Planning five days in Tuscany Italy can feel like a challenge—where do you even begin in a region so packed with beauty? On my two visits, I faced the same dilemma: trying to visit the very best hilltop towns without rushing through the serene charm Tuscany is known for.

In this article, I’ll share a realistic and balanced itinerary that blends world-famous highlights with lesser-known gems.

From rolling vineyards in Chianti to the medieval streets of Siena and the picture-perfect Val d’Orcia countryside, this plan will help you enjoy Tuscany at its best.

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Tuscany 5 Day Itinerary

Day 1: Florence – The Renaissance Hub

river with bridge with buildings in florence tuscany

I recommend starting in Florence. Skip Florence’s expensive accommodations, shorten your travel time to countryside destinations and spend only one night here.

Morning: Start early at the Duomo and climb its 463 steps to take in the sweeping views of Florence. Walk through the historic Old Town visiting its piazzas and narrow streets.

Afternoon: Focus on art in the afternoon and head to the Uffizi Gallery, where Botticelli’s The Birth of Venus will leave you speechless or the Accademia to see Michelangelo’s iconic David. Opt for a guided tour to save time and gain deeper insights into the artwork.

Evening: End the day at Piazzale Michelangelo, a popular spot for panoramic views of Florence, where you can watch the sun dip behind the city’s skyline, casting a golden glow over the Tuscan hills.

For your reference:

⚫Are you still undecided about visiting Florence? Here are the reasons why you should visit Florence.
⚫Want to know how to spend a day in Florence? Use this 1-day itinerary as your guide.

Day 2: Chianti Wine Region and Hilltop Villages

cobblestone square with view to door and planters in tuscany
building with doorway with ivy growing on wall in tuscany

I recommend renting a car in Florence for the remainder of your trip. Stay two nights in Siena.

  • Morning: Spend about an hour exploring Radda, a quiet sleepy village, then stop in Poggibonsi to visit its impressive medieval fortress and take in views of the surrounding countryside.
  • Afternoon: Take a guided vineyard tour in Chianti, where you will learn about winemaking and taste a variety of local wines paired with regional bites. I recommend the stunning Albola Castle near Radda.
  • Evening: Late afternoon visit Monteriggioni, a walled town that feels untouched by time, and enjoy dinner at a cozy trattoria while watching the sunset over the Tuscan hills.

For your reference:

⚫Want to know a bit more about Radda? Use this guide on why to visit and what to expect to see there.

Day 3 Siena – The Medieval City

tall tower attached to city hall building in siena tuscany
  • Morning: Start in Piazza del Campo and take in its unique shell shape before climbing the Torre del Mangia for beautiful city views.
  • Afternoon: Visit Siena’s stunning cathedral, with its intricate striped marble and mosaic floors.
  • Evening: Enjoy a simple but delicious Tuscan dinner in a charming restaurant and end your evening with a walk through the city’s dark streets for that extra ambience.

For your reference:

⚫Want to know how to spend one day in Siena? Check out my 1-day Siena itinerary.

Day 4: Val d’Orcia – The Quintessential Tuscany

tuscan countryside with rolling hills and trees

Next, I recommend you leave Siena and head to the Tuscan countryside. For this part of your Tuscany road trip, I recommend you stay in Montepulciano so that you will be within one hour of some of the best hilltop towns.

  • Morning: Start the day in Pienza, a UNESCO World Heritage Site, wandering its charming streets, sampling pecorino cheese at local shops, and enjoying panoramic views of the Val d’Orcia countryside.
  • Afternoon: Head to Montalcino, where wine enthusiasts can tour historic cellars and sample world-renowned Brunello wines, pairing them with light bites at a family-owned vineyard.
  • Evening: End the day in Montepulciano, savouring a leisurely dinner at a local trattoria, paired with a glass of Vino Nobile while overlooking the twinkling lights of the town.

For your reference:

⚫Want to know if Pienza is worth visiting? Find out the reasons to visit.
⚫How to spend a day in Pienza with this list of the best things to see and do.
⚫Want to know how to spend your time in Val d’Oricia? Check out my 3-day itinerary chock-full of recommendations for boutique wineries and restaurants.

Day 5: Montepulciano and Thermal Baths

stone archway with view to narrow street with cobblestones and green shutters in tuscany
rolling hills with trees and blue sky in tuscany
  • Morning: Begin the day exploring Montepulciano’s medieval streets, visiting artisan shops, and enjoying views from the Piazza Grande and the town’s historic walls.
  • Afternoon: Take a short trip to nearby Bagno Vignoni or Terme di Chianciano to relax in natural thermal spas. Or spend your afternoon sipping on delicious wine on one of these wine tasting tours from Montepulciano.
  • Evening: Return to Montepulciano for dinner at a local trattoria, paired with a glass of Vino Nobile, and stroll through the softly lit streets before calling it a day.

For your reference:

⚫Want to know if Montuplicano is worth visiting? Find out the reasons why it is!
⚫Find out everything to see and do in Montepulciano.

Alternative Suggestions for Your 5 Days in Tuscany

hillside with village atop and blue sky with clouds in tuscany

If you’re looking to mix up your Tuscany itinerary, there are plenty of alternative day trips to consider.

Pisa is a natural swap for Florence, where you can visit the iconic Leaning Tower and its surrounding square. Lucca, with its perfectly preserved Renaissance walls could be added to your day when visiting Pisa.

Arezzo is known for its antique market and stunning frescoes by Piero della Francesca and might be a quiet and more authentic alternative to Siena for art and history lovers.

And if you prefer seeing more smaller hilltop towns over Chianti’s vineyards, San Gimignano, with its medieval towers, is a day trip worth substituting into your itinerary.

Tailoring your days with these options can create a unique Tuscany experience that matches your interests.

Final Thoughts

This 5-day Tuscany itinerary balances iconic landmarks like Florence’s Duomo and Siena’s Piazza del Campo with quieter, off-the-beaten-path gems like Radda and Montepulciano.

It’s designed to give you a taste of Tuscany’s history, art, and food while leaving room for moments of relaxation, like at a thermal spa or sipping on local wines.

However, the best itineraries are the ones that reflect your travel style, so feel free to adapt this plan to match your interests, pace, and preferred destinations. Tuscany is all about embracing the journey.

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Founder, Creator of Dream Plan Experience

Renee Hannes is a European travel specialist with over 35 years of experience exploring France, Germany, Italy, Portugal, and Spain. Having lived in Germany twice, she combines her deep knowledge and passion for slow travel to craft tailored itineraries and destination guides that uncover hidden gems and authentic cultural experiences. She also offers personalized trip planning services and hosts retreats, helping travellers savour the art of slow, immersive European travel.