Where to Stay in Tuscany 20 Something Honeymoon

Where to stay in Tuscany, with or without a car

I have spent a considerable amount of my life in this region. I just love it.

I ended up even buying a small house, a boutique (read tiny) hideout.

But I still remember the first trip there with no clue on where to stay in Tuscany.

In this guide, you will find the best places to stay in Tuscany, including the best towns and the countryside too, with or without a car

But let's get straight into it

Table of Contents

1 Best places to stay in Tuscany – In a nutshell
2 Where to stay in Tuscany for art – Florence
3 Best place to stay in Tuscany on a budget – Pisa
4 Where to stay in Tuscany for Family – Lucca
5 Best town to stay in Tuscany for a local experience – Arezzo
6 Most beautiful town to stay in Tuscany – Siena
7 Where to stay in Tuscany for wine tasting
8 Best places to stay in Tuscany without a car
9 Where to stay in Tuscany countryside
- 9.1 Val D'Orcia and the South of Tuscany
- 9.2 Chianti Area
10 Best places to stay in Tuscany with a car
11 Best areas to stay in Tuscany – A little summary

You can read also

The Ultimate Guide to Tuscany (really all you need to know)
Best itineraries of Tuscany, from 3 days to a 2 weeks stay (with maps and detailed daily plans)
My suggested places to visit in Tuscany, including a few hidden gems
Where to stay in Florence
Best towns to stay in the Cinque Terre

Best places to stay in Tuscany – In a nutshell

Tuscany Map with attractions, towns, villages

Best towns to stay in Tuscany: I personally have three favourites. The first one is Siena, the most gorgeous of all. It is however, very popular with plenty of tourists around. The second one is Arezzo, still unknown to the most and that's probably part of the appeal. And finally, I want to add, of course, Florence, which is more of a small city (380,000 people), a must-visit for art lovers. Read more on the towns below.
Where to stay in the Tuscany countryside: I suggest two areas. South of Siena in the Val D'Orcia for the most picturesque landscape. Alternatively, in the Chianti Area for its amazing wineries and the vicinity to both Florence and Siena. Read more tips on a countryside stay.
Where to stay in Chianti: this is a well know area for its wine production and the best area to stay in Tuscany if you plan to book your accommodation in a winery. There are a few options of which the Viticcio is one of my favourites. You can read below more about Chianti and the true Tuscan life.
Best places to stay in Tuscany without a car: the best choice is to book your accommodation in a town and from there experience also the countryside with local day trips. Florence and Siena are popular spots. Arezzo is the hidden secret. Read more below for a stay without car.
Best places to stay in Tuscany with a car: the easiest solution is to book in the countryside and take day trips to the towns. Otherwise, follow the unusual itinerary I list in the below chapter.
Where to stay in Tuscany for art, culture and history: you will find history everywhere in Tuscany, from the small medieval village perched on one of the many hills to the most renowned destinations. Florence is with no doubt the town/city with more art and cultural attractions, from the Cathedral to the Uffizi Palace. A must visit for any trip to Tuscany. Read more about Florence below
Best areas to stay in Tuscany for a quiet weekend: the area south Florence is probably the handiest place to stay, close to most attractions and in the middle of the Chianti winery region
Where to stay in Tuscany for honeymoon: start with Florence and then go south to Montalcino, Montepulciano and Val D'Orcia, the most romantic part of Tuscany
Best winery stays in Tuscany: the Chianti area has probably the highest concentration of wineries that offer also accommodations, including a few stunning ones. The Castello di Fonterutoli is one of the best around, but often full (book well in advance). Another option is the Viticcio winery.
Best wine towns in Tuscany: I could say all of them 🙂 I think it goes down to a personal choice and taste. I love Montalcino for its Brunello wine and Montepulciano for its Nobile. Both expensive wines but so unique and amazing.
Best town to stay in Tuscany on a budget: I usually suggest Pisa, especially for a short stay. Why? Most of the low-cost airlines land in the Pisa Airport (well connected to the centre). You will have plenty of art and culture to experience around, of which the Leaning Tower is probably one the most iconic attractions of Tuscany (and Italy). Accommodations are cheaper than in many other Tuscan towns. Pisa is also so well connected to the expensive Florence (day trip) and Lucca, besides being a stone away from the beach, in case of a hot summer day. Read more about Pisa below.
Where to stay in Tuscany for couples: if you are after a romantic stay then head down to the Val D'Orcia area, really unique. Alternatively, book a room at Castello di Bibbione for a unique stay in a castle in the Chianti area. If you prefer to stay in a town, then you should check out Arezzo, off the beaten path, a great romantic destination close to Cortona.
Best town to stay in Tuscany for a local experience: my choice here goes to Arezzo, so underrated, mostly unknown to mass tourism, still as beautiful and unique as other more famous towns. It's also very well connected to Florence and a stone away from Cortona. Read more about Arezzo below.
Where to stay in Tuscany in winter: it's a time of the year when temperatures can go below zero and you may experience also some snow. Most of the small/medium wineries are closed for business, however, the most popular ones are open on the weekend. In winter I suggest staying in the town centres where you will mostly have a local experience without the many travellers that visit Tuscany in spring and summer. Restaurants, bars and shops are typically open all year around.
Where to stay in Tuscany for wine tasting: Montalcino and Montepulciano are my favourite towns. You will have the possibilities to organise your wine tasting in a few shops in the old centre or you can visit a few of the exceptional wineries around town. Siena has a few spots for wine tasting, however, they are more tourist-oriented. Greve in Chianti is also another option, being a beautiful town.
Where to stay in Tuscany for Family: I would personally suggest spending most of your time in the Tuscan countryside if you can drive. The farmhouses have usually playgrounds and/or swimming pools and you can leave your kids running around. Lucca is the most family friendly town in Tuscany with its wide pedestrian only area.
Where to stay in Tuscany with a toddler: Florence and Pisa are pretty flat and you will be easily able to move around with a pram. Lucca is also a great option as you will be able to walk over the huge walls (pedestrian area). Most of the other towns are more challenging. The Tuscan countryside is, of course, a good place to stay too.
Stay in Florence or Tuscany: this is a question I recently received. My guess, the question was more about staying in Florence or the countryside? If you are after art then Florence has to be (you can always organise a day trip to a winery region). If you are a nature lover, then book your place in the Tuscan countryside. Mix the two for the best experience.
Where to stay between Florence and Siena: I would say both 🙂 but if I have to choose one then Florence for a first time trip in Tuscany, Siena if you have been already in the region.
Agriturismo vs farmhouse vs hotel: the differences between an agriturismo and a farmhouse are so tiny, however so important to understand. It's mostly related to the food provided by the accommodation. If interested, read more on my full comparison short guide.

