5 days in Tuscany itinerary 

What’s the first image that enters your mind when you hear the word Tuscany? 

Is it its rolling green hills dotted with Cypress trees, its renowned wine culture or its charming Tuscan villages? Maybe it’s all the above plus much more. 

Whatever comes to mind when you think about Tuscany, the region appeals to so many visitors and across different demographics. 

A versatile region that attracts wine lovers, outdoors enthusiasts and gastronomes, visiting Tuscany is essential for any Italy itinerary. 

In this article, I’ll be sharing an easy to follow 5 days in Tuscany itinerary. It will outline a day-by-day planner of the best places to visit in Tuscany and in a short timeframe. 

A local’s guide to the best Tuscany trips, use this resource to help plan your Italy trip. 

Where is Tuscany? 

Tuscany is situated in northern central Italy. It's surrounded by Liguria and Emilia-Romagna to the north and Umbria and Lazio to the west and south. 

How many days to spend in Tuscany? 

There’s no right or wrong answer to how many days to spend in Tuscany. Some people choose to spend 3 days while others may have the luxury of spending 3 weeks in Tuscany. 

Another option is a road trip. This 4-day Tuscany road trip itinerary excludes the larger cities and focuses on smaller towns and countryside.

The beauty about this Tuscany itinerary is that while it’s written for 5 days, it can also be extended. 

Mix and match the destinations included in this Tuscany travel guide and reduce or increase the number of days. Ultimately, it’s your itinerary to customize as you wish. 

What is Tuscany best known for? 

Tuscany is known for several things. Some of the region’s best-known characteristics include: 

Its Renaissance heritage  

The capital of Tuscany, Florence, is home to Michelangelo's David, Botticelli's The Birth of Venus and works by Leonardo da Vinci. 

Wine  

Tuscany draws visitors to the region to try wines like Chianti, Brunello di Montalcino and Vino Nobile di Montepulciano. 

The Tuscan countryside and villages 

Rolling hills and cypress tree-lined roads are iconic features of the Tuscany countryside. The region is filled with charming villages and towns like San Gimignano and Lucca. 

What is the best time of year to go to Tuscany? 

The answer to what is the best time of year to go to Tuscany all depends on individual choices.

Personally, I enjoy visiting Tuscany in late spring (late May/June) or during the fall months (September, October (see 'Italy in September' and 'October')). 

The Tuscany Italy weather is still warm and sunny enough to explore cities, towns and villages around the region. 

My guide on when is the best time to visit Italy covers this topic in greater detail.

What is the best area to stay in Tuscany? 

Again, there’s no straightforward answer to what is the best area to stay in Tuscany? Florence is good for first-time visitors given its many attractions and conveniences within the city.  

On the other hand, places like Pienza or Arezzo may be preferable if looking for a less touristy Tuscan experience. 

Is driving in Tuscany difficult? 

You may find driving in Tuscany difficult unless you’re used to driving through narrow streets and parking in tight spaces. 

While Tuscany has plenty of wide, winding roads, it also has plenty of the above throughout Tuscan towns and villages. 

5 days in Tuscany itinerary 

Day 1

Start in Florence 

The birthplace of Renaissance art and architecture, it’d be a crime for first-time visitors to leave Florence off the list.  

However, feel free to skip this part if you’ve already visited Florence or prefer to see other parts of Tuscany. 

We spent 2 days in Florence, and it was a good amount of time to comfortably visit the top attractions. However, given this is a 5 days in Tuscany Italy itinerary, I recommend reducing this to 1 or 1.5 days.  

Should you plan to spend 7 days in Tuscany, you can comfortably extend this to 2 full days in Florence. 

One of the biggest advantages of having Florence as a base for a Tuscany itinerary is that it’s well connected. It makes it possible to create a Tuscany itinerary by train or to plan a Tuscany road trip. 

Cities in Tuscany you can visit by train from Florence 

• Pisa (54mins) 
• Livorno (1hr 26mins) 
• Arezzo (54mins) 
• Pistoia (33mins) 
• Siena (1hr 15mins) 
• Grosseto (2hrs 40mins) 

Organize Florence attractions 

Like many tourist-heavy cities across Italy booking main attractions in Florence is essential. Some of the most popular sites even require booking a month or so in advance. 

