There’s a reason Italy is one of the world’s most popular countries to visit. From the ancient history of Rome to the vineyards of Tuscany and the gorgeous Amalfi Coast, there’s just about something for every type of traveler. While it’s just about impossible to cover all Italy has to offer in one trip, the following seven sites are among the country’s must-sees from north to south.
The Dolomites
In a country that’s famously home to the highest number of UNESCO World Heritage Sites on Earth (59), one site that’s exponentially lesser known than, say, Venice or Rome is also among the most striking. The 18 peaks that make up the Dolomites, a sub-range of the northern Italian Alps, passed UNESCO’s Outstanding Universal Value test thanks to “a variety of spectacular vertical forms such as pinnacles, spires and towers, with contrasting horizontal surfaces including ledges, crags and plateaux,” among other standout features.
But it’s not just the astonishing nature that makes these mountains unique: Having once belonged to Austria, a swath of this region retains much of that heritage — as you’ll discover if you’re visiting one of the local ski resorts during the snowy season, when the best refueling options include goulash, dumplings, and strudel. And though winter in the Dolomites is also magical for all the intimate, tucked-away holiday markets — complete with local takes on glühwein — the summer hiking among these dramatic peaks and valleys is equally tempting.
Trevi Fountain – Rome
Considering the famous legend surrounding this stunning Baroque fountain (toss a coin in, and you’ll return to Rome someday), it’s fitting that the origins of the monument also pack plenty of lore. The official version of events holds that Roman architect Nicola Salvi won the rights to the project in a 1730 design contest. But there’s a backstory: Alessandro Galilei — yes, same family as Galileo — won first. But since he was a Florentine, the local outcry was so great that Salvi was awarded the commission instead.
As for the fountain’s waters, even their original source — an ancient aqueduct called Acqua Vergine — comes with its own mythology. The sixth-century senator Cassiodorus once reportedly said, “The Aqua Virgo runs with delightful purity… as a never-clouded sky.” Either way, this water was so special that the Vatican used to have a standing order. No longer potable, what fills the fountain now boasts a different value: around $1.6 million in visitor coinage annually. Popularized by Frank Sinatra’s 1955 rendition of “Three Coins in the Fountain” in the film of the same name, the traditional Trevi toss helps fund everything from local food pantries to shelters.
Il Duomo – Milan
At almost 110,000 square feet and with room for 40,000 people, this gothic cathedral is Italy’s largest church. But Milan’s Il Duomo goes big on more than sheer size: The construction took nearly six centuries to complete, from 1386 to 1965, and to this day requires fresh supplies of Candoglia marble to touch up the stunning yet susceptible rosy-white facade. Then there are the big names involved in the project, from Leonardo da Vinci (one of many artists and architects who attempted a design for the difficult lantern tower) to Napoleon Bonaparte, whose coronation here spurred the completion of the facade.
A standout figure of a different kind? The tally of resident statues, said to outnumber any other church in the world There are more than 3,400 in all — including an estimated 2,000 on the roof, where walking tours through the iconic spires tend to note the most prominent saints (the golden Madonnina), the least expected celebrities (20th-century heavyweight champ Primo Carnera), and everyone in between. For some visitors, however, the church’s biggest draw is actually quite small: a single nail believed to have come from Jesus’ cross.
Bridge of Sighs – Venice
Rare is the span of limestone (or anything, for that matter) that inspires an opera, a Pittsburgh prison, and a bid for eternal love. But rarity is Venice’s calling card, so if such a bridge were to be found anywhere, why not above the narrow canal that separates the courts of the Doge’s Palace from the prisons?
However apocryphal, the backstory is as follows: when Venetian convicts got their last glimpse of the city as they crossed this 17th-century Baroque bridge to their subterranean fate, audible sighing routinely ensued. Thanks at least in part to one very famous translator — Lord Byron, who dubbed il Ponte dei Sospiri (“the Bridge of Sighs”) in an 1812 poem — the arch took hold of the popular imagination. Among the homages built in subsequent decades, Pittsburgh’s version was the only to link a jail to a courthouse.
A slightly more romantic take on the bridge emerged in 1861 with Jacques Offenbach’s operetta “Le Pont des Soupirs” (the French translation of its name) in which the bridge played a central role. But the most romantic possible appropriation of the bridge is now a time-honored Venetian tradition: Drift underneath in a gondola at sunset, as the bells of St. Mark’s Basilica toll, and kiss your beloved to ensure everlasting bliss together.
Boboli Gardens – Florence
Hidden behind Florence’s Pitti Palace is one of the most extraordinary examples of the Italian garden — a Renaissance fixture that became the fashion at every European royal court from Luxembourg to Versailles to Peterhof. Blending geometrically arrayed landscape elements with architectural installations, monumental statues, and various water features, these 111 acres have since become an open-air museum, with centuries’ worth of expansion and revision represented.
Though work on the grounds began in the 1400s, the gardens didn’t get going in earnest until 1549, when Eleanor of Toledo — wife of the Grand Duke of Tuscany Cosimo I de’ Medici — bought the estate with grand-scale alfresco entertainment in mind. Medici court artist il Tribolo worked on the initial design, until his death ushered in a whole series of successors. Some of their most notable additions include the Buontalenti Grotto, the amphitheater’s obelisk (originally from Luxor), and, not least, the famed 18th-century rococo-style pavilion called the Kaffeehaus. While you won’t find refreshments there, you’ll at least find drinking fountains in some incredibly scenic spots, such as the Grotto of Adam and Eve, the Meadow of Columns, and the Garden of Madama.
Arco Naturale – Capri
Ubiquitous on bucket lists and honeymoon itineraries, Italy’s island of Capri is famous for its breathtaking natural beauty, and perhaps nowhere is that on better display than the island’s Arco Naturale (Natural Arch). It starts with the journey there: a leisurely stroll from boutique-lined Via Camerelle to Via Tragara — home to luxurious hotels and private villas. The street ends in a large terrace offering incredible views of the sea, the Amalfi Coast, the island’s mountaintops, and the famous Faraglioni rocks. From there, you’ll follow the narrow, coastline-hugging Pizzolungo footpath to the spectacular arch.
Located on the eastern coast on the island, the Arco Naturale dates to the Paleolithic era and is all that remains of a deep, underground grotto that was only discovered in the aftermath of a landslide. The arch spans 39 feet and is about 59 feet high — a natural bridge of limestone framing a postcard-perfect view of the Mediterranean’s sparkling blue water. While there, don’t miss the Grotta di Matermania, a cave where sacred rituals were believed to be practiced thousands of years ago.
Teatro Greco – Taormina
Boasting dramatic views of the Ionian coast and nearby Mount Etna (one of the tallest active volcanoes in Europe), this ancient Greek theater on the east coast of Sicily was carved directly from the rock of Mount Tauro sometime around the third century BCE. Though originally built for dramatic performances by the Greeks, the Teatro Greco was later taken over by the Romans in the second century CE and repurposed for gladiator contests. The stunning amphitheater holds upwards of 5,000 spectators, making it the second-largest ancient theater in Sicily, after one located in Syracuse.
The massive stone structure is divided into several distinct parts: a scene (stage) where the actors perform which features six Corinthian columns raised in the 1800s, an orchestra where either the musicians sat or gladiators fought, and a cave where spectators were seated. Though it’s nearly 2,500 years old, the theater continues to host performers such as Elton John, Bob Dylan, and Sting, and is also home to the Taormina Film Fest each June.
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