Where to stay in Tuscany - The best countryside, towns and villages

Where to stay in Tuscany for art – Florence

Florence is great for

Unique art and culture
Short stay (up to 4 days)
Base to visit other destinations (Pisa, Lucca, Siena, Arezzo, etc..) on a day trip
A stone away from the Chianti area

Florence is the only actual city in Tuscany with a population of almost 400,000 people.

It is very well connected to Rome, Milan and Venice with a quick train (under 2 hours)

It has also an airport, used mostly by the major airlines.

There are so many things to do and places to see in Florence that you can be busy for a week or more. Cultural events, museums, churches, amazing architecture, parks and so much more.

Florence is a magical city, however, avoid visiting it by car.

The centre is open only to the residents and finding parking is a real challenge.

If you are visiting on a day trip, you better park your car close to a train station outside the city and take a short trip to the centre. It will save you a big headache, besides some money.

From Florence, you can easily reach Lucca and Pisa with a short train trip, and Siena by bus (1.5hours).

If you plan to visit the Chianti area or the South of Tuscany, then you better rent a car or join an organised tour.

Accommodation in Florence can be quite expensive, but it's a unique city and unmissable on any trip to Italy.

I wrote a special guide to Florence with the best areas to stay, for couples, families, nightlife and more.

Here below just two accommodations that really stand out.

The Canto degli Scali has an amazing selection of apartments and double rooms, decorated in a very stylish way with plenty of space to move around (check the photos here)

Check availability at the Canto

The Elisa Guest House is also a great place to stay in Florence. Minutes from the Duomo and the train station.

The perfect base to explore all of the attractions of the city. So practical and so well priced.

Check the latest deal at Elisa Guest House

Florence - Elisa Guest House — Florence – Elisa Guest House

Best place to stay in Tuscany on a budget – Pisa

Pisa is great for

Budget trip
Short stay or weekend (low-cost airlines airport)
A family trip with toddler/pram

Pisa hosts the airport for the low-cost airlines (and now also for a few big names) flying to Tuscany.

