I compiled a list of 50 once in a lifetime experiences in Italy to help you plan your dream trip for when the right time comes.

50 once in a lifetime experiences in ItalyThe list is by no means exhaustive, as there are just too many things to see and do in Italy that would fit into the “once in a lifetime” category. I came up with at least one hundred more ideas while drafting this article, but then I thought it would become too much of a load and decided to cut it. In any case, I think I’ve come up with a good mix of art, nature, history, and culture.

So, here are my recommended once in a lifetime experiences in Italy, in no particular order:

1. Take an epic train ride aboard Italy’s Trans-Siberian railway, the historical line that travels through the incredible landscape of Abruzzo and Molise, which resembles the legendary Moscow-Vladivostock scenery. Think deep gorges, stunning aqueducts, valleys, ancient hamlets perched atop mountain peaks to be admired from fully restored vintage carriages that climb as high as 1,268 meters. If you’re curious to know more, read this article about my experience on the Italian Trans-Siberian train.

The Italian Trans-Siberian railway2. Enjoy Venice’s Grand Canal from aboard the #1 Vaporetto water bus, which connects Piazzale Roma to Lido. It offers a fabulous panoramic trip for a tiny fraction of the price of a water taxi or a gondola ride. Along the way, you’ll enjoy excellent views of such highlights as the Rialto Bridge, the glorious Church of Santa Maria della Salute, and the town’s finest palaces. If this trip is on your bucket list, make sure to read all my Venice tips.

3. Discover what daily life was like back in the Roman Empire with a visit to Pompeii and Herculaneum, two ancient port towns near Naples where time was brought to a standstill following a mighty eruption of Mount Vesuvius in 79 AD.

4. Visit one of Italy’s top wine districts and learn more about the story behind some of our best blends as well as the history of our territory directly from the winemakers – no one knows this better than they do. On the blog, you can read articles about the Langhe wine region in Piedmont and a wine tasting tour in Oltrepò Pavese

A view of the hills covered in vineyards in Oltrepò Pavese, one of Italy's top wine districts5. Take a road trip through Abruzzo, the region known as the “green heart of Europe” because of its extraordinary natural treasures. These include the Gran Sasso and Laga Mountains National Park, one of the largest in Italy, and the endless pastures of Campo Imperatore, known as Italy’s Little Tibet. Another jewel in the park is Rocca Calascio, a fascinating fortress built by the Normans to protect something richer than any other treasure in the world at that time: herds of sheep producing wool, the only fiber able to keep people warm!

6. Enjoy a fabulous tour of the Fenestrelle Fortress, Europe’s biggest fortification and the second-biggest masonry construction in the world after the Great Wall of China, covering an area of 1350000 sqm.

7. Visit the extraordinary cave town of Matera, whose history dates back to over 30,000 years ago. A must-see is the Crypt of the Original Sin, an ancient cave with an extraordinary cycle of paintings dating from the 8th century that won it the nickname of “Sistine Chapel of Rupestrian Art”.

A view of the ancient cave town of Matera in Basilicata8. Go island-hopping in Lake Maggiore and discover the three splendid Borromean Islands, which form an enchanting microcosm of exquisite gardens, baroque palaces, and quaint lakeside corners just off the elegant town of Stresa.

9. Learn that there’s more to Liguria than pretty seaside resorts with a trip inland, where you’ll find lots of quaint villages with intriguing stories. These include Triora, a medieval hamlet where legend has it that a shocking witchcraft trial took place in 1588; Bussana Vecchia, the hamlet that a group of international artists brought back to life in the 1950s after being damaged by a violent earthquake; Seborga, the tiny village that thinks of itself as a micronation, complete with a crown council that claims independence from Italy. If you’d like to know more, check out my articles about exploring Liguria beyond the usual routes and the self-proclaimed state of Seborga.

10. Visit a museum of the Italian Association of Company Archives and Museums (Museimpresa) to learn about some of the greatest brands that significantly contributed to the growth of Made in Italy all over the world. Examples are the Lavazza Museum in Turin, the Ducati Museum in Bologna, and the Branca Collection in Milan (if you are a fan of Fernet Branca, then take a look at this article).

