Last updated on March 3, 2024 by Stefano Ferro, founder of MEL365, following extensive travelling in Tuscany

Four or 5 days in Tuscany, itineraries with things to do based on your type of holiday

This region offers some of the most charming historic towns in Italy, as well as amazing countryside and unique wine, so popular in the whole world.

But are 4 or 5 days in Tuscany enough to enjoy all?

Trust me. A minimum of 7-10 days is needed to experience Tuscany. This region is one of Italy’s largest.

The good news is that if you plan ahead, you will be surprised at the number of things you can do and the number of places you can visit during your 4 or 5 days in Tuscany.

The guide will help you tailor your itinerary to meet your interests, whether you are into a countryside experience, family adventure, romantic getaway or famous historical sights.

Now let’s get started

You can read also

Four or 5 days in Tuscany – in a nutshell

In my personal opinion, don’t switch locations more than once if you are staying for only four to five days, except if you really want to experience everything (a tiring trip, but so much to see).

As a result, you will not have to spend time packing and unpacking your luggage, nor check into and out of hotels or Airbnb.

There are two major airports in Tuscany:

  1. Florence Airport is well connected to the city centre by bus (20 minutes)
  2. Pisa Airport (mostly low-cost airlines), is well connected to both the Pisa Centre (15 minutes) and Florence Centre (1h15m with Sky Bus or Autostradale Bus)

Trains and busses connect well in most of the Tuscan towns, however, realistically you will need to rent a car in Tuscany for a DIY Tour in the countryside. 

I highly suggest using DiscoverCars.com, a price comparison website that offers the best hiring rates (read cheapest)

The map below shows all the major towns and attractions that will be described in this guide.

In every plan, I outline what you can skip in case you have just 4 days for your trip

Map with Tuscany itineraries and attractions
Map with Tuscany itineraries and attractions
  • 4 or 5 days in Tuscany for art & history: you can think to split your stay in Tuscany between Florence (3 days) and Siena (2 days). These are the two most spectacular cities/towns in Tuscany, full of art and culture. Plenty of historical buildings, museums, galleries, cathedrals, and of course the outstanding historical centres. Losing yourself among the streets and lanes is what you should focus on most. Read more below for the art & history 5 days plan in Tuscany
  • Five days in Tuscany countryside: I highly suggest renting a car in Tuscany and organising your DIY trip. It will be easier, you will have a better experience and also it will be much cheaper. With 5 days in Tuscany, you can think of splitting your stay between the Chianti Area, south of Florence, and the Val D’Orcia, south of Siena. Read more below for the countryside 5 days itinerary.
  • 5 days in Tuscany for couples: I suggest here a couple of options. The first one is about splitting your stay between Florence (3 days) and Siena (2 days), both so romantic. The second possibility is to do Pisa (3 days) and Siena (2 days), for a budget option. Read more below on a full romantic itinerary
  • For families: also, in this case, I suggest splitting your stay between Florence or Lucca (2 days) and the countryside (3 days) that you can explore with a rented car. Your kids will love the scenery, the walks and most of all the playgrounds that you will find quite often in the agriturismo, the best place for sleeping and eating local products. Read more below on a family 5-day stay
  • For a bit of everything: During this itinerary, you will be able to get a taste of art, culture, nature, and of course some wine. The lot. Read below for more details

I have also included a few organised experiences in a few itineraries.

It’s pretty common (if not the norm) for them to allow cancellations without penalty. It is very advantageous to book now and cancel later if your plans change. 

My tip here is that you should plan ahead for the most popular experiences such as the Uffizi or Michelangelo’s David Accademia because the queues can be extremely long

Beautiful rolling hills of Tuscany
Beautiful rolling hills of Tuscany

Four or 5 days in Tuscany for art and history

Florence and Siena are the most iconic cities/towns in Tuscany, for a good reason, they are just outstanding

Besides having a super charming historical centre, they both offer so much in art and culture.

5 days in Tuscany for Art & Culture
4 or 5 days in Tuscany for Art & Culture

With 5 days I suggest splitting your stay between the two, starting with Florence.

