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Exploring Florence and the Rustic Charm of Tuscany Villas

January 31, 2021

Your Italy travel itinerary is incomplete without experiencing the natural beauty of the Italian countryside. Stay in charming Tuscany villas, taste the wine of famous wine houses, visit the Pienza and Val d'Orcia, and marvel in the picturesque districts of Florence. Here, we recommend some of the best places to go when making your Italty travel list.

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Tuscany, Italy is a globally-known tourist destination famous for its unique countryside lifestyle, picturesque nature landscape, vineyards, wines, food, tradition, history, nobility, and of course, the beautiful cities in region bannered by its capital city, Florence, and the equally beautiful Siena. The distinct character of the region made Tuscany a renowned destination for people seeking a peaceful and relaxing escape from the hustle and bustle of the city life.

The Tuscan Region is rich in history and heritage. Renaissance art and architecture is evident both in the cities and the countryside where old farmhouses and castles can be found. Most wines produced from these places often bear the castle or the house’s name. Original masterpieces of prominent Renaissance figures can also be found in Tuscan cities and has remained a popular attraction to tourists and locals alike.

Tuscany has a lot of things to offer and frankly speaking, we might as well write a whole book about it because a couple of pages won’t suffice to describe what Tuscany is all about. But just to give you a better appreciation and insight on what awaits you if you visit this part of Italy, allow us to give you, in no particular order, the top must-go points of interest when in Tuscany.

Visit and Explore Florence

Florence is the capital city of the Tuscan Region. Arguably the most famous of all the cities in Tuscany, Florence is home to some of most notable Renaissance pieces of art and architecture. Michaelangelo’s The David’s Statue, Botticelli’s works such as the “The Birth of Venus”, and Leonardo da Vinci’s “Annunciation” can all be found in this city exhibited in the Uffizi Gallery. The city’s most prominent and iconic structure is the Duomo.

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Climb 463 steps of the Bell Tower and you’ll get a sweeping and panoramic view of the entire city of Florence. If it’s not enough, marvel at the charming beauty of the Ponte Vecchio Bridge and snap a picture-perfect photo as souvenir.

Timeless Magic of Siena

You can't just visit Florence without visiting Siena. Enjoy a hearty authentic Tuscan cuisine and its exquisite art. Once a major banking, trading, and military power prior to the rise of Florence, Siena to this day has preserved its timeless beauty and gothic identity with the Renaissance influence still very much prevalent and visible adding to its distinct historic charm.

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Apart from the famous fan-shaped central square - Piazza del Campo, Siena is also home to the world’s wildest horse races, the Il Pallo. The Mangia Tower is the city’s tallest structure and easily the most visible landmark. With 300 steps up the tower, you’ll be rewarded by a commanding view of the city and the nearby Tuscan countryside.

The Leaning Tower of Pisa

Pisa is a small northwestern Tuscan city best known for the famous “The Leaning Tower of Pisa.” The tower was built during the 12th century and started leaning prior to its completion. With the advent of technology and modern architecture and structural design in the 20th century, the tower was stabilized and now provides a picture-perfect image to the liking of many tourists.

The Piazza del Miracoli in Pisa

While it’s incomparable to the likes of Florence and Siena in terms of diversity and variety of things to do and places to go, Pisa is a good base for tourists heading to the beautiful and rustic city of Lucca.

You can also pamper yourself with authentic Tuscan food and other local delicacies. The train station is just nearby but walking would be more advisable to fully explore the city and its offerings.


Lucca is another lovely city in Tuscany known for its Renaissance-era walls encircling the Piazza dell'Anfiteatro which used to be an amphitheater back in the days. These walls are testament of political and military power during the Renaissance but have become a popular tourist destination for despite its sturdy nature, the inside Piazza offers a different level of charm. The elliptical shaped Piazza has become a favorite chill-out spot for many tourists where they can enjoy al fresco dining dotted inside the Piazza for some authentic Italian and Tuscan meals.


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Lucca is also metaphorically referred to as the city of 101 churches, not because it has 101 churches but because it simply has a lot of religious buildings scattered throughout the city. To get the most of the Lucca, walking and biking is recommended.

Wine Tasting at Chianti

The Chianti Region in Central Tuscany is famous for medieval castles, vineyards and wineries. Almost all castles in this area have their own wineries and wines bearing their own name.

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Located between Florence and Siena, the Chianti Region is a favorite destination for wine tasting. From red wine to white wine and its derivatives, this beautiful, soulful, and relaxing region with panoramic view is a must-visit when in the Tuscan Region. Any trip to Tuscany without having to drop by the Chianti area is incomplete. The world’s finest wines are produced here and wine tasting is a must!

The Chianti region is also a great place to relax and enjoy the countryside. You can opt to rent private Tuscany villas for a day or two to get the whole Tuscany experience.