It's an interesting university town with one of the most famous attractions in the world, the Leaning Tower of Pisa.

This tower is located between the Arno and Serchio rivers. It is said that it was planned in that place because the soft soil would preserve it from possible earthquakes' damages.

Unfortunately, they later found out that one side of the soil was much softer, which explains the leaning.

In the last 20 years, the local government has conducted a series of work to secure the tower and today it's a much safer attraction to visit than it used to be.

Interestingly enough, Pisa town is very flat, making it a perfect base if you are travelling with a toddler and a pram. Most, if not all, of the Tuscan towns are hilly, if not steep.

The town itself is attractive, with a local young feeling, more economical in price for both restaurants and hotels, however, not as spectacular as Florence, Siena or Lucca.

It's a great destination if you are planning a short stay on a budget from which to explore Florence and other attractions.

The Relais Lorebian is an amazing value accommodation that can work very well for 1 or 2 nights. It's in an old property with lots of character. Service is great and parking is available.

Check the latest deal at the Relais Lorebian

The leaning Tower of Pisa — The Leaning Tower of Pisa

Where to stay in Tuscany for Family – Lucca

Lucca is great for

A family trip
A second or third trip to Tuscany to experience the unusual Renaissance architecture

Lucca is one of my favourite town, if not my favourite, in Tuscany.

Here are the main reasons.

the architecture is different from the other places in Tuscany, more from the Renaissance era and not the medieval time
if you spend weeks and months in Tuscany, as I did, you get used to the medieval towns and villages. Lucca is definitely something else.
the centre is still designed in a grid, as in the original plan from the Roman Empire. Different from the square concept of the other Tuscan towns
the original Renaissance wall still protects the town, all around the perimeter
best of all, the entire wall has been reorganised as a pedestrian area with a bike path. You can literally walk all around town, without the worry of any car. Fantastic if you are travelling with kids (my suggestion is to rent a bike, plenty of options around)

The Casa Paolina is an amazing property including 1 and 2-bedroom apartments with all you need for a short or long stay.

It's located right in the centre of town and minutes away from the station, the medieval walls and most of the attractions. It's a perfect place for families with kids.

Check availability at Casa Paolina

Best town to stay in Tuscany for a local experience – Arezzo

Arezzo is great for

A local esperience
A romantic trip
A unique historical experience

Arezzo was one of the most important Etruscan cities and you can see evidence of it all around town.

Interesting enough, Arezzo joined the Tuscany "touristic revolution" only in the last few years. It used to live only of agriculture and handcraft.

And this comes as a surprise because the town is really beautiful, with the main square, Piazza Grande, and the Cathedral being the top attractions.

Arezzo is somehow still off the beaten path and if you are looking for more of a local experience then it can be the best town to stay in Tuscany.

It has still that nice local feeling that places as Siena have somehow lost.

It's the perfect spot for couples that are looking for a romantic destination still a bit stuck in the Tuscan past.

The Cento Passi dal Duomo B&B is the perfect accommodation to explore Arezzo. Close to all you need. You forget about the car and you walk all through the town.

Nice spacious rooms and great service. Breakfast could be improved though. Price is a bargain.

Check the value for money at Cento Passi

Most beautiful town to stay in Tuscany – Siena

Siena is great for

Just wondering around, such a lovely town
The most antique horse race in the world
Wine tasting
Proximity to many attractions and destinations (San Gimigliano, Montalcino, Montepulciano, Val D'Orcia, etc)

How can you not fall in love with Piazza del Campo and the whole historic centre of Siena?

Impossible.

In fact, it has been added to the UNESCO World Heritage Site list.

Siena has also probably the oldest horse race in the world, the Palio, which started in medieval time and still runs on the 2nd of July and the 16th of August.

This is the race that stops the nation. Everyone in Italy is in front of the TV, watching this crazy event where the horse wins, doesn't matter if the jockey is still riding it.

Every horse represents a neighbourhood of Siena and all the locals are absolutely crazy about it.

Piazza del Campo is the stage for the race, changed and reorganised just for the event.

You may have seen the race in the famous movie "007 Quantum Of Solace".

There is however something to be said about Siena.

It is today one of the most visited sites in Italy and it suffers the same issue as Venice and other popular Italian destinations.

It can be really really busy with tourists, up to a point where the small lanes become too crowded.