With only 4 days I would opt to book the accommodation uniquely in Florence and have a day trip to Siena instead (this will save some time with check-in/out, bags, etc)

  • Florence – Day 1: You’ll start your day with a visit to the Uffizi Gallery, one of the world’s most important art museums. Here, I recommend joining the Priority Entrance Tour, a great way to save time, besides having a knowledgeable guide who will explain everything you need to know in a small group. Take a break for lunch at Panini Toscani, then walk through the old city centre, from the surprising Piazza Antinori to the Basilica of Holy Trinity, before ending at Piazza della Signoria. Follow the beautiful Borgo dei Greci Street to Piazza di Santa Croce. From there, continue north towards Piazza del Duomo. It will be a busy afternoon wandering around the Historical Centre.
  • Florence – Day 2: Continuing your tour of Florence, you will start with the Piazza Duomo and the Cathedral, but I suggest that you first climb the Dome with the Priority Entrance, skipping the main crowds. The included tour guide will make all the difference in understanding the history of the dome and the cathedral (which you will visit after the Dome). After lunch, cross the Ponte Vecchio Bridge, an arched Roman/Medieval river bridge that is an absolute must-see in Florence. The neighbourhood on the other side of the Arno River is called the Oltrarno. Turn right and proceed to the St Trinity Bridge by walking up Borgo S. Jacopo Street. Return across the bridge to the Historical Centre and visit the Gothic Basilica of Holy Trinity. Afterwards, follow Borgo Santi Apostoli Street and get lost in the maze of small lanes.
  • Florence – Day 3: In the morning, visit the Medici Family’s home, the Palazzo Vecchio, built in the 13th century during the Republic of Florence. Today, this building is home to some of the world’s most exceptional works of art. I recommend buying the ticket in advance for this visit to avoid the usual queues. You will also receive a complimentary audio guide that will be extremely helpful. Enjoy your lunch at the PizzaBar Gustarium. Two options are available in the afternoon. You can explore the Santa Croce neighbourhood (east of San Giovanni), where you can experience more of Florence’s local life with small shops and markets. Try to pay a visit to the National Central Library (they are currently hosting a free exhibition dedicated to Leonardo Da Vinci; check their website for details). Alternatively, you can walk through the Oltrarno neighbourhood to Forte di Belvedere (free entrance), a 15th-century fortress with a panoramic view of Florence and regular art exhibitions.

If you have just 4 days:

  • Florence – Day 4: Visit Siena, Pisa, San Gimignano, and the Chianti area. An excellent day tour organised by Tour & Travel covering some of the most famous art destinations in Tuscany. 

If you have 5 days:

  • Siena – Days 4: Pack your bags and take the train to Siena (1h40m). Check-in your hotel and have a walk around the historical centre. For lunch, head to Tigella Emilia for great handmade pasta. In the afternoon, keep walking to visit Piazza del Campo, the Pubblico Palace and the Duomo Cathedral (skip-the-line tickets are again highly suggested). If you have still some time, you can check out the nearby Baptistery of St John. Dinner at the Osteria Permalico, a charming restaurant in a wine cellar.
  • Siena – Day 5: A more relaxing day to visit the Castle of Brolio and the hilltop town of Radda in Chianti with an organised tour that includes also a visit to a couple of wineries as well as a beautiful lunch made of local products in the Chianti Area.

Accommodations and experiences:

Read more options on where to stay in the Florence area.

Locals and Florence
Locals and Florence

Five days in Tuscany countryside

If you plan to venture into the countryside, you will need a car.

Although trains and buses run between the Tuscan towns, moving around in the countryside can be challenging with public transportation

In the Chianti area, for example, getting around by bus would require way too much time and effort. 

