Explore beautiful Florence then head into the Tuscan countryside for food, wine and relaxation

Personalised journeys from start to finish

Every trip helps support Conservation

Every detail taken care of

  • Personalised journeys from start to finish

  • Every trip helps support Conservation

  • Every detail taken care of

Suggested places to visit

What's included

  • Luxury accommodation throughout
  • Private transfers
  • Private experiences focused around Italy's wonderful food and wine
  • Full support from your travel designer and concierge before, during and after your trip
Use this itinerary to inspire your bespoke journey

At a glance

Think of Italy and you think of food. It has long been considered to have some of the best, if not the best food in the world. From pasta and Parmesan to gelato and tirimasu, Italian food is simply irresistable and with every province, town and village having their own regional specialties, a trip to Italy is endlesslly fascinating, and very satisfying.

This ten-day trip takes you to the heart of Tuscany, an area known for its wonderful food, wine and beautiful countryside. Your culinary adventure starts in the magical city of Florence. Explore its Renaissance history at the Accademia Gallery, home to Michaelangelo’s David, the duomo and the outdoor sculpture gallery, Piazza della Signoria. You’ll also get to see how Italian gelato is made and taste a whole myriad of flavours – this is so much more than just ice cream.

You’ll then head to Cortona, where you’ll discover the wines of Montalcino and Montepulciano, two charming hilltop towns. It’s then time to unlock the secrets of Italian cooking with a hands-on class in a local restaurant where you’ll master the art of pasta making.

The final three nights of your trip will be spent at the beautiful Castello di Casole property. Explore the wineries of Chianti, go foraging for truffles and explore the medieval cities of Siena and San Gimignano – but be sure to set aside some time to simply soak up the views from the hotel’s infinty pool that looks out over the Tuscan countryside, a truly magical sight.

Example trip itinerary

Days 1-4


Flights & transfers


Private transfer to your hotel in Florence

Accommodation in Florence

Cathedral Santa Maria Del Fiore, Florence, Italy
Three nights in Florence Three nights in Florence

Surrounded by rolling Tuscan hills, the beautiful city of Florence is one of Europe's most enchanting and historically influential cities. If anywhere in the world can claim to have shaped modern Western consciousness, it is Florence's grand piazzas and palazzos. The world's greatest Renaissance artworks and sculpture can be found at every turn in the historical centre, an area that can be traversed on foot in under an hour but would infinitely longer to properly explore.

Classical Florence walking tour Classical Florence walking tour

Explore Florence’s Renaissance past with this guided walking tour of the city's historic centre. The Accademia Gallery is home to Michelangelo's ‘David’, one of the finest sculptures ever created, and though there are many copies across the city, this is the real deal. You'll also visit the church of Santa Maria del Fiore – the famous Duomo - to view Brunelleschi’s magnificent dome; the nearby Campanile of Giotto (bell tower); and Ghiberti’s enchanting ‘Gates of Paradise’, the door to the Baptistry. Continue to the Piazza della Signoria, centre of Florentine politics and home to a captivating outdoor sculpture gallery. Shopping, architecture and history will collide as you stroll over the Ponte Vecchio.

Gelato tasting Gelato tasting

This tour is all about gelato - Italian ice cream. Learn how gelato was invented, see how it is made on the premises of a gelato parlour, and naturally, lots of flavours will be tasted and compared.

Boat trip along the River Arno Boat trip along the River Arno

Glide along the Arno River, floating by the Uffizi and passing under the Ponte Vecchio. You'll see the city in a new way as you drift towards the Santa Trinita bridge and Carraia bridge as your guide recounts amazing stories about the city and its architecture.

The boat is steered manually by a Florentine ‘renaiolo’ (boat captain), meaning there is no engine noise. This wonderful experience on the river is also characterised by the absolute absence of city noise. The boat tour lasts about an hour, then you will hop ashore where your guide will continue showing the city’s monuments from different perspectives, ending with a visit to the Santa Croce church with the tombs of Michelangelo, Machiavelli, Galileo and Rossini.

Flights & transfers


Private transfer to your hotel in Cortona

Days 4-7


Three nights in Cortona Three nights in Cortona

Cortona is a small town located in the southern Tuscan province of Arezzo. Surrounded by stone walls and perched atop a hill, the town offers sweeping views out over the surrouning valley as far as the waters of Lake Trasimeno. Wander its cobbled streets, stop at one of its charming cafes for coffee or a glass of wine, or head out to visit the Girifalco Fortress.

Wine tour in Montalcino and Montepulciano Wine tour in Montalcino and Montepulciano

Montalcino is a beautiful hilltop town set within a full circle of fortified walls. Located in the Val d’Orcia National Park and surrounded by rolling hills and olive groves, it is home to an impressive fortress and is well known for its Brunello wine. You’ll also visit Montepulciano, one of the highest hill towns as 665m. It is filled with pretty squares and offers spectacular views across the surrounding countryside. It is famous for its Vino Nobile wines. In both towns you will visit wineries and enjoy tasting their beautiful wines.

Filling the pasta dough
Cookery class in Cortona Cookery class in Cortona

Learn how to cook like an Italian at this cookery class, held in a local restaurant in beautiful Cortona. You'll prepare a four-course Tuscan meal including a starter, pasta dish, main course and dessert. You'll be rewarded for your hard work as you sit down to enjoy the food you've made along with a glass of wine.

Flights & transfers


Transfer from Florence to your hotel in Tuscany

Days 7-10

Tuscan Countryside

Accommodation in the Tuscan countryside

Three nights in the Tuscan countryside Three nights in the Tuscan countryside

Rolling hills dotted with rustic farm houses, Medieval towns, dark green cypress trees and ranked vines, there are few views more quintessentially Italian than that across the Tuscan countryside. Spend your time here getting acquainted with an enviable culinary tradition, fine Chianti wines, beautiful towns and warm locals.

Truffle hunting Truffle hunting

Join in the fun of searching for truffles at a local farm, using trained dogs who will help sniff them out. You'll head into the woods where your guide will explain the techniques used to successfully find them. You'll then enjoy a truffle tasting and a light lunch.

Wine tasting in Chianti Wine tasting in Chianti

Explore the charming Chianti area, a place renowned for its red wines and rolling hills. Visit a local winery, walk among the vines and, of course, taste some delicious wine.

Medieval Tuscany tour: Siena and San Gimignano Medieval Tuscany tour: Siena and San Gimignano

Built on three steep hills and unchanged since medieval times, Siena is one of Tuscany’s most beautiful towns. Admire its major sites like the Piazza del Campo, where the famous horse race takes place every year, as well as explore quieter backstreets to appreciate Siena's complex and rich history. You will be introduced to the stunning Gothic cathedral, where you’ll enjoy a panoramic view from the Facciatone.

Continue on to San Gimignano, famous for its medieval skyscrapers, high walls and narrow streets that typify the image of a Tuscan hill town.

Flights & transfers


Private transfer to Florence airport

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A Foodie Adventure through Tuscany

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Every trip helps support Conservation.

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