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Calling all foodies, history enthusiasts, wine-appreciators, and romantics. Are you planning a trip to Tuscany and wondering what the best route would be, or how many days to spend here?
During my Italian honeymoon, we spent five days discovering the dreamy Toscana countryside. I spent months (or was it years?) planning this dream vacation. It had forever been on my bucket list, and answering “yes” to all of the above labels, I simply knew we had to visit the area during our three-week love extravaganza. It quickly became my favorite part of Italy. I continue falling more and more in love with Tuscany each time I return.
Have you also been dying to adventure around this part of the country? Then, take this nifty 5-Day Tuscany trip itinerary and use it well. I’ve outlined the perfect five days, covering iconic cities, towns, and villages in between. In my opinion, you won’t find a better itinerary which combines the best of Tuscany: historic sightseeing, wine excursions, travel times, and the absolute best places to dine.
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Getting around Tuscany
Good to know: While it may seem like there’s a lot of travel in between, the Tuscan region is small and easy to get around. You can always choose just one base, for example, Fiesole or Siena, and move around from there. This is especially easy if you’re hiring a car. We usually choose this option, basing ourselves in Fiesole, and driving each day to all the destinations outlined in this Tuscany trip itinerary.
But that’s because we love to road trip around new places. It all depends on you as the traveler. For this Tuscany trip itinerary, I have outlined it as staying overnight in new cities. But, ultimately, the choice is yours.
The trains are also efficient if you’re on more of a budget. For the major cities, there are train stations (including Fiesole). But to reach the medieval villages, you’ll need to train-ride to the nearest town/city and catch a local bus. That’s why we usually find hiring a car the easiest.
Day 1: Florence/Fiesole
This Tuscany trip itinerary starts things off in none other than Florence, the capital city of the Tuscany region. It’s a convenient base to land in, whether by plane, car, or train, and get organized. I suggest hiring a car in Florence.
Morning
Without a doubt, the first item on your Italian agenda has to be the iconic 18th-century Uffizi Gallery. It would be very silly to travel to this part of the country and miss out on one of the most famous museums in the world — unless it’s not your vibe at all. Before your trip, organise skip-the-line tickets to avoid spending your entire first day waiting impatiently in queues. This will also be your only major art gallery stop during this Tuscany trip itinerary. Take advantage.
After three to four hours here (the hours slip away when you’re warped in a world of art masters), it’s lunch time. Here are some of my top picks of the best restaurants in Florence:
- ORA for exquisite plant-based and vegetarian food, including a 100% vegan charcuterie!
- For a taste of the old neighborhood of Florence, lunch at Alimentari Mescite Di Vini — a favorite Florence restaurant serving traditional Tuscan cuisine.
- or fall into pasta heaven at Trattoria Sostanza, which has been around since 1869.
Then, if you have time, quickly head to the Duomo to admire it’s famous dome, and take a bunch of photos.
Local tip: Another option is to ditch the ristoranti vibes completely and pig out on a whole bunch of the best street food in Florence, from schiacciata (don’t miss All’Antico Vinaio) to coccoli to panino con il lampredotto.
Afternoon
Next, head 15-20 minutes out of the city to Fiesole. Home to farm houses and countryside, spending one night surrounded by nature was blissful. I highly recommend it. You get the main town center, and below this, the farm/agritourism stays. If you have rented a car, it makes exploring very easy.
Explore history dating back eons at the Archeological Museum of Fiesole. This specifically focuses on the Etruscan period. The many ruins are fascinating. The main town square also has a glass-covered wall feature that protects and exhibits some of these ancient ruins. If that doesn’t interest you, book a pasta-making class instead!
Evening
Enjoy the best plate of gnocchi of your life (true story) at Terrazza 45. Not only are the terrace and window views breathtaking (overlooking all of Florence), but the food is chef’s kiss. I always recommend the langoustine gnocchi. It is consistently my best meal in all of Italia. For antipasti/starters, we ordered bruschetta with slithers of anchovy and French butter, and a salad. Out of this world!
