8 Most Beautiful Cities & Towns in Tuscany (+How to Visit)
This post may contain affiliate links, which means that we may earn a small commission, at no cost to you, for qualifying purchases. More info: Disclosure.
Planning a trip to Tuscany, Italy, and wondering what are the best cities and towns in Tuscany? In this article, we are highlighting only the most beautiful, best towns in Tuscany that are worth your time the most.
These are one by one amazing places that are well worth a visit. We also included suggestions for the best things to do in each town, as well as the best places to stay. Find out!
There are few places in the world like the Tuscany region in Italy. It really has it all: the most beautiful rolling-hills landscapes, medieval historical towns, Renaissance art, Italy’s best wineries, amazing food, and good weather.
No trip to Europe would be complete without visiting at least some of Italy’s most beautiful towns. But did you know that some of the most enchanting towns and villages in Italy are actually located in Tuscany?!
However, with so many beautiful towns and villages in Tuscany, one more beautiful than another, how do you decide where to go if you only have limited vacation time?
Let’s face it – unless you have at least 2-3 weeks in the region, you won’t have the time to visit every Tuscan town and village. It took us multiple trips of over a week each to really discover the region. So in this article, we are only focusing on the VERY BEST ones, the most beautiful towns of Tuscany that are worth your time the most. Find out!
The good news is that the most beautiful cities and towns of Tuscany from our selection are located within a relatively short driving distance from each other. Therefore, you can see many of the best towns in Tuscany without having to spend too many hours in a car.
Here you can find our suggested Tuscany itinerary. But first, let’s take a look at what you can expect to see when visiting the most beautiful towns in Tuscany.
TIP: If you are short on time, it’s possible to visit several Tuscan towns in a day. In that case, it’s best to base yourself in Florence and take organized tours to the other towns. Here is the best and most popular multi-town tour which brings you to Pisa, Siena, and San Gimignano with lunch and wine in Chianti.
If you are looking to get a bit off the beaten path and visit some smaller Tuscan towns, check out this great tour that visits Pienza and Montepulciano, plus includes Brunello di Montalcino wine tasting.
Best towns in Tuscany – OVERVIEW
These are the best, must-see towns and cities in Tuscany:
1. Florence
Firenze (Florence) is the cultural capital of Italy with a great collection of some of the most famous art in the world.
Without a doubt, Florence is one of the most beautiful places in Italy and the best town in Tuscany region. No matter how much time you have in Tuscany, Florence should definitely be on your itinerary.
While you can easily spend several days in Florence, most tourists only visit this most famous town of Tuscany for a day or two. Below, you can find more information about the main sights, and here you can find our detailed itinerary and tips on how to see the best of Florence in 1 day.
Here are our suggestions for the best things to see and do in Florence:
Duomo of Florence
Basilica di Santa Maria del Fiore, the Duomo, is the most famous landmark in Florence. Visit the cathedral, go up inside its spectacular dome and check out Campanile – the bell tower.
TIP: If you don’t want to spend the whole day waiting in line, get skip-the-line tickets for Brunelleschi’s Dome. Alternatively, I recommend this popular tour that includes everything: Florence Cathedral and The Opera del Duomo Museum: Tour with Brunelleschi’s Dome. Either way, have to book in advance!
Uffizzi Gallery
The Galleria deli Uffizi hosts works of art by Botticelli, Michelangelo, Raffaelo and Leonardo da Vinci, just to name a few of the most famous artists. Perfect place to escape the heat of the day in summer.
If you visit just one museum in Tuscany, make it the Uffizzi Gallery. It’s a must!
TIP: Just as everywhere else in Florence, crowds at Uffizzi Gallery are huge, especially in high season. It’s best to get a timed entrance ticket. Timed entrance tickets are the best way to avoid the long wait, but you really have to make sure to be there in time so that you don’t miss your slot.
Ponte Vecchio
Florence’s oldest bridge, the 14th-century Ponte Vecchio is more impressive from the distance. Apparently, Ponte Santa Trinita is a good place to take pictures of this famous medieval bridge.
San Lorenzo Market
Whether you have the whole morning or just a few minutes, San Lorenzo market is a great place to explore for the whole family. The market is comprised of two separate markets. An indoor market, Mercato Centrale, is a food market. The outdoor market is where you’ll find leather, clothing, and souvenirs.
Piazza della Signoria
Piazza della Signoria is one of the most beautiful town squares in Florence. Admire the architecture and many beautiful sculptures. If you have time, visit Palazzo Vecchio and/or climb the Arnolfo Tower for some of the best views in Florence.
