Where to Stay in Tuscany
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My home region, lovely Tuscany, is world famous and millions of people visit every year from all across the world. Places like Florence, Siena, San Gimignano, and Pisa are practically household names now.
Despite all this, Tuscany is still full of places that are relatively little visited. Go a little off the tourist trail and you'll find quiet medieval villages that still move to ancient rhythms, hamlets practically unchanged in centuries, and proud cities unconcerned with tourism.
But why am I talking about this? It's because there are lots of places worth considering as bases when you visit. And many of them aren't the obvious ones that all the influencers and travel bloggers recommend!
So, with this article I hope to introduce you to Tuscany's main areas, help you think about which you might be interested in visiting, and then help you pick where you should base yourself.
Shall we take a look?
Table of Contents
What to consider when choosing where to stay
I could just jump into a list of the "best bases in Tuscany”, but doing so wouldn't really make any sense. How can we talk about where to stay without first talking about where to visit? There's no point in my telling you about 3 great towns in the Val d’Orcia if you're planning on visiting Florence and Chianti!
And beyond that, there is no singular town or city in which you can base yourself and do day trips to all the rest of Tuscany. This is a big region, and if you're coming for more than 3-4 days, you'll need to have a couple of bases.
There's lot to think about, but here are the 5 main questions I think you should ask yourself:
1. What you want to do while here and which places interest you?
Why are you visiting Tuscany? Do you just want to hit the highlights and then carry on to other parts of Italy? Or are you planning on settling down for an extended? Do you want to see our great cities or roam the bucolic countryside? Are you hoping to hit some thermal baths? Or maybe you're just here to taste wine and relax.
Different regions of Tuscany offer different things and where you should stay depends on what you want to do.
2. How many days will you be here?
Tuscany is a large region and much of it is quite rural. So, if you want to see a lot of it, you'll need at least 5 days (and that's assuming you've already been to Florence). If you want to see the Tuscan countryside and visit Florence, then give yourself at least a week.
If you're coming for a first visit and planning on seeing highlights like Florence, Siena, San Gimignano, Pisa, and the Chianti wine region, then give yourself 5 days and plan on either basing yourself only in Florence and doing day trips, or choose a base in Florence and then another in Siena (or the countryside nearby).
If you've got a week, now things can get a bit more interesting, but you should still resist the urge to try and see too much.
3. How many bases do you want to have?
This question depends both on how much ground you want to cover and how well you tolerate packing and unpacking your bags.
If you want to try and see various parts of Tuscany, you'll need 2-3 days. Florence or Siena will let you also cover Chianti, but if you want to see the Val d’Orcia or Cortona, you'll need to consider somewhere like Montepulciano. For visiting the Maremma coast, you'll need to look at places like Livorno and Grosseto. And while Lucca can be visited from Florence, if you want to get into Alpi Apuane mountains of northwest Tuscany, you'll need yet another base.
With 5 days, I'd recommend 2 bases. With a week, you could stick to 2, but 3 is probably more convenient (and will help you spend less time in the car). Once you have more than 7 days, then you start to have all sorts of options.
Also keep in mind that lots of hotels in the countryside are really lovely, so you want to give yourself some time to enjoy the place you're spending all that money on! Some hotels have their own wineries, others have thermal baths and spas, and most have beautiful grounds. The purpose of staying at these places is to unwind, so budget some extra time for that.
4. How do you plan to get around?
Whether or not you'll have a car is probably the single biggest factor in deciding where to stay while in Tuscany. While public transport between the major Tuscan cities is excellent (via train), the countryside is connected only by bus and service is infrequent, rarely direct, and time-consuming.
If you're planning on getting around via the bus/train, this will significantly limit which towns and cities are realistic options.
For those planning on using public transport for their day trips, Florence and Lucca are you best two cities. Arezzo also has decent transit connections. Siena is centrally located in the region, but bizarrely poorly connected.
Another thing to consider is that most of the towns in the countryside are quite small and you can usually visit 2-3 (and sometimes more) in a single day. So, if you choose a well-located base, you can normally fill out a few days of touring with relatively minimal driving distances.
5. What type of environment do you want for your home base?
Tuscany has no large cities outside of Florence (which is hardly large), but it does have quite a few mid-sized ones (Lucca, Pisa, Livorno, Arezzo, Grosseto, and Pistoia) that all have pros and cons as potential bases.
