Tuscany Holidays

Rolling vineyards and medieval towns


Cheap Flights to Pisa

Return Flights in April and May starting from just €50!

Whether you fancy checking out the famous Leaning Tower or want to travel onwards to beautiful Tuscany or the Cinque Terre, the city of Pisa opens up a world of adventures in Italy! Example departure dates: 02/04/2019 – 09/04/2019 – €50 02/04/2019 – 11/04/2019 – €50 06/04/2019 – 11/04/2019 – €55 30/04/2019 – 08/05/2019 – […]


Relaxing Tuscany Break

4 Nights in Authentic Guesthouse Incl. Flights and Breakfast

Enjoy a stay in one of Italy's most beautiful regions! Book this relaxing Tuscany break for 4 nights and return flights for just €194pp


Holiday to Tuscany

1 Week in Great Country Hotel incl. Return Flights

Want to live the good life? Then head to Tuscany and take things slow in beautiful surroundings with this awesome deal - click here for more!


Great Value Tuscany Holiday

5 Nights in Well-Review Apartment incl. Return Flights

Take things slow and enjoy the finer things in life in what is truly one of the most picturesque regions in all of Italy. Click here for more!


Tuscany Spring Holiday

5 Nights in Great 4* Hotel incl. Flights

Discover the beautiful landscapes and mouthwatering food of this classic Italian destination with this Tuscany spring holiday deal!


Tuscany Getaway

6 Nights incl. 4* Hotel, Breakfast & Flights

I found you this Tuscany Getaway in October 2017! Get 6 Nights incl. 4* Hotel, Breakfast & Flights for only €251pp!


Luxury Tuscany Getaway

6 Nights in Excellent 4* Resort incl. Breakfast & Flights

Dreaming of bella Italia? Then why not jet off to a luxury Tuscany getaway in an excellent 4* resort for some proper relaxation?


Tuscany Spring Break

1 Week in Superb 4* Hotel incl. Breakfast & Flights

Travel to one of Italy's most beautiful regions with this fantastic offer for a 4* Tuscany spring break - the perfect time to go!

Browse the best holiday deals to Tuscany at Holidayguru.ie!

Pine forests, cypress trees, olive trees, vineyards, and beaches – a varied landscape characterises Tuscany. If a break in Italy is coming up, the choice of where to go usually lands on a holiday in Tuscany. Here, you have everything that a holiday heart needs to relax. The coast is over 300 kilometres long and it delights holidaymakers with its countless spots for swimming. Get ready for the beach holiday of your dreams. The many thermal springs make Tuscany a popular destination for a wellness holiday. Northern Tuscany is ideal for active breaks. The Apennines provide an impressive backdrop for hiking. Just add the tasty food and Italy is perfect for everyone.

Popular destinations for a holiday in Tuscany

This holiday region is well-known for its culture, art, wine, and history. For many people, going to the beach and sightseeing is a perfect holiday combination. Others love sauntering through charming cities. Whereas others want to keep active surrounded by nature. I’m going to tell you which marvellous places you should see here.

Florence – a Tuscan tourist magnet

The number one holiday destination in Tuscany is Florence. The capital and the biggest city of the region is particularly popular for a city break in Italy. There’s no beach here, but you can’t help but lose yourself in the attractions that the city has to offer. In previous centuries, Florence was one of the richest cities in the world. Great artists left their mark here and shaped the history of the city. There is Renaissance architecture around every street corner. One of the most famous buildings is the Uffizi Gallery, which houses a collection of world-renowned classical art. You can never tire of looking at the many grand palaces. You can feel the atmosphere of the town in the parks and the squares. Take a walk on the banks of the river Arno and prepare yourself for more sightseeing. The historic town centre of Florence isn’t a UNESCO World Heritage Site for nothing. Don’t forget to visit the Palazzo Vecchio, the Piazza della Signoria, the Galleria dell’Arte and much, much more! No other city has such a huge number of sculptures, squares, churches, memorials, and museums as Florence. Come to the city of art and marvel at its masterpieces.

Pisa – more than a leaning tower

When you hear the name Pisa, an image of the Leaning Tower of Pisa comes straight to mind. It is the symbol of the city and known all over the world. Even people, who haven’t seen it in real life, have heard of it. But, the Leaning Tower isn’t the only sight, which attracts tourists to Pisa on their holiday in Tuscany. Pisa is also home to the oldest Botanic Garden in the world and numerous other sights. Other historical buildings include the Church of Santa Maria della Spina, the Church of the Santo Sepolcro and the Santa Maria Assunta Cathedral. Wander through the city’s winding alleys, which are lined with houses with the yellow facades typical of Pisa, to the museums. The city on the River Arno is the birthplace of many famous people, but Galileo Galilei is definitely the most well-known. The scientist was the reason that Pisa developed into one of the most important university towns in Italy.

In the province of Pisa, you can also find the village, Volterra. The centre is in a great location on a 550-metre high mountain ridge. Surrounded by a breath-taking landscape, it’s great for clearing your head. As in many other Italian small towns, historical and sacred buildings characterise Volterra. The Archaeological Museum, and the oldest town hall in Tuscany, as well as the remains of the town walls, are some of the town’s highlights. You should definitely take a trip to Volterra, if you’re in Pisa.