Travel tip: If you want to make the most out of Firenze in a day, and are not keen on staying in Fiesole, delve into my 1 Day Florence Itinerary instead for the duration of your first day in Toscana.
Day 2: Chianti
Wake up early to make the most of your day. Either enjoy breakfast (typically pastries and espresso) at your stay. Or, head to one of the cafes in Fiesole’s town, or a cafe in Florence (if you opted to stay overnight in the city).
Morning
You have two options for getting to Chianti. The fastest way is via the highway. However, the road less traveled is often the prettiest. Case in point: the Chianti Way, i.e., the SS222. Naturally, this is the route we always choose, veering along tiny winding roads, passing through little towns, villages, and farms overhead.
Feel free to stop over at any of these along the way. Either for a coffee refuel, a bite to eat, or an olive oil tasting.
Drive through to Greve, where you’ll stay for Night 2 of our Tuscany trip itinerary. We usually stay at the Borgo del Cabreo, which is heaven on earth. You don’t need to sleep at a winery — but this part of Italy is perfect for them.
Afternoon
If arriving in Greve on the weekend, quickly amble through the Weekend Market. I bought a tres chic vintage pinstripe collared shirt for my hubby here. Then, it’s off for some wine tasting! You’ll also do lunch at the winery.
Some excellent options include Azienda Agricola Altiero, Panzanello Winery, Ca di Pesa, and Lamole di Lamole.
Afterward, walk off the food and vino during a two-kilometer walk (30 mins) from Greve to the medieval village of Montefioralle. You can, of course, drive here (5 minutes). Instead of a winery around Greve, choose the Montefioralle Winery, right here in Montefioralle.
Evening
Lap up some downtime back at your accommodation, and get ready for dins. We had a couple of Michelin reservations during our trip, and chose Vitique whilst in Greve. We opted for the eight-course tasting menu!
Day 3: Siena, Val D’Orcia
Today we’re setting off for UNESCO-listed Siena, just short of an hour’s drive from Greve in Chianti. If you can picture the map of Italy, you’ll be traveling south, and Siena is below Greve. This medieval town is one of the most iconic places in Tuscany. There are plenty of guided tours through Siena, too, if you’d rather have someone explaining its dense history to you as you move from A to B.
But half the fun of traveling is discovering things on your own, I always say. You’re also going to spend the night of Day 3 of your Tuscany trip itinerary in Siena.
Morning
Now, as you enter Siena, you arrive into the city via a set of escalators! It’s the trippiest thing, and never before have I ever entered a city this way. You can also park your car at the back of the city.
As you hop off the escalators and enter Siena, stop at the Church of San Francesco for some architectural snaps. From here, the roads are lined with boutiques of all sorts, from local Italian designers to well-known labels. The road leads to the prominent shell-shaped Piazza del Campo. (Unlike most Italian squares, this one is a half circle, and runs downwards.)
Don’t miss the world-famous historical horse race in the Piazza del Campo if you’re visiting on July 2 or August 16 — a tradition since the 6th century!
Afternoon
There are loads of restaurants and cafes around the Piazza for lunch. However, I recommend another one of my favorite restaurants in Italy: Michelin-listed Ristorante Campo Cedro for a fusion of Japanese and Italian.
Grab a gelato and continue trekking the streets. Siena was one of my best destinations for medieval architecture! The walls, buildings, and structures are mesmerizing. Don’t miss the Italian Gothic-style Duomo di Siena. You’ll spot the similarities in design to Florence’s Duomo.
If you’re up for it, drive to the postcard-perfect Val D’Orcia (45 minutes from Siena) for Cypress-tree-lined scenes. Here, Pienza, Montalcino, and Montepulciano await. These towns are renowned for their wine. Or, chill out at your accommodation for a little while before dinner. Osteria Degli Svitati, Ristorante Gallo Nero, and Taverna di San Giuseppe are all great restaurants.
Day 4: Monteriggioni, San Gimignano, Volterra
Day 4 is perhaps my personal favorite. But that’s because today we’re off to San Gimignano — one of the most surreal and unique villages I’ve visited in Italy. I guess this leg of the Tuscany trip itinerary is a dedication to medieval discoveries. Tuscany is famous for it, so you won’t want to pass up the opportunity. As cliche as it sounds, it feels as if you’re traveling back in time.
