Ultra Luxury Tuscany Holidays
Some of the most prominent historic and cultural attractions of the region are found in the cities of Florence and Pisa. The ideal start to any tour of Tuscany, these two cities are so full of art, historical monuments, and beautiful sights, you’ll need at least a few days in each to do them justice.
Florence is home to Michelangelo’s David sculpture, as well as the Duomo cathedral. While the iconic Leaning Tower, Clock Palace, and The Square of Miracles await in Pisa. Lovers of Renaissance art and architecture are sure to be in sightseeing heaven as they explore the pretty squares and winding streets of both cities.
Foodies will find there’s not a single village, town, or city in Tuscany that doesn’t offer truly exceptional cuisine. It’s difficult to pick favourites, as there are so many gourmet hotspots dotted across the countryside and urban areas alike. However, Chianti is a great place to start, with towns such as Greve holding weekly markets where you can pick up local cheeses and cured meats. And of course, the famed Chianti wine.
It’s not all vineyards and green valleys though. Fans of the seaside are going to love the Tuscan coastline, which stretches for 500 km. It boasts everything from quaint fishing villages and family-friendly beaches to quieter pebble and rock stretches.
Some of the most prominent historic and cultural attractions of the region are found in the cities of Florence and Pisa. The ideal start to any tour of Tuscany, these two cities are so full of art, historical monuments, and beautiful sights, you’ll need at least a few days in each to do them justice.
Florence is home to Michelangelo’s David sculpture, as well as the Duomo cathedral. While the iconic Leaning Tower, Clock Palace, and The Square of Miracles await in Pisa. Lovers of Renaissance art and architecture are sure to be in sightseeing heaven as they explore the pretty squares and winding streets of both cities.
Foodies will find there’s not a single village, town, or city in Tuscany that doesn’t offer truly exceptional cuisine. It’s difficult to pick favourites, as there are so many gourmet hotspots dotted across the countryside and urban areas alike. However, Chianti is a great place to start, with towns such as Greve holding weekly markets where you can pick up local cheeses and cured meats. And of course, the famed Chianti wine.
It’s not all vineyards and green valleys though. Fans of the seaside are going to love the Tuscan coastline, which stretches for 500 km. It boasts everything from quaint fishing villages and family-friendly beaches to quieter pebble and rock stretches.
Some of the most prominent historic and cultural attractions of the region are found in the cities of Florence and Pisa. The ideal start to any tour of Tuscany, these two cities are so full of art, historical monuments, and beautiful sights, you’ll need at least a few days in each to do them justice.
Florence is home to Michelangelo’s David sculpture, as well as the Duomo cathedral. While the iconic Leaning Tower, Clock Palace, and The Square of Miracles await in Pisa. Lovers of Renaissance art and architecture are sure to be in sightseeing heaven as they explore the pretty squares and winding streets of both cities.
Foodies will find there’s not a single village, town, or city in Tuscany that doesn’t offer truly exceptional cuisine. It’s difficult to pick favourites, as there are so many gourmet hotspots dotted across the countryside and urban areas alike. However, Chianti is a great place to start, with towns such as Greve holding weekly markets where you can pick up local cheeses and cured meats. And of course, the famed Chianti wine.
It’s not all vineyards and green valleys though. Fans of the seaside are going to love the Tuscan coastline, which stretches for 500 km. It boasts everything from quaint fishing villages and family-friendly beaches to quieter pebble and rock stretches.
Tuscany is renowned for its food and wine. And roasted meats and red wines are just some of the treats that will make you feel like a true Tuscan.
Tempt Your Tastebuds
Tuscany is renowned for its food and wine. And roasted meats and red wines are just some of the treats that will make you feel like a true Tuscan.
From green hills and forests to ancient towns and sandy beaches, Tuscany's diverse landscapes are simply breathtaking. And you won’t be able to avoid falling in love with them!
Divine Nature
From green hills and forests to ancient towns and sandy beaches, Tuscany's diverse landscapes are simply breathtaking. And you won’t be able to avoid falling in love with them!
A wealth of Renaissance art is on show in Tuscany’s capital, Florence. Marvel at Michelangelo’s David at the Galleria dell'Accademia and Botticelli’s Birth of Venus at the Uffizi Gallery.
Art Lover’s Rejoice
A wealth of Renaissance art is on show in Tuscany’s capital, Florence. Marvel at Michelangelo’s David at the Galleria dell'Accademia and Botticelli’s Birth of Venus at the Uffizi Gallery.
Start Your Journey
Before you book your holiday to Tuscany, discover more with these insightful reads and holiday ideas.
10 reasons to book with Winged Boots
You'll soon understand why we're a leading luxury travel specialist
22 quotes from our customers about Winged Boots
Who could say it better than the very people who have experienced the complete Winged Boots travel service?