Siena – horse racing and Gothic masterpieces

One of the most beautiful cities for a holiday in Tuscany is Siena. The town isn’t far from Florence and is famous for a horse race called the Palio di Siena. It takes place on the Piazza del Campo, or Il Campo for short, every year. This square is considered the most beautiful square in all Italy and, for some, even the whole world. The imposing cathedral, which every tourist has to see inside and out, is in this square. Other buildings in the main square of the Medieval city are the majestic town hall and the former civic hospital, Santa Maria della Scala. Cloisters, museums, and church towers dominate the entire cityscape and create a wonderful atmosphere. The Gothic-style buildings impress not only architects, but also holidaymakers, who are interested in history. Siena’s surroundings are perfect for escaping into nature on a day trip. The city is in the hills in the Chianti region, surrounded by vineyards and olive groves.

In the province of Siena, you can find a Medieval gem – the small town of San Gimignano. Because of its tower houses in the historic centre, which date back to the Middle Ages, the town is also known as the ‘Town of Fine Towers’. The whole centre is a UNESCO World Heritage Site and is definitely worth a visit. San Gimignano stands out because of its Medieval buildings and its lovely atmosphere. A huge fortified wall surrounds it. I would recommend finding a tall building, where you can enjoy a panoramic view over the town.

Chianti – vineyards and fine wines

What I mean by Chianti, is the chain of hills in the middle of Tuscany. Chianti is also famous for the region’s red wine. Here, you can spend an idyllic holiday surrounded by nature and indulgence in the midst of olive trees and grapevines. Hikes and bike tours are on the daily itinerary. The trails lead you to lovely places and picturesque villages. During your discovery tour, you should head to Vagliagli, where the oldest vineyards in the region are. The Palazzo Ugolini and the Etruscan necropolis are the stars of Castellina. Castles, monasteries, and, above all, vineyards are the main attractions of a holiday in Tuscany in Chianti. There are lots of holiday rentals available in the region. You can find one in the countryside or in a central location in lovely, old houses. If you need more space, a holiday home with a big estate is advised.

Lucca – an Italian shopping paradise

Near the Mediterranean coast there is a city, which attracts the attention of many holidaymakers. Lucca is another Tuscan gem and is ideal for a break. It is the perfect place to relax. Visit a couple of vineyards and try a good Italian tipple. The city centre is home to lots of tourist attractions. Take a look at the marketplace, which was built on the ruins of a Roman amphitheatre. The Duomo di San Martino and many other sacred buildings characterise Lucca’s cityscape. Here, you’re in the right place for a shopping trip. Lucca used to dominate the textile industry and you can still feel that today. In the narrow lanes, there are shops and boutiques where you can still find beautiful textiles today. Take a day trip to the sea and leave all your worries behind you. The cities of Pisa, Florence, and Siena aren’t far away and you should include them in your excursion plans.

Livorno – a historic port town

The second-biggest city in Tuscany is a magnet for beach lovers. Livorno has a great beach location. If you want to relax, you can find beautiful spots along the coast. Swim in the Mediterranean and enjoy the Italian sun. The old town also has something to offer. The port is especially well-known as it is the biggest port in Italy. You can expect to find the most beautiful ship in the world, here, as well as a maritime atmosphere. The port is the centre of the city and is definitely worth a visit. The city’s cathedral towers high over the Piazza Grande. It’s not to be missed. The symbol of the city, the Memorial of the Four Moors, is another highlight. Impressive churches and museums allow you to dive into the past. In addition, the port town is famous for the two fortresses Fortezza Vecchia and Fortezza Nuova. Livorno is perfect for combining a beach holiday with sightseeing. Look for a holiday rental and enjoy La Dolce Vita. Alternatively, there are lots of hotels in the centre.

Arezzo – back in time to the Middle Ages

If you go northeast from Siena, you reach Arezzo. The Middles Ages are still alive here. Churches, patrician houses and palaces are spread across the whole city. Twice a year, the main square, Piazza Grande, turns into an arena for the Joust of the Saracens. If you’re in Arezzo in June or September, you can see it. It a show which you’ll never forget. Art and crafts have a central role in the city. You can get hold of jewellery and other hand-made pieces in some lovely shops in the old town. The markets are also very enchanting – they offer goods ranging from accessories to clothes and even furniture. You can also see a different type of art in the historical buildings and churches. For example, there are frescoes from the past here, which are second to none. Arezzo is the place to go for fans of architecture, art and culture.

The best offers for your holiday in Tuscany

Tuscany is one of the most popular holiday destinations in Italy. If you want to see Bella Italia’s best side, you should head here for your break. The region has lots of world-class hotels. I provide the best offers on this page. If you’d prefer to rent a holiday apartment instead, I also find great offers for them every now and again. Alternatively, there are many different holiday apartments in the region. I also look for offers for different resorts. You only have to decide where you want to go. Tuscany is a destination which you can head to at any time of the year. Take a look at my offers regularly, to make sure you don’t miss out on any great Tuscany deals.

The best travel times for a holiday in Tuscany are the months of March, April, May, June, July, August, September, October, and November. You can have a dreamy beach holiday or an exhilarating active holiday at these times of the year.