Charm & Romance in Italy’s Countryside: Tuscany and Umbria Tour

Beautiful view of Medieval town of Monteriggioni in Tuscany, Italy

What to expect on this itinerary

Your 10-day romantic adventure of Tuscany and Umbria will keep your love at the forefront on your personalized Italy tour. Enjoy a passionate embrace on a vineyard, drift down the Tiber River dining on delectable dishes, and climb to the top of a medieval tower for unrivaled views. Take the chance to sneak a kiss around every corner, and fall in love anew amidst the beauty of Italy.

Countries Visited

Italy

Places Visited

Rome, Spoleto, Assisi, Montefalco, Volterra, Florence, Orvieto, Monteriggioni

Suggested Duration

10 Days

Customizable Itinerary

Expand All
Day 1

Rome – Arrive in Rome and the Tiber River

Rome is known as the “Eternal City,” and embodies the tenants of Italian culture, from leisure to history, artistic aesthetic to a devoted relationship with romance. Your private transfer will greet you at Rome’s Fiumicino Airport and escort you to your boutique hotel at the heart of the historic city. Ivy drapes over the façade as nearby, the water cascades beneath the empowering figure of Oceanus posing at the center of the Trevi Fountain.

After taking a moment to settle into the comforts of your beautiful hotel, you can make your way to the banks of the Tiber River at Saint Angelo’s Pier and board an elegant boat. The lights over the river will flicker on the water and bring an ethereal glow to Rome while your four-course meal introduces an enticing array of aromas as you bask in the romance listening to the soft strumming of a guitarist. You may have an unadulterated view of the dome of St. Peter’s Basilica soaring above the city as you cruise by on a perfect first night in Rome.

What's Included:

Accommodation
Transfer
Tour
Dinner
Day 2

Orvieto – Visit Terni, Narni and Marmore Falls

Day 3

Spoleto – Travel to Spoleto for a Couple’s Cooking Class

Day 4

Spoleto – Venture to the Lavish Basilica of Assisi

Day 5

Montefalco – Tour a Quiet Winery and an Olive Oil Farm

Day 6

Montalcino – Traverse the Pristine Val d’Orcia region

Day 7

Siena – Delight in Renaissance Atmosphere

Day 8

Siena – Indulge in Medieval Allure

Day 9

Florence – Embrace Historic Beauty and Opulence

Day 10

Florence – Depart for Home

Trip Highlights

  • Indulge in the romantic atmosphere and delicious cuisine during a four-course meal on a scenic cruise down the Tiber River in Rome
  • Delight in the flavors during a private wine and olive oil tour through the secluded and stunning countryside of Umbria
  • Climb to the top of Torre Grossa at nearly 175 feet above the cobbled lanes of San Gimignano for an unparalleled view of the Tuscan countryside
  • Deilght in luxury, charm, and romantic ambiance in unrivaled accommodations across Umbria and Tuscany
  • Bask in the simple yet captivating flavors of Umbrian cuisine with a private couple’s cooking class near Spoleto
  • Immerse yourself into the fairytale setting of the medieval towns that decorate the lush hilltops covered with olive groves, chestnut orchards, and vineyards
  • Marvel at grand design and intimate details of Michelangelo’s David in Florence before listening to the melodic Gregorian chants at a secluded church above the city
  • Visit the Basilica of St. Valentine in Terni, home to the tomb of the patron saint of lovers, St. Valentine, for whom Valentine’s day is named

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.

4.9

Verified Traveler Reviews

Based on 2191 reviews

Review: Italy Family Vacation, Milan, Rome, Florence, Venice, Parma, Modena, San Gimignano, Lake Como, Dolomites Snowmobiling

Thanks for helping me organize my family (of 10 with diverse age from 15 to 63) trip to Italy, from Dec 17 to Dec 31. Whilst different member of my family have different expectation and requirement, I would like to comment you and your team on having planned an excellent trip that not only met each and everyone's interest and expectation but truly exceeded it.