Europe
Timeless elegance, rich history, and unparalleled luxury - Europe is a tapestry of breathtaking landscapes, world-class cuisine, and cultural wonders. From Parisian romance to Tuscan vineyards, experience the extraordinary.
Italy
Experience Italy's timeless allure, where centuries of history, art and superb cuisine meet modern life. From ancient ruins to charming piazzas, indulge in Italian living at every turn and discover its hidden treasures.
Our Half-Day Wine Tasting Experience Through An Exquisite Italian Vineyard
Indulge in Italy’s finest wines on this Tuscan countryside tour. Explore vineyards near Siena, learn about winemaking, taste exquisite wines, and enjoy a seasonal lunch. Hotel pickup and drop-off included for a seamless experience.
next trip today
Our expert team of personal travel managers are ready to craft your perfect journey. From business trips to luxury leisure holidays, simply put your pin in the map, and we’ll make it happen.
START A WHATSAPP CHATLuxury Tuscany Hotels
Luxury Tuscany Hotels
Rosewood Castiglion del Bosco
Montalcino, Tuscany
Nestled in a private vineyard, Rosewood Castiglion del Bosco exudes authentic Italian charm. Stay in exquisite villas, savour world-class dining, and immerse yourself in the relaxed Tuscan lifestyle of this historic estate.
Nestled in a private vineyard, Rosewood Castiglion del Bosco exudes authentic Italian charm. Stay in exquisite villas, savour world-class dining, and immerse yourself in the relaxed Tuscan lifestyle of this historic estate.
Nestled in a private vineyard, Rosewood Castiglion del Bosco exudes authentic Italian charm. Stay in exquisite villas, savour world-class dining, and immerse yourself in the relaxed Tuscan lifestyle of this historic estate.
Castel Monastero
Siena, Tuscany
Cradled in the heart of Chianti’s rolling hills, Castel Monastero blends historic charm with Tuscan elegance. Picture luxurious suites, artisanal-style dining, and lush vineyards. This is where Italy’s beauty and rich past takes centre stage.
Cradled in the heart of Chianti’s rolling hills, Castel Monastero blends historic charm with Tuscan elegance. Picture luxurious suites, artisanal-style dining, and lush vineyards. This is where Italy’s beauty and rich past takes centre stage.
Cradled in the heart of Chianti’s rolling hills, Castel Monastero blends historic charm with Tuscan elegance. Picture luxurious suites, artisanal-style dining, and lush vineyards. This is where Italy’s beauty and rich past takes centre stage.
16 tips for a perfect European ski break
There's nothing quite like a ski trip, and once you fall in love with the sport, there's no going back. A successful ski trip requires keen planning though. Read on for our top tips.
Six alternative destinations to visit on your next European break
Been to Ibiza, Paris, Rome, Athens, Istanbul or the Algarve? It's time to try something different...
Tuscany in a nutshell
Tuscany is one of the most celebrated wine regions in Europe. So you couldn’t possibly leave without sampling the dry red wines that it’s known for. There are countless wine tours and tasting sessions available across Tuscany. And whichever you pick, you’ll not only get to sample wines, but also learn about cheese pairing and just how breathtaking the region’s landscapes are.
Nothing compliments a good Tuscan wine like some Pecorino Toscano. A speciality of this corner of Italy, this cheese is made using 100% whole sheep milk and is renowned for its creamy flavour. Book a tour at Fattoria Pianporcino, a dairy farm in Pienza, to learn more about how the cheese and other pecorinos are produced.
Tuscany has a global reputation for being a hub for Renaissance art and architecture. Its capital, Florence, is home to some of the most famous pieces of art in the world, including Michalengelo’s David. Also visit the Duomo cathedral and the Uffizi Gallery to view Botticelli’s works. Another fantastic city of culture is Pisa, with the Leaning Tower a top landmark to tick off your sightseeing list.
Throughout the year in Tuscany there are festivals and carnivals as old as the Etruscans. One of the most popular is the Giostra del Saracino, or the Saracen Joust, held in Arezzo's Piazza Grande twice a year. Expect colourful processions, knights’ tournaments, and plenty of medieval fare.
A day trip to Cinque Terre is practically mandatory, with each of these five seaside towns having their own wonderful features and unique personality. Get ready to fall in love with the sight of clusters of colourful houses perched high above the water, quaint streets and harbours, and terraced vineyards. An unmissable feature for couples is Via dell’Amore. This stunning walkway links the villages of Riomaggiore and Manarola and is where you can make your love everlasting with a lock or inscription on the rock face.
For a family-friendly day out at the seaside, the beaches of the Pisan coast are hard to beat. Some of the best include Marina di Pisa, Tirennia, and Calambrone. Those at Maremma are especially known for their clear waters and sandy stretches.
Not quite beaches, the thermal springs and pools of Saturnia are a must for relaxation lovers. Believed to have therapeutic properties, the waters remain at a constant 37.5 degrees, meaning the baths can be visited all year round.