For those who prefer villages and small towns, Tuscany has these in abundance. And, because it is both a wealthy region and a heavily touristed one, these little towns often have services that would be impossible to find in similarly small places elsewhere. You'll find great hotels, terrific wineries, and Michelin-starred restaurants in places with barely 3,000 inhabitants!
And then, of course, you have beautiful rural areas that all offer different things.
Chianti is fantastic for wine tasting, hiking, cycling, and exploring tiny little villages. The Val d’Orcia offers incredible panoramas, thermal baths, and interesting gastronomic traditions. The Maremma coast has phenomenal beaches while the Alpi Apuane mountains have terrific trekking and blissfully crowd-free corners. For off the beaten path exploring, the Crete Senesi area offers a sleepy and sun-baked slice of Tuscany that few visitors encounter.
And for anyone wanting a few days of "vacation from their vacation” you even have a few resort-style hotels in the hills outside of Lucca.
Quick overview of Tuscany's geography
Before we discuss the best places to base yourself in, let's go over a bit of Tuscan geography. Like I said before, this is a big region and its attractions are spread all over, so before you decide where to stay, you need to think about where you'll be visiting.
For most first-time visitors, I think you should consider the following areas when planning your trip:
Florence metro area
Chianti
Val d’Orcia
Lucca and the northwest
Grosseto and the Maremma coast
Florence metro area
This is exactly what it sounds like - the area immediately surrounding the city of Florence, Tuscany's capital. Despite being home to Tuscany's largest city and one of the most visited places in Italy, the surrounding area doesn't actually have very many places of touristic interest. The main places that you're likely to be interested in are the Chianti wine region, the charming little village of Fiesole, and the medieval city of Pistoia.
Other places within day trip range of Florence are San Gimignano, Volterra, Siena, Pisa, Lucca, and Arezzo.
Chianti
The Chianti area, sometimes also called the "Chianti Classico” is a hilly region that lies in between Florence and Siena and is famed for its production of Chianti wine (made of Sangiovese grapes).
It's made up of 8 little medieval towns that dot the forested hilltops, the most famous of which are the ones whose names end with “in Chianti": Radda in Chianti, Castellina in Chianti, Panzano in Chianti, Greve in Chianti, and Gaiole in Chianti. While the towns themselves are very cute, the main reason to visit this part of Tuscany is to see vineyards, taste wine, and enjoy the rural countryside.
For those who want to enjoy a bit of rural Tuscan life, staying in/around any of these little towns can be very nice. However, the entire region is also easily visited from Florence or Siena, taking 30-60 minutes to get to. Note, however, that you will need a car to visit.
Val d’Orcia
The Val d’Orcia is a rural region of rolling hills and valleys in southern Tuscany. It begins about 45 minutes to the south of Siena and includes famed towns like Montalcino, Pienza, and Montichiello. Montepulciano, although not technically within the "valley”, is right on its eastern edge and usually included as part of it.
Like Chianti, this a major wine-producing area and it's home to some of Tuscany's most prized wineries, some of which produce that most famous of nectars, Brunello di Montalcino.
Although the villages here are, as with Chianti, quite small, both the architecture and the surrounding terrain is quite different. Where the Chianti towns are predominantly medieval and rather humble in scale, the towns of the Val d’Orcia feature grander buildings, Renaissance flourishes, and they overlook wide open plains of golden wheat and grains.
Lucca and the northwest
The main cities of northwest Tuscany are Lucca, Pisa, and Livorno. Just a bit west of Lucca, you also have a clutch of seaside resorts that are quite popular with Italians and wealthy foreign visitors - Viareggio, Forte dei Marmi, etc. The surrounding countryside has many serviced villas as well as a number of large resort-style hotels.
Although millions visit the beach towns, cities, and resorts, the countryside here is almost entirely unknown to foreign visitors.
And even visitors to the cities rarely stick around for long. Livorno is a major port of call for cruise ships, but almost everyone who arrives immediately heads off for more famous parts of Tuscany. Visitors to Pisa tend to come on day trips from Florence or just stop over to see the Leaning Tower while on their way to the Cinque Terre. Lucca receives some overnight visitors, but is also primarily a day trip destination.
The Maremma coast
The Maremma coast is Tuscany's southern coastline (and its most beautiful). Many of the beaches here are gorgeous and some look more similar to what you find in Sardinia than the rest of mainland Italy. Much of it also lies within protected nature reserves, so provides access to a relatively unspoiled coastline.