Piazza Santo Spirito
The perfect place to end your day in Florence is Piazza Santo Spirito. With many cafés, bars, and restaurants it comes alive every evening. It’s more of a locals’ place with reasonable food prices, live music, and a great atmosphere in the evening. Don’t miss it!
Piazzale Michelangelo
Piazzale Michelangelo, located in the Oltrarno district, is the most famous square of Florence with a magnificent panoramic view of the city. It’s a very popular place for sunset. Alternatively, check out some of the best rooftops in Florence, with great (sunset) views from most of them.
LEARN MORE: Best Things to Do in Florence
Where to stay in Florence
Luxury: The Westin Excelsior (with the best rooftop terrace in town!) or Ville Sull’Arno (outside the city center) – luxury at affordable rates.
Mid-range: Croce di Malta (rooftop terrace, pool, great location).
Lower mid-range: B&B Le Stanze del Duomo (great price-quality-location).
Budget: Hostel Archi Rossi.
READ ALSO: Florence Hotels with Rooftop Terrace
2. Siena
Tuscany’s second city, Siena, is a smaller and more intimate town than Florence. Yet it has so much to offer.
The historic center of Siena, a UNESCO World Heritage Site, is never as busy as its rival Florence. However, Siena is one of Tuscany’s most visited towns, so be prepared for the crowds.
The historic town center isn’t that big, so you can easily see the best of Siena in a day. Below you can find a short overview of the best things to do and places to see in Siena.
Piazza del Campo
Piazza del Campo (also called Il Campo) is the principal town square of Siena. It is one of Europe’s finest medieval squares. Il Campo is the heart of the city. It’s the place to relax, take in the views, sit down for some cappuccino or Italian gelato. You can climb the bell tower of Torre del Mangia for beautiful views over the historic city center.
Palazzo Publico is also not to be missed in Siena! The interior is stunning and you only need about half an hour to visit. It’s absolutely worth it!
Interesting to know: Il Palio, the world’s most famous historical horse race, is held on Piazza del Campo. Twice a year, 2nd of July and 16th of August, Il Campo is transformed into a horse racetrack, just as it has been for centuries, since 1644. If you are coming for Il Palio, you may want to stay in Siena for 3-4 days, as there is so much to see and do in the days before the race.
Duomo di Siena – Siena Cathedral
The beautiful cathedral of Siena has no equal in the whole of Central Italy. It’s stunning; both, on the inside as well as on the outside. If you visit one church in Tuscany, make it this one!
Inside, you can also visit the stunning library Biblioteca Piccolomini, the Crypt, and the Baptistery. Don’t miss the fabulous city views from the New Cathedral Façade.
TIP: It’s best to book your skip-the-line tickets for Siena Duomo Complex in advance.
LEARN MORE: Siena Cathedral (what to see and tips for your visit)
Historic city center of Siena
Stroll around the historic city center of Siena and admire its many Renaissance buildings, and visit some churches or museums. But if there’s one place you really cannot miss, it’s the Duomo – see below.
How to visit Siena: You can drive to Siena (parking is problematic though) or take a train. If you are short on time, the easiest way to visit Siena is by joining one of the organized tours from Florence.
LEARN MORE: Best Things to Do in Siena
Where to stay in Siena
Luxury: Grand Hotel Continental.
Mid-range: B&B Il Corso.
Budget: B&B San Francesco.
For families: Il giardino di Pantaneto Residenza D’Epoca.
3. Lucca
Lucca is our favorite town in Tuscany. It’s hard to explain why exactly because other Tuscan towns are just as beautiful from a tourist point of view… But it has such a great atmosphere and there is just something really special about Lucca.
I know many people who feel exactly the same way – Lucca is one of the nicest, coziest, most beautiful towns of Tuscany. You really have to experience it.
Below you can find some of our suggestions for the best things to do in Lucca.
City walls of Lucca
Whether you do the whole 4 km of panoramic walkway overlooking the city of Lucca or just walk a part of it, the 16th-century walls surrounding the old town of Lucca are not to be missed. They are so wide that you can even explore by bike (there are many bike rental shops offering cheap hourly or daily rates).
Families with children will love the playgrounds and recreation areas with picnic tables in the shade just outside the city walls.
Amphitheatre Square
Piazza dell’Anfiteatro, the oval square built around the elliptical structure typical of Roman amphitheaters, is a not-to-be-missed jewel from Roman times. It’s a lively place with shops and restaurants and various events and concerts.
