5 days in Tuscany: three fantastic itinerary ideas you’ll love

5 days in Tuscany itinerary ideas: easy to follow itinerary ideas to see the most beautiful destinations in Tuscany and travel tips for each [2025 Update].

Tuscany is one of the most beautiful regions in Italy and a destinations many have on their Italy bucket list, and rightly so!

The areas is blessed with pretty much anything a visitor can ask for.

Beautiful countryside, historical hilltop villages, the art powerhouse of Florence, thermal baths, wonderful food: this and much more you can experience in Tuscany.

But with so much to see, how can you make sure you pick the best destinations ans truly see the best of Tuscany?

There are many ways to go about it, depending on personal interest and mean of transport.

Today, I share Tuscany itinerary ideas for a five days stay, so you can see what’s possible.

Why you should trust me? Good question!

I am from Rome and I have been visiting Tuscany regularly since I was a child.

We visit Tuscany every year and, over time, have seen many places, participated in many experiences and taken many tours.

On the basis of this first hand experience, I have crafted these ideas for itinerary for 5 days in Tuscany that I believe are perfect for a first visit and will allow you to see the best scenery and villages in Tuscany at a reasonable pace.

I have included three itinerary to allow for different approaches:

• One Tuscany home base (with car)
• Tuscany without a car
• Road trip idea

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Five Days in Tuscany Itinerary 1: small towns, wine, cooking

This first Tuscany itinerary ideas requires a car and is ideas for people who want to stay put, enjoy beautiful accommodation in the countryside and take day excursion to beautiful locations.

This itinerary works best with accommodation in the area of Florence or Siena. Places I recommend you look at are Tenuta Chiudendone, Castelfalfi, Mormoraia, Podere Spedalone, Terre di Nano, Diacceroni (fantastic with kids).

Day 1 – Explore Chianti

I like to start this itinerary with a day in Chianti, a stunning part of Tuscany famous for its delightful wine, beautiful vineyard and castles.

Places I recommend to visit are Castello di Brolio (castle and vineyard), Castello di Ama (Castle and wineyard), La Volpaia (ancient Borgo, now also wine producing ) and the pretty town of Montefioralle.

If you are in Tuscany with kids, a day at La Palagina Farm in this area is a lovely way to have a family friendly wine tasting experience and for the kids to see animals and learn about farm life.

If you are into meat, this is also the area where you find Dario Cecchini’s restaurants!

Day 2 – San Gimignano and Monteriggioni

On day two I recommend you visit two of the prettiest hilltop towns in Tuscany, Sam Gimignano and Monteriggioni!

San Gimignano is Unesco World Heritage Site and one of the most visited places in the regions. Despite the high affluence of visitors however, it is still very much worth visiting, especially if you come here early in the morning, before the busload of tourists arrive (or at sunset! Either approach works).

Monteriggioni is an even smaller village but is very special as it is a castle town!

Monteriggioni is still entirely walled and is a delight: if you are not afraid of heights, you can climb up the village bastions and enjoy stunning views over the countryside.

If this is not for you, you can enjoy the adorable main square of the town and have a meal or a drink soaking up the medieval atmosphere of this tiny village.

Good to know! If you are traveling with kids, Monteriggioni has a lovely medieval museum with costomes they can try on!

Between the two, i recommend you stop for lunch with wine and a view in Tenuta Torciano, just outside San Gimignano.

This is a Tuscany road trip itinerary so you will need a car. However, we have kept the driving time to a minimum for each day so you can spend the time exploring and not behind the wheel!

Day 3 – Farm to table experience at Tenuta Chiudendone

On day three, I recommend you take it easy in term of traveling and settle in beautiful Tenuta Chiudendone, a fabulous country home that hosts a great farm to table experience.

Tenuta Chiudendone is in the North of Tuscany, so you may find it is a bit of a drive from where you are (potentially) but it is a very special place so I recommend it because I feel it is really worth it: people even come here from Rome, it is so special!

The Tenuta is a private, family estate which opens their doors to guests for a farm to table experience.

During a day with them, Francesco and Isabella show you around the estate, they explain all about their production of extra virgin olive oil and wine; they then bring you to the vegetables garden to pick fresh produce and cook with you, before partaking of a stunning meal all together.

After that, in summer you can even lounge at their pool!

This is a fantastic way to experience the Tuscan Countryside and real Italian hospitality while resting and taking it easy for a day.

Good to know: the experience is kid-friendly!

Day 4 – Siena and Bagno Vignoni

This is one of my very favorite days on this itinerary as it mixes a visit to stunning Siena and relaxing time in pretty Bagno Vignoni and its thermal waters.