The area's main city is the pretty Renaissance town of Grosseto which, perplexingly, receives very few visitors. Other places that you may have heard of are the town of Pittigliano, the Terme di Saturnia thermal baths, and the Monte Argentario peninsula and its main beach town of Porto Santo Stefano.
My 7 favorite bases in Tuscany
Below I've given 7 areas that I think make for ideal bases for both first-time and returning visitors.
You'll notice that I've listed some places, like Chianti and the Val d’Orcia, as entire regions rather than specific towns. This is these are rural areas with tiny little villages and I don't think which one you stay in is all that important. When choosing a base in these areas, you should focus more on the hotel than the town itself.
The 5 cities that I've recommended range in size from small to mid-sized (there are no truly large cities in Tuscany) and each of them is a regional hub, conveniently located for day trips to other interesting places and with decent public transport connections.
1. Florence
Tuscany's capital city and its main transit hub, almost every visit to the region starts in Florence.
A Renaissance masterpiece filled with more art and architecture than you could see in a dozen visits, Florence is home to the world renowned Accademia and Uffizi museums, monuments from the Medici family, and works of art by masters like Michelangelo, Donatello, Caravaggio, Botticelli, and Giotto. To soak all of that up, you need a minimum of 2 days in the city.
Florence also makes for a convenient base from which to explore much of the surrounding region. Places like Lucca, Pisa, and Siena are all reachable via public transport within 1.5 hours. If you'll have a car or plan to book tours, you can also take easy day trips to the Chianti countryside, Volterra, and San Gimignano.
My recommended hotels
Hotel Palazzo Guadagni - Housed in a historic building, the rooms here have been wonderfully furnished while still maintaining their original Renaissance design. The result is sumptuous, delicious, delightful, decadent, and lots of other nice "d” adjectives. This might be my favorite hotel in the city. $300-400 per night.
Hotel Calimala - You can't get more central than this. Surrounded by historic palaces and monuments, this modern boutique hotel with an artistic touch is perfect for getting a taste of Florence's Renaissance history. $300 per night.
La Maison du Sage - An absolutely gorgeous mid-range boutique hotel that is probably my favorite in Santa Croce. The location, adjacent to the Basilica di Santa Croce (with some rooms looking out onto it), is unbeatable. $250-350 per night.
Room Mate Luca - Modern mid-size hotel with big rooms that are colorful, a bit playful, and very comfortable. It's a bit boutique and a really nice place. $150-300 USD.
Hotel Silla - A really good value hotel with pretty rooms near Piazzale Michelangelo. The neighboorhood here feels a bit more local, but is still close to everything. $150-$200 per night.
Locanda de Ciomp - A small, cozy inn right in front of one of the city's most energetic nightlife streets. If you can get a room (it's often fully booked), it's excellent value. $150-200 per night.
Reisdenza San Gallo 79 - A very nicely renovated B&B just a quick walk north of the Duomo area. Rooms are big and bright, with high ceilings. $100-200 USD.
2. Chianti
Covering a small area of hilly and forested countryside between the cities of Florence and Siena, Chianti is Tuscany's premier wine-growing region. If you've seen photos of wavy hillsides carpeted in neat rows of grapevines, you've almost certainly seen Chianti.
The area comprises 8 little medieval villages: Gaiole, Radda, Panzano, Greve, Castellina, Barberino Val d’Elsa, San Casciano in Val di Pesa, and Castelnuovo Berardenga. Half of the villages are closer to Florence, while the other half are nearer to Siena.
The appeal of staying in Chianti is to enjoy the bucolic countryside, tour vineyads and do wine tastings, and spend time leisurely hopping between the pleasant little towns. With a great network of gravel and paved roads, cyclists have fantastic biking opportunities and hikers also have a good selection trails. When in the car, the winding country lanes make for great road trips. Photographers will also find themselves with simply too many panoramas to capture.
A few of these towns are bigger than others and have a little more to see and do in them, but it really doesn't matter which you stay in. Moreover, most of the good accommodation options are actually in the surrounding countryside (not in the towns themselves), often housed in renovated castles and noble palazzi.
You have an excellent choice of hotels here, ranging from rustic farmhouses and small B&Bs to really luxurious estates. Many high-end properties also have their own wineries, so you can do tastings on-site and your room is likely to overlook vineyards.