Churches of Lucca
Lucca is sometimes also called the city of 100 churches. Obviously, it’s impossible to visit them all, but don’t miss the cathedral, Il Duomo, Basilica of San Frediano and San Michele in Foro.
The Guinigi Tower
Have you ever seen a tower with trees growing on top? Don’t miss the famous Torre Guinigi which stands out over other buildings in Lucca. make sure to climb the tower for the beautiful views of the city.
Delle Ore Tower
Another tower you should visit when in Lucca is the medieval clock tower, Torre Delle Ore. If you climb just one tower in Lucca, I’d go for the latter. It’s less busy than the Guinigi Tower and provides magnificent views, also of the nearby Guinigi Tower.
How to visit: Lucca is best visited by car or public transport. There aren’t that many tours that come here most go to Siena or Pisa instead). This is one of the best guided tours from Florence that visits Lucca and Pisa.
Where to stay in Lucca
Hotels: Hotel Alla Corte degli Angeli.
B&B’s: B&B Arena di Lucca.
For families: B&B Villa Corte Degli Dei.
4. Pisa
After Florence, Pisa is probably one of the best-known towns of Tuscany. Who hasn’t heard of the Leaning Tower of Pisa…
But not many first-time visitors know that there is so much more to Pisa than the famous tower. Below you can find some suggestions for the best things to see in Pisa.
Piazza dei Miracoli & the leaning tower of Pisa
Before we visited Pisa, I have never even heard of Piazza dei Miracoli. It’s a beautiful square with many truly impressive buildings. It appears that the Tower of Pisa is just one of the many monuments of Miracle’s Square. Make sure to also visit the Cathedral, the Baptistery, and the graveyard.
TIP: Keep in mind that pretty much everyone who comes to Pisa wants to visit the tower, so the waiting times can be really long. If you want to climb the tower, it’s best to reserve your timed entrance tickets in advance.
What to see in Pisa, other than the Pisa tower
Also the town center of Pisa is well worth a visit. The number of tourists decreases exponentially the further you go from Miracle’s Square. So take your time to explore the old town center of Pisa. It’s the best way to escape the crowds and it’s really worthwhile!
Borgo Stretto is an ancient shopping arcade is a nice lively (with locals) place to have lunch or do some shopping.
Make sure to take a walk on the Arno promenade following the Arno river. A tiny picturesque church of Santa Maria Della Spina is also worth a short detour.
How to visit: Pisa can be reached by car or by train. There are also many Tuscan town tours that include Pisa in their itinerary.
Where to stay in Pisa
Mid-range: Hotel Bologna (best-value and very popular).
Lower budget: Hotel Alessandro Della Spina.
For families: B&B Tuscany Gallery.
5. San Gimignano
San Gimignano is smaller and lesser-known compared to the other famous towns of Tuscany. However, it’s definitely one of the most beautiful ones, so don’t miss it!
San Gimignano is famous for its fourteen medieval towers rising above the Tuscan countryside. Originally there were 72 towers in San Gimignano, all built by the patriarch families competing to display their wealth.
The town isn’t that big, so you can easily see the best of San Gimignano in just half a day. Stroll around the old town, don’t miss Piazza della Cisterna and climb to the top of the Torre Grossa and visit the Duomo. Dating from 13th century and 54 meters high, this is the tallest tower in San Gimignano and the only one that is open to the public. TIP – book a ticket in advance!
Good to know: If you happen to visit on Thursday, come VERY early as it’s a market day and the small town center tends to get very busy.
How to visit: San Gimignano is the most popular small town to visit in Tuscany, so it’s extremely busy here. Parking is a big issue too. If you can, it’s worth considering coming here in the late afternoon when the crowds have diminished. The easiest way to visit San Gimignano is with a tour. There are tons of tour options, mostly from Florence and Siena.
Where to stay in San Gimignano
Mid-range: Hotel La Cisterna (in town) or Hotel La Collegiata (in the countryside).
B&B: B&B I Coppi (stunning views).
For families: Agriturismo Macinatico.
6. Volterra
Volterra is a charming medieval town and while not as impressive as the previous five, I think it well deserves a place in this list of the best towns of Tuscany.
It’s a small town that you can visit in just a few hours and since it’s located very close to San Gimignano, you can easily visit both these towns in one day. Stroll down the historic town center of Volterra – it has a great atmosphere, especially in the evening.
