Traditions of Tuscany Tour

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Discover the Traditions of Tuscany


Tuscany – It’s like a dazzling diamond in the rough. Its diverse landscapes are filled with vineyards, olive groves, quaint hilltop towns and medieval castles. But it is also the central point for the birth of the Renaissance. Few parts of the world can claim such an abundance of art, history, architecture, culture, food and wine, or so intense a range of natural splendor.

And Tuscany, like all of Italy is filled with numerous ancient traditions. Each city or village plays host to various colorful religious rituals, historical pageants, medieval-style tournaments, unique traditional spectacles, food festivals, and much more. But in addition, routine tasks are tied to tradition – the daily ritual of making bread or coffee, farmers producing prosciutto, wine or olive oil, or artisans working or honing their craft. And like everything in Italy, these traditions seek to bring people together with good food and good wine at the table.

Such is the rich culture and heritage Tuscany. It’s small towns and villages move to a slower rhythm of life, connected to tradition, daily ritual, and the seasons. Its character and essence is deeply tied to its past. In some places, time seems to have stopped.

Taste of Italy Tour
Taste of Italy Tour

On this small group tour, you’ll play witness to the magical allure of these cultural traditions.

You’ll see the best of Tuscany in an experience that includes major historical sites as well as off-the-beaten path destinations, and of course, participating in its traditions and savoring the delicious regional cuisine.

With numerous destinations and an itinerary that allows for personal time to explore, we’ll discover the legendary cities Florence, as well as iconic Tuscan towns like Montepulciano and the small hilltop village of Cortona. We’ll attend a local medieval jousting festival, visit wineries and an ancient olive oil mill. We’ll learn how to make traditional Tuscan cuisine and watch artisans practice their time-honored craft.

This is a fully-escorted tour with all of your accommodations, excursions & tours, transportation and most of your meals completely arranged and included. However, we’ve left you some flexibility for free time to just read a book, take a swim, meander the small villages we will be visiting, or do some shopping.

Our “TRADITIONS OF TUSCANY” Tour this fall is an exceptional combination of activities, food, wine, and excursions that will give you an in-depth exposure to the traditional Italian lifestyle and the culture of the Tuscany region.

Martha F

Book your trip NOW!!! I had the most delightful trip. Everything was arranged perfectly. They really listened to what I wanted and didn’t want in my itinerary. We went to places I never would have found on my own. Worth every penny/euro. I have been telling all my friends that want to travel to Italy about Vitalia.

Martha F


Catherine, I can’t thank you enough for all the information! Great advice and insights! Thank you for all the travel and restaurant info as well. I have a feeling this is going to make the difference between a good stay and a great stay! You’re providing a great service! Thank you so much. So exciting and looking forward to trying your recommendations in Rome!



Our first trip to Italy and it won’t be our last! We initially had to cancel our trip due to a family emergency but then were able to reschedule it 9 months later. Catherine was very understanding and helped us through everything. What could have been a disaster, turned into the trip of a lifetime. We could not thank her enough for making this trip such a memorable one!

Taste of Italy Tour

Tour Highlights

  • ​10 Days/9 Nights
      - 4 nights in Arezzo
      - 5 nights in the Tuscan Countryside
  • Step back in time at a medieval jousting festival
  • Participate in a "Contrada" dinner
  • ​Discover the hidden gems of Florence
  • Visit a local antiques fair
  • ​Watch local artisan demonstrations
  • ​Wander the quaint Tuscan villages
  • ​Tour a Pecorino cheese farm with tasting
  • Enjoy a hands on cooking lesson of traditional Tuscan cuisine
  • ​Savor incredible Tuscan delights during one of our many food excursions
  • ​Visit an ancient olive oil mill
  • ​Shop the vibrant local markets
  • ​Sip delicious wines while taking in the views


Day 1 - Arrival Day/ Benvenuto!

Welcome to Italy! After arriving to the Rome airport (FCO), the group will be met for our private transfer to Tuscany.

Rest and unpack

Night in Tuscany. (D)

Day 2 - Traditions of Arezzo

After breakfast we'll meet up with our local guide for a private tour of Arezzo; stopping to visit the Piazza Grande, the Cathedral, and several other highlights.

Our private guide will fill you in on the history of this Medieval city, its Etruscan roots, and all of its fascinating traditions.

