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17 Most Beautiful Holiday Destinations in Italy

By Mike Kaplan · Last updated on January 23, 2025

When traveling to a country like Italy, you are likely interested in more than just the inside of a hotel room. While Italian accommodations can be as sumptuous as you might like, going on a vacation to this incredible region of the world usually carries interest in architecture, the Arts, history and local culture. Of course, for Italy and many of its visitors, the cuisine reigns supreme.

Street in Umbria

Below are some of the best vacation spots in Italy worth considering for your ultimate trip. All of these provide the history, culture and flavors you will enjoy, as well as uniquely special attributes for which each is adored.

17. Positano

Positano

Thanks to a short story by John Steinbeck and multiple movies, Positano is what many people dream of when envisioning the Amalfi coast of Italy. You will struggle to leave this seaside village yourself, a favorite songwriting escape for Mick Jagger and Keith Richards.

You may choose to stay in five star luxury comfort or simple surroundings while in this picturesque destination, but the accommodations are only one aspect of the romance and culture experienced among colorful hillside houses. Just bring your comfortable walking shoes, as hills prevail and there is so much to explore around this medieval port.

16. Venice

Venice

Venice is, of course, renowned for its architecture, artwork and gondola-navigated canals. It is a city of many nicknames, with the “Queen of the Adriatic” perhaps being its most appropriate descriptor. Venice is actually composed of 118 small islands linked together by beautiful bridges.

The birthplace of composer Antonio Vivaldi, this beautiful city has played a major role throughout history. Favorite tourist sites St Mark’s Basilica, the Grand Canal, and the Piazza San Marco will likely garner your attention and your camera lens.

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15. Portofino

Portofino

Because of its great harbor, Portofino started out as a fishing village. It’s much more than that, today, however, as it’s a resort popular with celebrities and artists who enjoy viewing the picturesque harbor. Located on the Italian Riviera, a must-see is Christ the Abyss, an underwater statue that protects fishermen and scuba divers.

Two churches stand out in the city: Church of St. Martin, which dates to the 12th century, ad Church of St. George, which has some saints’ relics. Portofino re-creations can be found at Disney Sea in Japan and Universal Orlando Resort in Florida.

14. Agrigento

Agrigento

Known as one of the greatest legacies of ancient Greece, Agrigento is a village on Sicily’s southern coast. In Agrigento, you are able to stand beneath towering columns of Greek architecture of remaining Doric temples dating back to the sixth century BC. Once the Greek city of Akragas, the Valley of the Temples near Agrigento provides many sightseeing wonders similar to those of Pompeii, Rome and even Athens, all within one location less traveled than those more popular tourist destinations.

Between the town of Agrigento and the Valley of the Temples sites, Museo Archeologico provides a wide array of exhibits of local finds, including immense statues and items from ancient graves.

13. Alberobello

Alberobello

Alberobello is a town in southern Italy that is famous for its architectural style that is truly unique. Many buildings there are trulli, named after a special type of stone hut that has a conical roof. The limestone buildings, which don’t require mortar to hold them together, were first made centuries ago and are still constructed this way today.

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The conical roofs are made from limestone slabs. When viewed from above, these roofs resemble egg-carton foam. You’ll want to spend time just wandering the small town’s narrow streets to view the trulli.

12. Procida

Procida

Procida is the place to go when you just want to chill out, enjoying water views. It’s the smallest island in the Bay of Naples and relatively untouched by tourists, except for August, the vacation month in Europe. The artist in you will want to break out a paint box to capture the picturesque views of sunwashed buildings lining the waterfront.

Be sure to stroll along the waterfront, perhaps stopping for a seafood meal in an outdoor café. The colorful Terra Murata in the historic center is well worth a visit; it also offers stunning views of the port below.

11. Montepulciano

Montepulciano

Located in southern Tuscany, Montepulciano is a well preserved medieval and Renaissance town. Foodies will like this place as it’s famous for its wine and food, including pork, lentils and honey. Its main street is a good place to walk and gawk, since it’s a pedestrian zone. Several wineries offer tasting stalls, and you can also see how an old jail was converted into a wine cellar.

Enjoy the Palazzo Tarugi, which is made of travertine, or visit the Cathedral of Santa Maria Assunta with its Assumption of the Virgin triptych Other churches have art that is just as marvelous.

10. Orvieto

Orvieto

Europe travel expert Rick Steves describes Orvieto as one of the “most striking, memorable and enjoyable” hill towns in central Italy. Located in Umbria, Orvieto is indeed just that. The old town, reachable by foot or escalator from the “new” town, is stunning. The town’s cathedral is an elaborate Gothic structure that seemingly reaches to the sky.

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Be sure to visit the Chapel of San Brizio with its colorful frescoes. More spiritual art can be found at the Palazzi Papali, a collection of medieval palaces. Don’t miss the town’s underground, a collection of Etruscan caves and tunnels.

9. Florence

Florence

Florence, also known by its Italian name Firenze, is the capital of Tuscany. Once one of the wealthiest cities in Europe, Florence was the location of medieval trade and commerce. It was once ruled by the renowned and powerful Medici family. Culture, monuments, architecture and Renaissance art draw millions of visitors each year to this popular destination in Italy.

