Ultimate Travel Guide to Tuscany – My 4 Day Itinerary

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.

Exploring Tuscany in four days offers the perfect blend of culture, history, and breathtaking landscapes. This itinerary takes you through medieval towns, rolling hills, and culinary delights that will immerse you in the charm of the region.

Day 1: Siena & San Gimignano – Medieval Marvels

Start your journey by visiting the iconic towns of Siena and San Gimignano. San Gimignano, known for its well-preserved towers, offers a glimpse into medieval architecture and stunning panoramic views of the Tuscan countryside. Siena, with its impressive Piazza del Campo and Gothic cathedral, immerses you in rich history and art. End the day with a traditional Tuscan dinner and soak in the local atmosphere.

Morning: Discover San Gimignano

Guide to visit San Gimignano

• 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

Guide to visiting Siena

• 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

The Val d’Orcia region embodies the essence of the Tuscan countryside, with its rolling hills, cypress-lined roads, and charming villages. Explore towns like Pienza, famous for its pecorino cheese, and Montepulciano, renowned for its vineyards. This day offers countless photo opportunities and the chance to indulge in the region’s culinary specialties.

10 Best Instagram Spots in Val D’Orcia.

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.

Day 3: Florence – The Heart of the Renaissance

Florence, the capital of Tuscany, is a must-visit for art and architecture lovers. Discover iconic landmarks such as the Cathedral of Santa Maria del Fiore, the Uffizi Gallery, and Ponte Vecchio. The city also offers excellent shopping opportunities and a lively street atmosphere. End your day with dinner at one of Florence’s many authentic restaurants.

10 Best Instagram Spots in Florence for great photos.

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

Wrap up your Tuscan adventure in the Chianti region, known for its vineyards and stunning landscapes. Take part in wine tastings at local wineries and learn about the production of the world-famous Chianti wine. Enjoy the peaceful atmosphere and reflect on the unforgettable experiences of your four days in 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

• Official Tuscany Tourism Website
• Best Tuscan Wineries to Visit
• How to Get Around Tuscany
• Weather Forecast for Tuscany
• Best Restaurants in Tuscany