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Assisi, Umbria Region - Italy - Photo by Jesse Andrews
Harvest Time in Tuscany
Chianti at Harvest Time
Chianti at Harvest Time in Tuscany - Celebrate Colour
View of Florence from Tuscan Countryside - Photo by Jesse Andrews
View over Florence from Piazza Michelangelo, Florence - Photo by Jesse Andrews
Historical Centre of Florence Italy - Photo by Jesse Andrews

Tuscany & Umbria: Exclusive Small Group Tour Including Florence Back

  • Tour Code : TUR-00326
  • Type : Semi-Private
  • Duration : 7 days
  • Departs from : Florence


This deluxe small group tour through Tuscany and Umbria offers our guests the possibility to experience two of Italy's most beautiful wine regions as well as Florence.  There are many highlights on this tour including a private cooking class with a local Tuscan Chef as well as dinner at a farm in the heart of Chianti wine territory. 


This journey through Tuscany and Umbria begins and ends in Rome.  Gourmet meals including select wines are included in the package price.  

The properties where we stay in each location are some of the finest hotels each destination has to offer.  



Day 1 - Siena & San Gimignano

Where we visit : Siena, San Gimignano
This morning you will meet your tour escort and group at the Piazza Barberini in Rome where will begin our journey north through the Umbria region into Tuscany The drive itself is a magnificent path along the roads of Tuscany, where it is possible to enjoy the view of hills covered by vineyards, olives tree, small villages and original bell towers. The first stop is Siena, probably Italy's loveliest medieval city, for a walking tour with a local guide. Siena's heart is Il Campo or Campo's square, where the famous horse race Il Palio takes place two times each summer. The town offer magnificent masterpieces and incredible views. Enjoy a wine tasting with cheese and salami. Continue to Florence and en route stop in San Gimignano. The town is listed as a World Heritage site and fascinates for its medieval look. Its high towers create a unique skyline. Enjoy the village on your own. Arrival in Florence late afternoon.Free time for dinner. Overnight in Florence.
Meals : Breakfast, Lunch

Day 2 - Florence

Where we visit : Florence
In the morning, enjoy a walking tour of the city with guide with Accademia. Lorenzo de Medici transformed Florence into the cradle of the Renaissance by attracting the best artists, architects and writers of the time such as Leonardo da Vinci, Michelangelo and Botticelli to whom he commissioned various works. Visit Piazza dellaSignoria, Palazzo Vecchio, the Dome with Giotto's bell tower, Ponte Vecchio, Santa Croce. Spend the afternoon at leisure exploring Florence on your own, visiting the Uffizi or taking the opportunity to visit Chianti or Lucca. Overnight in Florence.
Meals : Breakfast

Day 3 - Dinner in Chianti

Where we visit : Chianti
The day is free at leisure. There are many optional tours available: Pisa with its leaning tower, Montepucliano and Montalcino, Cortona, Assisi and Perigia and many other. In the late afternoon, transfer to Chianti area for a unique experience. Enjoy the view of the beautiful hills covered by vineyards and have a fantastic dinner in a farm house, accompanied with Chianti wine. Return late evening at hotel. Overnight in Florence.
Meals : Breakfast, Dinner

Day 4 - Pisa

Where we visit : Pisa
After breakfast, meet your expert driver guide and continue to Pisa. Here, meet you local guide and visit the city. Pisa is most famous for its Leaning Tower, but the old Maritime Republic offers incredible sights like Miracles’ square, the beautiful Battistero and many other masterpieces. At the end of the excursion, proceed to Cortona, where you will spend the next 2 nights. Dinner will be served in a typical restaurant. Overnight in Cortona.
Meals : Breakfast, Lunch

Day 5 - Cortona

Where we visit : Cortona
After breakfast, start your unforgettable cooking experience in Cortona with your local expert. Cortona is a small charming town in the Valdichiana, in southern Tuscany. 
The city, enclosed by stone walls dating back to Etruscan and Roman times, sits on the top of a hill about 600 meters above sea level. This dominant position over the valley offers a spectacular view from all over the town of the surrounding valley and even Lake Trasimeno. IN the morning, you will have the possibility to visit the fresh market to learn about the local ingredients, then you will have an exciting cooking class to learn the secrets of Tuscan cuisine. Then, you will eat what you have prepared with your own hands. Evening at leisure. Overnight in Cortona.
Meals : Breakfast, Lunch

Day 6 - Assisi & Perugia

Where we visit : Assisi
Breakfast In the morning meet your driver guide and proceed to Assisi, where you will have free time to discover the town. Continue to Perugia. Your lunch will be served in a nice farm house in the countryside. Upon arrival in Perugia, meet your guide for a visit. At the end, continue to Rome. Your dinner will be served at hotel.
Meals : Breakfast, Lunch, Dinner

Day 7 - Time to Say Arrivaderci!