Siena probably needs to introduction!

The town is world famous Unesco world heritage site and is home to one of the most beautiful piazzas in Italy, Piazza del Campo, as well as one of Italy’s most stunning cathedrals: Duomo di Siena.

Enjoying Siena is as easy as taking a walk around its medieval streets: no tour needed to soak up the unique historic atmosphere of this stunning town.

Bagno Vignoni is lesser known than Siena but it’s a place that capture the heart of visitors as it truly is unique: a tiny historic village with a main square developed over a large fountain of thermal water!

Bagno Vignoni is a place you visit in less than 10 minutes but it has lovely thermal baths you can access with a day pass (At Hotel Posta Marcucci) and several lovely lunch places perfect for a platter, glass of wine or aperitivo. Absolutely worth going! Find my guide here.

Day 5 – Pienza and Montepulciano

On day five I recommend you visit two of my favorite towns in Italy: stunning Montepulciano and picture perfect Pienza.

Montepulciano is probably my most favorite Tuscan town of all.

Perched on a hilltop, Montepulciano is medieval in appearance and feel and has lovely streets, a stunning piazza, Piazza Grande, fantastic food and great wine. It is the ideal places to visit for a half a day and soak up local beauty.

Pienza is a Renaissance town and while a little less authentic than Montepulciano (it is popular for weddings especially from abroad, so this impact on the overall atmosphere) is it so beautiful, it has to be seen!

Here, not to be missed are the views for the town bastions, a walk to the ‘Gladiator Cypresses’ and an aperitivo sampling the local cheese, Pecorino di Pienza!

To make the most of the stunning countryside of this area, I recommend you have lunch at Podere il Casale which has unparalleled views over the rolling hill of Val d’Orcia.

Five days in Tuscany without a car: itinerary idea

If you don’t have a car, you trip to Tuscany will look very different from what I showed above as the vast majority of these towns do not have the train and even bus connections can be hit and miss.

I therefore recommend you plan you time as follows, instead, using Florence as your home base.

I encourage you to red here >> Tuscany without a car, what to expect

Day 1 – Florence city center

Florence needs no introduction and while using it as a base will give you the chance to experience it well, it is paramount to also devote at least a full day to it, so you can soak up the beautiful atmpsphere of its center.

Depending on your interest, you may include a visit to the Uffizi (in which case, factor in a few hours) or to the Accademia (this is a shorter visit than Uffizi) you could do something fun, for instance a gelato class (gelato was born in Florence!) or just stroll and take in the open air museum feel of the place following our Florence city center itinerary.

Day 2 : spend a day in the country at Tenuta Chiudendone

Experiencing the Tuscan countryside without a car is not easy but there is a way!

Tenuta Chiudendone is a fabulous country home that hosts a great farm to table experience you can access without a car (they give you a meeting point and they come get you)!

The Tenuta is a private, family estate which opens their doors to guests for a farm to table experience.

During a day with them, Francesco and Isabella show you around the estate, they explain all about their production of extra virgin olive oil and wine; they then bring you to the vegetables garden to pick fresh produce and cook with you, before partaking of a stunning meal all together.

After that, in summer you can even lounge at their pool!

This is a fantastic way to experience the Tuscan Countryside and real Italian hospitality while resting and taking it easy for a day.

Good to know: the experience is kid-friendly!

Day 3: Lucca (and potentially Pisa)

One of the easiest and prettiest towns to visit by train from Florence is Lucca, a delightful, historic walled town with fantastic churches and ad an adorable car-free center.

Lucca is super easy to reach by train and can be visited in a day or even less, depending on how you like to travel.

If you like to cover a lot of ground or you have a burning desire to see Pisa, you can also reach pIsa from here. Just one word of warning, as I know Pisa is controversial for many!

Pisa is all about the architecture of the piazza, a piazza which is without a doubt one of the most unique and beautiful in Italy.

If you love architecture and you are the type of person who travels for the sheer beauty of a church, you’ll love it!

However, you will not love it if you go all the way for the lean of the tower!

If you only go for that, there is a huge chance you’ll be disappointed because yes, the tower leans… but so what? You’ll be done in ten minutes and will join the throngs of people who say Pisa is not worth it. If you go, go for the right reason ad I promise you will NOT be disappointed!

Day 4 – Siena

Siena is easiest visited by car but if you have a full day, you can also come here by train or bus from Florence and it is really worth it!

Siena is one of the mos beautiful small towns in Tuscany and Italy in general and has such impressive vestiges of its important history it entered the list of UNESCO world heritage sites in the mid 1990s.