The medieval wall surrounding Volterra was built in the 13th century and six gates allow entry through the wall into the center of the city. Don’t miss Porto All’Arco.
Take a quick look inside the Cathedral and the Baptistery. Palazzolo dei Priori, Pinacoteca and Museo Civico are worth a visit as well.
Acropolis houses several buildings and the foundations of two ancient temples. There are many Roman remains to visit as well, like the Roman Theatre and the Medicean Fortress.
How to visit: The easiest way to visit Volterra is by car. There are just very few tours that come here. This has nothing to do with the town itself, more with the fact that most tours visiting this area opt for San Gimignano instead.
Where to stay in Volterra
Mid-range: Hotel San Lino or Hotel La Locanda, also for families.
Lower budget: Volterra In.
7. Montepulciano
Best known for its ruby-red wines, Montepulciano is a beautiful hilltop town in one of the prettiest areas of the Tuscan countryside. It might not be as popular as the other towns and villages in Tuscany mentioned above, but it’s quite well-known and attracts lots of tourists.
If you are looking for some smaller towns or charming villages to visit in Tuscany, Montepulciano should definitely be on your list.
The town isn’t very big, so you don’t need that much time to get acquainted and enjoy the cozy atmosphere. On the other hand, it has a lot more to offer than it looks at first sight. So I recommend that you decide what you’ll want to see and do as that will determine how much time you’ll need.
As you enter the historic town center, you are transformed into a different era. It’s truly like taking a trip back in time. Walk around the main streets and all the way to Piazza Grande, the main square in town. Here, you can visit the Cathedral, and climb the tower of Palazzo Comunale for some amazing 360° views of the surroundings.
Just outside the center, you can also visit the Sanctuary of the Madonna di San Biagio. It can be reached on foot, by a little tourist train, or by car.
No trip to Montepulciano would be complete without tasting the famous Vino Nobile di Montepulciano. if you have an hour to spare, visit one of the underground wine cellars. Built deep inside the mountain, these wine caves are absolutely impressive! We recently visited this wine cave and it was the most memorable experience in Montepulciano!
How to visit: Montepulciano can be visited by car, but expect it to be very busy. Finding a parking spot late in the morning is really challenging. So try to arrive before 10 am or after 3 pm.
Alternatively, you can visit Montepulciano with a tour. There are tours from Rome, from Florence, or from Siena. Often, they visit at least a few Tuscan towns in a day and some also include a visit to a winery or a wine cellar.
Where to stay in Montepulciano
While the majority of tourists only visit Montepulciano for (half) a day, it could be a nice place to stay if you want to explore it without the crowds of day-trippers, taste wine without having to drive, and not have to worry about finding parking (assuming your accommodation has one).
Within walking distance from the center, with parking: Il Rondò Boutique Hotel or Albergo Ristorante San Biagio (uphill walk to the center).
LEARN MORE: Best Things to Do in Montepulciano
8. Pienza
Pienza is a stunning renaissance town located in the heart of the most picturesque part of Tuscany – Val d’Orcia. Just like most smaller towns and villages in Tuscany, Pienza was built high on the hill. This means that you can enjoy the most incredible views from here. The rolling hills of Tuscany with cypress trees are all around you.
What distinguishes Pienza from any other town in Tuscany is that from the beginning, it was built with a plan of becoming a ‘perfect’ town. The town center was designed by Bernardo Rossellino (15th century). He thought of every detail, placing all the main buildings and monuments along one main street, and foreseeing a stunning walkway that overlooks the most beautiful scenery with Val d’Orcia in the distance.
Even the street names here are suited for the perfect town, e.g. Via dell’Amore (the street of love) or Via del Bacio (the street of a kiss).
The main place to see in Pienza is Palazzo Piccolomini. The interior is incredible, but no pictures are allowed. Also the views from the balcony and the hanging gardens are unparalleled. You get an audio guide but can only visit here with a staff member whose main task seems to be to check that nobody is taking pictures. You can get tickets online, but normally it shouldn’t be an issue just getting them on the spot.
Good to know: The same ticket also includes a visit to the underground crypt and the labyrinth under the Cathedral, as well as the entrance to Diocesan Museum (Palazzo Borgia). Here, you can see some beautiful paintings by the famous 14-15th centuries artists from Siena.
If you have more time in Pienza, a nice thing to do is rent an e-bike or join a guided e-bike tour and explore the surrounding countryside.
How to visit: Pienza can be visited by car, but parking is extremely limited here. So you either have to get there very early (ideally before 10 am) or arrive in the late afternoon when people start leaving.
