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Tuscany and the Wine Country

Florence, San Gimignano, Chianti, Pienza, Montalcino, Montipulciano, Arezzo, Cortona and Siena
$6600/person


This tour is priced for a minimum group of 8 people. Per person. Double occupancy. Please inquire about a single-supplement room price. ​Get a group together and let's get something on the calendar! 

​Please join Tour Director Sandy Gregory for this wonderful adventure through Italy, or contact us to help you create your own independent travel experience in Italy with our Concierge Travel Services. 
Join us to experience la bella vita. We know that the decision to spend your valuable time and money traveling is a costly investment. Call on us to create the perfect guided or independent travel custom itinerary. We work closely with groups who want a personalized, private experience. Che Bella Tours is Creative Travel, and the partner you want when planning a remarkable family vacation, destination wedding, trip of a lifetime or other special occasion. Contact us for more information. We'll be happy to send you the detailed itinerary for this tour. 
Day 1. Arrive in Florence.
Bienvenuti a Firenze! 
Rooms are usually available after 2 pm, so your Tour Director will get you oriented with the city and direct you to some great lunch choices.

The afternoon is yours to explore as everyone gets settled. We’ll then get together for passagiatta, or the evening walk, on our way to our private rooftop sunset toast looking over the city of Florence and enjoy our 
Included Welcome Dinner.


​Day 2. A Day in Florence
Florence is one of the most preserved Renaissance cities in the world. Boasting over 40% of the world’s great masterpieces, the city is considered the art capital of Italy. The city is compact and walking is definitely the best way to see it. Our walking tour will take us to the small, but poignant Galleria dell’Accademia. There, we’ll learn about the Renaissance, highlighting Michelangelo’s life and masterpieces, including his David, “Unfinished” Slaves and Pieta. We’ll then move on to the Duomo Santa Maria del Fiore, Dante's House and Piazza della Signoria, finishing on the Ponte Vecchio. 

The afternoon is yours to explore Florence. I’d like to invite you to walk with me and spend all the time you need to browse the city’s couture stores and famous San Lorenzo market, where you’ll be able to pick up a great leather jacket, stock up on colorful scarves and purses, or wander through the Mercado Centrale for typical Tuscan delicacies. And don’t forget those shoes! Or you might want to use this time to dig into the vast art collections of the Uffizi Gallery, Palazzo Vecchio, Pitti Palace or the Medici Chapel. You also might want to spend the afternoon at the Boboli Gardens, the Galileo Museum, Palazzo Vecchio or go on a gelato crawl ... then burn off those calories by climbing the Duomo or Giotto’s Campanile. 


Day 3. Florentine Delicacies 
Today we’ll enjoy a private tour with a different angle on Florence - wine and food. As we wind our way through this historic city, our guide will craft a tale about the role wine and food have played in the history of the Florentines. We’ll begin at one of the most beautiful cafès in the city to learn how local Florentines do breakfast, learn about coffee and try a traditional schiacciata. We’re then off to the local market where we’ll try a selection of tasty Tuscan cheeses and salami, as well as prosciutto, the famous Tuscan ham, and a variety of olive oils while you sip a quality Tuscan wine. As we wind through medieval Florence, we’ll sample a taste of lampredotto, tripe sandwiches, and porchetta, the most famous Florentine street foods, paired a glass of good Chianti. We’re then on to Procacci to enjoy more wine varietals with October’s Italian treat - truffles. We’ll then finish with gelato master who will bring us back in to the laboratory to learn a bit about how they make gelato. With lsamples, of course! 

Optional: Tuscan Wine School
Enjoy a 2 hour wine-tasting experience, where their sommelier will walk you through the fascinating tradition of Tuscan wine making and olive oil production. You will learn about the wine regions and the most important grapes of the area. You’ll enjoy some great Tuscan wines, including Vernaccia di San Gimignano, Chianti Classico, Nobile di Montepulciano, Brunello di Montalcino and finish with Vin Santo. I have been working with Rebecca and her group for years and they do a great job. It’s a fun way to start your evening.

