One Week in the Tuscan Countryside Tour

Photo courtesy of: Hotel Castello di Casole © Belmond.

What to expect on this itinerary

Italy’s countryside is teeming with hilltop towns that are speckled across the breathtaking region of Tuscany, which you will explore on this handcrafted 7-day tour. Under the Tuscan Sun, you will appreciate the endless beauty of the emerald hills that roll from Montepulciano in addition to admiring the ancient architecture of the cultural heritage sites in San Gimignano. From town to town, you can find beauty in every charming destination against the beautiful countryside backdrop.

Countries Visited

Italy

Places Visited

Rome, Tuscany, Montepulciano, Pienza, Montalcino, Siena, San Gimignano, Volterra, Castello, Fiumicino

Suggested Duration

7 Days

Customizable Itinerary

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Day 1

Rome - An Introduction to Italy

Rome is a treasure trove of historical landmarks set within a mesmerizing architectural cityscape. The city showcases Ancient Roman design that is imbued with sophisticated and contemporary characteristics. You will touch down, drop off your belongings at your accommodation, and have the opportunity to tour classic Rome. During your initial discovery, you will visit Italian boutique stores, delicious gastronomic specialties, and fabled heritage sites within Dolce Vita, such as the Pantheon and the Spanish Steps. Afterward, you will enjoy local culinary dishes for dinner before returning to your room.

What's Included:

Transfer
Accommodation
Tour
Day 2

Montepulciano - Tour the Ancient Eras

Day 3

Montepulciano - Bucolic Pastures

Day 4

San Gimignano - A Surreal Stop in Siena

Day 5

San Gimignano - Breathtaking Tuscan Hills

Day 6

Fiumicino - Serendipitous Moments

Day 7

Fiumicino - Departure

Trip Highlights

  • Peruse the spirited city of Rome, visit Italian boutique stores, discover delicious dishes, and tour iconic landmarked locations within Dolce Vita
  • Unravel the history of Ancient Rome that is etched in the astonishing architecture of The Colosseum, Roman Forum, and Palatine Hill
  • Tuck into mouth-watering cheeses produced at a local dairy farm in Pienza
  • Cherish the history and beauty of the architectural details that surround the culturally significant Il Campo piazza in Siena
  • Lap up world-class wines and saffron-infused dishes at San Gimignano’s beloved Fattoria
  • Escape to a sought-after wine estate stationed on the staggering Chianti hill in Castello for an elite tasting experience in Tuscany
  • Take some time to enjoy a few moments in the bustling and characterful city of Fiumicino in addition to tucking into authentic Italian cuisine

Starting Price

$3,200 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.

4.9

Verified Traveler Reviews

Based on 19 reviews

Travel Review: Italy Tour, Milan, Tuscany, Venice, Siena, Lake Como, Lake Garda

Our agent, Lisa, did an excellent job of providing great accommodation throughout 4 cities in Italy, each one beautiful and unique, and exactly what we asked for. She listened to our requirements and quickly provided revisions to the plan to suit what we were looking for. On top of this, all of the connections were seamless and stress-free, allowing us to relax and enjoy the trip. Thank you.

We ate at some really lovely restaurants. Unfortunately I can not remember the names of them. We also stayed at amazing hotels. We especially loved our stay at Hotel Kriss at Lake Garda and Garden Hotel in Siena. Such great places to stay. Loved it.

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Luxury Italy Family Vacation Review: Florence, Rome, Sorrento, Amalfi Coast, Pisa, Orvieto, Capri, Siena, Pompeii, San Gimignano

Our agent at this Italy travel company was very helpful at every step. She put together a wonderful itinerary for us that was very balanced. We stayed in Rome, Sorrento, Florence, and Orvieto. We had private guided tours in Rome, Pompeii, Amalfi Coast and Florence, and group tours to Siena/San Giamagnano/Pisa and Capri. Everything was planned out perfectly. We were extremely happy with every accommodation. We did use the trains, and drivers met us at each destination so we did not need to worry about cabs. For the most part, we were able to avoid large groups. This was a wonderful way to see Italy. 