Alternatively, you can visit Pienza with a guided tour from Rome, from Florence, or from Siena. Most tours include at least a few of the nicest Tuscan towns in their itinerary.
Where to stay in Pienza
Since Pienza is a very small town, you don’t really have to stay here in order to see it. But its location is phenomenal and it could be a good base for exploring the Val d’ Orcia region and visiting other small towns and villages nearby. In that case, here are some accommodation recommendations (be sure your hotel has parking if you are staying close to the town center!):
Within walking distance from the center, with parking: Hotel San Gregorio or Piccolo Hotel La Valle.
Outside of town (stunning location): Agriturismo Marinello.
So, this is our list of the most beautiful towns in Tuscany. This stunning Italian region has much more to offer than these amazing towns, but if you are visiting for the first time and want to see the very best of Tuscany, then this list is all you need.
TIP: You really cannot go wrong with any of these Tuscan towns. However, if your time is limited, start with Florence and work your way down this list; we listed the very best towns first. On the other hand, if you are looking for smaller, more charming towns in Tuscany, you may want to start at the bottom of our list.
READ ALSO: Tuscany Itinerary & What to Eat in Tuscany
More inspiration and tips for your trip to Italy:
- Where to go: Best Places in Italy & Best Cities in Italy
- How to plan your time: 2-Week Italy Itinerary
- Rome:
- Venice:
- Florence:
- Bologna:
- Milan:
- Verona:
- Naples:
If you found this post helpful, don’t forget to bookmark it and share it with your friends. Are you on Pinterest? Pin this image!
More travel inspiration for Italy:
- Cinque Terre:
- Italian Lakes:
- Dolomites:
- Amalfi Coast:
- Emilia Romagna:
- More… Here you can find more tips for a big variety of destinations in Italy.
If I want to spend a week in Tuscany and see all these beautiful towns, where do you recommend me staying as my base – Florence or Sienna. Thanks!
Hi Muriel, please take a look at our 1-week Tuscany itinerary for some suggestions (also on where to stay).
If you are not renting a car, then indeed, Florence or Siena are both good options and there are plenty of day tour possibilities to explore the surrounding countryside from both of these towns. Or you can also stay in each town for a few nights. Florence has so much to offer in itself that you can easily spend 3 days in the city alone. Siena is much smaller and 1 day is enough.
Tuscany is huge and the possibilities are endless. So it really depends on which other places you want to visit and how you are planning to travel around. The best way to decide where to stay is to indicate on the map which places you want to see, how you can get there (if not renting a car), and then it will become clear where to base yourself.
Good luck with the planning!
@Jurga,
Thank you very much! Planning to follow your itinerary and seeing the towns you listed.
In that case, it’s probably best to stay in Florence, close to the station. You can find some hotel suggestions in this article.
If you are taking tours, you can visit a few places outside the city in a day (e.g. this tour visits Siena, San Gimignano, and Pisa in just 1 day), which leaves you more time to explore Florence or add a few other places to your itinerary.
Good luck with the planning and have a great trip!
My apologies but one follow-up question to my recent post…If we did make a stop in Pisa for a few hours – would you know if are there lockers or a place to store our luggage at the train station in Pisa?
Hi Steve, yes, as far as I know, there are lockers where you can leave your luggage at Pisa Centrale station. It’s about 25-30 minutes walk to the Leaning Tower from there.
Jurga, thank you so much for your blog…my family is planning a trip to Italy in June and your sample itineraries and places to visit are fantastic. I have two questions for you:
Number 1 – we are planning to do a day trip from Florence to spend in the countryside. We are renting a car as we like to explore on our own time rather than in a tour group. You mention a wine tour in Montepulciano which looks great but do I need to book a tour beforehand or is it like California wine country where there are many different options of wineries to stop at? Would we be able to just pick one that looks good to us or do we need to make arrangements before we arrive?
Number 2 – we are also planning on going to Portovenere for an evening from Florence via the train. I was thinking I could book our train tickets to allow for time to see Pisa. Is 4-5 hours enough time or would we need more? And how hard would it be to get to Lucca as part of that (or am I just trying to do too much)?
Thanks,
Steve
Hi Steve, to answer your questions:
1. Wine tour. It really depends on the place and the season when you visit. If you want to be able to plan your time a bit, it’s best to book in advance. Otherwise, even if available, you may have to wait a few hours. Also, there are some places where it looks like you could just stop, but you may not even find anyone when you arrive without advance booking. Plus, you may not find anyone speaking English… So it really depends.