After lunch, visit the Arezzo Antiques fair (Fiera Antiquaria), which is the oldest and largest fair of its kind in Italy. This busy and colorful market has always been considered the biggest and the most beautiful among all the outdoor antique markets placed in in the extraordinary settings of Piazza San Francesco, Piazza Grande, the Vasari Loggia, and along the street of the historical center - the Corso Italia

Hundreds of exhibitors offer locals and international visitors alike,  their art objects, furniture, jewels, clocks, books and antique prints, scientific and musical instruments, toys and all kinds of collectibles. For those who are not interested in antiquities, the fair offers a vast assortment of modern and vintage products as well.

Visiting the Antiques market can be the perfect opportunity to discover the history and artistic wealth of one of the most beautiful cities in Tuscany.

Enjoy the rest of the afternoon for some free time to continue to explore the fair, visit churches & museums, shop or just relax in the Piazza Grande with an aperitivo.

In the evening the group will enjoy a special dinner event. (B, D)

Day 3 - Traditions of the Giostra di Saracino

Today we will enjoy all the excitement and pageantry that surrounds this twice annual festival - The Giostra di Saracino!

We'll gather and join the crowds lining the main corso as we watch the the grand parade in all its colorful pageantry wind its way through the town's historic center to end at the jousting arena in the Piazza Grande. There will be drummers, fifers and flag throwers, noble families and of course, the knights.

Following the parade, we'll attend one of the most ancient traditions that Tuscans love to celebrate - the Giostra del Saracino, or Joust of the Saracen (Moor). The Giostra is a beautiful medieval festival that animates Arezzo every year with colors, sounds and flavors that dates back to a time long, long ago.

The event has its origins in the Middle Ages, and it can be considered an evolution of the military training exercises for knights. It was supposed to simulate battle: the knights practiced using their lance on a “puppet” who represented the bad guy.

In Medieval society, jousts and tournaments were the means to celebrate any special event and in Arezzo records indicate this particular one was very popular and repeated on special occasions.

And nowadays, the whole town turns up for this special festival in medieval costume to recreate the atmosphere of medieval Arezzo as each of the quarters of the city compete against each other in a joust (2 knights each) to win the coveted prize of the Golden Lance.

Night in Tuscany (B, L)

Day 4 - Traditions of Artisans & the Tuscan Kitchen

We'll spend the first half of the day visiting local artisans in their workshops, where you’ll meet the people behind century-old traditional handicraft and artisan products.  We'll have the opportunity to watch and interact with them as they craft.

Later in the day, roll up your sleeves for a hands-on cooking class where you will be learning to prepare a full multi-course traditional Tuscan dinner:  From appetizer, to pasta, main course (secondi or meat), and finally, dessert. At the end of the class we will sit down together to taste all the delicious food we have prepared during a nice dinner that will be enjoyed in the atmosphere of a wine-aging cellar.  (B, D)

Day 5 - The Tradition of Saints & Olive Oil

Today will be a full day of experiencing the local countryside life.

First we will visit one of the most famous sanctuaries of St. Francis of Assisi. Enjoy a tour with an opportunity to visit the gift shop with items made by the Franciscans such as honeys, chocolates, soap, & liqueurs.

After, visit an ancient olive oil mill with a tour, tasting & lunch with the owner.

Finally we'll stop in a quaint village that hasn't changed since the medieval ages.

After this amazing day, we'll transfer to our agriturismo villa set in the Tuscan countryside, for the next 5 nights.

(B, L, D)

Day 6 - Traditions of the Val D’Orcia & Pecorino Cheese

After breakfast at our agriturismo, we will depart for a tour of two of Tuscany’s most famous towns: Montepulciano & Pienza set in the Val d’Orcia – what many view as the “quintessential” Tuscany.

Montepuliciano – home of the famous Nobile di Montepulciano wines. Pienza – Birthplace of Pope Pius II. Pienza is also known for its many sheep farms producing the famous Pecorino cheese.

We'll have a cheese tasting at a local producer and then enjoy lunch with a view overlooking the Val d'Orcia.(B, L, D)

Day 7 - Traditions of Florence

This morning we will transfer to Florence - the birthplace of the Renaissance.

Upon our arrival you'll enjoy a private “Introduction to Florence” walking tour. On this 3-hour tour, we’ll be hitting all of the highlights while learning about the mystery, seduction, and history of Florence, which includes the Renaissance, its important noble families, and its famous artists.

We’ll uncover the many secrets and treasures found within the historical walls as this tour lays out the foundation of what made Florence the fascinating city it is today.