Four or 5 days in the Tuscany countryside
Four or 5 days in Tuscany countryside

With 5 days I would suggest splitting your trip between the Chianti Area (3 days) and the Val D’Orcia (2 days)

  • Chianti Area Day 1Pick up your car from the airport (Florence or Pisa) and drive to the Chianti area. Start your journey in Greve in Chianti, the gateway to the Chianti Area, and visit Piazza Matteotti, the town’s central square. Wander through the streets and stop at a wine shop for some tastings. Visit Il Vinaio for lunch, where you can sample more wine. After lunch, take a stroll to the Azienda Agricola Manetti Leonardo, one of the best wineries in town. In addition to tasting more wines, you will also learn more about the area. After that, you can visit the Wine Museum where, of course, you can taste more wine. You may also drive to the Castello di Uzzano for a visit and a walk among the wineries.
  • Chianti Area Day 2: This is a day devoted to driving through one of the prettiest locations in the world. After breakfast, drive to Montefioralle, a picturesque village perched upon a hill between medieval walls. Amazingly beautiful. Take the SR222 south (direction Siena) to the Castello di Panzano in Chianti and the town of Panzano, where you can have lunch. Drive along the iconic SR222 in the afternoon to Castellina in Chianti, another delightful medieval village. Make a visit to the Chianti Area Archaeological Museum for its interesting exhibitions and of course some wine tasting.
  • Chianti Area Day 3: Another great day for exploring the Chianti Area by car. For a beautiful walk in the hills, drive to Albola Castle. You can also visit the winery and taste some wine. Afterwards, visit Castello di Brolio, which has a spectacular view and some of the country’s best wines. Plan your lunch at Locanda del Tartufaio, then head to Chianti Sculpture Park for an arty afternoon. Finish the day driving to your next accommodation in Val D’Orcia
  • Val D’Orcia Day 4: Have a drive to one of these 3 panoramic viewpoints to appreciate how beautiful is this area of Tuscany (SP18 Viewpoint, Cipressi di San Quirico and Cipressi di Monticchiello). They are all so close to another famous cinematic spot, the Gladiator Point, where they filmed the famous scene of the Gladiator between the cypresses. This is going to be a beautiful morning exploring the countryside. Have lunch at Podere Il Casale, for the lovely local food and once again the picturesque view of the Val D’Orcia, unbeatable. In the afternoon, have a short drive to Montepulciano, one of the most beautiful medieval villages in Tuscany, famous for its magnificent wine, the Nobile di Montepulciano. Have a walk in the streets, full of wine shops where you can have some tasting too. If you still have some spare time, you should visit the Vecchia Cantina di Montepulciano, where you can do more wine tasting with the local producer and buy a few bottles at a bargain price.
  • Val D’Orcia Day 5: Drive to the Thermal Bath of San Filippo for a unique morning in the hot water. This spa area has been famous since the Roman times. Back then it was visited by wealthy and noble people. Today is open to everyone, free of charge (yes, no ticket, it’s a natural wonder of Tuscany). You have two options for lunch, either the local Osteria Lo Spugnone (great local food) or drive 10 km to the Bar Fontevecchia, one of the hidden secrets of the Val D’Orcia. Family run, it looks more like a community bar, they have a small selection of very tasty dishes, of course using only local products, all at a bargain price. In the afternoon have a drive to Montalcino, another amazing medieval village, famous for its iconic Brunello di Montalcino wine. Similarly to Montepulciano, you will be able to taste some wine in one of the few shops in the historical centre. Some spare time? Why not visit the boutique winery Azienda Tornesi (call in advance), just outside the town, where you can have more wine tasting?

If you have just 4 days in Tuscany, I would suggest skipping day 3 in the Chianti Area. It’s going to be a pity, but you need at least 2 days in Val D’Orcia.

Accommodations:

5 days in Tuscany for couples

You have a couple of options, based on your budget and style

Four or 5 days in Tuscany for couples
Four or 5 days in Tuscany for couples

Florence & Siena (romantic but more expensive)

The first possibility is to stay in Florence (3 days) and Siena (2 days)

This is one of the most romantic places on earth, especially with the nightlights.

True, Florence and Siena are probably the most expensive places in Tuscany, however, they are so charming.

In 5 days, you can visit most of the 2 cities as I described in “Five Days in Tuscany for Art and History” above.

