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Luxury Tuscany Holidays 2022 & 2023
Plan your dream Tuscany holiday with the help of our expert Personal Travel Managers. We offer Tuscany holidays from £695pp
Luxury Tuscany Holidays 2022 & 2023
Plan your dream Tuscany holiday with the help of our expert Personal Travel Managers. We offer Tuscany holidays from £695pp
Luxury Tuscany Holidays 2022 & 2023
Plan your dream Tuscany holiday with the help of our expert Personal Travel Managers. We offer Tuscany holidays from £695pp
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Better known as the darling of Italy, this region is one of the greatest in Europe for history, art and food. With traditions and buildings dating back to the Etruscans, the area is a charming mix of medieval-style villages and 21st century cities set into rolling green hills, mountains or quiet seaside bays. With so much going for it, you’re bound to find the perfect luxury holiday in Tuscany, no matter what your ideal getaway looks like.
The most famous of the area’s attractions are found in the culture capitals of Florence and Pisa. The ideal start to any tour of Tuscany these two cities are so packed with incredible art, historical monuments and beautiful sights, you’ll need at least a few days in each to really get to grips with it all. Florence is home to Michelangelo’s “David” sculpture as well as the Duomo cathedral while Pisa offers the iconic “Leaning Tower”, Clock Palace and Square of Miracles. Culture vultures will love getting their claws in here.
What goes hand in hand with superb art? Incredible food, of course, and Tuscany is definitely not short on this either! Food fanatics will find that there’s not a single village, town or city in the entire region that doesn’t offer truly exceptional cuisine, with different delicacies and recipes at each stop that will send your taste buds wild. With so many gourmet paradises we can’t put forward any one area for foodie delights but we can recommend the undisputed champion of wine as Chianti, the most renowned area for quality and traditional production.
It’s not all vineyards and green valleys though, water babies are going to love the Tuscan coastline which has everything from fishing villages on the rocks and pebble beaches to sandy stretches and charcoal-black shores. So whether you want to dive into the fascinating reefs or just get your holiday tan top-up, there’s an ocean-front spot for you.
WINGED BOOTS WISDOM
Walking at a snail’s pace but can’t get a real feel for the area in a car? Get on board with the local custom of cycling from place to place! The purchase of a bike as well as a variety of hiring options are available for almost nothing everywhere.
The most famous of the area’s attractions are found in the culture capitals of Florence and Pisa. The ideal start to any tour of Tuscany these two cities are so packed with incredible art, historical monuments and beautiful sights, you’ll need at least a few days in each to really get to grips with it all. Florence is home to Michelangelo’s “David” sculpture as well as the Duomo cathedral while Pisa offers the iconic “Leaning Tower”, Clock Palace and Square of Miracles. Culture vultures will love getting their claws in here.
What goes hand in hand with superb art? Incredible food, of course, and Tuscany is definitely not short on this either! Food fanatics will find that there’s not a single village, town or city in the entire region that doesn’t offer truly exceptional cuisine, with different delicacies and recipes at each stop that will send your taste buds wild. With so many gourmet paradises we can’t put forward any one area for foodie delights but we can recommend the undisputed champion of wine as Chianti, the most renowned area for quality and traditional production.
It’s not all vineyards and green valleys though, water babies are going to love the Tuscan coastline which has everything from fishing villages on the rocks and pebble beaches to sandy stretches and charcoal-black shores. So whether you want to dive into the fascinating reefs or just get your holiday tan top-up, there’s an ocean-front spot for you.
WINGED BOOTS WISDOM
Walking at a snail’s pace but can’t get a real feel for the area in a car? Get on board with the local custom of cycling from place to place! The purchase of a bike as well as a variety of hiring options are available for almost nothing everywhere.
Better known as the darling of Italy, this region is one of the greatest in Europe for history, art and food. With traditions and buildings dating back to the Etruscans, the area is a charming mix of medieval-style villages and 21st century cities set into rolling green hills, mountains or quiet seaside bays. With so much going for it, you’re bound to find the perfect luxury holiday in Tuscany, no matter what your ideal getaway looks like.