I really do think that for Chianti you should choose where to stay based on the hotel and its general location and not by specific town, but below I've given a quick breakdown of the various towns.
For more info, see my guide on where to stay in Chianti.
Greve
Greve is the largest of the Chianti towns and has ta decent selection of hotels, restaurants, and bars. It's closer to Florence than to Siena, and therefore busier. You have a few hotels in the town itself.
Radda and Castellina
Radda and Castellina are right next to each other and both are tiny, but very charming. They have a few restaurants and bars, so you'll have a few options in the evenings. They are both also just 15-30 minutes to Siena and you have a couple of hotels in both towns’ centers.
San Casciano
San Casciano is a rather work-a-day place. Its countryside is lovely, but the town itself is neither historic nor charming. Its location near to Antinori's famed winery (and its proximity to Florence) are convenient if you plan on visiting either place.
Barberino
Barberino is a charming hamlet, but it's just one road and far from the rest of the Chianti towns. The only reason to base yourself here is if there are specific wineries you want to visit nearby (like Antinori) or if you want to stay at the 5-star Castello del Nero hotel.
Panzano
Panzano is the smallest town in Chianti (just 1,000 inhabitants), but it has a gorgeous location and is actually one of the more visited towns, in large part due to the fame of Dario Cecchini's famous butcher shop and restaurant. The countryside surrounding it is gorgeous.
Gaiole
Gaiole is the most rural and "wildest” place in Chianti. It has just a handful of restaurants (although one my favorites - La Gorgia), two bars, and a couple of hotels. It has good wineries nearby though, some charming stone hamlets that don't even count as towns, and is deep in the woods. There are also 2 or 3 excellent 5-star hotels just 15 minutes away. It's not the right choice for most people, but is great if you're looking to get away from it all.
Castelnuovo Berardenga
Castelnuovo Berardenga is a pleasant partialy walled village just 20 minutes from Siena. It sits in an interesting location where the forested hills of Chianti give way to the dry "badlands” of the Crete Senesi. It's also home to the impossibly pretty hamlet of San Gusmé. You have no hotels in town and most people who chose to stay here do so at the nearby 5-star Borgo San Felice.
My recommended hotels
Castello del Nero - Frescoes and other medieval splendor abound at this luxurious 12th-century castle and wine estate outside Tavarnelle Val di Pesa. They have two restaurants, one with a Michelin star, a fabulous pool, a great spa, and an absolutely stunning view from their back terrace. From 700 euros.
Borgo San Felice - Just outside the town of Castelnuovo Berardenga and only 20 minutes from lovely Siena, this 5-star property is among the most beautiful in Tuscany; resembling a small medieval village, which it once was. It has two excellent restaurants (one with a Michelin star), as well as its own vineyards and a beautiful cantina and tasting rooms. From 600 euros.
Villa Le Barone - A count and countess pamper guests at their manor house outside Panzano. From 300 euros.
Badia a Coltibuono - A stylishly converted abbey is set in a nature preserve high above the town of Gaiole. From 180 euros.
Castello Vicchiomaggio - The 700-year-old wine estate near Greve has hosted Leonardo da Vinci and other luminaries and now houses guests in a storybook, castle-like manor house and a beautifully restored priory. From 180 euros.
B&B Castello di Fonterutoli - Guest rooms in stone houses scattered around a rural hamlet outside Castellina are stylish and relaxing. From 170 euros.
Palazzo Leopolodo - This palace full of medieval salons and beamed guestrooms in the heart of Radda opens to a village square on one side and sweeping countryside on the other, providing in-town convenience along with rural beauty. 120 to 140 euros.
3. Siena
Located about 1.5 hours south of Florence, Siena is one of Tuscany's most beautiful cities. A stunning example of medieval architecture, the city's red brick buildings and narrow pedestrianized streets are an absolute pleasure to wander. An evening in Siena is one of the most atmospheric experiences you can have in Tuscany. The city's cathedral is also one of the most impressive in all of Italy.
Although many tourists just visit the city as part of a day trip from Florence, this is a real shame and I always recommend spending at least one night here.
Siena is also a really good base for making day trips. Getting to the wineries of Chianti takes as little as 20 minutes, and you're only 1-1.5 hours from all of the following: San Gimignano, Volterra, and the Val d’Orcia towns of Montalcino, Pienza, and Montepulciano. It's an ideal choice for those who will have a car, are happy to do day trips, and want to avoid changing home bases frequently.