Hill Town of Cortona

Cortona is one of the oldest hilltop towns in Tuscany made famous by the book Under the Tuscan Sun which later on became a movie adaptation.

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The town is known for its Cortona’s Etruscan walls that surround the town’s historic center. One of the attractions in Cortona is Piazza della Republica – one of the town’s main squares and is home to Cortona’s 13th century town hall and clock tower. You also have Cortona’s Renaissance Cathedral and Museums.

Inside the walls, you can stroll along the narrow medieval streets and explore the cafes and restaurants and other establishments in the Piazza to get the most of this lovely town.  Near the walls, you’ll get a rewarding view of the valley below.


Arezzo is a small city in Tuscany settled at about 80 kilometers away from Florence. It is home to the Arezzo Cathedral where Piero della Francesca’s mural of the Mary Magdalene can be found.



The main square of the city is Piazza Grande. Here, you’ll be treated with a string of cafes and restaurants offering authentic Italian cuisine.


Experience a relatively slow-paced lifestyle in this part of Tuscany and savor its different vibe as opposed to the likes of Florence and other major cities in Italy where life has caught up with modernity.

In June and September, tourists are treated with an actual jousting tournament participated by the residents of the different neighborhoods in the city.


Elba is a Mediterranean Island in Tuscany famous as the place of exile of Napoleon Bonaparte during the early 1800’s. Apart from Napoleon’s name, Elba is also popular for its beaches and of course, the food.

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Walking and biking are also popular activities in the Island as there are existing trails crossing the entire Island which is perfect for those wanting some time off the water. You can also visit the small villages where you can shop for almost anything you can think of.

The Towers of San Gimignano

A mainstay in every tourist’s itinerary when in Tuscany, San Gimignano is a hill town which boasts 14 medieval towers popularly known as the Belle Torri or Beautiful Towers, set on the hilltop and visible from the neighboring countryside. It rises above the vineyards of its own wine-growing area which is one of the very few in the Tuscan region that focuses on white grapes.


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Of all destinations in the Tuscan Region, the medieval towers of San Gimignano provides a unique and distinct skyline set apart from the rest of Tuscany. It also has its own encircling walls typical of the cities in Tuscany.

The area has many visible remnants of the Romanesque and Gothic architecture. It also prides itself of being home to a UNESCO World Heritage Site in “The Historic Centre of San Gimignano.” As you explore the area, you’ll be rewarded with numerous beautiful secular buildings and churches providing a pseudo time lapse to the medieval times.

Complete your Italian rustic experience with a complimentary stay in luxurious and charming Tuscany villas.

Pienza and Val d'Orcia

Also a protected World Heritage Site by UNESCO, Val d’Orcia is home to Tuscany’s most beautiful and picture-perfect untouched landscape. Grains or sunflowers cover its endless rolling hills with the green valley encompassing the Orcia River.

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Val d’Orcia is composed of several lovely towns but one that stands out the most is the town of Pienza, also referred to as “The Ideal City”.

Pienza is another town in Tuscany that has that time lapse effect that seems to take you back to the medieval era as you wander in its narrow charming streets.

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In the town’s main square, you’ll find the Palazzo Piccolomini, the Cathedral of Santa Maria Assunta and the Town Hall. In the Palazzo, you can’t help but marvel at the impressive stone and marble architecture which was the home of the Piccolomini family until 1962 and therefore contains the old and original furnishings. Tourists are enchanted by the picturesque images of this small town.

Apart from these 10 destinations we mentioned, there are other notable places that deserve to be included in this list like the walled city of Montepulciano, one of Tuscany’s highest towns – Montalcino, and Montecatini Terme – one of Italy’s top spa towns known for its thermal waters.

Toscana villas

Dotting the evergreen hills of Tuscany are secluded villas and cottages that offer accommodation to traveling tourists. Most of these private villas, like the centuries-old structures in Florence, have retained their original architecture - most of which are in the signature reddish brick-and-wood build of the Romanesque style. The homes are typically surrounded by olive and old oak trees, inviting guests to enjoy a commune with nature.

Staying in one of these Tuscany villas means waking up to the cacophony of unique rustic sounds, enjoying a walk in lush gardens, and taking a break from the heat by dipping in the private pool.

Speaking of the heat, if you don't want to ruin your vacation with too much sun, the best months to visit the Tuscan region is during April, May, June, September, and October when the weather is relatively pleasant. The temperature can get crazy high around July and August so if you're doing your Italy tour during these months, it's highly recommended to include some sunscreen and water in your travel pack when visiting the Tuscan region.


Exploring Florence and the Rustic Charm of Tuscany Villas



Florence, Italy
120 € / night    
1 bedroom1 bathroom4
Florence, Italy
On request
2 bedrooms1 bathroom6-6
Florence, Italy
On request
2 bedrooms2 bathrooms4-4