Italy (Tuscany)

From rolling green hills and dramatic coastline to classic cities and seemingly hidden villages, Tuscany is a combination destination that offers a journey through beauty and history.

As the birthplace of the Renaissance, Tuscany provides insight to the nation’s past at every turn, with artistic influence spanning from the museums of Florence to the streets of medieval hill towns and beyond.

Across the oft-painted countryside, geothermal hot springs, truffle fields, endless vineyards, and olive groves embody the roots of Tuscan culture and epitomize Italian countryside living. Embracing the essence of its fertile land, a beloved food scene united by a trio of promises (local, seasonal, and sustainable) makes this region of central Italy not only a beauty to behold, but also a pleasure to smell, touch, and taste.

Tuscany’s capital city Florence is a treasure trove of art. Riverside avenues, narrow alleyways, medieval churches, exceptional museums, and grand piazzas all share a Renaissance flair which unites the compact city. To walk Florence is to step into the history of a city that has preserved its centuries-old culture, as originally shaped by masterful artists such as Leonardo da Vinci, Dante, and Michelangelo. Their stamp on Florence is immediately evident and everlasting, but many of their best works are presented in collections across the city at museums and galleries such as the Uffizi, Palatine, Museum of San Marco, and Accademia. Art unites with fashion and history is met with modernity, as many of these classic works neighbor shops of designer boutiques. Stroll to your content, and eventually head up to the hills for a hike to San Miniato al Monte to capture breathtaking panoramic views of this time-capsule Renaissance city.

Just an hour west of Florence, Pisa is home to one of the world’s most recognizable landmarks in its namesake tower. The Piazza dei Miracoli (Square of Miracles) contains a slew of Tuscan museums and sacred monuments that offer insight into Tuscan history and culture, capped by the infamous Torre de Pisa (the Leaning Tower). A first-time visitor can easily spend a day in and around the Piazza, but much of the city’s modern charm lies outside of this frequented square.

Home to one of the best universities in Italy, Pisa is fueled by education, and the resulting cafe and bar scene is incredibly lively and unique throughout all of Tuscany. Take an afternoon pause to chat travels and traditions with friendly locals before a leisurely stroll along the Arno River which boasts views of colorful palaces on one side and breathtaking mountains and forestry on the other.

With its Gothic buildings indicative of medieval times, Siena appears unchanged from its long and rich past, while coming off as a bit older and with more varied terrain than its Florentine neighbor to the north. Siena and Florence have feuded for power across centuries, and in the late 13th century, Florence would rise to prominence and steer the Renaissance movement. It was at this time that Siena would set in its ways, both geographically and culturally, and modern Siena is a unique gem because of this shift.

Visit the Duomo and Piazza del Campo to witness the level of medieval detail that Siena has become so synonymous with, and climb to the top of the Torre del Mangia for a 360-degree view of the cobbled city below. The golden-hued streets of Siena are a stark contrast against the decidedly decorative Renaissance roads of Florence – get lovingly lost among them via a self-guided walking tour.

Just south of Siena and near the Renaissance gem of Pienza, Val d’Orcia is the postcard version of Tuscany brought to life. Its rolling green hills and golden wheat fields are dotted with medieval castles, well-preserved farmhouses, endless rows of vineyards and cypress trees, and an assortment of hill towns that share history, beauty, and traditions. The landscape throughout the entire valley is part of a natural and cultural park and has even been recognized as UNESCO heritage site.

Smaller cities such as Lucca and Arezzo make for perfect day trips while providing authentic insight into aging societies. One of the most notable is coastal Livorno, a busy beach town and bustling port hub which combines the best of a Tuscan city with the allure of a Mediterranean destination. Its water sports, salt-scented air, and glowing sunsets are even home to Europe’s very first official bathing establishments hundreds of years ago.

Back in the countryside, hill towns like San Gimignano, Cortona, and Volterra are sure to capture your heart with breathtaking views, classic architecture, genuine hospitality, and farm-fresh foods. Chianti has become world-renowned for its wine and olive-oil productions and is one of Tuscany’s most ideal areas for a self-guided road trip considering its concentration of wineries, restaurant, and luxury hotels.


Tuscany is idyllic in late spring and early autumn, when the weather just seems to work in harmony with the land. Warm days, crisp evenings, readily available outdoor dining, and a range of events (like grape, olive, and music festivals) to keep things exciting. Summer is high season throughout most of Italy and Tuscany follows suit, with an influx of visitors throughout July and August.

If wine is of top focus, definitely aim to visit between September and October, when dewey valleys begin harvest festivals. Consider visiting in winter (outside of the Christmas holiday) for the lowest annual rates and fewest crowds, which can be especially beneficial if you’re hoping to visit popular sights like Michelangelo’s David.