Your planning have brought us to the lovely cities of Parma, Modena, Florence, Orvieto, Civita Di Bagnoregio, Naples, Rome, Venice, Cortina d'Amprezzo and back to our starting point Milan. Throughout the trip, we have a well balance itinerary that covered

- beautiful churches such as the Duomo in Milan, Rome, Florence,

- archeological site like Pompeii, Colosseum, Roman Forum, Pantheon, Pisa, Verona (learning more about romeo and Juliet)

- great local eating places (recommended by the guides you chose)

- lovely country side and unique sight in San Gimignano, Civita Di Bagnoregio, Orvieto, Lake Como,

- great gallery likes Uffizi, Academia

- Interesting activity such as Snow Mobile excursion in Cortina, Learning Cooking 

- Shopping activities

With so much, yet your team immaculate planning never have us rushing from sight to sight, we were both able to enjoy and learn as much as we can of each sight and at times added more activities.

The team of guides you chose, have truly turn stone and history into exciting stories that the provided the group deeper understanding of the sights we visited and saw. Really like to thank each on of them like our guides in Florence, Pisa, San Gimignano, Orvieto and Civita Di Bagnoregio, Naples and Pompeii, Rome, Verona, Venice and Milan.

But most importantly, thank you for getting our driver, he truly ensure our comfort whilst driving steadily through jams on our way to Naple and snow storm on our way to Cortina d Amprezzo and also took very good care of us ensuring we know what to do where we have no guides and leaving us clear instruction when we needed help. He is truly a wonder.

I will definitely tell my friends heading to Italy about this company.... A wonderfully great experience.

See more

Italy Travel Review: Perugia, Orvieto, Rome, Cooking Class, Cuisine, 1 Week
"Zicasso’s travel company did an excellent job designing our trip and provided support when we needed to make last-minute modifications."

See more

Review: Luxury Italy Family Vacation, Rome, Venice, Florence, Tuscany, Chianti, Verona, Milan

My husband and I, along with our 2 children (age 20 and 17), enjoyed a wonderful Italian vacation booked through Zicasso and this travel agency.  Our travel consultants listened to my ideas and arranged for us a fantastic custom itinerary.   They stayed within the budget allotted, offered choices for beautiful hotels and private tours, and made several revisions as per our request.  We departed from New York on our 25th anniversary, and spent 10 days traveling the country within the month of November.  This off-season time proved to be a great decision as reservations were easy to obtain, crowds were minimal (mostly all locals), and the weather was conducive for walking and sightseeing (average 60 degrees F).  Transportation and the personal drivers were top notch; with Mercedes SUVs or minivans to take my family from Milan-Chianti-Florence-Verona-Venice and then the high speed train down to Rome.  Accommodations arranged for us were phenomenal!  We stayed in a 12th century castle in Chianti, in the heart of the city center in Florence, and near the Spanish Steps in Rome.  The personal tour guides were friendly and knowledgable, and were happy to recommend eateries preferred by locals.  All in all, everything was flawless. We plan to return some day to see the Amalfi coast, Positano and Capri.  We would absolutely recommend these travel consultants, and the travel company team to anyone who is looking for a personalized Italian vacation.

See more

Italy Trip Review: Venice, Assisi, Florence, Rome, Tuscany, Uffizi Gallery, Victor Emmanuel Monument, Vatican, Cooking Class

My husband and I wanted this "trip of a lifetime" to Italy to go well and I didn't have the hours to research and then be sorry if I didn't choose right so our Italy travel company's customized travel plan was perfect!  I had put my name into Zicasso to say where we wanted to go and 2 travel agencies that specialize in Italy contacted me to find out what we wanted to do (go to Venice, Florence, Assisi and Rome) and then they contacted us with their suggested itinerary.  We chose our agency because theirs was a much more detailed itinerary and they definitely had a better knowledge of Italy.  Our agency booked our hotels (which all included breakfast), transportation and some tours and we were on our own for whatever else we wanted to do.