The town is world famous Unesco world heritage site and is home to one of the most beautiful piazzas in Italy, Piazza del Campo, as well as one of Italy’s most stunning cathedrals: Duomo di Siena.

Enjoying Siena is as easy as taking a walk around its medieval streets: no tour needed to soak up the unique historic atmosphere of this stunning town.

Day 5 – Chianti (with driver)

On the last day of this Tuscany itinerary, I recommend you get a trip to Chianti, so you can admire its stunning hills, taste its wonderful wine and see a part of the region that is different from all the others you’ve seen so far.

My favorite way to visit Chianti is with a day tour with LivTours, which offers a wonderful, upscale and entirely customizable experience. Find info here.

What I love about this tour is that they show you different Chianti realities: Castello di Verrazzano (one of the places I also recommend in the self guided itinerary) and a smaller, family run winery, all with the help of a bilingual chaffeur.

5 days in Tuscany itinerary (road trip): road trip idea for small town and thermal baths lovers

Another fun way to experience Tuscany is to have a road trip that allows to explore different areas.

While road tripping will come with the downside of having to pack / unpack and check in and out of accommodation, we found it was fun to so as it meant we could stay in several accommodations that we wanted to experience, for instance Castello di Meleto (Chianti), Terre di Nano (Montepulciano / Pienza), Castelfalfi, Diacceroni.

Not having to always head back to the accommodation also meant we could add additional stops such as Saturnia, which is most easily reached on the way to Rome or from the coast.

• Day 1: San Gimignano and Monteriggioni
• Day 2: Siena and Bagno Vignoni
• Day 3: Pienza and Monticchiello
• Day 4: Montepulciano and San Quirico
• Day 5: Pitigliano and Saturnia

Our 5 days in Tuscany road trip recommended itinerary

Day 1: Monteriggioni and San Gimignano

Tuscany is famous for wonderful hilltop villages so what better way to start a road trip in this wonderful region that with two of the most scenic of all?

The two villages for this first day are Monteriggioni and San Gimignano, both located in the countryside between Florence and Siena and easily reached by car from either city.

San Gimignano is a wonderful hilltop town, enlisted as UNESCO World heritage Site for its beautify and peculiar history.

The town thrived during the Middle Ages and the Renaissance and the wealth and power of its most important families gave the town the characteristic that still makes is stand out from the rest: an incredibly high number of towers!

San Gimignano can be visited in a matter of hours and it is a wonderful day for a morning and early afternoon.

Find our guide with what to see and travel tips for San Gimignano here.

I recommend you then have lunch in Tenuta Torciano, nearby, then make your way to Monteriggioni.

Monteriggioni is a tiny hilltop village still entirely surrounded by medieval walls and offering sweeping views over the countryside below.

The village is tiny and I should probably call it a ‘castle’, rather than a town however, the word castle can evoke elegant interiors and regal chambers, which is not what Monteriggioni is about

Monteriggioni is a castle in the sense that it is a fortified village with a central piazza still entirely surrounded by mighty walls.

Entering the village is like stepping back in time to the Middle Ages.

Take your time to have a snack in the piazza and explore its picturesque alleys and take in its small yet perfectly formed beauty: even better, spend the night so you can truly enjoy the slow pace and views of this gorgeous town.

You can find our guide to Monteriggioni here

Day 2: Siena and Bagno Vignoni

I recommend you spend your second day road tripping in Tuscany visiting Siena and then relaxing in the nearby thermal village of Bagno Vignoni,

Siena is one of the mos beautiful small towns in Tuscany and Italy in general and has such impressive vestiges of its important history it entered the list of UNESCO world heritage sites in the mid 1990s.

You can visit Siena in a day or a little less: Piazza del Campo and the Duomo will be unforgettable!

You can find our guide to a day in Siena here.

After the beautiful yet busy town of Siena i recommend you take the short dive to nearby Bagno Vignoni.

Bagno Vignoni is a tiny, delightful village famous for natural hot springs and a central town square with a hot pool!

The town is a little more than a congregation of houses but it is a perfect place for an afternoon and a nigh under many accounts

Here you have lovely thermal resorts (some budget friendly), a picturesque central square and also the chance to taste the food and wine of this area, famous for world renowned wines such as Rosso, Brunello di Montalcino and Morellino di Scanasano

Staying in the village for the night it a great way to experience this slow pace village and to go wine tasting without having to drive.

You can find our guide to Bagno Vignoni and recommended hotels here.

If you prefer a bigger center and do not care for thermal baths, then Montalcino can be a great option too, also perfect for wine lovers.