You may want, however, to swap

  • one of the Florence days with a Tour in the Chianti Area, where you get to see the picturesque wineries, and rolling hills, and taste some wine while you are there. There’s more to it than drinking, it’s about understanding the culture of the area.
  • one of the Siena days with the Vespa & Chianti Tour in the Tuscan Hills. Take a Vespa scooter ride through the picturesque hills of Tuscany along the peaceful roads. Discover the sights of Chianti and stop along the way for a wine-tasting and delicious lunch. A really memorable day.

If you have only 4 days, split your stay evenly between Florence and Siena

Accommodations and experiences:

Ponte Vecchio at sunset
Ponte Vecchio at sunset

Pisa & Siena (practical on a budget)

Pisa is a great base if you are on a budget or you are on a second or third trip to Tuscany.

It works also very well, of course, if you fly to the low-cost Pisa Airport.

Pisa is a University town, with a nice young vibe around. 

It is not as picturesque as Florence, far from it, however, it has one of the most iconic attractions in the world, the Leaning Tower.

Prices of accommodations and restaurants are usually cheaper than in any other town in Tuscany.

  • Pisa Day 1: visit Pisa with a nice DIY walking tour. Start with a tour of the iconic Leaning Tower and, of course, the Cathedral. These are both popular attractions and I highly suggest buying a skip-the-line ticket to not waste any minute in the long queues. Another possibility is to book a fully guided tour and add the Leaning Tower after that. For lunch head into town at I Porci Comodi, a small bar offering fantastic sandwiches and lovely antipasti dishes with cured meats and local products. In the afternoon, you can either explore the old part of town starting from Piazza della Pera and the Museo della Grafica, or you can take a Self-Guided Bike Tour with a handy App.
  • Pisa Day 2: catch the train (1 hour) to Florence, for a day trip to explore the lovely and picturesque city. Start the visit with the Uffizi Gallery, however, remember to book in advance the Priority Entrance Tour to skip the line and avoid spending the day queueing at the door. Then have a walk to the Cathedral for the Dome Climb with the Priority Entrance, again skip the long queue, a real-time saver. The last iconic place to visit for the day is the Ponte Vecchio, the Roman/Medieval arched river bridge. Such a romantic and unmissable spot.
  • Pisa Day 3: catch the train (30 minutes) to Lucca, a Renaissance town with medieval walls transformed into a gigantic pedestrian area. Start your visit from Piazza Napoleone with the 15th-century Ducal Palace. Make sure to add to your must-visit list the Tower Delle Ore, Guinigi Tower, the oval Piazza dell’Anfiteatro, the boutique Domus Romana Lucca and, of course, have a walk along the walls.
  • Pisa Day 4: catch the train to Siena (1h40m) for a day trip.
  • Pisa Day 5 (if available): visit the Chianti area and a few wineries for some oil and wine tasting with this Guided Tour.

Alternatively, spend days 4 and 5 in Siena. It will be more expensive, however, Siena is such an unmissable destination that you will fully enjoy in the evening, with the romantic street lights, without the day tourists.

Accommodations and experiences:

The leaning Tower of Pisa
The Leaning Tower of Pisa

4 or five days in Tuscany for families

Within a short distance of both airports, you will find Florence and Lucca, probably Tuscany’s most family-friendly town.

Here below are a couple of possible plans.

Four or 5 days in Tuscany for families
Four or 5 days in Tuscany for families

Florence and the Chianti Area

Even if you are travelling with a pram, Florence is a fun destination for 2 days with family and kids.

The area surrounding the Oltrarno is hilly, sometimes steep, but the historical centre is relatively flat.

You can explore Florence for a couple of days. 

In the remaining 3 or 2 days, rent a car and venture into the Chianti area.

For an amazing time with kids book at the Orlando in Chianti Glamping Resort. Your children will love the massive swimming pool and all the sports facilities. Such a great family-oriented accommodation.

AirBnb/Holiday Homes in Florence:

Lucca (only if you fly to Pisa) and the Chianti Area

Spend a couple of days in the town of Lucca, a beautiful, flat place with a large pedestrian area running around the old centre, over the medieval wall.

You don’t have to worry about leaving the kids running around.