Florence International (FLR) and Pisa International (PSA) offer convenient airport access to two of the most well-renowned areas in Tuscany. Italy’s capital city, Rome, is another viable entry option – often with more affordable airfare – and travel between Rome and Florence is simple and easy (less than 1.5 hours at a typical cost of $20). Once in Tuscany, a car is undoubtedly the best way to explore and enjoy the very best that the region has to offer. If driving is out of the question, a reliable network of trains, operating under the Trenitalia name, connect popular cities like Florence, Pisa, Siena, Grosseto and more.


Journey Through Renaissance Art – Bridging the gap between the Middle Ages and the modern era, the Renaissance period shifted European culture and shaped societies for centuries to come. Italy is the birthplace of the Renaissance, and Tuscany cradled the movement, with its profound artistic style resonating everywhere from cities like Florence, Pisa, and Siena to smaller hamlets like Pienza and San Gimignano. The entire region feels like an open-air museum, with emblematic paintings, sculptures, and architecture found throughout villages, churches, side alleys, and abbeys. For a more focused approach, visit the Uffizi Gallery and Accademia Gallery in Florence.

Natural Wellness – Tuscany is Italy’s leader for natural therapy, led by the mineral-rich thermal springs that are found throughout the region. Thermal baths have been favorited by everyone from former Popes to Napoleon himself, and can be found everywhere from city suburbs to coastal resorts. Seek out the free natural hot springs in San Filippo and Parco dei Mulini for a warm dip surrounded by open nature as a perfect place to relax and rejuvenate. For a more polished experience, visit an established spa, like Borgo Scopeto Relais, to indulge in a vinotherapy session. Natural grape baths, exfoliating skin scrubs, vine extract candle massages, and more await – as does a healthy glass of organic vino, if preferred.

Wine Trails and Olive Grove Roads – Without a doubt, a large part of Tuscany’s appeal can be credited to its dreamy countryside. Drive into it with a mission to explore the wine and olive farms which shape these fertile lands. Fun, informational tastings can be had just about anywhere, and a lifetime appreciation of the product is only a part of your reward.

Quality production isn’t hard to come across – with frequent informational signs leading to tasting centers, exhibitions, and organic farms – but one specific route still manages to stand out. The Chianti Classico, between Florence and Siena, passes through small cobblestoned towns with medieval castles, classic churches, museums and more, but its highlights are undoubtedly the world-renowned wines (Chianti Classico DOCG) and extra virgin olive oils that are produced from the land. Guided tours (like Grape Tours) often depart from Florence and are a worthy consideration to maximize time.

Visit a Food Market – True Tuscan cooking is done in the home and begins in the market. The thriving nucleus of nearly every Tuscan town, food markets offer more than the culinary delights that represent the region’s prosperous land – they are also one of the easiest ways to immerse into the ways of Tuscan living.

Share in this ritualistic shopping experience alongside chattering locals to find fresh goods ranging from cheese, wine, oils and breads to meat, fish, fruits and vegetables, and even clothing and handcrafted souvenirs. Your resulting best meal will likely be your most authentic and certainly most affordable. Markets are not hard to spot or plan around, but a few of our favorites include the San Lorenzo Central Market in Florence and the farmers’ market of La Lizza in Siena.

Ride Bicycles – Tuscany’s instantly recognizable landscape can be appreciated on foot or by car, but there’s something about the rhythmic motions of cycling that better connects you with the scene. The smell of harvesting grapes, sound of distant cowbells across the pastures, gentle breeze on your body, and the endless beauty of the land around you; cycling in Tuscany offers an exhilarating engagement of your senses.

Hop on a rental to leisurely explore hilltop towns from a different perspective, or base an entire day around biking through a coastal park (like Maremma Regional Park), where crystal-clear waters await as a reward. Much of the Tuscan region is connected via intricate bike trails that allow for multi-day excursions with nightly rests at luxurious hotels (an active cyclist’s dream) through all-inclusive tours such as Divine Tuscany Bike Tour.

On the other hand, day trips (around 10 miles in total length) make packaged tours more approachable, where groups like Tuscany Bike Tours depart daily for the country roads of Chianti from Florence.


Enoteca Pinchiorri – Florence’s only 3-star Michelin restaurant delivers a delicious and memorable dining experience. Authentic local recipes are re-interpreted with an innovative approach to create dishes that are lighter, crispier, or simply more surprising than what your palate might expect. Served on the ground floor of a Florentine palace by an impeccable staff, the restaurant’s multiple tasting menus ensure that every diner leaves satisfied. Dress code is required, but – given the restaurant’s high status – we find it comparatively casual.