Spend the rest of the afternoon exploring this magnificent city with time to shop, visit art galleries or museums, or just soak in the vibrant life of one of the many piazze while having a caffè or spritz.

Return to our agriturismo in the evening.

(B, D)

Day 8 - Traditions of Cortona

Morning departure for Cortona, made famous by Frances Mayes’ book & movie “Under the Tuscan Sun”. Cortona which also has its roots in Etruscan history, is a quiet and romantic town nestled in the beautiful hills of the Val di Chiana in the province of Arezzo.

It is surrounded by a countryside planted with olive trees, in which lavish villas are surrounded by large gardens, and hosts many monasteries, churches and monuments. The 13th century town hall and clock tower are in one of Cortona's main squares, Piazza della Republica, and there are cafes nearby for enjoying the piazza life.

We'll have a gentle walking tour to explore this quaint town followed by a wine-tasting experience. Then it's lunch on your own - there'll be no shortage of excellent choices.

In the afternoon, enjoy some free time to shop Cortona’s fun & interesting shops, visit the Etruscan(MAEC) or small Diocese museums, peruse galleries, have a caffè in a local bar, sample some gelato or just wander the alleys and streets. (B, D)

Day 9 - Traditions of Chianti

After breakfast, our private driver will meet us at our accommodations to whisk us into the Chianti region! This region of Tuscany made famous by the red wine of the same name, is a beautiful area of terra-cotta-roofed towns and winding roads leading through miles of vineyards, with cypress and olive groves stitching sun-dappled rolling hillsides – this is classic wine country.

We'll stop at a local farm that produces olive oil, and wine. After our tour, we'll enjoy a typical lunch showcasing all their products, including of course, their Chianti Classic!  (B, L, D)

Day 10 - Departure Day

Breakfast is provided depending on your time of departure. We'll say our goodbyes.

Private transfer to Rome Airport (FCO).

Bid "Arrivederci" to Italy! could do an add-on tour of Rome or Venice.

Key: B = Breakfast / L = Lunch / D = Dinner​,  included

*Itineraries are subject to change. Vitalia Tours and its partners will strive to provide you with the best possible tour and experience. It is our intention to adhere to the outlined itinerary as published. However, please be advised that it may be occasionally necessary to substitute an activity due to events that cannot be predicted. Therefore, Vitalia Tours reserves the right to make changes in accommodations, tours or excursions, meals, and itineraries at any time should it become necessary or desirable.

This Tour Includes:

  • Small group size: Maximum of only 6-10 travelers
  • 4 Nights in Arezzo in a 16th c. Relais and winery farmhouse
  • 5 Nights in an agriturismo villa set in the Tuscan countryside
  • All breakfasts, buffet style
  • 4 Lunches
  • 8 Dinners
  • Regional wines with most meals
  • Private full-time tour escort and interpreter 
  • Private bus/van w/driver for our daily excursions
  • Guided walking tour in Arezzo
  • Guided walking tour in Florence
  • All excursions and entrance fees as outlined by the itinerary
  • Giostra di Saracino VIP seats
  • Cooking class
  • Artisan demonstrations
  • Winery tours and tastings
  • Cheese & olive oil tastings
  • Airport Transfers (From/To FCO)
  • Pre-trip information packet
  • Local VAT taxes and government fees, gas, highway tolls, city access licenses and permits, and parking fees​​​​

Not Included:

  • Airfare
  • Travel insurance*
  • Travel documents & fees: i.e. passport and visas (if required)
  • Any meals not outlined in the itinerary
  • Any telephone, cell, data & internet usage**
  • Items of a personal nature​
  • Travel-related expenses outside of the tour itinerary
  • Any food or beverage ordered by traveler that is not included or presented during meals including: wine and other alcoholic or non-alcoholic drinks & gelato
  • Any taxes on personal items purchased
  • Optional tips to guides, staff or drivers. These are not required and are given at your discretion.​

* We highly recommend purchasing trip insurance to protect your investment. This is to ensure that you are covered in the event of loss of deposit and cancellation fees, medical emergency or health expenses, personal accident, flight cancellation or delays and to protect your luggage against any loss or damage.​ ​​​​​​ ​

** There is free wifi at our accommodations


Dates: Choose your dates
10 Days/9 Nights

Where: Tuscany

Tour Cost: $3,995.00 USD per person/double occupancy
Single Supplement: $500 USD

Deposit: $1000.00 USD at time of booking to reserve your spot

Balance due: 60 Days prior to tour start

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