It works great if you fly to Pisa (30 minutes by train), but I don’t recommend it if you fly to Florence (too far away).

Lucca is also within reach of Viareggio (25 minutes), one of Italy’s trendiest beach spots.

Take a trip to Chianti on the remaining 3 or 2 days.

Again, I highly suggest booking at the Orlando in Chianti Glamping Resort, the best place to stay with kids in the Chianti Area.

AirBnb/Holiday Homes in Lucca:

Lucca main square
Lucca main square

Four or 5 days to explore everything

This itinerary offers a bit of everything, from historical sites to the countryside.

Four or 5 days in Tuscany for everything
Four or 5 days in Tuscany for everything

The best place to start your trip is Florence, rich in art and culture.

You can organise this trip by renting a car or by public transportation.

This is probably the most tiring itinerary of all, however, you get to experience a lot.

  • Florence Day 1: The Uffizi Gallery should be the first stop on the tour, but make sure to book the Priority Entrance Tour in advance to avoid spending the entire day queuing. Then skip the long queue for the Dome Climb at the Cathedral with the Priority Entrance; another great time-saver. Ponte Vecchio, the romantic arch bridge over the river Arno, is the last sight of the day. 
  • Florence Day 2: catch the train (1h) to visit Pisa, the Leaning Tower, the Duomo and the historical centre.

With public transportation

  • Florence Day 3: You can visit the picturesque wineries of the Chianti Area, enjoy the rolling hills, and even taste some local wine. It’s not just about drinking, it’s about experiencing the local Tuscan life.
  • Siena Day 4: Take the train (1.5 hours) to explore the second most popular destination in Tuscany, Siena, where you will spend the last two days. Join the 2 hours walking tour (including the Skip-the-Line Duomo) to appreciate most of Siena’s iconic sites. In the evening have a stroll around the historic centre with the beautiful street lights. Dinner at the Osteria Permalico, a charming restaurant in a wine cellar.
  • Siena Day 5 (if available): the last day is dedicated to the Tuscan countryside, with this great tour of Val D’Orcia and San Gimignano

If you rent a car

  • Chianti Area Day 3: Pick up the car and make your own Chianti Tour. Explore Greve in Chianti by taking the SR222. Continue on the SR222 and stop at Castello di Panzano in Chianti and Panzano for lunch. Afterwards, drive to the picturesque town of Castellina in Chianti and take time to explore the Chianti Archaeological Museum where you can find interesting exhibits and sample some of the region’s best wines. Book your accommodation in the Chianti Area.
  • Siena Day 4: Keep driving on the SR222 till you are in Siena where you will spend your day and evening there. Book your hotel in town and make sure you can drive there (the historical centre is close to the traffic, check with the hotel)
  • Val D’Orcia Day 5 (if available): the last day is dedicated to the exploration of the magical Val D’orcia. In the morning drive to one of these viewpoints (SP18 Viewpoint, Cipressi di San Quirico and Cipressi di Monticchiello). The Gladiator Point, where they shot the famous scene of the Gladiator between cypress trees, is also close by. A beautiful morning awaits as you explore the countryside. I highly recommend having lunch at Podere Il Casale, for the lovely local food and the beautiful view of the Val D’Orcia. Visit Montepulciano, one of Tuscany’s most famous medieval towns, and enjoy the iconic Nobile di Montepulciano, a stunning and prestigious red wine. Enjoy some wine tasting at one of the many wine shops along the streets. Visit Vecchia Cantina di Montepulciano to do more wine tasting with the local producer and buy a few bottles at a great price, if you still have time.

Accommodations and experiences:

Siena - Palazzo Pubblico & Torre del Mangia
Siena – Palazzo Pubblico & Torre del Mangia
Stefano Ferro - MEL365.com Founder and Editor

About the Author

Stefano is a seasoned travel expert and the visionary founder of MEL365.com, a leading travel website with traffic across 6 continents. With a rich background in the travel industry, Stefano spent four pivotal years at Amadeus Travel Distribution System, gaining invaluable insights into travel technologies and distribution.

Leave a Comment