Lorenzo – Consistently the best restaurant in town, and considered among the finest in the entire region, Lorenzo has set the Italian dining standard for quality food and outstanding service since opening its doors in 1981. Located in beautiful Forte Dei Marmi, diners particularly enjoy the staple seafood pasta and extensive wine list, hand-picked by Lorenzo himself, who is known to greet each table personally.

Buon Gusto Gelateria – While you likely won’t come across lousy gelato anywhere in Italy, Tuscany’s very best is Buon Gusto in the idyllic village of Pienza. Everything in the tiny shop is homemade, and the creative shopkeepers rotate flavors daily. Expect everything from classic flavors like mint and salted caramel to more obscure gelato tastes like basil and beetroot.

La Taverna di San Giuseppe – With tradition and creativity as the soul of their menu, La Taverna di San Giuseppe in Siena has become a regional classic. The setting – an original Etruscan house at the top of a narrow street – will instantly have you feeling as if dining with family. Inspired cuisine – from sirloin with fresh truffles to wild boar stews, fresh vegetable pastas and more – is beyond worthy of the restaurant’s Michelin star.

Il Falconiere – Overlooking the hills of the Tuscan countryside, the restaurant Il Falconiere – part of the luxurious Relais & Chateaux property of the same name in Cortona – delivers an enchanting experience that is wholly worthy of its fairytale-like setting. Finding the restaurant can be tricky, but the dusty drive along scenic backroads on a hot afternoon is part of the charm. Our pick is to visit for lunch and to opt for the seasonal tasting menu.


Villa Cora – Located in a centuries-old park on a hill that overlooks the city of Florence, Villa Cora is an opulent, aristocratic residence that embodies the exquisite architectural style and artistic detail that Florence is renowned for. Passionate and personal service round out the grand feel, the poolside bar is elegant and chic, and the guest rooms (45 in total) are designed with Renaissance flair. The quick shuttle ride into Florence is a breeze, but the hotel scene may be difficult to detach from.

Il Salviatino – Combine the best of the Tuscan countryside with the attractions of historic Florence by staying at Il Salviatino on the hillside of Fiesole, a fast-and-free fifteen-minute shuttle ride from downtown Florence. The immaculately restored 15th-century villa is the stuff of Tuscan fantasies, with exquisite frescoes, antique art, and impeccably groomed gardens all across the property’s 12+ acres. A team of aromatherapists awaits at the standout spa, heated infinity pools provide breathtaking views of Florence below, and the hotel’s restaurant serves hearty Tuscan favorites like spinach gnudi and swordfish fillet. Breakfast is included, and 24-hour room service is available.

Borgo Pignano – Recently crowned as the best hotel for sustainability in Europe and in the Mediterranean, Borgo Pignano sits proudly in the center of a 750-acre organic estate outside the hill towns of Volterra and San Gimignano. Solar panels and wood-fired boilers (fed from the estate’s own forest) provide hot water and heat the 23-room hotel, which itself is built of locally sourced stone and slate. Filtered rainwater feeds the gardens, which supply the onsite restaurant with its organic and seasonal produce.

If sustainability interests you, the staff will take you behind the scenes and explain everything from organic soap-making to honey production. If you prefer to appreciate these efforts from a distance, an array of holistic activities – like yoga, pilates, horseback riding, painting, and wine tasting – are offered as well. Arrive early if you can, and plan to spend a minimum of 30 minutes photographing the grand entrance.

L’Andana – A proud member of the prestigious Leading Hotels of the World collection, L’Andana provides a touch of elegance to the otherwise rustic countryside of Tuscany’s southern Maremma region. Seclusion is a crucial element to the atmosphere here, with nothing but olive and vine-studded rollings hills as far as the eyes can see. Relax and soak in the scene for a laidback getaway, or take advantage of the hotel’s proximity to the Tyrrhenian sea where boat excursions and hidden bays await. On-site tennis courts and a golf course are available if you fancy some sport, and included mountain bikes are the perfect way to explore the seemingly endless surrounding hillside and vineyards.

After a day’s worth of adventure, a visit to the Espa spa – with a mineral-heated pool, hammam, and thalassotherapy pool – is sure to put you in the right mood before dressing up for dinner.

La Bandita Countryhouse – In the famed and UNESCO-protected Val d’Orcia region of southern Tuscany, La Bandita Countryhouse is the result of a New York City couple who quit their high-profile jobs to fulfill their Tuscan fantasies. The Countryhouse resultantly offers everything you’d want in a Tuscan hotel – like outdoor dining, endless panoramic views of golden pastures, and a surrounding sheep farm for authenticity – while managing to feel like the humble, lived-in home of a close personal friend. Daily breakfast, an infinity pool, access to a private gourmet chef, and highly personalized service round out this dream stay.