- Days 1-4Florence
- Days 4-7Cortona
- Days 7-10Tuscan Countryside
- Days 1-4Florence
- Days 4-7Cortona
- Days 7-10Tuscan Countryside
A Foodie Adventure through Tuscany
Sip and savour your way through the heart of Tuscany on this ten-day sojourn, discovering the magic of Florence before heading into the Tuscan countryside for food, wine and relaxation.
Trip highlights
- Uncover Florence's Renaissance history
- Get a behind-the-scenes look into making Italian gelato
- Taste traditional dishes paired to excellent wines in Cortona
- Unlock the secrets of Italian cooking with a hands-on class
- Visit the renowned wineries of Chianti
- Go foraging for truffles in the Tuscan Countryside
Our bespoke trips include
We design one-of-a-kind journeys incorporating luxury in all its forms. Our bespoke trips include:
- Luxury accommodation throughout
- Privately guided tours
- Private transfers
- Meticulously selected experiences
- Expertise and support from your Jacada Concierge
Itinerary in detail
Every Jacada trip is tailored to your personal preferences and interests. Below you’ll find a sample itinerary to inspire your own custom-designed journey.
Days 1-4
Fall in love with Florence
Think of Italy, and you think of food. It has long been considered to have some of the best, if not the best, cuisine in the world. From pasta and Parmesan to gelato and tiramisu, Italian food is irresistible. And with every province, town and village boasting distinct regional specialities, a trip to Italy is endlessly fascinating and immensely gratifying.
Surrounded by rolling Tuscan hills, the elegant 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
At every corner of its historic centre, turn to some of the world’s greatest Renaissance artwork and sculptures. While it is an area traversable on foot in under an hour, it would take you infinitely longer to uncover its secret wonders and little-known sights.
Where you could stay
Make it mine
On Foot
Through Taste buds
By Boat
Discover the treasures of classical Florence
Explore Florence’s Renaissance past through the city’s historic centre. The Accademia Gallery is home to Michelangelo’s ‘David’, one of the finest sculptures ever created, and while 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, the 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.
Sample silky smooth gelato
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, plenty of freshly made flavours will be tasted and compared.
Drift along the River Arno
Glide peacefully 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 fascinating tales about the city and its architecture. The boat is steered manually by a Florentine ‘renaiolo’ (boat captain), meaning no engine noise.
After the tour, hop ashore, where your guide will continue showing the city’s monuments from different perspectives, ending with a visit to the Santa Croce church, housing the tombs of Michelangelo, Machiavelli, Galileo and Rossini.
Days 4-7
Charming 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 surrounding 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.
Flavours of Cortona
Food
Wine
Join an immersive culinary class
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 alongside a glass of tasty wine.
Flit between wineries 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 in Italy. It is filled with pretty squares and offers spectacular views across the surrounding countryside. Montepulciano is famous for its Vino Nobile wines. In both towns, you will visit wineries and enjoy sampling their delicious wines.
Days 7-10
Wind down in the Tuscan Countryside
Rolling hills dotted with rustic farmhouses, 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, exquisite Chianti wines, beautiful towns and warm locals.
Discover more
Turn back time
Forage
Swirl & Savour
Siena and San Gimignano: relive medieval Tuscany
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.
Go 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.
Sip fine wine 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.
Why book with Jacada
Personalised design
We’ll plan your trip around your personal interests, tastes and preferences, providing honest advice based on first-hand knowledge.
Authentic experiences
Our expert guides and brilliant Concierges are hand-picked for their ability to bring your destination to life with care and passion.
Positive Impact
We seek out unforgettable experiences that benefit both local communities and the environment.
We had a once in a lifetime trip to Italy! Everything was curated and planned perfectly.