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Travel Review: Family Tour of Italy, Rome, Florence, Sorrento, Pompeii, Amalfi Coast Tour, Cooking Lesson

The trip was wonderful. Our travel company did an excellent job of asking our needs and then meeting them. I really appreciated the fact that each day of the trip was planned out and sent to us in great detail so that we knew where we needed to be and at what time. Not only did this help us effectively see the things that we wanted to see, but also allowed us to know when our leisure time was and plan accordingly. This was our first trip to Italy and since we were travelling with our three children, including a seven year old, we needed a trip that was well arranged and thus low stress. In 8 days, we saw Rome, Sorrento, and Florence. Having pre-arranged transportation to pick us up from airports, train stations, and hotels was perfect. We had the same drivers in each location so we felt very relaxed. We arranged for at least one tour or activity each day not lasting more that 4 hours. This gave us time afterwards to explore the cities at our leisure.  We stayed in small hotels which were Bed and Breakfast places. It did take some time to understand the way these places work but overall, we enjoyed them. We had tour guides waiting for us when we toured places such as Pompeii and the heart of Florence.

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Travel Review: Anniversary Vacation in Italy, Rome, Sorrento, Puglia. Matera, Capri Boat Tour, Colosseum & Forum Tour, Wineries

My wife and I have wanted to travel to Italy for almost a decade, so picking the right travel agent was a very important step for us. Zicasso connected us with several agencies. We ultimately selected this company and worked with this travel agent to plan our trip. We could not have been more pleased with our experience.

One of the reasons we selected this travel agent was because she was based out of Italy. We felt more comfortable with someone living in the country as opposed to a travel agent who had simply visited Italy. Her expertise definitely improved many aspects of our trip. Our must-haves included a multi-night stay in Rome and Pompeii. Our agent crafted a 11-day vacation for us that included Rome, Pompeii, Sorrento, Matera, and Puglia. Each detail of our trip was planned perfectly.

We were picked up by private automobile transport at the airport and had private tours through almost our entire trip. Our tour groups ranged in size from just us to 10 people. The tour guides that our agent selected were incredibly knowledgeable and personable. They were enthusiastic and clearly very passionate about their tours. She also recommended a variety of restaurants and made reservations for us for every evening we were in Italy. She offered options for each day and we were able to select the tours that best suited our interests (Roman Catacombs, Food tour, Jewish Ghetto, etc.). We had 4-star accommodations throughout the trip. Not only were all the hotels great, they were in perfect locations in the center of the cities we visited.

When it was time to travel to Sorrento, our agent arranged travel by train and then private automobile pickup to our final destinations. We spent a day in Sorrento, another day in Capri, and our last day touring the Amalfi coast. We were able to take a boat tour around Capri and visit multiple cities along Amalfi. We tried our first ever Michelin rated restaurant and it was delicious. We couldn't believe that she arranged for a private driver to spend 12 hours with us along the Amalfi Coast (he dropped us off at designated cities and picked us up an hour or two later).

For our next step, our agent took us off the common tourist path and had us visit Matera and Puglia. It was a great cultural contrast to Rome and Sorrento. We slept in a Grotto (hotel) in Matera and had splendid views of the country and old city. In Puglia, we visited a winery and dined along the Adriatic Sea.

It was a memorable trip that we could not have been more thankful for. During multiple times on the trip, my wife and I remarked how lucky we were to have a travel agent so knowledgeable.

Our agent called us several times to check-in on us and immediately remedied a situation where our itinerary was forced to change. We had her number 24-7 for any needs. We had a stress-free trip. We could not have planned this trip on our own, so we are grateful to have had our agent's wisdom. We had contemplated doing our own research, but we could not have recreated the magic of this trip.

When we travel to Italy again, we will definitely be using this travel company!

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Italy Travel Review: Rome, Florence, Venice, Pisa, Tuscany, Chianti, Siena, Cinque Terre, Vatican, Coliseum, Sistine Chapel

The overall experience in planning a trip with this Italy travel agency was exceptional. From the start our dedicated travel agent set a precedence to ensure we would have a trip of a lifetime.  We requested for her to plan an itinerary from Rome to Siena to Florence and Venice. The level of detail that she planned our trip was amazing! She went above and beyond to find the best (and cost effective) manner to travel between areas, to knowing when to coordinate private vs. group tours to even specifying what restaurants to go to. Our agent even provided us with a more detailed itinerary with contact information and addresses for everything we had planned. This was extremely helpful when asking for directions or taking a cab somewhere. Our agent really met all our needs and more. I have already recommended her to all my friends and family. If you want a memorable vacation to Italy with no worries, then our agent is the right person for you. 

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Travel Review: 7- Day Italy Vacation, Rome, Florence, Local Food & History
Had a wonderful trip to Italy, visiting Rome and Florence.  Travel company did a great job creating an itinerary that included the right balance of guided tours with time to explore on our own.   All guides and transportation provided were very professional and the guides were very knowledge able and spoke excellent English.  

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Customizable Itinerary

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

28,000+ Verified Traveler Reviews