The most famous of the area’s attractions are found in the culture capitals of Florence and Pisa. The ideal start to any tour of Tuscany these two cities are so packed with incredible art, historical monuments and beautiful sights, you’ll need at least a few days in each to really get to grips with it all. Florence is home to Michelangelo’s “David” sculpture as well as the Duomo cathedral while Pisa offers the iconic “Leaning Tower”, Clock Palace and Square of Miracles. Culture vultures will love getting their claws in here.
What goes hand in hand with superb art? Incredible food, of course, and Tuscany is definitely not short on this either! Food fanatics will find that there’s not a single village, town or city in the entire region that doesn’t offer truly exceptional cuisine, with different delicacies and recipes at each stop that will send your taste buds wild. With so many gourmet paradises we can’t put forward any one area for foodie delights but we can recommend the undisputed champion of wine as Chianti, the most renowned area for quality and traditional production.
It’s not all vineyards and green valleys though, water babies are going to love the Tuscan coastline which has everything from fishing villages on the rocks and pebble beaches to sandy stretches and charcoal-black shores. So whether you want to dive into the fascinating reefs or just get your holiday tan top-up, there’s an ocean-front spot for you.
WINGED BOOTS WISDOM
Walking at a snail’s pace but can’t get a real feel for the area in a car? Get on board with the local custom of cycling from place to place! The purchase of a bike as well as a variety of hiring options are available for almost nothing everywhere.
The most famous of the area’s attractions are found in the culture capitals of Florence and Pisa. The ideal start to any tour of Tuscany these two cities are so packed with incredible art, historical monuments and beautiful sights, you’ll need at least a few days in each to really get to grips with it all. Florence is home to Michelangelo’s “David” sculpture as well as the Duomo cathedral while Pisa offers the iconic “Leaning Tower”, Clock Palace and Square of Miracles. Culture vultures will love getting their claws in here.
What goes hand in hand with superb art? Incredible food, of course, and Tuscany is definitely not short on this either! Food fanatics will find that there’s not a single village, town or city in the entire region that doesn’t offer truly exceptional cuisine, with different delicacies and recipes at each stop that will send your taste buds wild. With so many gourmet paradises we can’t put forward any one area for foodie delights but we can recommend the undisputed champion of wine as Chianti, the most renowned area for quality and traditional production.
It’s not all vineyards and green valleys though, water babies are going to love the Tuscan coastline which has everything from fishing villages on the rocks and pebble beaches to sandy stretches and charcoal-black shores. So whether you want to dive into the fascinating reefs or just get your holiday tan top-up, there’s an ocean-front spot for you.
WINGED BOOTS WISDOM
Walking at a snail’s pace but can’t get a real feel for the area in a car? Get on board with the local custom of cycling from place to place! The purchase of a bike as well as a variety of hiring options are available for almost nothing everywhere.
Better known as the darling of Italy, this region is one of the greatest in Europe for history, art and food. With traditions and buildings dating back to the Etruscans, the area is a charming mix of medieval-style villages and 21st century cities set into rolling green hills, mountains or quiet seaside bays. With so much going for it, you’re bound to find the perfect luxury holiday in Tuscany, no matter what your ideal getaway looks like.
The most famous of the area’s attractions are found in the culture capitals of Florence and Pisa. The ideal start to any tour of Tuscany these two cities are so packed with incredible art, historical monuments and beautiful sights, you’ll need at least a few days in each to really get to grips with it all. Florence is home to Michelangelo’s “David” sculpture as well as the Duomo cathedral while Pisa offers the iconic “Leaning Tower”, Clock Palace and Square of Miracles. Culture vultures will love getting their claws in here.
What goes hand in hand with superb art? Incredible food, of course, and Tuscany is definitely not short on this either! Food fanatics will find that there’s not a single village, town or city in the entire region that doesn’t offer truly exceptional cuisine, with different delicacies and recipes at each stop that will send your taste buds wild. With so many gourmet paradises we can’t put forward any one area for foodie delights but we can recommend the undisputed champion of wine as Chianti, the most renowned area for quality and traditional production.
