a week, or longer.

Where to Stay in Tuscany

For a quick visit to Tuscany (3 days or less) pick one location. Florence is your best option, since you will spend a day or two visiting the sites in Florence. The next best choice is Siena, a large town that is well connected to many places in Tuscany by public transportation.

With more time, I recommend spending two to three nights in Florence and then picking a location outside of Florence, either Siena, a Tuscan villa, or a centrally located Tuscan hill town.

On our most recent trip, we spent ten days in Tuscany, dividing our time between Villa Le Prata (in Val d’Orcia), Siena, and Florence.

Tours of Tuscany

Joining a tour takes out the hassle of renting a car or figuring out your transportation options. It also allows you to visit several Tuscan towns in one day or do something unique, like truffle hunting or dining in a vineyard.



Frequently Asked Questions

How many days should I spend in Tuscany?

If you want to explore several hilltop towns, go wine tasting, road trip through the beautiful landscapes of Val d’Orcia, plan on spending at least three days in Tuscany, with another day or two for Florence. You could easily spend a week in Tuscany and never run out of things to do.

What is the best month to visit Tuscany?

If you want to see Tuscany with the lush, green landscapes that make it look like a Renaissance painting, plan your visit for the month of May. By mid-summer, the landscapes turn a golden yellow and in late summer, some of the fields are tilled.

Do you need a car in Tuscany?

Many of the larger towns, such as Siena, San Gimignano, Pisa, and Lucca, are very easy to get to using public transportation. But if you want to visit the smaller towns or spend time photographing the landscapes, you will need to rent a car, because some smaller towns are very difficult or time consuming to get to using public transportation.

Visit More Wine Regions Around the World

FRANCE: Spend 3 days on the Alsace Wine Route, visiting small towns like Colmar, Eguisheim, and Ribeauville.
FRANCE: Spend 10 days in the French Riviera and Provence.
PORTUGAL: The Douro Valley is the oldest wine region in the world. Plan your visit with our Douro Valley Travel Guide and best wineries to visit in the Douro Valley.
AUSTRALIA: Go wine tasting in Barossa Valley and McLaren Vale.
NEW ZEALAND: Visit New Zealand’s largest wine region, the Marlborough Wine Region on the South Island.
CHILE: Visit the wine regions around Santiago, Chile.
ARGENTINA: Explore the wine regions around Mendoza, Argentina.

More Information about Tuscany

TUSCANY ITINERARY: Learn how to plan your visit with our Tuscany Itinerary, which has sample itineraries, whether you have 3 days, 5 days, or an entire week in Tuscany.

TUSCAN HILL TOWNS: Check out our detailed guides to Siena, Montepulciano, Pienza, Montalcino, San Quirico d’Orcia, San Gimignano, Monteriggioni, Lucca, Volterra, Arezzo, and Cortona.

FLORENCE: If you are planning your first visit to Florence, don’t miss our guide to the 10 Best Things to Do in Florence and how to spend two days in Florence. We also have guides about the best rooftop bars in Florence, the best viewpoints in Florence, and how to visit the Florence Cathedral.

DAY TRIPS FROM FLORENCE: Here are 15 day trips to take from Florence, with practical information on how to plan your day.

If you have any questions about the best things to do in Tuscany, let us know in the comment section below.

More Information for Your Trip to Italy

BEST OF ITALY: In our guide to the Best Places to Visit in Italy, we list 25 beautiful destinations to consider for your next trip to Italy.

ITALY ITINERARIES: If you are just beginning to plan your Italy itinerary, take a look at our 10 Days in Italy Itinerary for five different ways to spend 10 days in Italy. We also have a detailed 10 day itinerary that includes Rome, Florence, the Cinque Terre, and Venice and a 10 day southern Italy itinerary that includes the Amalfi Coast, Matera and Puglia.

ROME: For a list of the top experiences in Rome, read our article Best Things to Do in Rome. Learn how to put these together in our 2 Day Rome Itinerary and 3 day Rome Itinerary. And don’t miss our guides to the Best Views of Rome, best Rooftop Bars in Rome, and our Rome Restaurant Guide.

