Tuscany holidays – Itinerary for 7 days of architecture and love

Florence, Image by Alex Berger via Flickr

Tuscany is the most famous region of Italy; it’s even better known than the one which contains the eternal city of Rome. This region of Italy is renowned for its incredible landscape, unique wines, and ageless arts. There are numerous ways to approach visiting this land, and planning your itinerary for your perfect Tuscany holidays can be difficult. Choosing what to prioritize and what to put aside when planning an itinerary can be heartbreaking. That’s why I’ve created this 7-day itinerary for exploring Toscana.

Length: 7 days
Start and End Point: Starts in Florence and ends in Siena
Cities: Florence, Siena, San Gimignano, Volterra, Montepulciano
Sights: Lots of Medieval towns
With or without a car: This route is perfectly doable either way, but everyone knows the Tuscan roads are undoubtedly best visited by car.
Best time: The months bordering Italy’s shoulder season (April, May, June, September, and October)
Best suited for: Arts and architecture enthusiasts.

(For those wondering, Rome is in the Lazio region.)

Day 1 – Florence

Florence is the ultimate destination for art lovers. During your two days here you will have the opportunity to visit several splendid churches and museums. On the other hand, given that you do not have all the time in the world, here is a quick overview of Florence’s must-sees.

Today, visit the city’s beloved monument, the most significant landmark of Tuscany: the Cattedrale di Santa Maria del Fiore (You’ll sometimes see it called the Duomo, as it simply means an Italian cathedral.) There is much to see and do in this church besides admiring its facade. After having appreciated Santa Maria del Fiore’s superb interior decoration, climb inside Brunelleschi’s Dome. Indeed, the spiral staircase is steep, but the 360-degree panorama of the city at the end is definitely worth it. If you want to admire the dome from the front row, opt instead to ascent the willowy campanile (bell tower) of the church. The Grande Museo del Duomo and the Baptistry are praiseworthy and demand a visit. Beware that certain parts of the Duomo require a ticket, such as the ascension of the dome. Buy tickets here. After that, pay a visit to Ponte Vecchio, the oldest bridge in Florence before WW2 and, at the same time, the only one that survived the war’s destruction.

If you’ve always dreamed of seeing a 17ft tall statue, here’s your chance! Continue your day at the Galleria dell’Accademia. Don’t be put off by the line there! Just know better and buy your tickets in advance; the line to get in for ticket holders is much shorter than for those who have to purchase tickets.

On a separate note, try the Pappa al Pomodoro if you ever happen to see it on a menu at the restaurant. This Tuscan bread soup will fill your stomach and heart with the best components of every Italian dish: tomatoes, basil, and garlic.

Uffizi, Image by KotomiCreations via Flickr
Cattedrale di Santa Maria del Fiore, Image by leeherrera_ca via Flickr

Day 2 – Florence

What’s on the menu today? More museums and architectural masterpieces, of course! Start with the Uffizi Gallery. You will find here the works of famous artists da Vinci and Michelangelo. (But also of Botticelli, Caravaggio, Giotto, Raphael and Titian.) You can now understand how this Medici palazzo is considered one of the finest art museums on earth.

Without a reservation, you could wait in line for several hours to get a ticket. I therefore strongly advise you to book in advance! Visiting the museum typically takes around 3 hours. For those who don’t want to see everything this gallery has to offer, know the best rooms are #2, #3, and #10 to 14. Pro Tip: Use the Rick Steve’s app (Rick Steves Audio Europe ™) instead of a paid guided tour. It might sound crazy, but I promise it’s all you need.

Then head to the Palazzo Vecchio, once inhabited by the Medici family. Just be aware that some rooms are only accessible through specialized tours. If you want to visit the tower of Palazzo Vecchio, make sure you come on a sunny day, since it closes in the event of rain.

Before leaving Florence, other great places to consider visiting are the Museo Nazionale del Bargello (an art museum), the Basilica di Santa Croce (which contains the tombs of Michelangelo and Galileo), and the Basilica of Santa Maria Novella.


Piazza della Repubblica, Image by Billy Wilson via Flickr
Ponte Vecchio
Ponte Vecchio, Image by Neil via Flickr

What is there to do in Florence besides churches and museums?

If you have “too much time on your hands” during your stay in Florence, there are plenty of activities for tastes: Head to Mercato Centrale to get a glimpse of the local flavor. The best viewpoints for sweeping views of Florence are at Piazzale Michelangelo and the Basilica di San Miniato al Monte right alongside. Otherwise, indulge in the local sport: the Passeggiata

Day 3 – Volterra

It’s time to leave the city of Florence and its art to go to Siena. However, we will combine this with a stop in Volterra. Volterra’s centerpiece is arguably the Palazzo dei Priori. It has the feel and look of the famous Palazzo Vecchio in Florence minus the heavy traffic.

For true history buffs, the Museo Etrusco Guarnacc is one of the best Etruscan museums in the country. Expect a different experience than the Uffizi Galleria (it’s naturally not as well funded), but it has an extensive collection of artifacts from the ancient people of Etruria. Moreover, for those whose thirst for art has not been satisfied during the first 2 days of the trip, you can go and admire the art collection of Volterra at the Pinacoteca e Museo Civico.