It’s not all vineyards and green valleys though, water babies are going to love the Tuscan coastline which has everything from fishing villages on the rocks and pebble beaches to sandy stretches and charcoal-black shores. So whether you want to dive into the fascinating reefs or just get your holiday tan top-up, there’s an ocean-front spot for you.
WINGED BOOTS WISDOM
Walking at a snail’s pace but can’t get a real feel for the area in a car? Get on board with the local custom of cycling from place to place! The purchase of a bike as well as a variety of hiring options are available for almost nothing everywhere.
The most famous of the area’s attractions are found in the culture capitals of Florence and Pisa. The ideal start to any tour of Tuscany these two cities are so packed with incredible art, historical monuments and beautiful sights, you’ll need at least a few days in each to really get to grips with it all. Florence is home to Michelangelo’s “David” sculpture as well as the Duomo cathedral while Pisa offers the iconic “Leaning Tower”, Clock Palace and Square of Miracles. Culture vultures will love getting their claws in here.
What goes hand in hand with superb art? Incredible food, of course, and Tuscany is definitely not short on this either! Food fanatics will find that there’s not a single village, town or city in the entire region that doesn’t offer truly exceptional cuisine, with different delicacies and recipes at each stop that will send your taste buds wild. With so many gourmet paradises we can’t put forward any one area for foodie delights but we can recommend the undisputed champion of wine as Chianti, the most renowned area for quality and traditional production.
It’s not all vineyards and green valleys though, water babies are going to love the Tuscan coastline which has everything from fishing villages on the rocks and pebble beaches to sandy stretches and charcoal-black shores. So whether you want to dive into the fascinating reefs or just get your holiday tan top-up, there’s an ocean-front spot for you.
WINGED BOOTS WISDOM
Walking at a snail’s pace but can’t get a real feel for the area in a car? Get on board with the local custom of cycling from place to place! The purchase of a bike as well as a variety of hiring options are available for almost nothing everywhere.
Special Offers
Tuscany Special Offers
- We've found 12 offers in Tuscany for you
- View All Offers
Offer
Kempinski Hotel Bahía
Spring 2023 escapes to MalagaFrom £859 pp
for 3 nights inc flights
for 3 nights inc flights
3 nights from £859 pp
inc flights
inc flights
Offer
Reid’s Palace, A Belmond Hotel, Madeira
Meet me in Madeira in Spring 2023From £769 pp
for 3 nights inc flights
for 3 nights inc flights
3 nights from £769 pp
inc flights
inc flights
Offer
Four Seasons Hotel Milano
Spring 2023 breaks to Four Season Hotel, Milano From £2,069 pp
for 3 nights inc flights
for 3 nights inc flights
3 nights from £2,069 pp
inc flights
inc flights
Offer
Anantara Vilamoura
Spring 2023: Three-nights in PortugalFrom £689 pp
for 3 nights inc flights
for 3 nights inc flights
3 nights from £689 pp
inc flights
inc flights
Offer
Rome Cavalieri, A Waldorf Astoria Hotel
Book a stay at Rome Cavalieri, A Waldorf Astoria HotelFrom £929 pp
for 3 nights inc flights
for 3 nights inc flights
3 nights from £929 pp
inc flights
inc flights
Offer
Shangri-La Hotel Paris
2023 holidays to the Shangri-La Hotel ,Paris From £2,149 pp
for 3 nights inc flights
for 3 nights inc flights
3 nights from £2,149 pp
inc flights
inc flights
Offer
Hôtel Barriére Le Majestic
Spring 2023 stays at Hôtel Barriére, Le MajesticFrom £1,599 pp
for 3 nights inc flights
for 3 nights inc flights
3 nights from £1,599 pp
inc flights
inc flights
Offer
Hôtel de Paris Monte-Carlo
Book and save at Hôtel de Paris, Monte-CarloFrom £1,199 pp
for 3 nights inc flights
for 3 nights inc flights
3 nights from £1,199 pp
inc flights
inc flights
Offer
Nobu Hotel Barcelona
Spring 2023: Spanish escapes to Nobu Hotel, Barcelona From £489 pp
for 3 nights inc flights