Our agency provided us with a detailed itinerary summarized with dates, times and phone numbers on one page and in the packet were our maps, tickets and vouchers for trains and tours.  We flew into Venice and had a map of where to get the private water taxi from the airport to our hotel.  From the dock in Venice we were very close to our Hotel which was easy to find and in a GREAT location.  The breakfast buffet was wonderful and service was very good.  We chose not to take the gondola ride and instead used the public water taxis and toured Venice on our own for 2 nights. On the third day we met our private water taxi driver at the same dock to take us to the train station in Venice to go to Florence.  

The first class train even had it's own computer for each person and lots of room.  In Florence we were met by our driver with a sign with our name and driven to our hotel with a view of the Duomo where we stayed for 3 nights.  This hotel had a private room and a shared suite with free snacks and coffee and tea and breakfast was around the corner at a pastery shop.  We followed the map provided to the tour office and toured the Uffizi Gallery, Streets of Florence Tour and a very fun cooking class with 4 course dinner and lots of good wine!  Our third day in Florence, we were met with a private driver at our door and driven around Tuscany, stopping at an abby and few small towns including Greve and eating on a veranda at a winery which we also toured. This was one of our favorite days of our trip.  

We wanted to go to Assisi and our travel agent said they do not have a place to store bags at Assisi (though the other agent who contacted me said there WAS but our agent was right!) so she at first had planned a private driver to take us to Assisi and wait for us and drive us to Rome but instead we decided to take the train to Assisi and stay overnight and take the train to Rome the next day.  The room in our hotel in Assisi had such a beautiful view we wished we had chosen to stay there another night!  

After taking the train to Rome,  our driver took us to our hotel which was just around the corner from the massive Victor Emmanuel Monument so within walking distance to all the major Rome attractions.  This hotel had a private elevator that opened directly into our suite and a little deck with a table and chairs to eat outside.  Breakfast was ordered daily and sent to our room (though they could not get our order right most days but the great location made up for this!)  For our 5 nights in Rome, our only scheduled tours were the Ancient Rome Tour and the Vatican tour.  All of our tours were with at most 10 other people and sometimes it was just us.  

In the itinerary our agent recommended restaurants and other places to see in each location which we did take advantage of and we used the Rick Stevens Guidebook extensively. Our driver picked us up right on time at the hotel the last day to take us to the airport.

We loved that we had some support but could explore on our own!  We highly recommend this Italy travel company!

See more

Travel Review: Anniversary Trip to Italy, Rome, Florence, Pisa, San Gimignano, Positano, Truffle Hunt, Cooking Class, Food Tour

Locations Visited: Venice, Verona, Florence, San Gimignano, Siena, Pienze, Rome, Pompeii, Positano

My husband and I planned this trip for our 10-year anniversary. I’m a person with high expectation and this travel agency exceeded all my expectations. The entire trip was dream.

We opted for personalized tours and transport for 95% of our trip. All of our drivers were wonderful. They arrived on time and made sure we made it to all of our destinations without issue. They had the contact information for the tour guides we were meeting. Upon arrival to our first hotel, a local cell phone and gift were given to us. Having the iPhone during our trip made any needed communication with our agent and his team a breeze. In addition, we used the phone apps for navigation throughout the cities we visited. We made a last-minute request for an additional private transport, and our agent was able to make it happen. We greatly appreciated their customer service.

We participated in a several unique experiences while in Italy. We went truffle hunting in Pienza, which was amazing. After, we were served a meal that highlighted truffles and the cheeses made locally. In addition, we did a cooking day in Rome. This was a private cooking class where we made pasta, several sauces, and appetizers. The one disappointment is that we never received the recipes from the chef (we were told by the chef that they would be emailed to us). However, this is a knock on the chef and not our travel agent. Once the class was done, we were served a meal in a private garden area. Lastly, we did a food walking tour in Rome. This was an amazing way to find local cuisine that we wouldn’t have known about otherwise. A wonderful experience.