With a population of about 50,000 people and a major university (Università di Siena), Siena is also always lively and never feels overwhelmed by tourism. Because most people only visit during the day, staying here gives the added benefit of getting to enjoy the city in the mornings and evenings when there are few tourists and the streets of the old town are surprisingly empty.
My recommended hotels
Grand Hotel Continental - This 5-star hotel is located across from Piazza Salimbeni right on Siena’s premier pedestrian street and just minutes from Piazza del Campo and the Duomo. The 5-star rating is a bit optimistic in my opinion, but the rooms are lovely and the location, smack in the center of Siena, is simply unbeatable. From 350 to 700 euros.
Campo Regio Relais – Stylish rooms in an old house look out to the magical cityscape and Duomo, and welcoming sitting rooms open to a sunny terrace. From 200 to 275 euros.
Il Battisero – Stylish rooms and suites in a former papal residence face the Baptistery and enjoy an in-house wine shop and tasting room. From 110 to 160 euros.
Palazzo Ravizza – A 17th-century Renaissance palazzo full of oil paintings, antiques, and beamed ceilings suggests an age of genteel travel, and a large garden enhances the atmosphere. From 100 to 175 euros.
Hotel Santa Caterina – A homey old inn just a few steps outside the city walls has cozy, wood-beamed guest rooms that overlook the countryside and a large garden. From 90 to 175 euros.
Casacenti — A converted family apartment now accommodates guests in four spacious rooms just behind the Duomo. From 70 to 110 euros.
4. Val d’Orcia
While not an official adminsitrative area, the Val d’Orcia is defined as the small southern Tuscan territory that encompasses five main towns: Pienza, San Quirico d’Orcia, Montalcino, Bagno Vignoni, and Radicofani. The region begins about 45 minutes to the south of Siena (1.5 hours from Florence) and is a sparsely populated agricultural zone. Although wine is grown on the hillsides around Montalcino, the defining characteristic of the Val d’Orcia is really its undulating fields of grain which are watched over by hilltop towns.
Montepulciano sits on the eastern edge of the area, technically at the start of the Valdichiana, but is usually considered part of it for tourism purposes. The hamlet of Montichiello, not large enough to be considered its own town, is another famous place in the region.
The main reason to visit the Val d’Orcia is really to enjoy its unique panoramas. The countryside, and the way the farmland has been subdivided among small landowners, has earned it a UNESCO World Heritage designation and the landscapes are both unique and quintessentially Tuscan.
In addition to great views, the small towns are pretty and historic, and their proximity to one another makes it very easy to visit many of them in a single day. For wine lovers, spending a day touring vineyards and tasting famous wines like Brunello di Montalcino and Vino Nobile di Montepulciano is another highlight. The restaurants of the region are also excellent and many of them are located in stunning settings, offering phenomenal views and al fresco dining.
To get a taste for the region, I generally recommend spending 1-2 days here.
As for where to base yourself, I personally think that you should choose a hotel in the countryside, focusing on somewhere that offers great views. Because this part of Tuscany can get very hot, having a pool can also be a major benefit.
If you want to stay in a town instead of the countryside, consider the following:
Pienza
Pienza is a Renaissance jewel with delightful architecture and a fabulous belvedere viewpoint that offers some of the most memorable sunsets of the region. It's the most popular town in the region, so has the most going on, but is also the most touristy.
San Quirico d’Orcia
San Quirico d’Orcia has a few hotels and a nice center and is mostly visited by day trippers, so becomes very quiet and pleasant in the evenings. It's very close to Montalcino, so convenient for those interested in wine touring.
Bagno Vignoni
Bagno Vignoni is miniscule, but it has two very nice hotels (both of which have their own on-site thermal baths) and a handful of good restaurants. If you're looking for spa treatments and pampering, it's great.
Montchiello
Montchiello is a tiny walled hamlet with a few streets, a couple good restaurants, and great sunset views. Its location is ideal for visiting places like Pienza, Montepulciano, and Bagno Vignoni, but avoiding the crowds.
Radicofani
Radicofani is your best bet for stayingb more “off the beaten path" in a sleepy little village. It's tucked away in an area of lovely forested land, which is very different from the wide open plains of the rest of the valley.