LAKE GARDA: Get started with our article Best Things to Do in Lake Garda. Learn how to plan your time with our Lake Garda Itinerary. We also have information about things to do in Sirmione and Riva del Garda.

DOLOMITES: For a list of where to go and what to do, read our article Best Things to Do in the Dolomites and Best Hikes in the Dolomites. Learn how to plan your trip with our Dolomites Itinerary Travel Planner.

We have TONS more information about Italy in our Italy Travel Guide, including Rome, Florence, Venice, Tuscany, the Dolomites, the Amalfi Coast, the Cinque Terre, Basilicata, and Puglia.


Tuscany Bucket List Italy


Header photo credit: shutterstock.com/Gaspar Janos

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Comments 16

  1. Avatar for Rich M
    Rich M

    My family and I are planning a first time 3-week trip throughout Italy. a couple of questions (as I have only passed through Rome, 1 time):
    Sadly, we can only take this amount of time beginning in June due to our teenager school schedule (understanding it will be warmer and potentially tourist busy):
    a) At the start of this Blog, where you list “Tuscany Bucket List”… from where was that picture taken and is publicly available? This is our ideal area that we would like to see live.
    b) We were thinking of allowing ourselves 4-5 days to see the Tuscany area… would you recommend Florence as our central home base (can either rent a car or take trains)… as we intend to see: Florence, Cinque Terre, Pisa, San Gimignano, Sienna…?
    c) Our trip can begin in either Venice to Naples (or the reverse)… High-level planning is looking like Venice > Tuscany Area > Rome Area > Naples Area (Amalfi, Pompei, Sorrento)…

    We love to hike, enjoy food, wine, futbol, cooking (my wife has a separate list for art/history/statues/etc.)… but we appreciate both the hustle/bustle of a city and also love the countryside.
    Any recommendations you have (or even itineraries), we would happily review with consideration to what a teenager may be willing to see is greatly appreciated.

    1. Avatar for Julie Post

      The header photo was taken in Val d’Orcia. I purchase it on shutterstock.com and the photo credit is given at the end of this post. Florence works very well as a home base for visiting Tuscany. The only challenge with Florence is parking, if you have a rental car, because rental cars are not allowed in the city center. If you have a rental car, you could spend 2 nights in Florence (only seeing Florence) and 3 night in Siena, using this to day trip to nearby towns. If you plan to use public transportation, then stay in Florence because it is well connected by train and bus to other cities. As for itineraries, take a look at our 2 week itinerary. This covers the places you want to see. You can then add more time into places like Tuscany, Rome, and the Amalfi Coast. And if you haven’t seen it yet, we have lots of info on our Italy Travel Guide. Let me know if you have any other questions. Cheers, Julie

  2. Avatar for Michele

    Hi Julie
    We are planning a trip to Italy (from Australia) late Sept to late October. We have confirmed plans to travel to Milan, Venice, the Dolomites and Puglia and we fly out of Rome 22nd Oct. We had also planned to go to Cinque Terra and Tuscany but now think that Cinque Terra may be too crowded to enjoy. I also wondered in Tuscany is similar to Puglia and therefore we could change our plans and go to Sardinia or elsewhere instead of Cinque Terra and Tuscany. I also wondered if Tuscany may be better in May when it is greener rather than late sept/early Oct when I suspect the vines are bare and earth tilled. What do you think?? Alternatives to CT and Tuscany or stick with the plan?? I really appreciate your advice as your website is absolutely fantastic.
    Thanks so much

    1. Avatar for Julie Post

      Hello Michele. Those are all great questions. From what I know, the Cinque Terre will be busy in October but not crazy crowded like it is in the summer. So, I wouldn’t keep if off your list just because of the crowds, but the later in October you can put it, the less crowded it should be. But if you are starting in Milan, it would make sense to do the 5Terre from here to avoid backtracking to central Italy after Puglia. However, Italy isn’t that big and it can be done. Tuscany will be somewhat brown during your visit (we had very similar timing in 2022 when we did Tuscany and then Puglia and then the Amalfi Coast). However, Tuscany is still beautiful. It is different than Puglia so you can do both on the same trip and it won’t be repetitive. The repetitive part will be touring town to town to town. We worried about that before our trip but we still had a great time. If you skip Tuscany and the Cinque Terre, you could go from Puglia to the Amalfi Coast to Rome, which is what we did. It’s kind of the reverse of our Southern Italy Itinerary. You can think about it and if you still have questions, let me know. Cheers, Julie

  3. Avatar for Lan Forbes
    Lan Forbes

    Hello from Wahington state,
    Enjoyed your blog tremendously! We’re avid amateur photographers and have been travelling in Europe for many years. Just a quick question: where did you stand to take that beautiful picture of San Gimignano at the distance? Love that angle so much.
    Thank you.

