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 5752 reviews.

Italy Trip Review: Guides, 9 Nights

Zicasso's travel agent created an itinerary and experience that was simply perfect. Every hotel experience, guide, and driver was excellent. She was kind, patient, knowledgeable, and made the perfect suggestions. I loved working with her! Thank you to our agent, the tour operator, and Zicasso for a wonderful trip!

Reviewed By Anita L.

Italy Vacation Review: Tuscany, Siena, Rome, Amalfi, Capri,...

Our Italy trip with Zicasso’s travel partner was nothing short of spectacular! Referred by a friend who had an amazing experience, we decided to give it a try and were not disappointed. Our agent was fantastic, always ready with answers to our questions and providing excellent support throughout our journey.

In Tuscany, we visited beautiful wineries and enjoyed a delightful lunch with the vintners, who were incredibly warm and welcoming. Her attention to detail was evident when she adjusted our plans due to weather changes and even checked in on us when we were slightly delayed for a tour.

Siena was breathtaking and our hotel in Rome was perfectly located, allowing us to walk to all the major sites. One of the highlights was a small boat tour around Capri from Amalfi—perfect weather and stunning waters made it unforgettable. The cooking class on the Amalfi Coast, set on the side of a cliff, was exceptional and having personal tours just for the two of us was an unexpected and delightful bonus.

We can't express enough how much we enjoyed our Italy trip. The travel partner exceeded our expectations and we highly recommend them for a truly memorable experience!

Reviewed By Kent S.

Italy Anniversary Travel Review: Tuscany, Local Cuisine,...

Zicasso’s trip coordinator and her team did a fantastic job, not only in planning the trip to meet our needs and wants, but also in personalizing it as needed. They were also available as we needed them to adjust things, such as pickups, and even made some dinner reservations for us. With our budget, they set us up in excellent hotels that fit our desire for the trip to be a wonderful anniversary getaway. Her staff were also very helpful. We would strongly recommend them for a trip to Italy!

Reviewed By Rajesh J.

Italy Family Trip Review: Lake Como, Amalfi Coast, 2 Weeks...

Zicasso's travel planner and her staff did a perfect job for our family of six. She made our trip seamless!

Everything she planned was perfect and no detail was left out. I would use them again and again for my travels to Italy.

Reviewed By Sally F.

Switzerland, Italy Solo Vacation Review: Zurich, Lucerne,...

My first solo trip was something I had dreamed about for years. I wanted it to be more than sightseeing. I wanted adventure, comfort, safety, and freedom without the stress of planning it all alone. Through Zicasso, I was connected to two specialists and Zicasso's travel consultant stood out immediately. She delivered an itinerary that gave me everything I asked for and more: maximum cities, maximum fun, and maximum value, all without compromise.

Before deciding, I researched and compared tours, packages, and individual prices online. The travel consultant’s proposal came out on top for value and content. While the other agent offered fewer cities and activities at a higher price, her plan was ambitious without being overwhelming. She booked my trains, arranged private transfers where needed, and selected boutique-style hotels that exceeded expectations. I was honestly surprised at how good they were. I stayed at hotels in Interlaken, Florence, and Sorrento. Each was clean, comfortable, and perfectly located for exploring. I had prepared myself for budget trade-offs, but instead, I found thoughtfully chosen hotels that balanced affordability with real quality.

Every document, train ticket, and activity confirmation was uploaded into the app. It became my lifeline throughout the trip, with every detail at my fingertips. The structure gave me confidence, while still leaving me free to explore.

Switzerland came first: Zurich, Lucerne, Interlaken, and Zermatt. Each city felt like stepping into a postcard. Interlaken gave me the adrenaline rush of skydiving, while Zermatt charmed me with its close-knit magic and alpine beauty. Italy unfolded with equal ease: Lake Como, Venice, Florence, Sorrento, Amalfi, and Rome. Every destination felt curated, yet natural, from gondola rides in Venice to boat tours on the Amalfi Coast.

What I loved most was the balance between structure and freedom. Pre-booked activities and restaurant reservations gave me a strong framework, but I could just as easily decide to spend an afternoon wandering Florence, eating gelato, or sitting in a piazza. The rhythm of the trip was perfect, structured enough to tick off bucket-list highlights, yet relaxed enough to feel like a real vacation.

Food was freestyle, but memorable. Highlights included a Japanese-Peruvian restaurant in Zurich with its elegant Japanese-Peruvian flavors, a different Japanese restaurant, a restaurant in Como with its modern fusion menu, an Indian restaurant for comforting classics, and international favorites like those in one of the restaurants in Rome. Between those meals and plenty of gelato and crepes, every stop added its own flavor to the journey.

As a solo traveler, safety mattered. I felt comfortable walking around in the evenings and was usually back in my hotel by 1am to stay rested for the next day. What really gave me peace of mind was the travel consultant’s constant support. Communication was fast and responsive. I never had to wait long for answers, whether through the app or email. There was a moment when I made a mistake with the trains and missed an activity. She immediately stepped in and worked to reschedule it or secure a refund that same day.

Earlier in the planning process, I also had a card issue due to an address error. Even though policy would not normally allow it, she and her team patiently waited until I received the refund before finalizing the booking, just weeks before my trip. That flexibility and care spoke volumes.

The difference was clear. She used my budget to its fullest potential, giving me more destinations, more experiences, and better hotels than the alternative option. She managed to combine the efficiency of a fully organized tour with the freedom of independent travel. Everything was planned, yet everything was still mine to shape.

This trip was everything I wanted: good food, beautiful views, safety, and absolute reliability. It was an organized journey with freestyle flexibility, which is exactly what solo travelers dream of. The travel consultant’s planning let me chase adventure while always knowing I had a safety net. Switzerland and Italy gave me memories I will never forget, but it was the behind-the-scenes planning that made it possible. If you want a trip that is your way, your budget, your pace, but without the endless hassle of managing it yourself, the travel consultant at this agency is the person who can make it happen. My first solo trip became my dream trip and that is the highest praise I can give.

Reviewed By tasmia S.

Italy Trip Review: Rome, Tuscany, 2 Weeks

Zicasso's was an excellent travel company. The attention to all trip details by our tour operator was amazing. We enjoyed all the tours, the guides, the accommodations, the drivers, the Italian train system, and restaurant recommendations, and his itinerary information that we downloaded on our iPhones was extremely valuable throughout our entire trip. I would not hesitate to recommend him to anyone. I would definitely consider using him for future travel.

Reviewed By Kathy D.

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