The city lies in a basin surrounded by low Apennine mountains. Featuring Roman era layout with primarily Renaissance influences, other eras are visible in its architecture and skyline. The Ponte Vecchio bridge over the Arno River is one you will want to visit, as it is the only bridge in the city to survive World War II and dates back to the 14th century. Uniquely positioned shops held up by stilts decorate the edges of the bridge.

8. Verona

Verona

Perhaps better known than Agrigento, Verona is the famed home of Romeo and Juliet, as well as the setting for two other Shakespeare plays. A city with about a million residents, Verona is situated on the Adige River of northern Italy. Verona is known for its Arts culture, with opera being a major draw to the Arena, an amphitheatre of ancient Rome.

Of course, you will not resist visiting Juliet’s own balcony and standing beneath it to profess your love to her ghostly memory. City history dates back to beyond the sixth century BC, so there is plenty of architectural and historic wonder to take in during your visit.

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7. Rome

Rome

The capital of Italy, Rome is the seat of modern Italian culture and Vatican City, the residential country of the Pope. Over two and a half thousand years of history are packed into Rome’s borders, including the famed Colosseum, magnificent Trevi Fountain, the Sistine Chapel and St. Peter’s Basilica with its highly treasured dome. You will be amazed by the juxtaposition of Rome’s ancient landmarks against the city’s modern business district where Dolce & Gabbana, Prada, Chanel, Armani and Versace are all at home.

For your stay, you can enjoy the most decadent and modern of hotel conveniences or choose to take in ancient surroundings in more historic accommodations. Whatever you do, enjoy the city’s own uniquely Roman cuisine.

6. Sorrento

Sorrento

Overlooking Southern Italy’s Bay of Naples, Sorrento is within eyesight of Mount Vesuvius, Naples and the Isle of Capri. The famed Amalfi Drive is a must-do for visitors with their own transportation, a narrow road weaving through the cliffs high above the Tyrrhenian Sea. The city serves as a wonderful and convenient hub, if you wish to explore other Italian cities easily reached by ferry, including Naples, Positano, Amalfi, Capri and Ischia.

A city of Roman origins, Sorrento is also a delightful village setting in which to explore the port of Sorrento, the Piazza Tasso, a 14th century monastery, museums, cathedrals, and Roman ruins at Punta del Capo. You can enjoy Sorrento as a standalone destination or as part of a broader travel plan.

5. Palermo

Palermo

The capital of Sicily, Palermo is widely known for its uniquely Sicilian history, architecture, culture and cuisine. The town is over 2700 years old. Situated by the Gulf of Palermo in the Tyrrhenian Sea, Palermo is at Sicily’s northwest point. Mediterranean weather will bathe your skin in sunlight and warmth as you enjoy exploring the city’s buildings and opportunities for shopping, sightseeing and dining. One well-known site to visit is Palermo’s vegetable and fish market in the heart of the city, known as Vucciria.

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For incredible period architecture, you will not want to miss the Palermo Cathedral or Church of Saint Catherine. Norman architecture is visible in the Palazzo dei Normanni, and several palaces and museums provide other manmade wonders to photograph or just view with awe. If you love the macabre, you will not want to miss the Capuchin Catacombs, where you can pay your respects to corpses in varied states of mummification.

4. Pisa

Pisa

Worth seeing for more than just the famed leaning tower, Pisa is another city of Tuscany known for its historic churches, palaces and bridges, as well as for its maritime history. Although Pisa’s direct origins and history are not completely known, the city was certainly a port of trade for the Greeks and Gauls. Even ancient Roman authors referred to it as an “old city.”

This lengthy history is evidenced throughout its streets, architecture and surroundings. While several dozen famed sights are awaiting your footsteps, you can also walk along the paths of many well known residents. Those include Andrea Bocelli, Galileo and many other notables from throughout history.

3. Capri

Capri

If you want to vacation like the ancient Romans, head over to Capri, an island in the Tyrrhenian Sea off the coast of Italy. It’s been a resort since the days of the Roman Republic. Capri is a popular day trip destination from Naples and Sorrento.

Once there, you’ll see the ruins of royal Roman villas. A must-see attraction is the Grotto Azzurra (Blue Grotto) where sunlight shining through an opening in a sea cave illuminates the cave’s interior. Another popular site is the rock formation I Faraglioni that is best viewed from a boat.

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2. Siena

Siena

Located in the famously romantic region of Tuscany, Siena is revered and highly visited due to its place in culinary, art and medieval history. Museums are a major draw for visitors, as is the Palio, a horse race held in the town square each year. Tuscany dates back to beyond the 10th century BC and much of its medieval past remains visible. The landscape around Siena is vast and hilly, harkening to paintings of great Masters.

Architectural wonders surround you in the town square, such as the Italian Romanesque-Gothic Siena Cathedral with its marble interior and vibrant ceiling frescoes. City gardens, festivals and delightful confections for which the region is known will make you want to spend more time walking Siena’s cobblestone streets.

1. Lake Como

Lake Como

Lake Como has been a popular vacation destination with rich and aristocratic travelers since the Romans. It is still a popular playground for celebrities today. Como is Italy’s third largest lake and one of the deepest in Europe. The lake is lined with villas, some of which were built by the Romans, and their gardens.

The lake itself is a good place to boat, or go wind- or kite surfing. An inspiring sight is the Sacro Monte d1 Ossuccio, a sanctuary that boasts 15 Baroque chapels. Ferry service is available between the cities on the lake.

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