Once you’ve finished exploring the winding streets of Volterra, pack your bags and head to your accommodation in Siena, your base for the rest of the trip.

But if you want to spend more time in Volterra, check out this city guide for extra things to do.

Drive to Volterra from Florence: 89 km, 1 hour 15 min.
Public transport: However you go about it, getting from Florence to Volterra by public transport will take around 2 hours and require a transfer.
Luggage Storage: You might have a hard time finding luggage storage in Volterra. However, if you don’t have a car, consider emailing the tourist office or see with a museum clerk to see if they can hold your luggage.
Drive to Siena from Volterra: 55 km, 50 min.
Public transport: 1 hour 45 min (Operated by Autolinee Toscane with a transfer in Colle Val D’Elsa)

Day 4 – Siena

Known for its magical medieval atmosphere, Siena is a wonderful base for exploring Southern Tuscany. Of course, Florence has more museums and attractions, but it remains an actual city with traffic and smog. Siena will allow you to unwind for the rest of your trip.

Start your city tour by going to Piazza del Campo. In the middle of this vast Piazza, it is easy to imagine the gatherings that could have happened here. You can then enter the Palazzo Pubblico and climb a bell tower for the umpteenth time: the Torre del Mangia. Take the time to explore the streets. If you’re lucky enough to encounter rain during your days here, notice the sandalwood smells that come out after the rain.

If you want to take a cooking class in Tuscany, the most famous is undoubtedly given at the Scuola di Cucina di Lella. If you’re looking for local flavor, the Acciughe sotto pesto hails from Siena and can be found all over town in restaurants, bars, and supermarkets.

If you come to Siena during the summer months, check the dates the Palio is held, as you might want to arrange your trip around those dates.

Palazzo dei Priori, Image by Ben Mason via Flickr
Volterra, Image by Christa Lohman via Flickr
Siena and the Torre del Mangia, Image by David Bramhall via Flickr
Palazzo Salimbeni, Image by Ray in Manila via Flickr

Day 5 – Montepulciano

For the 5th day of your journey, I suggest you temporarily leave the timeless Siena and go to a small town called Montepulciano. Perched on a cliff, the city is mainly known for its Vino Nobile.

Start exploring from the center of the city, at the Piazza Grande. Go up to the Palazzo Comunale and visit its terrace. Then wander through Montepulciano by walking down the village’s main street, Il Corso.

Many of the city’s best institutions are, of course, its wine estates and cantinas. But these are, of course, not the only things to see. The city museum, the Pinacoteca Crociani, has a rather fascinating history: in the 2010s, the actual author of one of its paintings: the famous Caravaggio. It should be noted, however, that most of his paintings will be by authors unknown to people not well-versed in medieval Italian artists.

Drive from Siena to Montepulciano: 65 km, 55 min. one-way
Bus: 1,5 hour, 2 daily (Operated by Tiemme)
Tour: Tuscan Escapes offers a Pienza and Montepulciano Tour for 160 EUR/person. This Siena-based tour company has stellar reviews. Their Website

I should quickly mention that Montepulciano was the filming location for the scenes set in Volterra in the Twilight series 2nd installment. It may be of interest to you.

Day 6 – San Gimignano

Leave Siena once again, and travel to San Gimignano, a village that remains seemingly untouched by time. The city once had more than 70 towers to signify its grandeur, a fun fact that will make many compare it to an old-world Manhattan.

First, go to the Palazzo Comunale. You can climb up the Torre Grossa to observe the town from its highest tower and visit the Museo Civico afterward. Then head to the Collegiata di Santa Maria Assunta, an 11th-century basilica whose beauty is recognized inside and out.

The city still has several museums: the Museo del Vino Vernaccia, the Museo della Tortura and the Galeria Continua (a renowned contemporary art museum)

Why wasn’t it a day trip from Florence? From Florence, you’d have to take 1 train and 1 bus to get to San Gimignano, versus only one bus from Siena.

Drive to San Gimignano from Siena: 43 km, 40 min one-way.
Bus:  1 hour (Operated by Autolinee Toscane), 10 daily, but none on Sundays

Montepulciano, Image by Timothy Brown via Flickr
Montepulciano, Image by Nora Kuby via Flickr
San Gimignano, Image by Chipps via Flickr
San Gimignano, Image by Avital Pinnick via Flickr

Day 7 – Siena

On your last day of travel in Tuscany, enjoy the tranquility of Siena one last time before thinking of returning home.

I have a question for you. Could you take a trip to Tuscany without a single stop at a vineyard? Meet at the Azienda Agricola La Lastra. The vineyard is 6 km outside Siena and offers an Educational Wine Tasting Tour that you will remember.

If you have yet to visit them, the Duomo di Siena and the Biblioteca Piccolomini are repeatedly ranked among the city’s highlights. The Pinacoteca Nazionale is similarly an excellent place to relax at the end of this week of travel before returning to Florence to take your flight home.

Giotto’s Campanile in Florence, Image by Gigi via Flickr

In summary:

Day 1FlorenceFlorenceFlorence
Day 2FlorenceFlorenceFlorence
Day 3VolteraFlorenceSiena
Day 4SienaSienaSiena
Day 5MontepulcianoSienaSiena
Day 6San Gimignano SienaSiena
Day 7SienaSienaSiena