What to Visit in Tuscany: My Perfect 5-7 Day Guide

There are certain places that are beautiful in photographs, and then there is Tuscany – a place that somehow manages to look even better when you are actually there.

It is the kind of trip where you catch yourself saying wow, this is beautiful an almost unreasonable number of times a day. One minute you are driving through endless green hills and vineyards, the next you are having coffee inside a tiny medieval town where it feels as though very little has changed for centuries. Add incredible food, some of the most famous wine regions in the world, cypress-lined roads, old stone villas and sunsets that make even a random drive back to your hotel feel cinematic, and you start to understand the obsession.

For me, the beauty of Tuscany is exactly in that combination. There is plenty to see, but it is also a place that constantly reminds you to slow down. And that is probably the most important thing to remember when planning a Tuscany itinerary.

If you are planning 5 to 7 days in Tuscany, my biggest advice would be: do not try to see everything.

Tuscany is a large region, and although many of the places you will want to visit look relatively close on a map, driving between them every single day quickly adds up. Technically, you can fit an enormous amount into one week. Whether you will actually enjoy doing that is another question.

For me, the perfect Tuscany road trip is a balance between exploring and actually experiencing where you are. I want mornings by the pool, a long lunch overlooking vineyards, a few hours wandering through an old town, perhaps a winery in the afternoon and dinner somewhere beautiful. I do not want every day to become a race against Google Maps.

If you are travelling by plane, Florence and Pisa are the two most convenient arrival points for this kind of Tuscany trip, and both are absolutely worth exploring while you are there. They definitely deserve separate guides of their own – with my favourite hotels, restaurants, things to see and everything else – but I still wanted to include them here, because dedicating a day to Florence and a few hours to Pisa fits perfectly into a 5–7 day Tuscany itinerary.

This guide is all about finding that perfect balance between the places you want to see and actually having time to enjoy Tuscany – a mixture of beautiful cities, countryside, medieval towns, wine and, if you are travelling during the warmer months, a little bit of the Tuscan coast.

One thing I would definitely do differently from a traditional one-hotel holiday is split the trip between at least two bases.

This makes such a difference.

Rather than booking one beautiful hotel and spending the entire week driving back and forth across Tuscany, choose one base for the more northern or central part of your itinerary and another further south, depending on the places you want to visit.

For example, staying around Chianti makes Florence, Greve in Chianti and several wineries very easy to reach. You can then move further south if Siena, Pienza and Val d’Orcia are priorities. If you also want a few days by the sea, the Versilia coast can become your final stop.

It is actually very common to change hotels two or even three times during a Tuscany road trip, and here it makes complete sense. Pack relatively lightly, choose beautiful properties you genuinely want to spend time in and treat the hotel changes as part of the journey rather than an inconvenience.

Now, onto the places I would put on the list.

It would be impossible to write a guide to Tuscany without including Florence. Even if the purpose of your trip is mostly vineyards, countryside and smaller Tuscan towns, I would always make room for at least one day here.

Florence is essentially an open-air museum – the Duomo, Ponte Vecchio, Piazza della Signoria and the Uffizi are only the obvious starting points – but what I love most is that you do not necessarily need a strict itinerary to enjoy it. Walk, stop for coffee, cross the Arno, have a long lunch and leave enough time for a little shopping. And if you are a true shopping lover and happily dedicate half a day to it, The Mall Firenze is around a 40-minute drive from the city and definitely worth adding to your itinerary for its selection of luxury designer outlets. If it is your first visit, give Florence a full day at minimum; if you love art, architecture and museums, you could very easily spend two or three. And if you are staying in northern Chianti, Florence is particularly easy to incorporate into your Tuscany itinerary without changing hotels.

If there is one landscape that immediately comes to mind when someone says Tuscany, there is a good chance it looks something like Chianti.

Rolling hills, vineyards disappearing into the distance, olive groves, cypress trees, old stone houses and little villages appear one after another as you drive through the region. Chianti stretches between Florence and Siena and has been intrinsically connected with wine production for centuries. The Sangiovese grape sits at the heart of Chianti Classico, and the region is dotted with wineries, castles and small towns.

