Planning a short trip to Tuscany? Whether you’re dreaming of cypress-lined roads, honey-coloured villages, or long lunches with a view, this 4-day Tuscany itinerary brings together the region’s most charming sights and experiences. From hilltop towns to wine tasting in Chianti, here’s how to make the most of your days in Tuscany.

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4-Day Tuscany Itinerary

This itinerary is perfect for a Tuscany road trip and works well as a standalone getaway or as part of a longer trip to Italy. You can fly into Florence or Pisa, rent a car, and explore at your own pace. We recommend staying in the Chianti region for all 3 nights to keep things relaxed. We stayed at La Valletta B&B in Panzano, which was a perfect base for exploring the region.

Day 1: San Gimignano

Start your trip in San Gimignano, one of Tuscany’s best-preserved medieval towns, famous for its skyline of ancient towers, hence the nickname of “Medieval Manhattan”. This charming hilltop town offers breathtaking views, rich history, and delightful local Italian flavours. You’ll find narrow alleys, stone towers, and sweeping views over the surrounding countryside. Yes, it’s touristy, but still incredibly atmospheric, especially in the early morning or late afternoon.

On your visit, make sure to climb the Torre Grossa for panoramic views of the Tuscan countryside. Relax in Parco della Rocca, a peaceful park with stunning views and ruins of the old fortress. The weekly market takes place on Thursday mornings at Piazza del Duomo and Piazza della Cisterna, perfect for browsing local cheeses, crafts, and souvenirs. If you’re visiting in June, keep an eye out for the Ferie delle Messi, a medieval festival with parades, flag throwers, and costumes. So atmospheric!

Visit early in the morning or late in the afternoon to avoid the crowds and enjoy a more peaceful experience

Don’t skip the award-winning gelato from Gelateria Dondoli. It’s a bit of a tourist magnet, but worth the hype

Craving something savoury? Try a delicious schiacciata sandwich next door at Vinaino Fiorenza

Day 2: Montefioralle & Wine Tasting in Chianti

This is the day Tuscany dreams are made of: winding roads, sleepy villages, and golden light over vineyards.

Montefioralle

This tiny hilltop village is known for its perfectly preserved medieval charm. Its small size and peaceful atmosphere makes it an easy but memorable stop. Wandering around this hidden gem feels like stepping into a peaceful postcard, with its old stone houses and serene atmosphere.

Because of its small size, you can easily combine Montefioralle with a:

Lunch at I’Desìo Ristorante in the village, or take a small trip to nearby Panzano and enjoy lunch or dinner with the prettiest views over the Tuscan hills at Ristorante Oltre Il Giardino

Wine tasting at a nearby vineyard. We enjoyed one at Le Cinciole in Panzano (highly recommend!), around a 20-minute drive from Montefioralle

Wine Tasting

The Chianti region is renowned for its wine production. Take a day trip to explore the vineyards, visit wineries for tastings, and enjoy the stunning scenery of rolling hills and vineyards. Don’t miss trying the famous Chianti Classico wine, which pairs perfectly with local dishes.

We had an incredible experience at Le Cinciole. The tour, wines, and warm hospitality made it unforgettable.

Day 3: Pienza & Montepulciano

Get ready for one of the most beautiful drives of your trip! The Val d’Orcia is postcard-perfect Tuscany, with curvy roads, wheat fields, and lone cypress trees.

Pienza

It’s safe to say that Pienza is one of our favourite villages in Tuscany. The architectural beauty combined with the breathtaking views of Val d’Orcia will make you fall in love instantly. Admire the Renaissance architecture in the center of the village, and wander around its beautiful streets and square. Via dell’Amore feels like stepping into a painting, with breathtaking views over the rolling hills and cypress trees. Be sure to try the Pecorino cheese, a local specialty Pienza is known for.

To make the most out of your day, make sure to explore more nearby gems such as Montepulciano as they’re only 20 minutes apart, and the iconic cypress-lined road leading to Farmhouse Poggio Covili, or Crete Senesi vista.

Montepulciano

A paradise for wine lovers! Montepulciano, your second stop, is a hilltop town famous for its Vino Nobile wines and has some of the best wine cellars in the region. We definitely recommend doing a taste tour at one of these cellars!

Enjoy a delicious schiacciata sandwich for lunch at La Schiaccia dell’Opio. It’s a great spot to refuel before exploring more of the region.