Dinner tonight is on your own - if you have room


NEW! Dig a Little Deeper Series. Need more? Inquire about one of our private optional tour excursions in Florence. Pricing will be based on number of participants: 

The Medici Tour. This afternoon tour examines the relationship between power and art, the political upheavals gave birth to the artistic revolutions of the Renaissance, and the humanistic impulse of one of the most interesting families in history, the Medici. We'll focus on the history and patronage of the family, visiting several key sites connected with them, including the Palazzo Vecchio, Medici Chapels and Medici Palace. We'll trace the family from the era of the Republic to the era of the duchy, and their rise from rich merchants to rulers of a kingdom. We will examine the work of Michelangelo, in the family chapel he created, which includes the tombs of Lorenzo il Magnifico and brother Giuliano.

Made in Florence Artisans Tour and Shopping. The Florentine tradition of producing artisanal goods has been in existence for centuries and remains one of the cornerstones of Florence's visual and social history. This unique tour supports local artisans and celebrates the tradition of craftsmanship. Florentine leatherworkers, silversmiths, shoemakers, and milliners continue to practice their crafts building upon methods passed down through generations. We will visit the private workshops of these distinguished individuals, providing a behind the scenes look at the current state of artisan production. Along the way, your guide will guide you to fashion items, jewelry, ceramics, culinary products and much more…
 
Galileo and Science in Renaissance Florence. The rule of the Medici family in Renaissance-era Florence led to an explosion of scientific progress, especially astronomy. Under their rule, Florence became a shining beacon for experimentation, which the Roman church was frantically trying to suppress with the Inquisition. At the same time, humanism, stemming from the study of ancient Greek and Latin texts, was a new way of thinking about a man’s place in the world, and became a recurring theme in Renaissance literature, art and society. This tour includes a visit to the Museo Galileo, where the most important Medicean collections of scientific instruments are preserved. After visiting the museum, we will head to the center of town in order to trace the role of humanism in Renaissance Florence; be it through a delve into the poetry of Dante and Petrarch, a discussion of the drastic changes in the art of the period or of the growing interest in the study of the traditional liberal arts.

Fresco Workshop. Learn the Fresco technique and create your own masterpiece with a local artist. Fresco means fresh in Italian, and is the revered art of painting on fast-drying damp plaster with water based pigments. During this 3-hour workshop, you'll learn basic fresco technique from a local Florentine artist, who will take you through the steps of preparing a surface, drawing and transferring a drawing (cartoon), and finally applying the paint. Be warned. It's difficult. It's also a lot of fun and you'll go home with our own hand-made fresco painting. Along the way, you'll gain a deeper, tactile understanding of the development, creation, and legacy of Renaissance art.

Optional Opera Experience:
1. The Three Tenors & Dinner: Featuring a trio of vocal talents as well as a superbly prepared Italian meal. Audience goers will be dazzled by a performance that evokes the famous concert of the 1990s which featured Luciano Pavarotti, Plácido Domingo and José Carreras. Including many well-known songs, the concert comfortably blends Neapolitan songcraft with Italian arias drawn from some of the most popular operas in the country.

