Piazza del Campo with gothic town hall building and tower in Siena, Italy

Tuscany Tour for Lovers: Siena, Cortona, Volterra, San Gimignano and Certaldo

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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

Siena, Cortona, San Gimignano, Volterra...

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Suggested Duration

8 Days

Medieval city walls and historic towers make each town in the Tuscan countryside feel like a fairytale, and you will feel like royalty. On your custom tailored Tuscany tour for lovers, each day takes you to the intimate villages and enchanting landscapes, from lush valleys to glistening seaside. Taste the traditions of elegant, regional cuisine and savor the treasured company of your partner. You will find the charms of history and the enchantment of sunsets over castle walls, sipping wine in...

Customizable Itinerary

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Trip Highlights

  • Stroll through charming medieval Tuscan towns off the beaten path that provide a more intimate exploration of the countryside
  • Revel in the enchanting atmosphere of historic artifacts in small museums housing captivating objects
  • Relish a beachside picnic on the Maremma coastline, with handpicked Tuscan flavors to enjoy
  • Delight in the celebrated views of hilltop Tuscan towns overlooking the famous rolling landscape
  • Savor the sensational wineries around Siena with an exploratory wine tour around the region
  • Satisfy your inner explorer and storyteller inside the ancient city walls of Volterra, filled with unique charm and botanical gardens

Detailed Description

The truth about Tuscany is that it has an endless amount of beauty emanating from the land itself. The countryside is picturesque, and the towns have stepped out of a photograph. Your 8-day Tuscany tour for lovers provides you the luxuries of romance and the tenderness of history, where the crowds fade away, and the horizon fills with possibility.

The honeymoon ambiance begins with your arrival at the Florence International Airport where your private transfer greets you. Soon you find yourself in the charming hillside town of Siena, known for the Palio horse races held in the summer. The rest of the day is for you and your partner to familiarize yourselves with the wonders of the cityscape and the charm spreading across the cobblestone streets. In the evening, you can embrace the romance with an intimate dining experience to welcome you to the city. The following day, your private guide meets you at the hotel eager to show you the beauty of Siena beyond the central meandering streets, showing you the treasures of the medieval city.

Outside of Siena, you travel to the Umbrian border to visit Cortona, an ancient town with Etruscan heritage. The city has lovely frescoes and a stunning panorama of the valley. On your way back to Siena, you can stop at any number of hilltop villages decorating the countryside, including Lucignano. In the towns of San Gimignano and Certaldo, you have a view of either city situated on the hills, exuding power and pride in medieval towers and castles. Once in the city of Volterra, you find unique charm wrapped around the historic city walls and exuding from the rich tales shared throughout the city. Follow your time in Volterra with a private guided tour of nearby wineries that welcome you like old friends.

The following day you travel to the coastline of Maremma, in the town of Grosseto. Savor the sweet scent of the sea and the delicious flavors of a picnic packed by an artisan salumeria. Visit the hillside charm of Castiglione della Pescaia overlooking the water. With a full day in Pisa, you will visit the celebrated Leaning Tower before stepping beyond the Piazza dei Miracoli to experience the enchanting architecture and ambiance of the former grand coastal power. Upon your return to Siena, you can indulge in the traditional flavors of the region at a romantic candlelit dinner. On your final day, your private transfer meets you at your hotel and escorts you to Florence International Airport for your flight home, where you can watch the Tuscan countryside fade. 

Be sure to browse the additional tours in Tuscany section on Zicasso.

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.

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