All of our tour guides were excellent. They were knowledgeable, friendly, and familiar with the cities. We had one guide that really went into the details and reasons for expressions in the art. We didn’t care for that, but we didn’t specify that ahead of time or to the guide. It was wonderful seeing her excitement and passion for all of the amazing working works of art and sculpture that we saw.

Overall, I would highly recommend this travel agent and his team if you are traveling to Italy!! You will not be disappointed. We gave him our wish list of activities, accommodation preferences, etc. ahead of time and he made sure we got them all! Thank you for such a wonderful and memorable trip. If we are able to return to Italy, you will be hearing from us.

See more

Travel Review: Memorable Vacation to Italy, Florence, Tuscany, Siena, Antinori Winery Tour, Rome, Vatican Tour
Giuliana of this Italy travel company guided us every step of the way and created one of our most memorable vacations. The most impressive thing at the outset was how quickly she responded to our initial inquiry. We had never been to Italy, had not done a great deal of research, and had only a general idea of what we wanted beyond the dates (mid-May) and the cities we wanted to visit (Florence and Rome). Within a day, Giuliana submitted a detailed proposed itinerary based on a recent client request similar to ours. The proposal included various options that provided a great starting point for further discussion. She asked many questions, including our hotel preferences (small boutique, high-rise, how many stars, etc.) and suggested a number of venues that would expose us to Italy’s remarkable history and culture. The result was a vacation specifically suited to our personal tastes and interests. We spent four days in Florence and three in Rome. In Florence, we stayed at the Hotel Lungarno on the Arno River, a lovely small hotel in the heart of the city within walking distance to everything of interest, including the Uffizi and Academy museums, and the famous Duomo. It rained two nights, but we didn’t have far to go for a great dinner. The hotel restaurant was superb. One of the highlights of the Florence leg of the trip was a day tour of the Tuscany wine region that included a stopover in the historic town of Siena. We had lunch at the Osteria di Passignano, a restaurant at the Antinori vineyards where we were treated to a four course lunch and wine tasting and a tour of the winery. Fabulous. In Rome, we stayed at the Hotel Saint George. Another small, well appointed, boutique hotel, centrally located near the Tiber River, it provided access to all the essential venues, including the Vatican, Coliseum, Spanish Steps, etc. As in Florence, everything was in walking distance, including fine dining restaurants, pizzerias, espresso bars, and gelateria—and lots of places to shop. The hotel was comfortable, attractive, with a friendly and efficient staff, but we would not recommend the hotel restaurant. It was nice enough (although too brightly lit) but was virtually empty the night we were there and the food was just O.K. That wasn’t Giuliana’s fault since the hotel restaurant was not on her recommended list. We were just tired (it was our first night) and thought we’d give it a try. The hotel concierge made up for it, however, by recommending two great nearby restaurants for the remaining two nights. Neither was on Guiliana’s list, but they were terrific. A word about the logistical aspects of the trip: we viewed this as critical to the success of a customized tour with multiple venues and connections. We couldn’t have been more pleased. On arriving at Rome’s Fiumicino Airport, we were greeted by Aldo who drove us to the high-speed train to Florence. After sharing an espresso with us in the station café, he made sure we got on the right train, helped us with our bags, and took us to our seats. Similar service greeted us at every connection point during the trip. Our personal tour guides, Enza (Florence), Andrea (Tuscany), and Sylvia (Rome), were exceptionally knowledgeable, personable, and fluent in English. Giuliana telephoned us at several points during the trip to confirm that we had arrived at our destination, that the drivers were on time, and that the accommodations met our expectations. Very reassuring to know she was keeping such close tabs on things. In short, all elements of transportation and personal service were impeccable. Would we visit Italy again? Without doubt. The trip simply whetted our appetites. Would we use this company? We wouldn’t consider any other service. Next time, however, we’ll make more of an effort to visit the restaurants recommended by Giuliana.

See more

Customizable Itinerary

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

28,000+ Verified Traveler Reviews