The best time to enjoy Siena is at sunrise and at night when most of the tour buses have left.

June to August is the high season, expect plenty of people everywhere.

Winter is instead a great season to visit Siena, more livable, although it can be quite cold as well.

This does not mean that you should not visit Siena, just be aware that you will not be alone.

In Siena you will find also one of the most beautiful 5 stars hotels in the world, the Grand Hotel Continental.

Set in a historical palace, you may feel like stepping back in the glorious past of Siena.

Check availability at Grand Hotel Continental

Siena - Grand Hotel Continental — Siena – Grand Hotel Continental

Another more cost-effective option is the Hotel Palazzetto Rosso, a converted medieval palace refurbished with modern and comfortable rooms with amazing interior design.

The service is one of the best in town and the location as central as it can be.

Check the latest deal at the Palazzetto

Siena - Hotel Palazzetto Rosso — Siena – Hotel Palazzetto Rosso

The Hotel Italia is one of the best value for money in Siena. Great rooms, lovely breakfast and fantastic service.

It's just minutes away from the station and a 15-20 minutes walk from the centre of town.

Check price at the Hotel Italia

Where to stay in Tuscany for wine tasting

Most of the towns and villages of Tuscany offer wine tasting in some form or another

In saying that, there are three villages that literally stand out because of their amazing wine.

The first one is Montepulciano, famous for its magnificent wine, the Nobile di Montepulciano.

This is a lovely small medieval village that has not changed in the last 500 years.

This is probably the best place to stay in Tuscany if you are after a boutique wine and food experience.

It is reachable by both bus and train.

Then comesMontalcino, as medieval as Montepulciano, with another iconic Tuscan wine, the Brunello di Montalcino.

Unfortunately Montalcino does not have a train station and public buses are rare and far between.

This makes Montalcino less popular with tourism and probably a better option if you are travelling by car.

San Gimignano is another option, just outside Siena and easily reachable by bus or train.

This town is world famous for its Vernaccia di San Gimignano, one of Italy's finest white wines, famous since the Renaissance era.

This village stands out for its medieval architecture and unique towers, erected by the wealthiest families of that era.

It's a popular village to visit, however, it can also be quite busy, especially in July and August

Other villages to consider are:

Pienza: seating in the famous Val D'Orcia, between the incredible rolling hills that have made Tuscany world famous. It should be on the bucket list
Pitigliano: one of the most characteristic villages in Tuscany, also called the little Jerusalem, seating on a huge tufa rock surface. Once you approach the town you will literally be open mouth

Best places to stay in Tuscany without a car

This region can be absolutely visited without a private or rented car.

It may take more time, it may require planning it more carefully however you will be more relaxed during the trip, either on a train or a bus.

If you are planning two weeks or more, then you can also think to book a car just on those days where the destination is difficult to reach by public transportation.

The village of Montalcino is a typical example, not connected by train and not well served by public bus.

I have organised a few itineraries without a car for one week and 10 days. You can see more option for 3 or 5 days in my Tuscany itinerary guide.

Itinerary of Tuscany without a car

Where to stay in Tuscany countryside

If you are thinking to stay in the Tuscany countryside then you should plan to also hire a car.

I personally use a comparative website called DiscoverCars.com. They give the best deal analysing all the current prices from more than 30 rentals companies. Great unbeatable prices.

Check the best car price

Without a car, it may be very hard to move around as public transportation is good between towns and cities but it lacks when moving around the countryside.

The best places to stay in Tuscany with a car are the farmhouses or the agritourism. They can be really romantic, they provide local products and they are usually cheaper than the hotels in the towns.

Another alternative, especially if you are travelling with a group of friends or with kids, is to book a villa.

Val D'Orcia and the South of Tuscany

The area south of Tuscany, down to Siena and Montepulciano, is probably the most spectacular part of the region, with those beautiful rolling green hills that you have already seen in many photos around.

Having a car will add a local pace, made of no timeline and breaks in hidden and unknown villages along the way

As an example, the trip from Montalcino to Montepulciano can be done in 1 hour with a bus or 1 day with a car, visiting the few villages between, driving through the beautiful hills and stopping for a few photos, making an excursion in a "Riserva Naturale" (National Park), having lunch in a local "trattoria" and so much more.