The Branca museum and distillery in Milan11. Join Neapolitans evoking protection during San Gennaro’s blood miracle, the great religious spectacle that takes place three times a year in the Duomo church – on the first Sunday of May, on 19 September, and 16 December (the day when Vesuvius erupted in 1631). Then, explore the saint’s treasure at the Museum of the Treasure of San Gennaro, one of the world’s most precious collections of jewels and artworks.

12. Take a sunset tour of Agrigento’s Valley of the Temples, a gem of Italian archeology, and explore the impressive remains of the ancient Greek town of Akragas, the nucleus of modern-day Agrigento. While you are there, take a quick detour to Scala Dei Turchi, one of Italy’s most astonishing stretches of coast.

13. Stroll through the fascinating remnants of the ancient Roman Empire in Italy’s capital and step inside the Colosseum, where emperors used to organize cruel fights and grandiose events to increase their popularity among the public.

View of the Colosseum in Rome14. Take part in the Mysteries of Campobasso, one of the many fascinating events taking place in Italy. It takes place on Corpus Domini day in June and consists of groups of people parading through town while portraying episodes from the Bible aboard special machines that a local artist built back in 1748. There are even children suspended on ropes and metal wires!

15. Take a thrilling ride on the Skyway Monte Bianco cable car and enjoy impressive close-up views of Mont Blanc, Italy’s highest peak (over 4800 mt). This mountain, which someone even compared to a gothic cathedral, is a true natural marvel of our country and offers an extraordinarily scenic landscape.

16. Spend a wonderful weekend amid the sublime natural landscape of Val D’Orcia, a Tuscan corner of tranquil villages, ancient abbeys, and countless shades of greens and yellows, dominated by the Radicofani Fortress. You’ll feel like you’ve just stepped into a painting. By the way, if you’re planning to visit Tuscany, here’s an itinerary for a 10-day road trip that I personally used.

The beautiful landscape of Val D'Orcia in Tuscany17. Deep dive into the world of Frederick II, the Swabian emperor known as ‘stupor mundi’ (the wonder of the world), with a visit to Castel Del Monte, his most famous castle. Located in the Alta Murgia National Park, the castle is one of Apulia’s most important cultural sites, boasting a unique octagonal design with particularly rich symbolism (if you’re putting together an itinerary around Apulia, do take a look at this article).

18. Forget strict travel schedules for a day and lose yourself in the magnificent treasures of the Vatican Museums in Rome. It’s one of the world’s most extensive art collections, with countless pieces spread across 7 kilometers of galleries! Please don’t leave without exploring the glorious St. Peter’s Basilica and climbing to the top of its dome, where some truly amazing views await you.

19. Spend Easter in Sicily and join Enna’s 16 confraternities in the epic procession that takes place through the town’s streets on Good Friday as part of the town’s local Holy Week traditions.

The Good Friday procession in Enna, one of the most amazing events of the Holy Week in Sicily20. Channel your inner Grand Tour traveler and discover the splendid historical villas of the Brenta Riviera aboard a burchiello, the traditional Venetian barge of the 17th century that cruises between Padua to Venice. The traditional boat has been replaced with a modern version for obvious reasons, but the itinerary retains all the enchantment of those times, with bucolic views and visits to architectural marvels like Villa Foscari (one of the masterpieces created by genius architect Andrea Palladio), Villa Widmann (which sports some beautiful frescos and a labyrinth), and Villa Pisani in Stra (the famous Doge’s Palace on the mainland).

21. Enjoy Italian opera in one of the country’s many historic theatres, from Naples’ Teatro San Carlo (Europe’s oldest opera house) to Milan’s Teatro alla Scala and Parma’s Teatro Regio (try to go there during the town’s annual Verdi Festival).

22. Witness all the power of Mother Nature in Castelluccio di Norcia, one of the villages almost completely destroyed by the earthquake that hit Umbria in 2016, where an extraordinary chromatic show goes on stage every year between late June and early July when the famous local lentils are in full bloom.

Colorful fields of lentils in fool bloom in Castelluccio di Norcia23. Marvel at the sheer beauty of the Royal Palace of Caserta, one of the finest examples of royal residences built in Europe during the 18th century. With over 1000 rooms and 11 acres of beautifully landscaped park, it’s a real architectural masterpiece.