It is also a particularly convenient area to use as a base if you want to visit Florence. Depending on exactly where you stay, many properties in the northern part of Chianti are only around 30-45 minutes from the city, meaning you can have countryside mornings and still spend an afternoon or evening in Florence.

One town worth stopping in is Greve in Chianti, particularly around Piazza Matteotti, its distinctive triangular main square surrounded by arched loggias, small shops and places to try local food and wine. Greve sits right in the Chianti Classico territory and works perfectly as a relaxed stop rather than something you need to dedicate an entire day to.

And, of course, you cannot really come here without visiting at least one winery.

One of the most impressive options is Antinori nel Chianti Classico in Bargino. The architecture alone makes it worth seeing: this is very much the contemporary, design-led side of Tuscan wine culture rather than the tiny rustic cellar you might traditionally imagine. I would book your winery visits in advance and plan them earlier in the day – something I learned is that Tuscany’s wineries are not necessarily places you casually arrive at for an 8 PM tasting.

My advice? Leave enough empty space in your Chianti day. Part of its charm is simply driving through it.

Siena feels different.

San Gimignano is incredibly charming, but Siena has the scale and energy of a proper city while somehow still making you feel as though you have stepped onto a film set.

Its historic centre is also protected by UNESCO and is considered one of the great examples of a medieval city, preserving much of the Gothic appearance it developed between the 12th and 15th centuries. The city was built around Piazza del Campo, which remains its extraordinary focal point.

And Piazza del Campo really is one of those places that photographs do not quite explain.

You emerge from one of Siena’s narrow streets and suddenly find yourself in this huge, sloping shell-shaped piazza surrounded by warm terracotta buildings. Sit down, order something, people-watch and give yourself time to take it in rather than immediately moving onto the next sight.

Unlike some of the smaller Tuscan villages, I would dedicate at least half a day to Siena, preferably stretching into the evening. Walk without too much of a plan, see the Duomo, explore the streets around Piazza del Campo, stop for an aperitivo and stay for dinner.

Siena becomes particularly beautiful as the day cools down and the city starts filling with people heading out for the evening. If your Tuscany itinerary only allows room for one larger historic town outside Florence, Siena would be very high on my list.

Certaldo was one of those places that reminded me that the smaller stops can sometimes become your favourites.

The town is divided between the newer lower part and Certaldo Alto, the tiny medieval village sitting above it. The easiest – and definitely most charming – way to reach the historic centre is via the funicular from Piazza Boccaccio. It runs up towards the old walled town, although you can also walk if you are feeling energetic.

Once you arrive, everything becomes wonderfully quiet and simple.

Do not come here expecting endless shops, huge restaurants or a long list of attractions. Certaldo Alto is a handful of beautiful old streets, brick buildings, little cafés and restaurants, local wine and the kind of atmosphere that makes you start wondering what life would be like if your biggest decision that afternoon was whether to order another coffee.

It is also historically important as the home of Giovanni Boccaccio, author of The Decameron and one of the major figures of Italian literature.

You really only need around two hours here. Take the funicular up, walk around, have a coffee or a glass of wine with some local cheese, enjoy the views and continue your journey.

If Certaldo happens to be reasonably close to your route, I absolutely think it is worth the detour.

If your Tuscany road trip takes you further south, Pienza is the place I would add to the itinerary – particularly if you are exploring Val d’Orcia.

Pienza is fascinating because it is not simply another beautiful medieval Tuscan town. Its historic centre is recognised by UNESCO as an important example of Renaissance urban planning. In 1459, Pope Pius II decided to transform his birthplace according to Renaissance ideas of the ideal city, working with architect Bernardo Rossellino. The result can still be seen around Piazza Pio II and landmarks including Palazzo Piccolomini and the cathedral.

In other words: if some Tuscan towns feel as though they grew organically over centuries, Pienza feels unusually harmonious because someone actually had a vision for how it should look.