2. Opera Florence is a delightful evening’s entertainment featuring some exciting and talented vocalists, the program includes operatic works for a soprano, a mezzo-soprano, a tenor, a baritone or a bass. The concert constitutes a thrilling odyssey through some of the best-loved arias drawn from Italian opera, including works by Giacomo Puccini, Gioacchino Rossini, Giuseppe Verdi and Wolfgang Amadeus Mozart. With such superb musicians plus a fabulously ornate and historic setting, there can be no finer way for music lovers to enjoy a selection of the best in Italian opera when staying in the city.
Day 4. Florence to the Villa.
This morning we head to our Tuscan villa. 
Enroute, you’ll make a short stop at the American WWII Memorial Cemetery. This is a well maintained and respectful cemetery just outside of Florence, with manicured lawns, acres of white crosses and a few stars. The presentation is very respectful of our soldiers, serves as a remembrance of the price of freedom, and captures the spirit of the sacrifices made by the men and women who fought during WW2. The American Battle Monuments Commission does an excellent job of maintaining the grounds and the attendant on duty is always
​
L’arte di non fare niente. This is a wonderful Italian expression which translates as “the fine art of doing nothing.” In Italy, the art of doing nothing - and doing it well - is what vacation is all about. Enjoy the day relaxing. Lounge by the pool. Hike the vineyard. Grab a bike. It’s the perfect day to enjoy your villa. Lunch is available for you at the villa or you can bike, walk or head to nearby San Gimignano.

THE VILLA. Our villa is in the hills of Tuscany near San Gimignano. It’s a beautiful location with swimming pool, sauna and steam, and air-conditioned rooms. Breakfast is included in your price. We'll enjoy our included dinner, a tasting menu that highlights the flavors of the local produce, olive oil and wines. 


Day 5. San Gimignano, Wine-tasting Tour and Lunch in a Castle 
Today we visit the Tuscan town of San Gimignano, where time seems to have stood still. As you stroll through the winding streets, you’ll see what Tuscan hill towns looked like in the Middle Ages. We’re then on for an afternoon of wine tasting and included lunch in a castle. You’ll be treated like royalty at this small, family-run winery where you will visit the cellars, historic rooms and finish in their beautiful dining room.  

We'll return to the villa in the late afternoon. You can arrange for a steam or sauna, a massage, hike the vineyard and watch the sunset. Dinner tonight is on your own at the villa or in nearby San Gimignano. 
Day 6. A Day of Winetasting: Montalcino, Montepulciano and Pienza
Montalcino is a small walled town that is perched on top of a hill in Val d’Orcia and the home of the famous wine called Brunello. Brunello wines are considered one of Italy’s best and most expensive wines and is the only Tuscan wine that is made from 100% Sangiovese grapes. At our winery, we’ll be pleasantly immersed in the harmonies of Mozart music, played across the rows of vines through a hundred speakers, in ecstasy with nature. This is not something born to amaze the visitor, but rather the result of serious agronomic and scientific research concerning the beneficial effects of musical frequencies on the vines (Vitis Vinifera), supported by the Universities of Florence and Pisa, the center of agronomic research of Arezzo, and sponsored by the prestigious company BOSE, specialized in the production of audio systems.

Montepulciano is a lovely Etruscan Tuscan town. As early as in Roman times, the Gauls were known to have travelled all the way down in the Italian peninsula to Montepulciano to enjoy their excellent red wines. Montepulciano reached its peak of fame and splendour in the 16th Century, with estates designed by the most famous Florentine architects. Their wines were served at the table of popes, cardinals and the Medici family and gained the fame of a very elegant “noble” red wine called Vino Nobile di Montepulciano, which literally means Noble Wine from Montepulciano. Your walking tour will include the most beautiful architectural gems such as the Duomo, the Palazzo Pubblico, Palazzo Contucci and Tarugi overlooking Piazza Grande before we enjoy an including wine tasting and lunch. 

After lunch we're on to one of my favorite Tuscan hilltowns, Pienza. It's one of the prettiest little towns in Italy and the perfect ending for those of us who 
love history, architecture and food. The city wall offers a wonderful walk around the perimeter of the town - perfect for our afternoon passagiata.  You'll then have time to explore the layrinth of streets and find a little cafe or restaurant for dinner (not included) before we are transferred back to the villa.