My recommended hotels
L’Olmo - This 4-star hotel is set in a stunning patch of countryside just a few minutes outside of Pienza and Montichiello. With only 8 rooms, a gorgeous pool, and surrounded by rolling fields and pasture, it’s one of the most relaxing places to stay in the region. It’s expensive (rooms start at 350 euros a night), but fabulous.
La Bandita Townhouse - The most chic accommodation in Pienza, and maybe all of the Val d’Orcia, this intimate hotel is stylishly and comfortably decorated and rooms have luxuries like deep soaking tubs. Their restaurant is also superb. From 300 euros a night.
Fonte Bertusi - Charming apartments, all with outdoor spaces, are set in cottages around an estate outside Pienza. Many of the ingredients of the excellent breakfast are from the farm gardens and orchards. From 180 euros.
Albergo Il Giglio - A centuries-old inn, with a cozy lounge for sipping Brunello, captures all the atmosphere of medieval Montalcino. From 160 euros.
Agriturismo Terrapille - A beautifully restored farmhouse outside Pienza houses guests in large suites and apartments. From 120 euros.
La Casa di Adelina - Antiques-filled rooms in an old house are as charming as the setting, the walled village of Montichiello. From 100 euros.
5. Montepulciano
Sitting at an elevation of almost 2,000 feet and overlooking vineyard-carpeted valleys on all sides, Montepulciano is perhaps the classic “Tuscan hill town". Located at the eastern edge of the Val d’Orcia and the western edge of the Valdichiana (two agricultural valletys), Montepulciano has a population of around 14,000, making it the largest town in the area. It also has the most impressive architecture, with a substantial city center made up of grand stone and marble buildings in a mix of medieval and Renaissance style.
Its strategic location, easily defendable on a hillside and surrounded by fertile farmland, has made it an important regional center since the Middle Ages. Like with Chianti and the Val d’Orcia, the hills around town also produce prized wines, in this case "Vino Nobile di Montepulciano".
You can visit the town itself quite easily in half a day (a morning or an afternoon is plenty), but if you're planning on also spending some time in the Val d’Orcia or visiting Cortona, you could use Montepulciano as your base for a couple of nights. Montalcino in the far west of the Val d’Orcia is a 40 minute drive, Cortona is the same, and even Siena is only an hour.
You have a good selection of hotels in the town center as well as a few just outside it. There is decent bus service to the Val d’Orcia towns, meaning if you won't have a car, this is really your only sensible base. You also have a couple of taxis here, so arranging transfers without the need to hire a driver is a possibility, unlike in any of the other towns.
I think there are five primary things to think about when considering Montepulciano as a base:
It's the largest town in the area with the best selection of restaurants, bars, and hotels
You have the best transit connections (although they're still not good) and there are taxi services
It's by far the most touristy and most visited town
It's very hilly
Parking can be an absolute nightmare
My recommended hotels
Palazzo Nobile di San Donato - An elegant Renaissance palace provides Montepulciano’s poshest accommodations, and the suites overlook Piazza Grande and the countryside below. From 300 euros to 400 euros.
Agriturismo la Bruciata - Well-appointed apartments on a farm at the edge of the Val d’Orcia are set on beautiful grounds with two swimming pools and views that give you a sense of being in a beautiful landscape painting. From 600 euros to 1,000 euros a week.
Meublé il Riccio - The Caroti family houses guests in style and comfort in their 800-year old palace off Piazza Grande (looking at the decorations, you’ll soon learn that “Riccio” means hedgehog). From 120 euros to 200 euros.
Albergo il Marzocco - One of the oldest palaces in town has been an inn for 150 years, housing guest in atmospheric, old-world comfort. From 140 euros to 160 euros.
Osteria del Borgo - Stylishly rustic accommodations in the highest precincts of town come with two perks—amazing views over the countryside, and homey Tuscan cuisine in the in-house restaurant. From 100 euros to 150 euros.
6. Cortona
Cortona sits on a high hill in the southernmost part of Tuscany, in the province of Arezzo, just north of Lake Trasimeno, Italy's 4th largest lake. It's 105 kilometers southeast of Florence, about 2 hours by train. It is also essentially on the border with the region of Umbria, and it's just 45 minutes to its capital city of Perugia.
Originally an Etruscan city, Cortona is one of the only places in Italy that has preserved the Etruscan city layout and urban design. Visibly, it's not that distinct from other medieval cities, but as you explore the town you'll probably perceive that something simply feels "different". It's a neat town and simply a pleasant place to spend time.