    1. Avatar for Julie Post

      That is a cool view, isn’t it? That photo was taken somewhere along Strada Provinciale 47 or SP60. We visited Volterra first and then drove that road to get to San Gimignano and I don’t recall our exact driving route to get that photo. I’m sorry I can’t narrow that down more. Cheers, Julie

  4. Avatar for Michelle Horak
    Michelle Horak

    Hello from Texas! I have been using your travel resources since 2018, and they have never let us down! Lots of people ask me for my itinerary for our travels, and I always just send them a link to your website.
    My question- we are staying at a winery/vineyard in the Tuscany region of Italy. We would like to visit Pisa & Siena for day trips. Would we need to rent a car for this? I’m not sure if we could access the train from this area. Maybe you would know. Thanks!

    1. Avatar for Julie Post

      Hello Michelle. Thank you for spreading the word about us! Pisa and Siena are very easy to get to by train. As for using the train, it really depends on what part of Tuscany you will be staying in, for ease of getting to a nearby train station. If you are staying in a villa or small town without train access, it might be worth renting a car. But if you are staying near a town with a handy train station, then you could use the train. It’s just hard to know without knowing exactly where you are staying. If you have your hotel/villa booked, you could also reach out to them for travel advice on getting to Pisa and Siena. Cheers, Julie

  5. Avatar for Ryan Swank
    Ryan Swank

    Quick question about the villa you stayed at in Tuscany. What made you settle on Villa le Prata, and were there other comparable options that you considered prior to booking? We love the idea of staying at an adults-only wine resort, but we haven’t been able to find a Google search term that works well for identifying other comparable options. Thank you!

    1. Avatar for Julie Post

      We found it on Booking.com, searching for villas that get good reviews. It had a great location for what we planned to do and the fact that it was Adults Only was a bonus. You could use Booking.com, put in a search area, and then filter the property type for country homes, or villas, or bed and breakfasts, and see what turns up. When I search for villas for Montalcino quite a few options come up. We prefer to book properties with a review score about 9.0 and of course the higher the better. Cheers, Julie

  6. Avatar for Beth
    1. Avatar for Julie Post

      That’s a great question. Unfortunately, to visit a lot of the hill towns, you will have to park outside of the city center and then walk in. In many towns, this is a hilly walk so it would be very tough for you to visit the smaller towns. Even in Florence, there is a lot of walking. I know there are towns and cities in Portugal that have tuk-tuk tours but I can’t think of any in Tuscany, but it would be something to Google/research, because that could be an option for you. Cheers, Julie

  7. Avatar for Kelly

    When renting a car to be in Tuscany, where should I rent? Also I keep hearing about acquiring a driving pass. Can you explain.

    1. Avatar for Julie Post

      Hello Kelly. I haven’t heard anything about a driving pass in Tuscany and I just did a very quick Google search and nothing came up. Tim and I were just in Tuscany in September 2022 and didn’t need a pass at that time. We rented a car from Avis in Siena on our first visit to Tuscany. You can also rent a car from the city you will be in just before traveling to Tuscany. For example, if you are going Rome to Tuscany to Florence, rent the car on the day you leave Rome and return it once you get to Florence. Cheers, Julie

    2. Avatar for Joyce
      1. Avatar for Julie Post

        Hello Joyce. On the How To Get Around Tuscany section of this post, the first thing I state is that having a car is the best way to get around. The train doesn’t go to every Tuscan town and taxis can be expensive, so if you plan to be in Tuscany for a few days and want the freedom to easily visit the towns that most interest you, renting a car is the best way to go. Cheers, Julie

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