for 3 nights inc flights
3 nights from £489 pp
inc flights
inc flights
Offer
W Algarve
Exclusive Offer: Save up to 20% at W Algarve Was £743
Save £124
Save £124
From £619 pp
for 3 nights inc flights
for 3 nights inc flights
3 nights from £619 pp
inc flights
inc flights
Offer
Kakslauttanen Arctic Resort
Stay at Kakslauttanen Arctic Resort this Christmas and save up to 10% Was £2,705
Save £246
Save £246
From £2,459 pp
for 5 nights inc flights
for 5 nights inc flights
5 nights from £2,459 pp
inc flights
inc flights
Offer
The Principal Madrid Hotel
April 2023: Five nights at The Principal Madrid From £749 pp
for 3 nights inc flights
for 3 nights inc flights
3 nights from £749 pp
inc flights
inc flights
Recommended Hotels
Our recommended
hotels in Tuscany
- We've found 2 properties in Tuscany for you
- View All Hotels
- Boutique accommodations offering 74 rooms and suites as well as a seven-person villa
- Two on-site restaurants serving authentic Italian fare overseen by Gordon Ramsay
- Extensive range of health treatments and programmes available in the hotel’s spa
- Boutique accommodations offering 74 rooms and suites as well as a seven-person villa
- Two on-site restaurants serving authentic Italian fare overseen by Gordon Ramsay
- Extensive range of health treatments and programmes available in the hotel’s spa
Call us on 0203 816 0985
to start planning your vacation
to start planning your vacation
- Rural escape comprising more than 20 rooms, suites and private villas
- Indulge in heated swimming pools and an on-site spa
- Get lost in the stunning landscape of the Tuscan hills with hotel organised tours
- Rural escape comprising more than 20 rooms, suites and private villas
- Indulge in heated swimming pools and an on-site spa
- Get lost in the stunning landscape of the Tuscan hills with hotel organised tours
Itineraries Available
Call us on 0203 816 0985
to start planning your vacation
to start planning your vacation
Recommended Itineraries
Our recommended
itineraries in Tuscany
- We've found 1 itineraries in Tuscany for you
- View All Itineraries
5 Nts Tuscany & 5 Nts Venice
5 Nts Tuscany & 5 Nts Venice
- International flights
- 10 Nights accommodation
- 10 x Breakfast
- 3 x Excursions
- Private transfers throughout
- International flights
- 10 Nights accommodation
- 10 x Breakfast
- 3 x Excursions
- Private transfers throughout
Call us on 0203 816 0985
to start planning your vacation
to start planning your vacation
- International flights
- 10 Nights accommodation
- 10 x Breakfast
- 3 x Excursions
- Private transfers throughout
Extra Mile Guarantee
Our Extra Mile Guarantee
We appreciate every Winged Boots customer and to prove this we want you all to receive a very high standard of customer service when booking with us. Our Extra Mile Guarantee is just that. A promise that no matter the destination, whether it is your first or your hundredth time using Winged Boots, you will be treated like a VIP from enquiry through to departure and even when you return home.
David Ox, managing director- Dedicated personal travel managers
Each with a minimum of 10-years’ experience
- Covid regulations, simplified
We explain complicated travel requirements
- Complimentary event invitations
Meet the team at our annual shoot day, O2 London, a private dinner and more
- Transparent price
No hidden fees, quotation costs or admin charges
- The human touch
Just honest conversations with real people
- Out of hours contact
Via email, direct dial and even on Whats’App
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Celebrating? Let us know and we may surprise you
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We’re licensed by ATOL and TTA
- We make it happen
Wherever, whenever, however and every time
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Tuscany in a nutshell
- Did you know that one of Tuscany’s nicknames is ‘The Pantry of Italy’? Well you do now and if that name alone doesn’t have you grabbing your cutlery and boarding the next flight out, we don’t know what will!