In this area, you can check out the following accommodations:

The Agriturismo Il Rigo is one of my favourite places in the whole of Tuscany. The location is really unbeatable, between wineries, old villages and thermal baths. The view is just unique (see photos here) and the interior design is so typical Tuscan style.
The Palazzo dei Diavoli is a great value farmhouse and boutique winery, just outside Montepulciano. The view is again spectacular (see photos here). The rooms are spacious, however, they do not have that amazing Tuscan interior design as Il Rigo above. In saying that, it comes much cheaper.
Villa Montalcino is a great place if you are travelling in a group or with kids (up to 8 people). It is basically a small castle (see photos here) in the middle of the Tuscan countryside. Close to the village of Montalcino and just 40km from Siena.

Check availability at Il Rigo Check price at Palazzo Check availability at Villa Montalcino

Chianti Area

Another possibility is to stay between Florence and Siena, the Chianti Area.

This will allow you to easily visit both cities on a day or half-day trip.

You can find here a few accommodations right in the Chianti wineries, which are absolutely a unique choice.

In this area, you can check out the following accommodations:

The Castello di Bibbione is a dream come true. Have you ever dreamt to sleep in a castle, possibly with a pool? Then you should book this place. Truly magnificent (see photos here). And the best is that it doesn't cost an arm and a leg.
The Viticcio is set in an actual working winery. It's a great place, with a pool, to experience the Tuscan life, oil and wine production and farming life. The rooms are beautifully decorated (see photos here) and the food is 100% local. It's all so Chianti style.
Villa La Coccola will make you feel a celebrity. The interior and exterior design mix the Tuscan style with a modern touch (see photos here). The swimming pool is the perfect spot for those hot summer days. Really a unique place for up to 8 people

Check price at Castello Check price at Viticcio Check availability at La Coccola

As I previously said, do not venture with the car inside Florence, unless you are looking for a headache which will start with the impossibility to park (unless you fork 30 euros, or more, for a day).

If you have a car and you want to visit Florence then I suggest parking it just outside the city at one of these two places:

Villa Costanza, this is the newest and best spot in my opinion. You don't even need to leave the "Autostrada" (highway). Tram #1 will take you directly to the city centre. The parking is less than 10 euro/day. Absolutely a bargain
Piazza Don Pietro Puliti in the town of Galluzzo. It's free parking, which is great. Walk to the next square, Piazza Acciaiuoli, and catch the tram 36 or 37 to the city centre.

TIP: Don't leave any bag in the car that people can see, even if there is nothing inside.

The tram tickets can be bought in a convenience store ("Tabaccheria") or at the newsstand. Remember to validate it once on board.

Siena has a ZTL area and you cannot drive inside the old centre.

If you are visiting the city on a day trip, consider parking the car outside the centre and get a tram or bus to go in.

It's cheaper and easier.

Do not venture into the medieval part of town, some of the streets can be quite narrow.

Best places to stay in Tuscany with a car

Having a car will give you more flexibility in the countryside, however, it will be also a headache in the city where the streets are narrow and parking is hard to find.

If you plan to stay mostly in the countryside, then check the previous chapter for all the options you have.

I have built 4 itineraries by car for one week and 10 days in Tuscany.

You can approach them in a relaxed way, with more chill-out time and longer stays in the destinations, or, more on the go, changing accommodation every second day or so.

It is going to be more tiring, however, you will experience so much more.

Is it not true that the trip to a place becomes the experience itself and not just a way to reach the destination?

If you stay in the cities, be aware that most of them, like Florence and Siena, have a ZTL area.

If your hotel is in the ZTL area then ask them, once you have booked your room, to provide the special pass.

As previously said, you may also consider parking your car outside the centre and commute by public transportation to the hotel

Siena - Piazza del Duomo — Pisa – Leaning Tower and Cathedral

Best areas to stay in Tuscany – A little summary

To make things easier, I always suggest seeing Tuscany as divided into 6 areas.

the Central area with Florence and the wineries around
the North with a mountain landscape (less characteristic, I would leave this area on a third or fourth trip to Tuscany)
the West with cities as Pisa (main touristic airport) and Lucca. They are both connected with a quick train to Florence and the beach.
the Coast with some good beaches great for a day tour in those hot days but I would not stay there
the South, from the Chianti area to Siena and other beautiful villages
the East with Cortona and Arezzo (opening more to the tourism in the last few years.

Where to Stay in Tuscany 20 Something Honeymoon

Source: https://mel365.com/where-to-stay-in-tuscany/