The city's main square is lined with restaurants and wine bars, steep and narrow staircases lead off in all directions, and a number of viewpoints offer vistas that extend as far as Lake Trasimeno. This is also a favorite town for local and foreign artists and artisans, so it has a good cultural scene (galleries, events, shows, etc.), is surprisingly cosmopolitan, and has lots of good shopping. Despite being small, it also has many good restaurants.
Cortona itself can be visited in half a day or even just a couple of hours if you don't stop to eat, but it can also be used as a good base for a night or two. Although Montepulciano and the Val d’Orcia are less than an hour away, I don't really recommend using Cortona as your base for visiting those places. Instead, I consider it somewhere to get a bit off the beaten path and to use as a base for visiting the western parts of Umbria. The under-the-radar Tuscan city of Arezzo is also 30-60 minutes away by train or car.
My recommended hotels
Villa di Piazzano - Just at the bottom of the hill that Cortona sits atop, Villa di Piazzano is a fantastic 5-star hotel set inside a noble villa with manicured gardens and grounds. Staying here feels a bit as if you’re on a weekend jaunt to your aristocratic friend’s unbelievable country estate. Daily rates run from 400 to 800 euros depending on the month.
Relais il Falconiere - The setting is rural but the accommodations are stylishly luxurious in this beautifully restored villa and several surrounding farmhouses. From 350 euros to 750 euros.
Monastero di Cortona - This boutique adults-only hotel offers rooms inside of a converted monastery right in town. It’s not as luxurious as the two options below, but it’s much cheaper, especially in the summer. You can find rooms from 280 to 500 euros.
Casa Zeni - Stylish apartments in a medieval house in the center of town are so attractive and comfortable that you will be tempted to settle in for a very long time. 200 300 euros.
Hotel San Michele - Old world charm prevails in a grand palazzo tastefully converted to welcoming guest quarters. From 90 euros to 150 euros.
Hotel Italia - A 15th-century palace is the setting for simple and atmospheric rooms just off the main square. From 100 euros to 140 euros.
Villa Borgo San Pietro - Comfortable accommodations in a villa and outbuildings are set on well-tended grounds in the countryside outside of Cortona proper. From 85 euros to 140 euros.
7. Lucca
In the northwest of Tuscany, Lucca is a lovely mid-sized city that sits on flat terrain along the banks of the Serchio River. Near to the coast and about 1.5 hours from Florence, it's also close to the cities of Pisa and Livorno.
Blessed with wealth since medieval times, Lucca is an elegant city of 90,000 with walkable city walls, cobbletone streets, pretty churches, and gorgeous villas in the hills beyond town. Located at the beginning of the impressive Apuan Alps (Alpi Apuane), the gentle rolling hills that you see elsewhere in Tuscany are replaced here by actual mountains.
There are no major “must visits”, but it's a very pleasant city, quite a bit less touristy than other Tuscan cities you'll visit, and the sensible place to base yourself if you're planning on visiting it, Pisa, Livorno, or the Cinque Terre. If you're here in the summer, it's also only 30 minutes to the coast, so you can combine some beach time with sightseeing.
One of its other major benefits is that it's well connected by train, with regular service to the rest of Tuscany and the city of La Spezia, the jumping off point for visits to the Cinque Terre. If you're planning to visit the Cinque Terre on a day trip from Tuscany, this is really the only city from which it makes sense to do so.
My recommended hotels
Palazzo Dipinto - This stylish and design-forward boutique hotel is right in the city center. It’s not cheap, but it’s quite nice. From 250 - 400 euros.
Grand Universe Lucca - A historic hotel that’s hosted visitors from John Ruskin to Chet Baker and has been redone with lots of contemporary-chic style. From 200 euros to 300 euros.
Hotel Palazzo Alexander - Plush rooms in this 12th-century palace honor the composer Puccini and even include a garret (a sort of attic) for a luxurious take on La Boheme. From 100 euros to 200 euros.
San Luca Palace Hotel - An old palace just inside the walls provides lots of old-world comfort. From 120 euros to 180 euros.
Alla Corte degli Angeli - Flower motifs, rich upholstery, and antiques make this fashionable old palazzo a top choice for an atmospheric stay in equally atmospheric Lucca. From 120 euros to 180 euros.
B&B Arena di Lucca - A comfortable and character-filled old apartments with a prime position on the Piazza dell’Anfiteatro. From 65 euros to 120 euros.
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