A Foodie Adventure through Tuscany
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
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Cathedral Santa Maria del Fiore in Florence
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Traditional Tuscan soup
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Getting lost amid the cobbled streets of Cortona
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Enjoying an authentic Italian cooking class
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View of Siena’s romantic, medieval town
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Vineyards in the Tuscan countryside
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Wine tasting at a local shop in Montepulciano
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
- Days 1-4 Florence
- Days 4-7 Cortona
- Days 7-10 Tuscan Countryside
- Days 1-4 Florence
- Days 4-7 Cortona
- Days 7-10 Tuscan Countryside
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.
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
Florence
Overview
Set amidst lush trees and terraced gardens, the Belmond Villa San Michelle enjoys the most perfect view over Florence from its hilltop position. Dating back to a 15th century monastery, the renaissance villa’s facade has been attributed to Michelangelo, as much a part of Italy’s heritage as the cathedrals and galleries down the hill. Today, Belmond Villa San Michele is recognised as one of the country’s finest boutique hotels.
Each of the 20 rooms and 25 suites are unique, with sumptuous antiques, along with cotto-tile flooring and bright Florentine textiles. Separate from the main building, the exquisite Limonaia Villa contains three suites located in the convent’s former orangery, all with incredible views. These can be connected together to create perhaps the most glamorous villa in Tuscany, a unique haven for families and groups of friends, or for a special occasion such as a wedding or exclusive party.
Belmond Villa San Michelle is naturally a favourite among honeymooners, however there are special services tailored towards family adventures, and world famous the cookery school is a destination in itself. A huge range of activities are on offer, such as exclusive historical tours and rafting under the Ponte Vecchio, and there is a complimentary shuttle to and from Florence itself. At the hotel, relax amongst the immaculate gardens and at the spa, swim in the panoramic pool or take part in one of the renowned culinary classes.
Dining options here include one of the best restaurants in Florence – the romantic La Loggia – and more laid back cuisine at the Pool Restaurant, each with their own bar, as well as the Cloister Bar in the old monastery.
→ Find out moreFlorence
Overview
A little north of the historic centre, the Four Seasons Hotel Firenze is an opulent oasis set within a walled 4.5 hectare (11 acre) park – the largest private garden in Florence.
The hotel is split between the main building – the 15th century Palazzo della Gherardesca – and a 16th century former convent. Original features abound, with ornate decorative flourishes, period oil paintings and antiques at every turn.
There are 116 rooms, including 44 suites, each individually finished with frescoes, friezes and hand-painted sculptures, all a symphony of silk, velvet and marble. Many enjoy Arcadian views out to the surrounding gardens while others look into the courtyard or over typically Tuscan streetscapes.
Services of a typically high Four Seasons standard and 37 rooms in La Villa are even attended to by a team of butlers. The spa is also one of the finest in the city.
The main restaurant, Michelin star winning Il Palagio, sits under vaulted ceilings in the main palazzo, as does the elegant Atrium bar, a spot for cocktails and delightful afternoon teas. By the pool, Al Fresco serves up lighter bites.
A selection of unforgettable dining experiences can be arranged, from intimate meals in the historic chapel or out in the garden, to an utterly extravagant dinner served on a private terrace atop the Ponte Vecchio bridge. Designed by Michelin-starred chef Vito Mollica this indulgent four-course affair is inspired by the boutique jewellers on the bridge and uses gold as an ingredient.
Further unique experience can be arranged, including rental of a new Ferrari or classic Alfa Romeo and Mercedes – all convertible, naturally – to explore the Tuscan countryside in style.
→ Find out moreFlorence
Overview
The Hotel Savoy could not be more centrally located if it tried, located on Florence’s Piazza della Repubblica, next to the Duomo, with all the famous attractions of the city within walking distance.
Interiors are the work of designer Olga Polizzi, combining sleek and contemporary Italian with the building’s historic form, along with some more playful touches throughout. There are 88 rooms and 14 suites, including the two bedroom Repubblica Suite and its spectacular view over the square, and the Brunelleschi and Signoria suites that each enjoy private steam rooms.
Hotel Savoy’s restaurant, Irene, is overseen by renowned chef Fulvio Pierangelini and offers authentic flavours using local seasonal products, with some light and healthy reinventions of Tuscan classics. During warmer months, guests can enjoy al fresco dining on the terrace and soak up the atmosphere.
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Make it mine
On Foot
Through Taste buds
By Boat
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.
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.
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.
Where you could stay
Tuscany
Overview
Tuscany is one of Italy’s most picture-perfect regions with its rolling hills, rows of vineyards and old stone buildings. Located with a 4,200-acre estate, the Belmond Castello di Casole is everything you would expect from a grand country residence.
The castle dates from the 10th century, when it was used to house political exiles from nearby Siena. Traditional construction methods and natural materials found on the estate were used during the restoration to ensure the castle maintains its authenticity and charm.
Despite its size, the castle has just 39 rooms and suites, giving it an intimate feel. Rooms have plenty of character with original wood-beamed ceilings and stone walls, luxurious fabrics and a mix of antique and contemporary furniture. Most have views of the Tuscan countryside, looking out over the estate’s vineyards and olive groves.
There are two restaurants with a focus on honest Tuscan food, so expect home-made pasta, organic vegetables and locally sourced fish and game. With over 100 acres of vineyards, this is the perfect place for wine lovers, and Tosca restaurant has a large wall displaying hundreds of vintages from leading wineries in Tuscany and around the world.
The former wine cellar now houses the spa and guests can relax and unwind with a treatment from a menu inspired by local ingredients such as rosemary, grapes and olive oil. Take a dip in the outdoor infinity pool and enjoy the views or take advantage of the activities on offer including cooking classes and truffle hunting.
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Discover more
Turn back time
Forage
Swirl & Savour
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.
