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

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

Ratings of Zicasso's Service
Customizable Itinerary

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

Countries Visited

Italy

Places Visited

Siena, Cortona, San Gimignano, Volterra...

See all

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

Expand All

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

$3,600 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

4.9 stars based on 5721 reviews.

Italy Tour Review: Wine Tour, Cooking Classes, Local Cuisine,...

Zicasso’s travel company was wonderful in planning our trip on short notice and in line with our requests and preferences. Their suggestions of what to do and where to stay were perfect. And when we accidentally got off on the wrong island, the travel company quickly got us new ferry tickets to get to the right place. It was all seamless.

Reviewed By Sherry G.

Italy Honeymoon Review: Rome, Sorrento, Cooking Class, Private...

This trip was the greatest week of our lives! Everything planned was better than I could have imagined. The private drivers being coordinated behind the scenes made the trip so easy and removed all the stress of trying to navigate a new country. Every driver and our tour guide was so nice and I feel like we made friends with all of them.

My favorite part of the trip was definitely the cooking classes and that every tour was private and intimate for my wife and I. The connections Zicasso’s travel agent hooked us up with made the trip the most memorable experience. Our travel agent and the travel company took special care of all the tiny details of the trip; our hotel knew it was my birthday and had a special surprise for me! I’m beyond thankful for the perfect honeymoon they provided my wife and I.

Reviewed By Branson S.

Italy Trip Review: Sorrento, Cooking Class, Local Cuisine,...

The accommodations and private tours were worth the extra money. Our drivers were professional and helpful.

Reviewed By Claudia R.

Italy, Greece Travel Review: Como, Bellagio, Wine Tour,...

The overall trip was great. The weather was terrific and the countries we visited had so much to see. Zicasso's tour company did a good job of balancing relaxation with fun. Each of the guides we had was so pleasant and shared so much information with us. They were very attentive to our needs.

Reviewed By Nisha V.

Italy Vacation Review: Florence, Rome, Truffle Hunt, Cooking...

Wow, where to begin. This trip was an absolute dream.

When I first spoke to Zicasso’s travel consultant, I told her my main travel concern: traveling with nine- and 15-year-old boys as a single mom in Italy. I was excited to take the trip with them, but I really needed something that was meticulously planned to take away the nerves of having to navigate alone with two kids. She listened and executed the most beautiful trip.

She planned activities that captured the attention and imagination of a fourth grader and a teenager. And the experiences were unique. Probably the highlight of the trip was a truffle hunt with the hunter and his dog in the countryside outside of Florence. My oldest wants to move to Florence and start hunting! We had a personalized cooking class, a private Vespa tour of Rome, and a delicious and informative art and food tour, among other amazing experiences. As we were sending photos back home, I got so many requests for our itinerary because it was so special and unique. Both boys were hard-pressed to choose which part they liked best.

The hotels she selected were beautiful, comfortable, and right in the heart of the cities and attractions we wanted to see. When we encountered a small hiccup (by our hotel, not our travel agent), I contacted her and she responded right away, getting us a free room upgrade and free dinner! We felt very taken care of.

Aside from the amazing activities and locations we saw, the trip was fantastic because everything was so seamless. We always had a private driver arranged, pre-booked train tickets, and even someone to make sure we made it on time for our flight home. I never had to worry about a thing. It was also telling that every tour guide we interacted with had only glowing things to say about our travel agent and her keen attention to detail and organization.

If you're planning on visiting Italy, this travel company is the travel agency you need to select. It takes any of the stress and guesswork out of the travel process, and all you have to do is show up and enjoy.

Thank you so much! You helped us make some amazing memories!

Stephanie

Reviewed By Stephanie S.

Italy Trip Review: Amalfi Coast, Herculaneum, Vatican, Capri,...

We had a fantastic time and Zicasso's tour operator did an excellent job organizing every detail of our trip. Drivers and guides were always punctual, and the itinerary was perfectly balanced—full days, without ever feeling rushed.

Some real highlights for us were Herculaneum, the Pantheon, the Vatican, and our unforgettable Capri boat tour. Our guide brought Pompeii's history to life in a way that made it feel like stepping back in time and the Naples street food tour was delicious and nostalgic—her pizza fritta instantly took me back to the calzones I grew up with in Niles, Ohio. Our driver was with us for several days and made every transfer feel effortless.

There was a small hiccup at the very end with a trip planner, but it was minor compared to the overall quality of the trip. The organization, communication, and attention to detail throughout made this a truly memorable experience and we wouldn’t hesitate to book with this tour agency again. We had a fantastic time and the tour company did an excellent job organizing every detail of our trip.

Reviewed By James T.

Your Dream Vacation

in 3 simple steps

  1. 1

    Describe your dream trip

  2. 2

    Get matched with top travel specialists

  3. 3

    Book the trip

Free service - no credit card required