Day 3 Val d’Orcia: Pienza and Monticchiello

On this day, you get into the heart of Val d’Orcia, one of the most scenic areas of Tuscany.

I recommend you start your thirds day in Tuscany visiting Pienza, a stunning hilltop village often refereed to as the ‘ideal city’.

The nickname is not a modern marketing hack but rather taps into the peculiar history of Pienza.

Originally a village like many others in the vicinity, in the XVI century the town as entirely redesigned by will of Pius II, who decided to turn his native town into the perfect example of the ‘Humanistic ideal town’

The result is wonderful!

Pienza is a delight and a beautiful place to explore for one morning.

You can find our guide to Pienza here

After Pienza, I recommend you take the short drive to Monticchiello, an off the beaten path, beautiful village in the middle of the Tuscan countryside.

Monticchielllo is a small gem of a place and a beautiful preserved medieval village with something special: in simmer, the town turns itself into a stage and host theater performances widely acclaimed n the arts world!

Monticchiello is along a dust road yet well kept road and the drive and village are north worth the effort.

I recommend you stop here in the afternoon and either spend the night in the village (find our guide to Monticchiello here) or, before dark, head to a nearby Terre di Nano and spend the night there: this is an agriturismo and winery so beautiful, it is a destination in itself and easily will stay as a highlight of your Tuscany road trip!

Day 4: Montepulciano and San Quirico d’Orcia

A short drive from Monticchiello lies the wonderful hilltop town of Montepulciano, maybe my most favorite of all!

Montepulciano is a historical medieval and renaissance town perched on top of a hill in between two of the most beautiful areas in Tuscany: Val D’Orcia and Val di Chiana.

The town develops vertically and it crowned by a stunning piazza, Piazza Grande, with beautiful palazzi and an unforgettable historical well.

The town is a delight to visit for a day and has some lovely food and wine worth trying.

I recommend you have lunch at Cafe Poliziano in town or you can drive out to Podere il Casale for lunch in the countryside before heading to our next stop: San Quirico d’Orcia.

San Quirico d’Orcia is a tiny village with wonderful Romanesque churches and a delightful central piazza.

Small and scenic, this is a lovely town to spend a couple of hours and a great place to call home for the night while tasting the delicacies of the area.

You can find our guide to San Quirico d’Orcia here.

Day 5: Pitigliano and Saturnia

I recommend you spend this last day heading a little farther South and exploring the stunning area of Maremma, in the south of Tuscany.

The first place I recommend you to see here is Pitigliano.

This is a wonderful hilltop village very different from the others in this list and possibly form anywhere else you have seen in Italy.

The town is perched on top of rock of tufo (a local stone) and blends in with the scenery so well, it looks as if it emerges from the ground itself!

The first glimpse of Pitigliano from the road is unforgettable however, the town itself is also worth exploring.

Home for centuries to the local Jewish community, it has a fabulous Jewish Quarter and Synagogue that is now open to the public and very interesting to visit and is a pretty village with scenic views, worth of your time.

Find our guide to Pitigliano here.

After Pitigliano, I recommend you go visit one of the most photographed places in the whole of Tuscany: Saturnia!

Satrunia is a locality known for thermal waters and while this has been a popular destination for decades, it seems to have only lately gotten international acclaim thanks to aerial shots of its wonderful Cascate del Mulino, a free thermal bathing area.

Indeed, the cascate are wonderful and one of the best thermal spring destinations in Tuscany.

They are a stretch of land where the hot water of the spring creates small waterfall and bathing pools with a white pearly color, where people can bathe for free.

They are a busy yet beautiful place to visit and a great locality to relax for awhile before saying good bye to Tuscany on your way back to Florence or nearby Rome.

You can find our guide to Saturnia hot springs here.

Additional resources for your time in Tuscany

No matter what season you are planning this road trip for, I highly recommend you book your rental car and accommodation in advance.

If renting a car, remember that in Italy we drive on the right and that car seats for children are compulsory.

Please find our tips for traveling in Italy safely here.

Remember that motorways in Italy are tolled. This itinerary keep you on non-paying roads most of the time however, you are likely to be on the motorway when close to Siena.

Always be prepared for tool booths with cash and cards. You can find all the info about Italian toll roads here.

Do not drink and drive: if planning wine tasting, make sure you select a place that allows you to stay the night, walk home or that can arrange a driver for you.

Do not drive at night: while the roads are well kept, many of the roads on this itinerary are country roads and can be dangerous in the dark

I hope you enjoyed these ideas for recommended itinerary for 5 days in Tuscany and that you will have a wonderful time. Safe travel planning!

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