Ultimate Travel Guide to Tuscany – My 4 Day Itinerary

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Tuscany is one of those places that steals your heart the moment you arrive. From sipping wine in the Chianti countryside to wandering the medieval streets of Siena, every corner of this region feels like a postcard. If you only have four days, don’t worry—I’ve got you covered with the perfect itinerary to make the most of your time. Ready for stunning views, incredible food, and unforgettable experiences? Let’s dive in!

Day 1: Siena & San Gimignano – Medieval Marvels

Morning: Discover San Gimignano

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  • Drive to San Gimignano, known for its medieval towers and incredible views.
  • Stay close by or drive there early to get there before the tour buses. I had it all for myself before 8:30. 
  • Climb the Torre Grossa for a panoramic perspective of Tuscany.
  • If you have a drone, flying over the city is allowed and give you the best perspective. 
  • Grab a scoop of Gelateria Dondoli’s award-winning gelato.

Afternoon: Explore Historic Siena

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  • Walk through Piazza del Campo, one of Europe’s most beautiful squares.
  • Visit the Siena Cathedral (Duomo di Siena), a stunning Gothic masterpiece.
  • Enjoy an espresso at Nannini, a famous local café.

Evening: Sunset and Dinner

  • Dine at La Mandragola, known for its delicious Tuscan steak.
  • Stroll the illuminated streets before heading to Val d’Orcia for a countryside stay. 

Day 2: Val d’Orcia – The Most Scenic Part of Tuscany

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Morning: Picturesque Villages and Rolling Hills

  • Visit Pienza, famous for its stunning views and pecorino cheese.
  • Stop by the Chapel of the Madonna di Vitaleta, a must-see photography spot.
  • Drive along the cypress-lined roads of Monticchiello.
  • Stop for a photo at Casa de “Il Gladiatore” made famous in the Gladiator movie.

Afternoon: Relaxation in Thermal Baths

  • Unwind in the natural hot springs of Bagno Vignoni or Saturnia.
  • Enjoy a slow lunch at Osteria La Porta in Monticchiello.

Evening: Farewell to the Countryside

  • Toast to your trip with a glass of Brunello di Montalcino.
  • Watch one last sunset over the Val d’Orcia hills before heading to Florence.
  • Poppi is a very charming village with a castle on the hill that is a great stop in the way to Florence.
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Day 3: Florence – The Heart of the Renaissance

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Morning: Discover the Best of Florence

  • Start your day in Piazza del Duomo—climb Brunelleschi’s Dome for breathtaking views.
  • Or Start your day early with a magical sunrise at Piazzale Michelangelo. The direction of the sunrise and solitude make this an even better option than sunset, if you can get up early enough.   
  • Explore the Uffizi Gallery, home to Michelangelo, Botticelli, and other Renaissance masters.
  • Walk across the Ponte Vecchio, the city’s iconic medieval bridge.

Afternoon: Cultural and Culinary Delights

  • Visit the Pitti Palace and wander through the Boboli Gardens.
  • Grab lunch at Mercato Centrale, a paradise for food lovers.
  • Explore the Oltrarno District, famous for artisan shops and relaxed vibes.
  • If you are in Florence in April do not miss the Giardino Bardini where the Wisteria bloom is magical. I went to Florence mostly to see this. 

Evening: Sunset at Piazzale Michelangelo

  • Hike up to Piazzale Michelangelo for the best sunset view over Florence.
  • Enjoy a Tuscan dinner at Osteria Vini e Vecchi Sapori.

Day 4: Chianti Wine Region – A Taste of Tuscany

Morning: Wine Tasting and Vineyards

  • Drive the scenic Chianti wine route, stopping for photos along the way.
  • Visit Castello di Verrazzano or Antinori nel Chianti Classico for an unforgettable wine tasting experience.
  • Wander through Greve in Chianti, a charming Tuscan village.

Afternoon: Tuscan Countryside Charm

  • Enjoy a leisurely lunch at a vineyard, savoring fresh pasta and local wine.
  • Explore Monteriggioni, a perfectly preserved medieval fortress.

Evening: Stay in a Tuscan Villa

  • Book a stay in a countryside agriturismo for an authentic experience.
  • Sip on local wines as the sun sets over the rolling hills.

FAQs About Traveling in Tuscany

1. What is the best time to visit Tuscany?

Spring (April-June) and fall (September-October) offer the best weather and fewer crowds.

2. Do I need a car to explore Tuscany?

Yes! Renting a car allows you to explore small villages and scenic countryside roads at your own pace.

3. What is Tuscany famous for?

Tuscany is known for its wine, historic cities, rolling hills, and Renaissance art.

4. Are the towns in Tuscany walkable?

Most Tuscan towns are compact and best explored on foot, but some have steep hills, so wear comfy shoes! And take a rental car there.

5. How much should I budget for 4 days in Tuscany?

A mid-range budget is €150-€200 per day, covering accommodations, meals, and attractions.

Additional Resources for Planning Your Tuscany Trip

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