24. Delve into the astonishing mosaic artworks of Ravenna, a town in Emilia Romagna with an extraordinary historical and artistic heritage. Once the capital of the Western Roman Empire, today it’s home to eight UNESCO World Heritage and countless other important cultural landmarks, including Dante’s tomb.

25. Treat yourself to a royal weekend in Turin, Italy’s first capital, amid royal residencies, fabulous museums, historic cafés, and sinful sugary pleasures. Check out my article about what to see and do in Turin in four days to plan a long weekend there.

View of Palazzo Madama in Turin at dawn26. Celebrate Carnival in Italy by attending one of the many festivals taking place across the country. From Sardinia’s Mamuthones and Issohadores (people dressed with black sheepskins and grotesque wooden masks) to Piedmont’s Battle of the Oranges, there are countless events that speak volumes about the country’s unique local traditions.

27. Climb on top of Mount Etna, Europe’s highest (and most active) volcano. Sicilians have a unique relationship with their “Muncibeddu” (a nickname for Etna that means beautiful mountain in local dialect). Its eruptions are greatly feared, but its volcanic soil creates excellent products, including the highly-regarded Etna DOC wine.

28. Venture off the beaten track in northern Molise and discover where most of the world’s bells come from, Agnone. It’s here that the Marinelli family has been casting bells since the 11th century. Visit their workshop means stepping into the fascinating world of Italy’s oldest family business, which received important recognitions throughout its history, including the privilege of using the Papal coat of arms on their bells. By the way, here are a few reasons why you should include Molise on your travel wishlist.

Inside the workshop of Marinelli Pontifical Foundry in Agnone29. Cruise down the Po River Delta, Italy’s largest expanse of wetlands located between Veneto and Emilia Romagna, to admire a unique ecosystem of rare birds, lush vegetation, lagoons, sand formations, fossil dunes, and coastal pine forests.

30. Become one of Juliet’s secretaries for a day and experience the magic of handwritten letters from across the globe at Juliet’s Club in Verona. Here’s a sneak peek of what to expect when visiting Juliet’s Club.

31. Visit Genoa, one of the key protagonists of the Mediterranean’s history where modern banking was born and the ancestors of modern hotel star rating (i.e., the Rolli) first appeared. The Ligurian capital also boasts a fascinating 76 mt lighthouse, which is believed to be the world’s third oldest lighthouse still in operation. Check out my guide on how to spend four days in Genoa.

Piazza Banchi in Genoa with a flower kiosk and the Church of San Pietro in Banchi32. Learn about Naples’ mysterious Cult of the Dead, the tradition of adopting anonymous bones and skulls (the so-called anime pezzentelle) and praying for their souls. Hotspots of such devotion are the Fontanelle Cemetery in the Sanità district and the Church of Santa Maria della Anime ad Arco in the historic center, both filled with thousands of remains of these poor souls.

33. Discover a unique side of Tuscany with a visit to Pitigliano, an ancient village carved out of tuff rocks in the heart of Maremma. Here, Tuscan customs perfectly blend with Jewish traditions, resulting in something truly unique to this part of the region. An example is the sfratto, a traditional biscuit that incorporates the ingredients of both cultures.

34. Tour South Tyrol, an incredible alpine region boasting 300 days of sunshine per year, 800 castles, and unique natural wonders like Lake Braies, the Three Peaks of Lavaredo, and some impressive earth pyramids. It’s also a thriving wine-growing region – just saying!

Lake Braies in South Tyrol35. Live an authentic Italian beach experience in Rimini, the birthplace of film director Federico Fellini and a favored seaside holiday destination in my country. Expect lots of colorful bagni (beach clubs), excellent food (try their piadina), a beautiful old town rich in history, and wild nightlife.

36. Browse one of the world’s greatest art collections at the Uffizi Gallery in Florence, the palace designed by Giorgio Vasari for Cosimo I de’ Medici in the 16th century. What was originally conceived as a space for the town’s legal and administrative offices now hosts masterpieces by leading Italian artists. Botticelli’s La Primavera and Birth of Venus, Leonardo Da Vinci’s Annunciation, Caravaggio’s Medusa, and Titian’s Venus of Urbino are not to miss.