Morning
Yet before you cross its medieval paths, Monteriggioni is first up from Siena. Completely surrounded by a (preserved) fortified wall, stroll the whole of this protected medieval village in under one hour — tops! Walking the 13th-century ramparts is kind of a must-do. Stop in the main square for an espresso, or, depending on the time, an Aperol. Shop the dozens of artisanal boutiques, with plenty of artsy fartsy pit stops and souvenirs to die over! You can even follow the “Monteriggioni in Arme” medieval weapons route!
Afternoon
Next up: San Gimignano, 40 minutes from Monteriggioni. Where does one even begin? Get your camera ready the second you start walking up the hill (no cars are allowed in the city, so you park just outside). Stepping through the city walls feels like stepping into a history book. And not one single brick has been changed since the 15th century – in fact, it’s illegal to do so!
The main road dazzles with delis, panifici (bakeries), pasticceria, osteria, and boutiques. There’s my favorite leather shop (Le Torri), where I usually shop till I drop, and my favorite deli is Mangius Enogastronomia (right near the town entrance). Don’t leave without a bottle of pomegranate balsamic!
Lunch at Ristorante Boboli (the wild boar ragu and classic Tuscan bread soup are heavenly), then wait in line for a taste of the World’s Gelato Champions — not even kidding — from Gelateria Dondoli. I’ve never eaten such a delicious mango sorbet before. From the gelateria, carry on straight where even more boutiques await, and landmarks like the Duomo of San Gimignano.
Heading back the way you came, slip down Via Piandorella and stop here for breathtaking views over Tuscany, and, of course, an Aperol Spritz in the alley.
Late Afternoon
Spend the night in San Gimignano, or escape to Volterra — the supposed “birthplace of…vampires!” Cue all the Twilight scenes.
Volterra is only 40 minutes from San Gimignano. It’s closer to Pisa, which is the final stop of our Tuscany trip itinerary tomorrow. So, it depends on how you want to split your travel time. San Gimignano to Pisa is one hour and 20 minutes. Some of my favorite sites in Volterra include Piazza dei Priori, Palazzo Incontri Viti, the Roman Theatre, and Fortezza dei Medici.
Day 5: Pisa
For your final day of this Tuscany trip itinerary, Pisa calls with its renowned Leaning Tower. It would be tragic to visit this part of Italy and not be able to tick it off your bucket list. Honestly speaking, Pisa is best savored for a day trip, in my humble opinion.
Apart from the landmark, there’s nothing else too wow to rave home about, hence we saved it for a daytime expedition.
Morning
Wake up nice and early to make the most of Day 5! Either depart from Volterra (a one-hour drive from Pisa) or San Gimignano. Grab a classic Italian breakfast to-go, i.e., shooting down an espresso at the coffee bar, and a Nutella-filled croissant (the brekkie of champions, no?), and off you go!
Start at the Square of Miracles (Piazza del Duomo). Climb 251 steps to the top of the famous Leaning Tower of Pisa. If you’re really stretched for time, I’d suggest doing the guided tour route, saving you time and effort.
Late Morning
Sightseeing done, there are a few choices for how to end your 5-day Tuscany trip itinerary.
Hired a car? See if your car hire has a drop-off point in Pisa if you’re going elsewhere afterwards, for example, up to Cinque Terre, or catching a train to Rome. Or, catch the train back to Firenze. It’s an hour journey or 50 minutes via the fast train. Otherwise, drive back to Florence (1h 25mins drive), and take things from there.
If you’re heading elsewhere in Europe, Pisa Airport is a major budget airline hub and you can actually grab very cheap flights across the continent.
Sitting on Tuscany’s border, Umbria is three hours from Pisa, or two hours from Florence. Or, instead of traveling back down the country, head further north to Milan (part of the Lombardy region). The fastest way to reach Milan from Tuscany is via train.
For any travelers planning a vacation to Italy in winter, don’t forget about snow-capped Aosta in the Italian Alps. All we’re saying is ski-day!
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