The following lists several of Florence’s best attractions. Many have free cancellation policies in place giving you peace of mind that full refunds are available. 

• Florence Duomo Cathedral skip-the-line guided tour 
• Tour Brunelleschi's Dome and Duomo 
• Florence Cathedral and Brunelleschi's Dome ticket and audio app 
• Basilica di Santa Croce di Firenze 
• Skip-the-line Uffizi Gallery timed entry ticket 
• Skip-the-line tickets for Michelangelo’s David 
• Pitti Palace 
• Reserved entry ticket to the Boboli Gardens 
• Reserved entrance ticket to the Medici Chapel 

Visit wine windows in Florence 

A social media favorite, the wine windows in Florence add a unique touch to your 5 days in Tuscany itinerary. Make a note of the following spots for your Tuscany trip itinerary. 

• Wine in wall, Via delle Belle Donne, 23 
• Osteria delle Belle Donne, Via delle Belle Donne, 16R 
• Il Latini, Via del Palchetti, 6r 
• Cantina De' Pucci (Restaurant & Wine Window / Buchetta del Vino), Via de' Pucci, 4 (this restaurant looks excellent) 
• Osteria San Fiorenzo, Borgo dei Greci, 1r 
• Ristorante Pietrabianca, Piazza dei Peruzzi, 5R 
• Fiaschetteria Fantappie, Via dei Serragli 47 
• Babae, Via Santo Spirito, 21r 

Where to eat in Florence 

Don’t spend time overthinking about where to eat in Florence. Take inspiration from the list below that’s been helpfully categorized according to popular Florentine dishes. 

Bistecca alla Fiorentina 

• Trattoria Osteria Dall'Oste SMN, Via Luigi Alamanni, ⅗r 
• Ristorante I Tuscani - L'arte della Bistecca alla Fiorentina, Piazza di S. Pancrazio, 2r 

Schiacciate (Tuscan sandwiches) 

• All’Antico Vinaio, Via dei Neri, 65r (famous sandwich shop in Florence) 
• Schiacciateria De' Neri 18r, Via dei Neri, 18/r 
• La Nicchietta in Calimaruzza, Via Calimaruzza, 12 

Day 2 

Pisa and Lucca 

Two of the most beautiful places in Tuscany to add to your Tuscany road trip itinerary are Pisa and Lucca.  

I suggest visiting Pisa first and Lucca after. Pisa attracts more visitors, and its attractions are likely to be far busier than in Lucca. 

If renting a car, the journey should take around 1hr 30mins from Florence to Pisa (not factoring in stops). Alternatively, it’s a 54-minute train ride from Florence Santa Maria Novella to Pisa Centrale.  

Consider booking skip-the-line tickets to visit the leaning tower of Pisa and the cathedral in advance. Pisa’s leaning tower (Torre di Pisa) is known around the world and reserved entry tickets will likely sell out. 

Next stop: Lucca 

A short distance from Pisa is the picturesque city of Lucca. With a journey time of around 28mins by car or 38mins by bus, Lucca is 100% worth visiting. 

Located on the banks of the Serchio river, Lucca is best known for its walls that surround the historic center.  

Fully intact, the Renaissance walls (Mura di Lucca) form a 2.6mi (about 4.2km) ring around the city. Now a pedestrian promenade, they provide a scenic route around the old town of Lucca. 

Other notable landmarks to visit in Lucca include St. Martin’s Cathedral, Giungi Tower, Napoleon Square and Mansi Palace National Museum. 

St. Martin’s Cathedral (Duomo di San Martino), Piazza Antelminelli  
Giungi Tower (Torre Giungi), buy tickets to reach the top of the tower (230 steps) to enjoy panoramic views 
Napoleon Square (Piazza Napoleone)  
Mansi Palace National Museum (Museo Nazionale di Palazzo Mansi), Via Galli Tassi, 43 

Where to stay in Lucca 

A pretty town to add to your 5 days in Tuscany itinerary, Lucca has several great hotels to consider booking. Some of my favorites include: 

• Il Cortile di Elisa (B&B in Lucca’s historic center) 
• L’Antica Bifore (beautiful B&B in historic center) 
• Palazzo Rocchi - Residenza D'Epoca (centrally located hotel in Lucca) 
• La Bohème (beautiful B&B in central Lucca) 

Thermal towns in Tuscany 

A unique theme for exploring Tuscany comes in the form of visiting its thermal towns. Essentially, they’re home to natural hot springs and have been popular since Roman times for their therapeutic properties. 