- Late spring through to mid-autumn is one of the busiest foodie periods in Tuscany’s year. A particularly prominent form of entertainment during this time are the regional ‘sagra’ festivals held in each town. These are food celebrations which showcase the harvest of each place, such as Lari’s cherry fair. If you don’t have time to visit all of them we recommend Bibbiena’s La Sagra Delle Sagre in June, which has mini-stalls representing all the regions produce so you can see everything in one place.
- Of course, you couldn’t possibly leave Tuscany without sampling at least one drop of wine. There are so many tours available your mind will reel with each offering fabulous additions like wine tasting sessions, gourmet meals, cheese pairings and more
- Did someone say cheese pairing? Nothing compliments a good Tuscan wine than a Pecorino formaggio. A speciality of this corner of Italy, the produce is made using 100 percent whole sheep milk and is renowned for its creamy texture and spicy flavour. To take a look at the production of this delicacy and grab a few wheels to take home, Monteroni d’Arbia in Siena is an ideal spot.
Soak Up the Culture
- You’ll be so full of culture by the time you leave Tuscany that you’ll be quoting Dante and waxing lyrical about the Renaissance for years to come. But when you’re not taking stock photos at ‘The Leaning Tower’ or next to the statue of David, there are a hundred other ways in which the Italians celebrate their history that you can get involved in.
- Throughout the year in Tuscany there are festivals and carnivals as old as the Etruscans which are the perfect way to get a little culture lesson in amongst a lot of fun. One of the most popular is the Giostra del Saracino, or Saracen Tournament, held in Arezzo's Piazza Grande twice a year. Expect colourful processions, knights’ tournaments and medieval fare.
- If you want to have a hands-on experience of authentic Tuscan culture and rub elbows with the locals, grab your mates and join in with the vendemmia (seasonal grape harvest). An iconic moment in the country’s calendar, this September reaping of the vines is a fun day with great company and rewards (in liquid form).
- A cultural site that’s saturated with romance and history, a day trip to Cinque Terre is a must for everyone. Particularly for couples, the area’s Via dell’Amore (The Way of Love) in Riomaggiore is a stunning walkway between two villages where you can make your love everlasting, like generations before you, with a lock or inscription on the rock face
- Although there are a multitude of beachy paradises awaiting you here, many of them require a payment before you’re allowed to access them whereas beaches signposted as spiaggia libera are ‘free’ for public use. This means there are plenty of places to escape from the crowds on private stretches which have all the facilities you need, already paid for!
- For a family-friendly day in the water, the beaches of Val di Cornia are sandy, sparkling and super-fun spiaggia libera that the little ones will enjoy for the rock pools and gentle currents and grown-ups will love for the sun worship opportunities.
- A recently discovered treasure by visitors to the Tuscan coastal route, Maremma’s beaches are popular among locals and offer diverse marine life along with gorgeous shores. An ideal spot for some scuba diving in the reef, you can indulge in any number of watersports here.
- Not exactly a beach but still worth taking a dip, the thermal springs and pools of Saturnia are a must for any aquaholics. Available all year round due to their toasty 37 degree waters, these Roman baths come with excellent opportunities for Instagram shots and scenic vistas.
Good to know
- FlightTime: 2 hours and 10 minutes from London
- Packing Essential: An insatiable appetite
Best time to travel
Average Temperatures
Jan: 7°c  | Feb: 8°c | Mar: 11°c  | |||
| Apr: 13°c | May: 17°c | Jun: 22°c  | |||
Jul: 25°c  | Aug: 25°c | Sep: 22°c | |||
| Oct: 16°c | Nov: 11°c | Dec: 8°c |
Location map
Get in touch with our team of personal travel managers to start planning your trip
- The human touch
- Complete concierge service
- 24/7 out of hours contact