It also sits on a hill overlooking Val d’Orcia, so this is where you get some of those almost impossibly perfect Tuscan landscapes – soft rolling hills, isolated farmhouses and rows of cypress trees that look like somebody designed them specifically for a postcard.

And there is another reason to come hungry: Pienza is famous for its pecorino cheese. A slow lunch involving local cheese and wine feels almost compulsory here.

I would combine Pienza with a drive through Val d’Orcia rather than treating it as an isolated destination. This is one of those days where the road between places is almost as important as the places themselves.

This one changes the mood completely – and that is exactly why I would include it.

If you are visiting Tuscany between May and the end of September and want to combine countryside and sightseeing with a little time by the sea, I would absolutely consider spending a day or two around Forte dei Marmi.

Forte sits on the Versilia coast in northern Tuscany and has been one of Italy’s best-known seaside resorts for generations. Think long sandy beaches lined with beautifully organised bagni, iconic beach cabins, elegant villas hidden behind greenery, restaurants, cafés and some seriously good shopping. The town is particularly known for luxury tourism and designer boutiques.

But what I liked most is that despite all of that, Forte still feels wonderfully relaxed. Everybody seems to be on a bicycle. The town is almost completely flat, compact and extremely bike-friendly, with cycling being one of the preferred ways for both locals and visitors to move between the beach, town centre and residential streets.

There is something very charming about leaving your car, getting on a bike in a summer dress and cycling between a beach club, coffee, lunch and the boutiques.

During the day, book one of the beach establishments and enjoy the sea. In the late afternoon, change for an aperitivo, walk through the centre, do a little shopping and head towards the pier around sunset. With the beach in front of you and the Apuan Alps rising behind the town, Forte dei Marmi gives you a completely different side of Tuscany – and after several days of driving between vineyards and medieval villages, a day spent horizontally under an umbrella can feel very well deserved.

Pisa is another very easy addition to a Tuscany road trip, particularly if you are flying in or out of Pisa Airport or continuing towards the Tuscan coast.

Of course, everyone comes to see the Leaning Tower of Pisa, but the entire Piazza dei Miracoli is worth your time – the cathedral, baptistery and monumental square together form a UNESCO World Heritage Site. The good news is that Pisa does not necessarily need an entire day. A few hours are enough to see the main sights, walk through the historic centre, have a coffee or lunch and continue towards your next stop. I would particularly recommend combining it with the beginning or end of your trip, rather than sacrificing a full Tuscany day just to tick the tower off your list.

Rent a car.
If your goal is to experience the Tuscan countryside rather than simply visit Florence and another major city, I genuinely think having a car changes the trip. The magic is often in the smaller towns, wineries, countryside hotels and roads between them. Public transport can work for certain destinations, but it will restrict how spontaneously you can build your days.

Book wineries in advance – and do not leave them until the evening.
One thing I had imagined very differently was winery timing. Many tastings and organised visits finish in the late afternoon or early evening rather than functioning like bars that stay open late. Check each winery individually and book ahead, particularly in summer. I would plan a winery for late morning or afternoon and save dinner for somewhere else.

Do not change towns every two hours.
This is probably my biggest tip. Yes, you could see three or four places in a day. I am not convinced you should. Tuscany is much better when you have enough time to sit down, order something and forget what time it is.

Choose your accommodation as part of the experience.
A beautiful Tuscan villa or countryside hotel with a pool is not simply somewhere to sleep. Especially during the warmer months, I would deliberately leave a few mornings or afternoons free to enjoy it. Have breakfast slowly, spend two hours by the pool and then head out later in the day. That balance made the trip infinitely more enjoyable for me.

For me, late spring to early autumn is the dream.
May through September would personally be my first choice, particularly if you want that classic Tuscany experience of green or golden landscapes, outdoor lunches, vineyards and long days. Summer can obviously be hot and busy, so May, June and September are particularly appealing if you want warm weather without always travelling at peak intensity.

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