2. Yes, you could certainly combine a visit to Portovenere with a stop in Pisa. You don’t even need 4-5 hours in Pisa. If you are only visiting Miracles Square and the Leaning Tower, a maximum 2 hours should be more than sufficient, plus some time to get there from the train and back. Also here, if you want to actually climb the tower, it’s best to book tickets in advance.
If you absolutely want to squeeze a visit to Lucca on the same day, it should also be doable. In that case, start early, plan everything really well, and be sure to check the train schedules. In that case, you’ll probably just walk around everywhere without really taking the time to explore deeper.
Hope this helps.
My husband and I are planning a Cinque Terre/Tuscany/Rome trip next year for approx two weeks. From CT, we will travel by train to Florence and stay 2 nights. Then would like to “base” in countryside to hike & bike/take in wineries/tour various small towns for 4 nights. You mention Montaione as a good central base if we don’t want to pack/unpack to visit other towns like Lucca, Siena, San Gimignano, chianti wine region… You mention Hotel Macine, which looked like a great option. We will need a car rental for this leg of the trip, so is that easy to do in small town of Montaione? From Tuscany area, we had planned to take train to Rome. Thanks for info!
Gail S
Atlanta, Ga
Hi Gail, if you are renting a car for a part of your journey, it’s always best to do that in the bigger cities/airports. There’s much more offer and the prices will be lower.
So you could best rent a car in Florence. I think you’ll find some car rental options in the city, but Florence airport is also very close by and can be easily reached by tram from the city center in about 15 minutes. So you could also rent a car from the airport. It’s usually cheapest to return the car to the same place, but I’m sure you could return it to Rome as well – check various options and see what works best for you.
Hi, which towns will I be able to walk around easily in my 26th week of pregnancy? If there are a few stairs, that’s okay, but if there are many steps, I’ll likely be very uncomfortable. Thanks!
Hi Yonit, it really depends on YOU and how your pregnancy is going and what you’re comfortable with. Also the weather.
All these towns are very walkable and all of them have cobblestones and some steps here and there. But – unless you start climbing every church tower, etc. – you can also explore a lot without having to do too many stairs. For example, in Florence, you can walk to the hilly areas, or you can just stay in the heart of the city center which is quite flat. Pisa, Lucca, Siena – all these are also rather flat. We also visited all these towns with two strollers when all 3 of our kids were little and never experienced any issues.
@Jurga, thanks so much for your helpful reply!
What I found most delightful about San Gimignano, other than the shops, was the walk all around the city walls. There’s a path just below the walls where you can circle the whole city and take photos of the stunning valleys below.
Thanks for sharing your experience, Pati! I agree – San Gimignano is amazing, the atmosphere is unique, and the surroundings – simply stunning.
Happy travels!
Sorry me again travelling alone with no car unless i get the courage to rent one
my itinerary is June
Florence 14 to 18th using as a base to do excursions out of the city
Umbria 18 to 25th
Tuscany 25 to 28 ???
Cinque Terre 28th to July 1
Milan 2 night fly home
My 2 questions are
Do I return to Florence again to use as a base on the 25 to 28th or do I
stay in the country side and if so which town do i stay in???
and should I add an extra day in CT? so just 2 nights in the hills and 4 nights in CT?
How far in advance do we need to book excursions?
All suggested appreciated
thank you Jurga
Hi Roma, sorry, but I really have no time to help with individual itineraries. There are just too many options and everyone travels differently.
I’d spend less time in Cinque Terre and more in Tuscany, maybe also add Bologna and Lake Como and/or Lake Garda to the mix. But it really depends on your interests. You can also see our Tuscany itinerary suggestions for some ideas.
If you don’t rent a car, yes, it’s better to stay in bigger cities like Florence, Milan, etc. and make day trips from there. Train connections are generally very good in Italy, and there are also lots of tours available, so it’s easy to get around between towns and cities. For smaller places – it’s often easier by car indeed and driving is in general not that challenging, but it all depends on what you are used to and where exactly you go.
For excursions – depends so much on the place and on what you want to do. Often, you can book last-minute too, and some activities like a boat ride between the villages in Cinque Terre can be booked on the spot too. But very often (especially in high season), you better plan for any longer tours at least a few weeks in advance. For places that are super popular (think Colosseum, the main museums in Florence, or Pisa Tower, etc.), you definitely need to book in advance.