Where we visit : Rome
In Rome, we conclude our services. A complimentary transfer to airport or railway station in Rome is included in this package. Should you like to have additional options in Italy post-tour, we would be delighted to provide you with some unique suggestions and assist you in anyway that we can.
Meals : Breakfast




Tour Highlights and What's Included

  1. Bus As Per Itinerary Tour Escort / tour host Welcome Cocktail
  2. 3 Nights In Florence
  3. 2 nights in Cortona
  4. 1 night in Rome
  5. 2Dinners, Wine included
  6. 1 Dinner in Chianti with wine tasting Cooking class in Cortona + 1 lunch, wine included
  7. 1 wine tasting with cheese and salumi in Siena
  8. Walking Tour Of Florence With Accademia, entrance fee included
  9. Visit of Siena And free time in San Gimignano
  10. Visit of Pisa Visit of Perugia and free time in Assisi
  11. Departure transfer from Rome hotel to FCO or railway station
  12. Luggage Handling At Hotel

What's Not Included

  1. Optional excursions during your tour
  2. Travel Insurance
  3. Arrival transfer
  4. Porterage at airport on arrival
  5. City Tax( 4€ per person per night, to be paid locally. The amount may change according to local policy ) Tips
  6. Beverages and meals not mentioned in the program

Sites and Locations Visited on this Tour

Pricing & Availability

Please contact us today by either phone or email for assistance with this booking.
Email :
Toll Free : 1-866-779-2565


Hotel Berchielli

A Florentine jewel the Hotel Berchielli has been welcoming visitors since 1890. Timeless elegance and sophisticated surroundings enriched with stained glass windows, chrome and wrought iron works by local craftsman, fine marbles and stone along with breathtaking views over the river Arno, Ponte Vecchio and SS Apostoli all combined with modern comforts make the Berchielli an ideal place to stay.

Hotel Pierre Florence

The hotel Pierre is located in a pedestrian only area of Florence, in a prime location that offers visitors sophisticated accommodations, fantastic buffet breakfast and knowledgeable and helpful staff. We have found over the years working with this hotel that they are truly one of the best in Florence for so many reason.

Hotel San Michele

Hotel San Michele is located inside of one of the oldest buildings of Cortona, the ancient Baldelli Palace, strategically located right in the heart of town. The Baldelli Palace is a 15th-century mansion restored according to its original features and considered by various guides a true example of Cortona's architectural splendour. The Italian Ministry of Art, declared the building hosting H

Hotel Villa Marsili

This impressive 18th-century residence is now a luxury hotel, which offers you spectacular views of the mountains, hills, and nearby Lake Trasimeno. You are guaranteed an outstanding service. Hotel Villa Marsili features original frescoes from the 14th-century church, which once stood on this site. It is set within the town walls of Cortona and boasts beautiful views across the picturesque town

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Client Testimonials

Dear Guiseppe and Jesse,
We just returned from our most wonderful vacation to Italy and wanted to first thank you for putting together such a wonderful trip, and second to provide some feedback for the future.

1. Hotel Sovestro in San Gimignano was wonderful. The staff were very friendly and helpful and made the first portion of our journey very stress free. They made us feel like we were part of their family. I would recommend it to anyone and would specifically ask for it if we were to make a return visit.

2. Hotel La Baia in Monterosso was nice and it's location was very good especially for us older folks humping luggage from/to the train station.

3. Hotel Lucchesi in Florence- what can I say expect FANTASTIC. The rooftop view at sunset is well worth it. Again very friendly and helpful staff. Would recommend it to everyone.

Wine Tour
Money well spent. We had a great time overall. The driver Mario was OUTSTANDING. He had lots of local knowledge as well as about winemaking. USE HIM AGAIN!!!

The various wineries we visited on tour:
Altesino- fantastic and they were not cheap on their pouring. Great experience.
Azienda Agricola Patrizia Cencion Sloaria- Again a great tour by one of the owner's daughters. We felt like we were the only thing on their mind although there were other customers there. A great way to complete the day.

Again we had a fantastic time and are very appreciative of everything you booked for us. We wish you continued success and if our travels should bring us back to Italy, we know who to call.

- Ron and Deb Crosby Read More


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