Day 4: Siena or Florence

Depending on your route back, you can finish your Tuscany itinerary in Siena or Florence. If you’re into medieval charm and less crowded streets, opt for Siena. If you’d rather end your trip with Renaissance art and vibrant city life, choose Florence.

Siena

Known for its Gothic Cathedral (Duomo di Siena) and the Palio on Piazza del Campo, a historic horse race held twice a year, Siena is a must-see on your Tuscany itinerary. Explore the winding streets, visit the impressive Siena Cathedral, and enjoy a meal at one of the local trattorias, where you can enjoy traditional Tuscan cuisine. Climb the Torre del Mangia for epic city views.

Get your Duomo di Siena tickets in advance

Florence

Florence, the capital of Tuscany, is a must-visit for any traveler. The city is home to some of the world’s most famous art and architecture, including the iconic Cattedrale di Santa Maria del Fiore (Duomo), Uffizi Gallery, and Ponte Vecchio.

Make sure to book your Duomo ticket in advance

Take your time wandering through the historic streets, head to Arno River to cross Florence’s oldest bridge, the Ponte Vecchio, enjoying gelato from local shops, and soaking in the Renaissance atmosphere.

Grab an affogato at Vivoli, one of the oldest gelato shops in the city

If you have more time, consider spending an extra night in either city to explore at a slower pace.

Tuscany Itinerary Map

Make sure to save this map to explore the highlights of Tuscany more easily!

How to Visit Tuscany

The most convenient airports for this itinerary are Florence (FLR) and Pisa (PSA). Both have international connections and car rental options. Florence is more central, but Pisa often has cheaper flights.

Tuscany’s rolling hills, medieval villages, and vineyard-covered landscapes are best explored at your own pace. While there are public transport options, the best way to see the region’s hidden corners is by car.

From the airport, you can pick up a rental car and start your road trip straight away. Alternatively, you can spend a night in Florence or Pisa and rent a car the next morning to avoid city traffic.

By Car

To follow this itinerary, we recommend renting a car. It gives you the freedom to explore at your own pace and reach countryside spots that trains don’t cover. You’ll find plenty of car rental options at Florence and Pisa Airports, as well as in the main cities.

Do keep in mind:

• Many historic centres have ZTL zones (Zona a Traffico Limitato), which are restricted traffic areas. Driving into these without a permit can result in fines. Better to save that money for pasta and wine!
• Parking is often just outside the town walls and requires a short walk to the centre, so wear comfy shoes!
• Country roads can be narrow and winding, perfect for scenic drives, but take it slow.
• Distances between villages vary,

Tip: A smaller car is often easier for navigating narrow village streets and tight parking spots.

By Public Transport

If you’re not keen on driving, you could visit some towns by train, but it will limit your flexibility. Tuscany’s real beauty is in its smaller villages and scenic backroads, which aren’t always accessible by public transport.

Purchase your train tickets in advance

By Tour

If you are basing yourself in one city and want to explore the surrounding countryside without a car, the best option is to take day tours. Many tours leave from the bigger cities like Florence, Siena, and Pisa and take you out into the Tuscan countryside to explore the wineries and hilltop towns.

When to Visit

Tuscany is beautiful all year round, but the best time to visit is during spring (April to June) and autumn (September to early November). These shoulder seasons offer the perfect balance: mild temperatures, golden light, fewer crowds, and dreamy landscapes.

• Spring brings blooming wildflowers, fresh green hills, and warm days that are perfect for exploring towns and vineyards without the summer heat.
• Summer can be hot and crowded, especially in major towns. While the countryside remains lovely, it’s good to start your days early and take a long siesta or wine tasting break in the afternoon.
• Autumn is harvest season, when the vineyards are full of colour and you can experience wine festivals and seasonal produce like truffles and chestnuts.
• Winter is quiet and atmospheric, especially in towns like Florence or Siena. While some agriturismos close for the season, you’ll find great deals and enjoy cultural sights without the crowds.

Where to stay on This Tuscany Itinerary

Here are a few suggestions depending on your route:

Tuscany offers a variety of accommodation options, from luxury hotels to charming agriturismos (farm stays). For a unique experience, staying in an agriturismo is definitely recommended.

We stayed in La Valleta Bed & Breakfast in Panzano in Chianti which was absolutely perfect. Just a 20-minute walk from Panzano, with breathtaking views of the Tuscan hills all around. The breakfast, pool, wine, and, most importantly, the views were exceptional.