When you see the word ‘terme’ in a name place it typically indicates that it’s a thermal town. 

And while in Lucca, it might be interesting to visit a Tuscan thermal town further north called Bagni di Terme. A popular thermal destination, baths like Terme Bagno Bernabò are ideal for health conditions as well as for general relaxation. 

Other popular thermal towns around Tuscany to consider adding to your itinerary include: 

• Saturnia (Maremma, southern Tuscany) 
• Montecatini Terme (between Lucca and Pistoia) 
• Rapolano Terme (central Tuscany) 
• Bagno Vignoni (Val d’Orcia) 

Tuscany Italy map

Day 3

Volterra, San Gimignano, Monteriggioni and Siena 

Day 3 of this 5 days in Tuscany itinerary includes some of the best places to visit in Tuscany by car.  

Consisting of medieval villages and towns where time has stood still, they provide an authentic insight into Tuscan local life. 

It's possible to spend a week in Tuscany without a car and plan everything by using public transport.  

However, given the limited number of days in Tuscany, the travel time using public transport will be considerably longer.  

Volterra 

Depart Lucca to visit the medieval town of Volterra. The distance between the two is around 43.5mi (70km) or approximately 1hr 20mins by car.  

Like Lucca, well-preserved city walls also surround Volterra’s historic center. 

Visitors flock to Volterra to see historical sites like the Palace of the Priory (Palazzo dei Priori) and its cathedral. The palace’s bell tower provides far-reaching views of Volterra and the Tuscan countryside.  

This Priory Palace and cathedral private walking tour is a great way to learn more about each site. 

A town center steeped in its Etruscan past, enter through La Panchina del Sole (arch) to begin your Volterra visit. 

Palace of the Priory (Palazzo dei Priori), Piazza dei Priori, 20 
Volterra Cathedral (Cattedrale di Santa Maria Assunta), Piazza S. Giovanni 

San Gimignano 

A short 40-minute drive from Volterra is the charming hilltop town of San Gimignano. It's best known for its many medieval towers that were built by wealthy families during the 14th and 15th centuries. 

Climb to the top of one of the town’s remaining towers to enjoy unspoiled views of the Tuscany countryside. 

San Gimignano’s most notable attractions consist of its cathedral (Duomo di San Gimignano) and the art museum (Palazzo Comunale Pinacoteca).  

Where to eat in San Gimignano 

Stop for lunch in San Gimignano to try its local dishes in some of the town’s best dining spots. 

• Spizzicheria Le Chicche Toscane (traditional Tuscan restaurant), Via S. Martino, 5 
• La Mandragola (Tuscan restaurant with a view), Via Diacceto, 23 
• Le Vecchie Mura (Tuscan restaurant), Via Piandornella, 15 
• RiccaPizza - San Matteo (pizza), Via S. Matteo, 5 

Monteriggioni 

Start your afternoon of day 3 of 5 days in Tuscany in the gorgeous town of Monteriggioni. 

A town in Tuscany whose impressive walled structure draws you in long before you arrive is a must see. 

At around 35 minutes’ drive or 16.2mi (26km) from San Gimignano, it’s an ideal addition to any Tuscany road trip planner. 

The grand walled exterior structure is slightly misleading as Monteriggioni is quite small once you enter through Porta Franca.  

Its main public square, Piazza Roma, is lined with several bars, restaurants, a church and a popular gelateria. But the best thing to do in Monteriggioni by far is to enjoy the views. 

Walk the pathway along the Monteriggioni walls to savor the splendid views of the walls and town from above. 

Monteriggioni Walls, (Mura di Monteriggioni – Camminamento) 

Siena 

I suggest spending a maximum of 1 hour in Monteriggioni (or less depending on your pace) before departing for Siena. 

With just 13mi (21km) (or 23 minutes’ drive) between the two destinations, there’s still plenty of time to explore Siena.  