Also, I just booked a few tours for our own trip in Italy in April, and noticed that the prices of a few tours were now quite a lot higher than a few weeks before. So we personally try to book as much as possible in advance (but always with the free cancelation option).
Hope this helps.
Ciao Jurga! I have been travelling to Italy for more than 50 years and just came across your blog. Due to the pandemic, my plans (like many) were cancelled this year. However, your article took me on a nostalgic journey the I really needed. I have been to all the places you mention and can’t wait to return. I hope you don’t mind me suggesting a visit to Montepulciano, which is probably my favorite hilltown in Tuscany. I usually visit once a year and was sad I couldn’t be there this year. Incredible restaurants, beyond incredible wine, what more can you want? I am so looking forward to 2021 when travel opens up again and am already planning my trip for this coming July! Thank you once again for allowing my mind to escape to my happy place!
Thanks for your suggestion, Norman. We still haven’t been to Montepulciano, but I heard great things about it indeed (and the wine is amazing too ;)).
Let’s hope that we can all travel and explore the world soon enough again!
Hi Jurga,
I am planning on going on a trip to Tuscany for 7 days with 10 friends. We will be 18 and we have found a really nice villa with a pool etc only about 1 km from the centre of Sienna. We like it because it has the feel of being remote whilst also being close to things to do. I am conscious that Sienna isn’t the biggest town, do you think 7 days is too long to stay there for some teenagers who want quite a relaxed holiday not doing too much each day or is there too much to do for us to get bored in that time in and around Sienna? If you think it’s not too long could you possibly suggest any enjoyable things to do maybe not necessarily in Sienna but in areas closely surrounding it too?
Thank you in advance!
James
Hi James, the distances in Tuscany aren’t that big and there is plenty to see and do in Siena and nearby (easily done as a day trip). So I wouldn’t worry about getting bored – you’ll find plenty to do if you feel like leaving the pool for a day.
In our Tuscany itinerary, you can find quite some suggestions for places to visit. We also stayed in just one place in Tuscany (although our location was probably a bit more central – Montaione area – but it was quite far from the highways…) and made day trips everywhere. It was so nice to be able to combine sightseeing with a nice relaxing vacation.
P.S. if you don’t find enough suggestions in my article, I highly recommend this Tuscany guidebook. It has everything that’s worth seeing and they use a great 3-star system, so it’s easy to decide which places are worth your time the most.
Hope this helps. Enjoy your trip.
We are headed to Montauto, small town overlooking San Gimigmano…. we are coming from Orlando Fl and wonder should we fly to Florence or Rime and take the train? Then rent a car or hire transportation to villa? We plan to do some amazing wineries and Florence. Any suggestions?
Hi Lynda, I’d just book the flight that is best suitable or best priced. It doesn’t matter much whether you fly to Rome or to Florence.
If you are staying outside of major towns, I would definitely rent a car to explore Tuscany.
For wineries, it’s better to take a tour so that you don’t drink and drive.
Hope this helps. Enjoy your trip.
Just as they say, “When in Rome, do as the Romans”, you HAVE to drive in Italy! And make absolutely sure it’s a convertible! That way you can enjoy all the sites and sounds with a full panoramic view. My wife and I rented a little Fiat convertible every time we went (we lived in Germany for 10 years) and believe me, it’s the only way to go! Plus you can stop and take pictures, without getting outa the car!
This sounds like the perfect Italian road trip, Jack! Wish we could do that… We have been dreaming of touring Italy or Greece in a convertible for so long, but with 3 kids, it ain’t going to happen any time soon. I’m jealous 🙂
Hello! That’s a great blog with such beautiful pictures. I have been to Rome and Venice, but never been to Florence and all these amazing pictures inspire me to plan my trip soon.
Italy is amazing – we can go back again and again! It’s always worth it.
Hi Jurga, I am assuming it is est to rent a car to visit these places most easily no? We are arriving in Rome but thought to just take the train from there to Florence as we have done in the past. I am not sure about driving in italy! It seems daunting!
Hi Jill, coming from Belgium, we always drive in Italy, with a big family van, and never had any issues anywhere. It depends a bit on the area, and parking is often hard to find in the most popular places, but for the rest, it’s just driving as anywhere else in Europe. You do need to be aware, though, that some very popular places have traffic restrictions and signs are usually in Italian, so in that sense, it’s not always easy. But you can always just ask people if you are not sure about something…
It’s possible to take a train between the bigger cities and you can always book an organized tour for the places that are more difficult to reach by public transport, but exploring by car definitely gives you more freedom. For places like Rome or Florence – you don’t need a car, so you can still take a train there and only rent a car for a day or two when you want to visit the countryside for example.
