Medieval town of Cortona in Tuscany, Italy

Tuscany Tour of Medieval Cities & Renaissance Preserves

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Customizable Itinerary

This is a sample itinerary to inspire a personalized trip designed with your travel specialist

Countries Visited


Places Visited

Florence, Pisa, Lucca, Cortona...

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Suggested Duration

8 Days

When you think of Tuscany, you can already imagine the green hills and practically taste the lingering pleasures of Chianti wine. Your custom tailored Tuscany tour of Medieval cities shows you the celebrated Italian province by taking you deeper into the cities you already know, and into the countryside towns protected from the toils of time like a secret. Let your private guide lead you to Renaissance artwork and down preserved streets of medieval villages holding close to heritage and tradition....

Customizable Itinerary

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Trip Highlights

  • Enjoy a private tour of the Renaissance artwork and architecture in the vibrant city of Florence
  • Experience the celebrated flavors of a local Pecorino cheese farm with a private visit to see the process of cheese-making from start to finish
  • Witness the marvelous landscapes of Crete Senesi, an overlooked, yet, sensational region outside the city of Siena
  • Discover the charms of Pisa, from its Roma roots to the Piazza dei Miracoli where the Leaning Tower stands
  • Climb to the top of the Guinigi Tower for an unparalleled view of the Tuscan countryside and the medieval city of Lucca
  • Revel in hard to reach historic towns filled with culture and unspoiled by time

Detailed Description

Cypress, oak, and olive trees rise and fall with the hillsides. Vineyards carpet the valleys. Historic towns watch over the landscape. These are the quintessential images of Tuscany. On your 8-day Tuscany tour of Medieval cities, you will witness gardens and towers, preserved ramparts and breathtaking cliffs. Each moment takes you one step beyond the classic splendor and immerses you in the past, present, and future wonders of the towns, cities, and countryside.

Your luxurious tour in Tuscany begins with your arrival at Florence International Airport. Your private transfer greets you at the airport and escorts you into the Renaissance city of Florence where you have the remainder of the day at your leisure. After breakfast the following morning, your guide meets you at the hotel for a private tour of Florence’s best-known, and lesser-visited treasures, for an all-encompassing exploration. Travel to Pisa where you can discover the remnants of the Pisan Republic, from Piazza dei Miracoli to the Church of Santa Maria della Spina.

In Lucca, you can stroll around the historic city walls and climb to the top of the central tower, which offers views of the red-tiled rooftops and surrounding lush landscape. The following day, you venture to the towns of Arezzo and Cortona, both providing enchanting characteristics of historic Tuscany dating back to the Etruscans. When visiting Siena and Monteriggioni, you find the captivating architecture of the Middle Ages and the exquisite landscape of Crete Senesi. Travel to Volterra for a day to traverse the cobbled streets of the medieval hillside town, followed by a private guided tour of a local Pecorino cheese farm.

When you arrive in Val d’Orcia, your guide leads you through numerous villages often overlooked by visitors both foreign and domestic. You can sip on famous wines in Montepulciano and Montalcino or venture into the stunning region of Maremma to visit towns such as Pitigliano and Castiglione della Pescaia. On your final morning in Florence, your private transfer meets you at your hotel after breakfast and escorts you to the airport for your flight home.

Starting Price

$2,859 per person (excluding international flights)

Your Zicasso trip is fully customizable, and this sample itinerary is a starting place for your travel plans. Actual costs are dynamic, and your selection of accommodations and activities, your season of travel, and other such variables will bring this budget guideline up or down. Throughout your planning experience with your Zicasso specialist, your itinerary is designed around your budget. You can book your trip when you are satisfied with every detail. Planning your trip with a Zicasso travel specialist is a free service.

What's Included

  • Accommodations
  • In-country transportation
  • Some or all activities and tours
  • Expert trip planning
  • 24x7 support during your trip

Your final trip cost will vary based on your selected accommodations, activities, meals, and other trip elements that you opt to include.

Reviews of Zicasso's Referral Service

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