Granted, Siena is much larger than Monteriggioni and with more attractions to visit. Saying that you might prefer to skip Monteriggioni altogether to spend more time here. 

At the heart of Siena is the mesmerizing Siena Cathedral (Duomo di Siena). Dating to the 13th century, the cathedral’s best known for its striking facade and its black and white marble design. 

Booking tickets to visit Siena Cathedral is highly recommended. While it doesn’t match the long lines of St. Peter’s Basilica in Vatican City, it still gets busy. 

Two Siena Cathedral entry ticket options include: 

• Cathedral complex pass with audio guide (self-guided tour with access to all parts of the church except the rooftop) 
• Siena Cathedral skip-the-line tickets and 2-hour walking tour (entry to the church and tour of Siena with knowledgeable guide)

Siena’s other piazza 

After exploring Siena’s Cathedral in Piazza del Duomo, head over to Piazza del Campo. A 2-minute walk away, the central square with its characteristic fan shape is home to more of Siena’s top attractions. 

One of the most notable is the public palace (Palazzo Pubblico), which today is used as the city’s town hall. Constructed in the late 13th century, the building reflects a Gothic architectural style. 

For me, its most striking feature is Mangia Tower (Torre del Mangia). Built in the 14th century, the slender tower stands at 334ft (102m) tall. Once regarded as one of the tallest secular towers in medieval Italy, the panoramic views will leave you speechless. 

Where to stay in Siena 

Spend the night in serene Siena by checking into one of these centrally located hotels. 

• Residenza d'Epoca Palazzo Borghesi (upscale accommodation, 2 minutes’ walk to the cathedral) 
• Hotel Palazzetto Rosso (Tuscan-style hotel, 5-minute walk to Piazza del Campo)  
• B&B Il Corso (Tuscan-style townhouse in historic center) 

Day 4

Grosseto, Montemerano, Saturnia, Pitigliano 

Discover the Maremma and more picturesque villages in southern Tuscany on your 5 days in Tuscany itinerary. 

Grosseto is the name of the province as well as the capital city of the Maremma. The journey time from Siena to Grosseto is around 1hr by car or 47mi (75km) and this doesn’t include stops. 

Public transport options are available either by bus or regional train and range from 1hr 15mins to 1hr 50mins. 

Things to do in Grosseto, Tuscany 

Like several of the towns and villages mentioned above, Grosseto is also famous for its well-preserved medieval walls.  

Presented in a hexagonal shape, the walls were built in the 16th century by the Medici family. Today, it’s an attraction that visitors can walk along the ramparts and enjoy views of the city. 

Other things to do in Grosseto is to visit San Lorenzo Cathedral (Cattedrale di San Lorenzo). The 13th century church has a striking facade and is a prime example of Romanesque-Gothic architecture.  

Other sights within close walking distance include Piazza Dante and the Natural History Museum of the Maremma. 

The former is lined with cafes, shops and bars while the latter are exhibitions showcasing the history of the Maremma. 

Natural History Museum of the Maremma (Museo di Storia Naturale della Maremma), Str. Corsini, 5 

Montemerano and Pitigliano 

Discover two incredible Tuscan villages in southern Tuscany by visiting Montemerano and Pitigliano. 

Two fine examples of Tuscan medieval villages, they’re a beautiful addition to any 5 days in Tuscany itinerary. 

Montemerano is a small, though incredibly charming borgo in Tuscany, and one you can comfortably visit in an hour. 

In contrast, there are plenty of things to do in Pitigliano and a visit can last a few hours. 

Lunch in Pitigliano, Tuscany 

While in another beautiful Tuscan borgo, sit down for a leisurely lunch to sample some of the region’s best dishes. 

Two of our favorite places to eat in Pitigliano include: 

• Hosteria del Ceccottino, Piazza S. Gregorio VII, 64; and  
• La Corte del Ceccottino, Via Vignoli, 204B 

Saturnia 

Approximately 30 minutes by car from Pitigliano is the thermal town of Saturnia.  

A trip here usually means a visit to its thermal baths (Terme di Saturnia).  

But bathing outdoors may not be as appealing in winter despite the thermal spring temperature remaining a constant 37.5°C (100°F).  

We visited in September and the weather was still warm and ideal to bathe in the thermal waters. 

