Ultimate 3-Day Tuscany Itinerary: Best Things to Do & See
Tuscany is a timeless landscape of rolling vineyards, medieval hill towns, and unforgettable flavors that capture the heart of Italy.
Day 1: Florence – Renaissance Art & Local Flavors
Morning
Start your Tuscan adventure at the Galleria degli Uffizi, home to masterpieces by Botticelli, Michelangelo, and Da Vinci, offering a journey through Italy’s artistic golden age.
Galleria degli Uffizi
Stroll to Duomo di Firenze, Florence's iconic cathedral, and climb Brunelleschi’s dome for sweeping city views.
Duomo di Firenze
Afternoon
Enjoy a Tuscan lunch at Trattoria Mario, a local favorite known for its authentic Florentine steak and lively atmosphere.
Trattoria Mario
Wander through the artisan workshops and boutiques of Oltrarno, Florence’s bohemian quarter, where tradition and creativity thrive.
Oltrarno
Evening
As the sun sets, sip aperitivo at La Terrazza Lounge Bar, perched atop Hotel Continentale, with panoramic views over the Arno and Ponte Vecchio.
La Terrazza Lounge Bar
Dine at Osteria Vini e Vecchi Sapori, a tiny, family-run gem offering classic Tuscan recipes in a convivial setting.
Osteria Vini e Vecchi Sapori
Day 2: Siena & Chianti – Medieval Streets and Vineyard Views
Morning
Begin at Piazza del Campo, Siena’s shell-shaped medieval square, famous for the Palio horse race and its vibrant atmosphere.
Piazza del Campo
Visit the magnificent Duomo di Siena, adorned with black-and-white marble and intricate mosaics.
Duomo di Siena
Afternoon
Lunch at Osteria Le Logge, a refined yet cozy spot serving creative takes on traditional Tuscan cuisine just steps from the square.
Osteria Le Logge
Drive into the heart of Chianti and enjoy a guided tasting at Castello di Ama, a storied winery blending world-class reds with contemporary art installations among the vineyards.
Castello di Ama
Evening
Dine at Ristorante La Cantina del Gallo Nero, set in a medieval cellar, and savor local specialties paired with Chianti vintages.
Ristorante La Cantina del Gallo Nero
Conclude your evening with a leisurely passeggiata through Siena’s softly-lit alleys, perhaps with a stop at Enoteca Italiana to sample more regional wines in a unique fortress setting.
Enoteca Italiana
Day 3: Val d’Orcia – UNESCO Landscapes & Hilltop Towns
Morning
Drive south to Montepulciano, a stunning hilltop town famed for Vino Nobile wines and Renaissance palazzi; don’t miss the panoramic views from Piazza Grande.
Montepulciano
Stop by the centuries-old Contucci Cantina for a tasting in evocative underground cellars right off the main square.
Contucci Cantina
Afternoon
Head to Pienza, the “ideal Renaissance town,” and sample world-famous pecorino cheese while wandering its charming lanes and scenic terraces.
Pienza
Enjoy lunch at La Porta in Monticchiello, a tiny stone hamlet, where creative local dishes come with sweeping Val d’Orcia views.
La Porta
Evening
Unwind in Bagno Vignoni, a unique village built around ancient thermal pools, where you can relax in thermal waters or enjoy dinner by the steaming square.
Bagno Vignoni
Finish with a gourmet meal at Osteria del Leone, renowned for its warm hospitality and seasonal, locally sourced Tuscan fare.
Osteria del Leone
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