Tuscany, Italy

12 Days of Summer in Tuscany – A Journey Through History, Hills, and Heritage

9/23/2025

A Brief Look at Toscana’s Past

Toscana (Tuscany) is one of Italy’s most enchanting regions, known as the cradle of the Renaissance and home to masterpieces of art, architecture, and winemaking. With roots stretching back to the Etruscans and later flourishing under the Roman Empire, the region blossomed during the Middle Ages and Renaissance, shaping Western culture through figures like Dante, Michelangelo, and Galileo. Today, it offers travelers a mix of medieval towns, rolling vineyards, thermal springs, and breathtaking coastlines.

Our Itinerary

We rented a car from Pisa and over 12 days stayed in four hotels and one apartment, giving us flexibility to explore both the famous highlights and hidden gems of Toscana.

Pisa

Our journey began in Pisa, famous for the Leaning Tower in Piazza dei Miracoli, alongside the Duomo and Baptistery. Beyond the landmark, Pisa offers charming riverfront strolls along the Arno and lively piazzas filled with student energy.

Lucca

A short drive away, Lucca enchanted us with its Renaissance-era walls, which can be cycled or walked for panoramic views. Inside, we wandered through narrow streets, admired the Guinigi Tower with its rooftop garden, and soaked up the peaceful atmosphere of Piazza dell’Anfiteatro.

Florence

No trip to Toscana is complete without Florence, the jewel of the Renaissance. We admired the Duomo with Brunelleschi’s dome, crossed the Ponte Vecchio, and visited world-class museums like the Uffizi and Accademia.

San Gimignano

Nicknamed the “Medieval Manhattan,” San Gimignano is famed for its skyline of towers. We enjoyed wandering cobblestone streets, tasting local Vernaccia wine, and indulging in what’s claimed to be the world’s best gelato.

Siena

Siena impressed us with its Piazza del Campo, heart of the city and stage for the Palio horse race. The Siena Cathedral is another highlight, with its black-and-white marble and intricate mosaic floors. The city has a medieval charm that contrasts beautifully with Florence’s Renaissance grandeur.

Montepulciano

Perched high on a hill, Montepulciano is a paradise for wine lovers, especially known for Vino Nobile di Montepulciano. We explored underground wine cellars, admired sweeping views of vineyards, and enjoyed the town’s elegant palazzi.

Val d’Orcia

Driving through the Val d’Orcia was like stepping into a painting—rolling hills, cypress-lined roads, and golden fields. We stopped in postcard-perfect towns like Pienza (famous for pecorino cheese).

Talamone

Our final stop was the coastal village of Talamone, a gateway to the Maremma region. Here we enjoyed sunsets by the sea, fresh seafood, and a slower pace—perfect for ending our adventure.

Tips for travelers

  • Rent a car: Toscana’s beauty lies in its countryside—vineyards, hilltop towns, and scenic roads that are best explored by car.

  • Book in advance: Popular towns like Florence and Siena can be crowded in summer. Reserving hotels and museums ahead of time is essential.

  • Pace yourself: With so much to see, don’t try to rush. Allow time to sit in piazzas, enjoy long meals, and soak in the atmosphere.

  • Wine & food: Each area has its specialty—from Chianti wines to truffle dishes in San Miniato and pecorino in Pienza.


Tuscany is a place where history and nature merge seamlessly—where every town tells a story and every landscape feels like art. Our 12-day journey gave us a taste of Renaissance cities, medieval villages, vineyard-dotted hills, and the Tuscan coast. It’s the kind of trip that lingers in your memory long after you’ve left.