Day 7. A Day at the Villa 
Enjoy a day at the villa and think about joining one of our optional activities:
- a day in San Gimingnano
​- Cinquecento! A guided driving tour of the Tuscan Countryside in a vintage Fiat 500
- hike the vineyards
- enjoy a spa treatment
- enjoy a cooking lesson in nearby Certaldo
​
Dinner tonight is on your own at the villa
Day 8. Arezzo and Cortona
Today we visit Arezzo and Cortona. We’ll start with a walking tour of Arezzo. Arezzo is a medieval city with a beautiful historic centre immortalized by Roberto Benigni in the movie Life is Beautiful.. It’s also known for the production of gold jewelry and of the famous artist, architect and art historian Giorgio Vasari. We'll enjoy a wonderful included lunch in the square. 

​We’re then our way to Cortona, one of the oldest hill towns in Tuscany. It's famous for its international athmosphere and Etruscan Museum. We'll enjoy a walking tour through the town before enjoying a jewelry-making demonstration where the master will demonstrate the ancient art of lost wax casting. You’ll have some time to explore the town and experience passeggiata - the evening walk - before we head to our included dinner in Cortona. Transfer back to the villa after dinner.​

Day 9. 
Siena and Farewell Dinner Overlooking The Campo
Transfer from the villa to Siena. 
Our private walking tour we’ll be taking us through the winding streets of the contrade (neighborhoods) to learn about the passion of Siena’s famous Palio horse race and the striped grandeur of St. Catherine’s Cathedral. You’ll have the afternoon for lunch on your own and to stroll through the winding streets and absorb the city’s rich medieval history. It’s a fun, vibrant town with some very good shopping. Beautiful ties, paper, fabrics, terracotta, gold jewelry, tapestries and wine are all produced locally in Siena. Via di Città is the main street of the city and has plenty of good shops selling bags, purses and leather items. 

Special for Che Bella Guests - a rooftop celebration. As the sun sets over Tuscany, we’ll head to the rooftop towering over the Campo to enjoy a buffet dinner of local Tuscan delicacies and of course, lots of wine - all while being seranaded by a guitarist and surrounded by breathtaking views. Please note that we can make arrangements to have a variety of Tuscan wines from various wineries available to you at this event to sample. After a buffet dinner and some dancing on the rooftop, we’ll be transfered back to our villa.

Day 10. Transfers back to Florence for Flights Out​

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  • Home
    • Sandy Gregory, Owner and Tour Director
  • WHERE WE GO
    • TOUR CALENDAR
    • CONCIERGE TRAVEL SERVICES
    • BOOK CLUB TOURS >
      • London and the English Countryside
    • ITALY >
      • Italian Dreams: Venice, Florence, Tuscany, Orvieto, Rome and the Amalfi Coast
      • A Taste of the North: Milan, Lake Como, The Cinque Terre and Bologna
      • Italy's Northern Lakes and Veneto Wine Road
      • Romantic Winter Getaway to Verona and Venice
      • PIEDMONT
      • Tuscany and the Wine Country
      • Siena's Palio & Tuscany
      • LE MARCHE, PERUGIA AND UMBRIA WITH THE PERUGIA CHOCOLATE FESTIVAL
      • Puglia, Naples and the Amalfi Coast
      • Sicily
      • Culinary Tours to Bologna, Florence and the Tuscan Countryside
      • Art Journaling in Tuscany
      • Destination Weddings: Italy
    • FRANCE
    • SPAIN
    • PORTUGAL
    • ENGLAND >
      • LONDON, WINDSOR, THE COTSWOLDS, BLENHEIM AND OXFORD
    • IRELAND & SCOTLAND
    • MARRAKESH
    • GREECE
    • GERMANY & AUSTRIA >
      • THE BEST OF GERMANY & AUSTRIA
      • The Passion Play 2020
      • CHRISTMAS SEASON IN GERMANY & AUSTRIA
    • PERU, Galapagos Islands and the Rainforest
    • THE MAJESTIC PARKS OF THE WEST
  • WHERE WE'VE BEEN
    • Photo Gallery
    • Trip Reports
  • Contact Us
  • The Bella Buzz