Curator’s statement
To someone from Corsica, Tuscany feels like a soulful sister — familiar yet endlessly enchanting. I road-tripped through this region with my best friend last year, and it was pure magic: medieval villages, rolling hills, long lunches and unforgettable moments. This itinerary is all about maximizing your time and soaking in the full Tuscan experience without rushing it. Think of it as your 10-day passport to la dolce vita, curated for travelers who crave depth, beauty and a little indulgence.
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Days 1–2: Pisa – Gateway to Tuscany
Arriving in Pisa, you can feel the excitement of the journey ahead. After landing at Pisa International Airport, pick up your rental car — something sturdy and capable of handling off-road terrain if you plan to explore the countryside, or, if you’re sticking mostly to city and hilltop towns, opt for a compact car for easier maneuvering and parking.
Where to stay
Bagni di Pisa Palace & Thermal Spa (5-star) – A luxurious spa retreat in an 18th-century palace, perfect for unwinding after your flight.
Hotel Bologna (4-star) – Elegant boutique hotel with a central location, making it easy to explore the city.
Rinascimento Bed & Breakfast (4-star) – Stylish and intimate stay in the heart of Pisa.
Must-sees & dos
Climb the Leaning Tower of Pisa (book tickets in advance to skip the lines!).
Stroll through Piazza dei Miracoli, where history whispers through its marble structures.
Wander through Borgo Stretto, a charming street lined with boutique shops and cafés — grab an espresso and soak in the Italian energy.
Where to eat
Osteria dei Cavalieri – Traditional Tuscan dishes with a local feel.
La Scaletta – Cozy trattoria with fantastic seafood.
Ristorante alle Bandierine – Homemade pasta heaven, perfect for your first authentic Italian meal.
Days 2-4: San Gimignano – The City of Towers
Leaving Pisa behind, you’ll drive just over an hour through rolling hills and cypress-lined roads to reach San Gimignano, a medieval gem that feels like stepping back in time.
Where to stay
Hotel La Collegiata (4-star) – A former monastery turned luxury retreat, ideal for relaxation.
Relais Santa Chiara (4-star) – Stunning countryside views and a tranquil atmosphere.
Villasanpaolo (4-star) – Spa hotel with panoramic Tuscan vistas, perfect for unwinding.
Must-sees & dos
Climb Torre Grossa for breathtaking panoramic views over Tuscany.
Visit San Gimignano 1300 Museum, where the town’s history comes to life through intricate models.
Enjoy a Vernaccia wine tasting at a local vineyard — this crisp white wine is a regional specialty.
Where to eat
Cum Quibus – One of Tuscany’s best fine-dining experiences, perfect for a romantic evening.
Ristorante Perucà – Intimate spot known for its decadent truffle dishes.
Gelateria Dondoli – Grab a scoop of award-winning gelato before a sunset stroll.
Days 4-6: Siena – The Heart of Tuscany
Just a 45-minute drive away, Siena welcomes you with its stunning Gothic architecture and lively piazzas.
Where to stay
Grand Hotel Continental (5-star) – The only five-star luxury hotel in the city, housed in a 17th-century palace.
Palazzo Ravizza (4-star) – A charming historic residence with a peaceful garden.
Hotel Athena (4-star) – Modern comforts with an unbeatable location near the city walls.
Must-sees & dos
Visit the breathtaking Siena Cathedral, a masterpiece of Italian Gothic architecture.
Wander through Piazza del Campo, the heart of Siena and home to the famous Palio horse race.
Discover Siena’s historic fountains, like Fonte Gaia and Fonte Branda, each with their own stories carved in stone.
Check out the Museo Civico, where stunning frescoes tell the city’s medieval story.
Where to eat
Osteria da Divo – Elegant dining in a unique, cave-like setting with inventive Tuscan cuisine. Perfect for a special night out.
La Taverna di San Giuseppe – Cozy ambiance and authentic Tuscan fare.
Antica Trattoria Papei – A great spot for bistecca alla Fiorentina, Tuscany’s legendary steak.
Gino Cacino di Angelo – A hidden treasure for what might be the best sandwich of your life, perfectly paired with a glass of local wine and the warmest welcome in town.
Days 6-8: Montepulciano – The Wine Lover’s Dream
An hour’s drive south brings you to Montepulciano, where rolling vineyards and Renaissance architecture set the scene for indulgence.
Where to stay
Etruria Resort & Natural Spa (4-star) – A wellness-focused retreat with thermal baths.
Villa Cicolina (4-star) – A boutique stay in a former noble residence.
Palazzo Carletti (4-star) – Historic luxury with frescoed ceilings and spacious rooms.
Must-sees & dos
Visit Cantina Contucci for an unforgettable Vino Nobile wine tasting.
Stroll along Corso, the town’s main street, lined with artisan shops and enotecas.
Check out the San Biagio Church, an architectural masterpiece set against the countryside.
Where to eat
Osteria Acquacheta – The best place for a massive Fiorentina steak.
Ristorante La Grotta – Refined dining next to San Biagio.
Le Logge del Vignola – Gourmet dishes in a romantic setting.
Days 8-10: Val d’Orcia – The Quintessential Tuscan Landscape
Just 30 minutes away, Val d’Orcia’s rolling hills and dreamy villages are pure magic. This is Tuscany at its most picturesque.
Where to stay
Rosewood Castiglion del Bosco (5-star) – One of Tuscany’s most luxurious countryside resorts.
Adler Spa Resort Thermae (5-star) – A wellness retreat with natural hot springs.
La Bandita Townhouse (4-star) – Chic, boutique stay in the heart of Pienza.
Must-sees & dos
Wander through Pienza, the "ideal Renaissance town" known for its charming streets and pecorino cheese.
Drive the scenic Cypress Avenue in San Quirico d’Orcia, one of Tuscany’s most photographed roads.
Stroll through the beautifully preserved town of San Quirico d’Orcia — don’t miss the Horti Leonini gardens and the Collegiata Church with its unique Romanesque architecture.
Relax in the natural Bagno Vignoni hot springs, a true hidden gem just a few minutes away.
Where to eat
Osteria La Porta (Monticchiello) – Fantastic countryside views and incredible wine selection.
Trattoria Toscana (La Foce) – Farm-to-table Tuscan cuisine at its best.
Ristorante Daria (Monticchiello) – Homemade pastas and traditional Tuscan specialties.
On day 10, it’s time to head back to Pisa (a scenic two-hour drive) for your flight home — or, if time allows, extend your adventure along the Tuscan coast!
Need to know
Driving in Tuscany means freedom, but also tight roads and lots of roundabouts. If you’re exploring mainly cities and hilltop towns, opt for a compact car as it makes narrow streets and parking much easier. For countryside adventures or unpaved roads, choose something sturdier like an SUV for extra comfort and traction. Always keep some euros on hand for parking meters and make restaurant reservations in advance, especially in smaller villages where spots fill up quickly. Pack layers, as, even in summer, evenings can get cool in the hills. And lastly, don’t overpack your days. Tuscany is best enjoyed slowly, with time to wander, sip wine and follow your curiosity. That is where the magic happens.
Travel Advisor
Alexa Mollicchi Casanova
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For more inspiration and insider recommendations, visit our Tuscany page.