Car rental in Italy is usually not too expensive, especially if booked well in advance.
It’s really your decision, I can’t really tell you how you’ll experience it, as everyone is different and a lot depends on what your previous driving/travel experience is.
Whatever you decide, I’m sure you’ll have a great trip. Italy is simply amazing.
Hi Jurga – thx for Full Suitcase – it’s very helpful. We (family of 4 adults) have 5 nights to spend in Tuscany in early July’19, before heading south to Amalfi. We’re thinking a couple of days in Florence and then several days at other smaller towns of interest. Trying to decide if we’re better off staying in a central villa (outside Florence, Siena, other?) and taking day trips – or staying in local hotels as we drive around. Is Cinque Terre a worthwhile day trip (or overnight stay)? Any suggestions on central location for a villa and/or must see locals, are appreciated.
Hi Russell, you can find some suggestions here – Tuscany itinerary. It also has some suggestions for where to stay.
Cinque Terre – you can see the best of it in one day – more info here: Cinque Terre in one day.
It’s really your choice – to stay in one place or change hotels every night. It’s definitely possible to just stay at one place, we did that, but it also means more driving up and down of course. So the choice is yours.
I’m sorry but I really can’t help you further because there are just too many options on how you can spend 5 days in Tuscany, so you’ll just have to decide which places interest you the most. Once again, please check our itinerary suggestions, it might help a bit.
Enjoy your trip!
Hello,
How about Cinnique Terre .. we are travelling next week with our 4 months infant baby. We have planned 2 nights stay at Florence and checking for day tour packages to Pisa and Cinnique Terre.
Also plwase suggest if car renting will be a good option in Florence.
Hi Bibhu, here you can find all the practical information for visiting Cinque Terre and here you can find our suggestions on how to see the best of Cinque Terre in one day. You should better take a train or a guided tour. Renting a car is ok, but it’s a bit a waste of money if you only visit Cinque Terre, since you’ll have to leave it at a train station in La Spezia anyway (and pay for the parking). I would only rent a car if you are traveling around Tuscany for several days, because in Cinque Terre it’s really useless.
Hope this helps.
Thanks for the quick reply Jurga. I need some further details as we are planning for a trip to Dolamite mountains from Venice . We have rented a car from Venice Mestre station and thinking for a day trip to Dolamite mountains.
The weather is not ao friendly as we are seeing now online. Would it be worth for a drive to the dolamite mountains with an infant around ?
Worst case we are thinking for sightseeing and then comeback if not to the mountains.
Kindly advise.
Thanks in advance!
Cheers
Bibhu
Hi Bibhu, we spent a week in the Dolomite mountains and haven’t seen a small part of them, so I really don’t know what to tell you in terms of a day trip. I guess you can always visit one place, but do some research up front where you want to go. I wouldn’t worry about the weather forecast – we also had rain and thunderstorms on the forecast every day when we visited, but in reality, it hardly ever rained. It’s usually very local and passes quickly. Check the specific hourly weather forecast for the place you want to visit the day before you go and you’ll have a much better idea how it is, but even then – it changes so quickly in the mountains.
If you rather visit something else, then consider Verona or Lake Garda. In one day, with a car, you could do the eastern side of Lake Garda, stop at a few places, don’t miss Malcesine. I think it would be easier and more enjoyable from Venice. Here you can find more information about Lake Garda towns.
Enjoy your trip!
Is Monteriggioni worth a visit? Looks beautiful from the air!
Hi Dan, I really wouldn’t know as we haven’t been there. I guess it’s nice to see if you have an hour or two to spare, although it looks really small from the pictures. On the other hand, sometimes little off the beaten path places can make for some of the best travel adventures and memories, so if you are nearby and have some time, why not just give it a try…
Great tips for Florence, so many wonderful museums and architecture – and many free to see too. Santo Spirito and other neighbourhoods across the Arno River are my favourite areas to see the ‘real life’ Florentines. I’ve written about this and other things you can do aside from the art and museums part of Florence: http://www.tripchow.com/traditional-trattoria-florence/
ooo you’re taking me back to our trip! Isn’t Tuscany just gorgeous! Although we never made it to Lucca which I would’ve loved to have visited so I shall save this page for when we do. Thanks
You’ll love Lucca! As I said, there is just something special about it… Thanks for leaving a comment, Alex!