Saturnia Thermal baths are located within a spa complex which includes the park, spa and golf resort and golf club. 

Hotels in Pitigliano, Tuscany 

Cozy up in Pitigliano by checking into one of these fine accommodations located in the historic center. 

• KM 0 Dal Centro – townhouse and winery located in the Jewish Ghetto  
• Dimor’à Rooms – modern guesthouse in Piazza della Repubblica 
• Da Titta – rustic rooms, breakfast included  
• B&B Locanda Il Tufo Rosa – cozy B&B with generous-size rooms 

Day 5

Montelpuciano, Arezzo, Greve in Chianti 

The final day of the 5 days in Tuscany itinerary includes smaller Tuscan cities and visiting the Tuscany countryside. 

Montelpuciano 

Wine enthusiasts should need no introduction to Montepulciano.  

The hilltop town is known for producing its namesake wine alongside its picturesque historic center.  

At the center is Piazza Grande, a large square that’s home to the town’s cathedral (Cattedrale di Santa Maria Assunta). Built between the 16th and 17th centuries, inside are several historical works of art and monuments. 

Unsurprisingly, there’s no shortage when it comes to historic wine cellars and wineries in Montepulciano. Some places worth noting down include: 

• De' Ricci Cantine Storiche in Montepulciano, Via Ricci, 13 – tours and wine tastings in an underground space  
• Talosa - Cantina Storica, Via Talosa, 8 – wine tasting in an underground historic setting 
• Cantina Crociani - Crociani Winery, Via del Poliziano, 15 – wine tasting in a pretty winery 

Alternatively, consider joining one of these Tuscany guided tours in Montepulciano. Offering a mouthwatering food and wine experience, these tours are a memorable way to explore the town.  

• Montepulciano wine tasting and cellar tour 
• Tuscan winery tour with wine tasting and meal 

Arezzo  

Heading back up north, it’s approximately a 48-minute drive (33mi/53.4km) to reach the city of Arezzo. 

The Italian city in eastern Tuscany is like an open-air museum of medieval and renaissance architecture.

All roads lead to Piazza Grande, a public square lined with 16th-century stone buildings, cafes and antique shops.  

Nearby is St. Francis Basilica (Basilica of San Francesco). The 13th century church houses historic frescoes by Piero della Francesca and the Crucifix of Santa Croce by Cimabue. 

For a quick, affordable and delicious lunch, consider stopping by Chiantineria. We enjoyed freshly made Tuscan-style sandwiches with a large dose of friendly service and big smiles.  

Chiantineria, Via di Seteria, 6 

Greve in Chianti 

The final destination before driving back to Florence is to visit the Chianti region.  

For this 5 days in Tuscany itinerary I’ve chosen Greve in Chianti, but this can be substituted for other towns. They include: 

• Panzano in Chianti 
• Gaiole in Chianti 
• Radda in Chianti 
• Castellina in Chianti 

Another famous wine region, driving around Chianti is an essential addition to any Tuscany countryside itinerary. 

The town’s origins date to the early Middle Ages. Piazza Matteotti, the principal town square, has a unique triangular shape and is lined with shops, bars and restaurants. 

However, the biggest draw to the Chianti region is to sample its famous wine. And one of the best ways to do this is by joining a Chianti wine tour.  

Some of the top tours worth a closer look include: 

• Chianti Wineries Tour with Food and Wine Tasting 
• Chianti half-day afternoon tour  
• Greve in Chianti wine tasting and winery tour 
• Tour and tasting at an organic winery in the Chianti Classico area 

My guide on the 10 best wine tours from Florence lists more options that might also suit your Tuscany itinerary. 

Return to Florence 

After 5 days exploring the best and most beautiful places in Tuscany, we return to Florence. 

As mentioned at the beginning, feel free to customize this itinerary in Tuscany according to your own preferences. Spend longer exploring the Chianti region or leave out the Tuscan borghi for another visit.  

What are your thoughts on this 5 days in Tuscany itinerary? Does it provide a good mix of different places to visit? Let me know in the comments below. 

Disclosure: This post may contain affiliate links, which means I may receive a commission if you click a link and purchase something that I’ve recommended. Thank you for your support.

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