Tuscany is one of the most celebrated wine regions in Europe. So you couldn’t possibly leave without sampling the dry red wines that it’s known for. There are countless wine tours and tasting sessions available across Tuscany. And whichever you pick, you’ll not only get to sample wines, but also learn about cheese pairing and just how breathtaking the region’s landscapes are.
Nothing compliments a good Tuscan wine like some Pecorino Toscano. A speciality of this corner of Italy, this cheese is made using 100% whole sheep milk and is renowned for its creamy flavour. Book a tour at Fattoria Pianporcino, a dairy farm in Pienza, to learn more about how the cheese and other pecorinos are produced.
Tuscany has a global reputation for being a hub for Renaissance art and architecture. Its capital, Florence, is home to some of the most famous pieces of art in the world, including Michalengelo’s David. Also visit the Duomo cathedral and the Uffizi Gallery to view Botticelli’s works. Another fantastic city of culture is Pisa, with the Leaning Tower a top landmark to tick off your sightseeing list.
Throughout the year in Tuscany there are festivals and carnivals as old as the Etruscans. One of the most popular is the Giostra del Saracino, or the Saracen Joust, held in Arezzo's Piazza Grande twice a year. Expect colourful processions, knights’ tournaments, and plenty of medieval fare.
A day trip to Cinque Terre is practically mandatory, with each of these five seaside towns having their own wonderful features and unique personality. Get ready to fall in love with the sight of clusters of colourful houses perched high above the water, quaint streets and harbours, and terraced vineyards. An unmissable feature for couples is Via dell’Amore. This stunning walkway links the villages of Riomaggiore and Manarola and is where you can make your love everlasting with a lock or inscription on the rock face.
For a family-friendly day out at the seaside, the beaches of the Pisan coast are hard to beat. Some of the best include Marina di Pisa, Tirennia, and Calambrone. Those at Maremma are especially known for their clear waters and sandy stretches.
Not quite beaches, the thermal springs and pools of Saturnia are a must for relaxation lovers. Believed to have therapeutic properties, the waters remain at a constant 37.5 degrees, meaning the baths can be visited all year round.
Tuscany is one of the most celebrated wine regions in Europe. So you couldn’t possibly leave without sampling the dry red wines that it’s known for. There are countless wine tours and tasting sessions available across Tuscany. And whichever you pick, you’ll not only get to sample wines, but also learn about cheese pairing and just how breathtaking the region’s landscapes are.
Nothing compliments a good Tuscan wine like some Pecorino Toscano. A speciality of this corner of Italy, this cheese is made using 100% whole sheep milk and is renowned for its creamy flavour. Book a tour at Fattoria Pianporcino, a dairy farm in Pienza, to learn more about how the cheese and other pecorinos are produced.
Tuscany has a global reputation for being a hub for Renaissance art and architecture. Its capital, Florence, is home to some of the most famous pieces of art in the world, including Michalengelo’s David. Also visit the Duomo cathedral and the Uffizi Gallery to view Botticelli’s works. Another fantastic city of culture is Pisa, with the Leaning Tower a top landmark to tick off your sightseeing list.
Throughout the year in Tuscany there are festivals and carnivals as old as the Etruscans. One of the most popular is the Giostra del Saracino, or the Saracen Joust, held in Arezzo's Piazza Grande twice a year. Expect colourful processions, knights’ tournaments, and plenty of medieval fare.
A day trip to Cinque Terre is practically mandatory, with each of these five seaside towns having their own wonderful features and unique personality. Get ready to fall in love with the sight of clusters of colourful houses perched high above the water, quaint streets and harbours, and terraced vineyards. An unmissable feature for couples is Via dell’Amore. This stunning walkway links the villages of Riomaggiore and Manarola and is where you can make your love everlasting with a lock or inscription on the rock face.
For a family-friendly day out at the seaside, the beaches of the Pisan coast are hard to beat. Some of the best include Marina di Pisa, Tirennia, and Calambrone. Those at Maremma are especially known for their clear waters and sandy stretches.
Not quite beaches, the thermal springs and pools of Saturnia are a must for relaxation lovers. Believed to have therapeutic properties, the waters remain at a constant 37.5 degrees, meaning the baths can be visited all year round.
frequently asked questions
When is the best time to travel to Tuscany?
Winters are mild and this time of the year can be perfect for sightseers as there are less tourists in popular spots like Florence, Pisa, Lucca, and Siena. Florence and Siena also hold Christmas markets at the beginning of December, so they’re perfect for getting you in the festive spirit.
Are direct flights available to Tuscany from the UK?
What are some interesting facts about Tuscany?
next trip today
Our expert team of personal travel managers are ready to craft your perfect journey. From business trips to luxury leisure holidays, simply put your pin in the map, and we’ll make it happen.