37. Get a taste of la dolce vita with a scenic road trip through Apulia, from country roads brimming with Trulli and enchanting whitewashed hamlets to gorgeous natural swimming holes and delicious traditional food. If you need some inspiration, read this post.

The conical-roofed Trulli of Alberobello in APulia38. Take part in a Palio, the century-old bareback horse race that sees the participation of the whole town. The most famous is the Palio di Siena, which takes place twice a year, but there’s one equally fascinating held in Asti in September.

39. Stand in awe at the Marmore waterfalls in Umbria, the highest in Europe (165 meters), and discover that they are not the work of mother nature but rather the product of ancient Romans’ engineering genius.

40. Swim in the transparent waters of Tropea, the pearl of Calabria’s “Coast of the Gods”, under the watchful eye of a monastery standing high above a rocky promontory. Then watch the sunset from one of the panoramic viewpoints scattered around town and join locals in their evening passeggiata. This is the itinerary I used to explore Calabria’s Tyrrhenian coast.

The church of Santa Maria dell'Isola, one of Tropea's icons41. Climb to the top of Milan’s iconic Duomo at sunset and admire the views amid countless statues and elegant pinnacles that have enchanted generations of travelers (Mark Twain defined it “a poem wrought in marble”).

42. Explore the Cinque Terre with a scenic hike through Sentiero Azzurro, a 12 km trail that connects the five villages and offers truly spectacular views. Alternatively, you can opt for the longer, less touristy Alta Via delle Cinque Terre, a 40 km path running from Levanto to Portovenere.

43. Immerse in Palermo’s unique atmosphere and incredible cultural heritage. Expect precious historical buildings, vibrant street markets with tons of local delicacies and loud sellers, and truly unique attractions like the Capuchin Catacombs under the city streets where hundreds of perfectly preserved corpses are exposed to the public, revealing a lot about customs and traditions of the local society between the 17th and 19th centuries. These are just a few examples of the top 15 things to see in Palermo I wrote about on the blog.

A colorful street market in Palermo44. Take a dip in the (free) natural thermal pools of Saturnia in Tuscany, where fabulous hot springs have been rejuvenating bodies and minds since ancient Roman times.

45. Head south to admire the picture-postcard sights of the Amalfi Coast, from enchanting villages clinging to rugged mountains and scenic hiking trails to beautiful villas and lovely little beaches – plus some of the craziest driving you’ll ever experience! Download my free Amalfi Coast Guide if you’re planning a trip there.

46. While touring the Amalfi Coast, please take some time to visit also Salerno. Its super attractive historic center features an ancient castle, Europe’s oldest botanical garden, and a lovely tree-lined seafront promenade. Oh, and the most beautiful crypt I’ve ever seen! Still not convinced? Read here.

Salerno-minerva-gardens47. Treat yourself to a beach holiday in Sardinia and its many gorgeous beaches, which honestly have nothing to envy to the Caribbeans. Some of the best spots include Cala Domestica, Mari Pintau, Cala Goloritzé, and Cala Spinosa.

48. Immerse in Burano’s gorgeous kaleidoscope of colors. Then, leave the crowds behind and jump on a little boat for San Francesco del Deserto, a pretty little island inhabited by Franciscan friars.

49. Take a deep dive into European prehistory with a trip to the largest collections of prehistoric rock art in Lombardy’s Val Camonica. You’ll find over 140,000 drawings realized during thousands of years, depicting agricultural scenes, hunters, warriors, and magic symbols. This was the first Italian site to enter the UNESCO World Heritage list.

50. And finally, put your guides away and just venture inside the first unpretentious trattoria you come across (no sign of printed menus is often a good sign, too). Chances are you’ll have one of your most memorable dining experiences of your life!


Ciao for now,

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1 Comment

Taylor 9 January 2021 at 16:47

I am proud to say that I have checked off some of these experiences. Italy is such an amazing country filled with so many amazing things to enjoy. Great article! 🙂

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Ciao! I’m Val

Ciao! I’m Val

Ciao! I'm Valentina, an Italian blogger with a huge passion for my country, its culture and traditions. My Italian Diaries is the online space where I share my expert knowledge of itineraries, activities and off-the-beaten path places to help you experience the best of Italy like a local.




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