Coast to Countryside: The Ultimate Italy Bucket List

Explore the belissimo world of Italy, from manicured vineyards to classic culinary creations and world-famous art with our must-do, must-see and must-try guide. 

Leaning towers, rich red vino and oodles of hand-rolled pasta – the boot-shaped peninsula is home to some of the most impressive archaeological, cultural and gastronomical feats to ever exist.

Whether you’re tempted by lush rolling hills or pristine coastlines, Italy offers an abundance of wonder and discovery at every twist and turn. Jump on the train, relax on a fully guided tour or organise a personalised road trip with TripPlanner – how you get around is up to you. Read on to be inspired by our ultimate Italy bucket list.  

Ready for your Italian adventure? Discover our handpicked collection of properties here. 

Ride a gondola in Venice 

Skip the vaporetti and cancel the taxi. Instead, take your time exploring the famed city of canals onboard a relaxing gondola. Glide along the populated Grand Canal and venture through Venice’s intricate waterways as you spot some of the city’s most iconic attractions, including the Santa Maria della Salute and Teatro La Fenice. If you’re lucky, your skilled gondola driver may sing a traditional tune as you float along the gentle current in the luxurious, intimate flat-bottomed boat.   

Looking for classic Venetian elegance? Look no further than Baglioni Hotel Luna Venice.

See the ancient wonders of Rome 

Hear tales of gladiators in combat at the magnificent Colosseum, climb up Palatine Hill and envision the city’s origin story, admire the well-preserved concrete dome and iconic pillars of the Pantheon and delve deep into layers of religious history within the breathtaking Basilica di San Clemente. Appreciate intricate designs, monolithic structures and crumbling ruins as you wander through one of Europe’s most visited cities. 

Stay close to Rome’s iconic landmarks at the luxurious Six Senses Rome.

Admire art in Florence  

It seems only fitting that the city regarded as the birthplace of the Renaissance would be the continued home of some of the most famous masterpieces. Find your way to Florence’s artistic pièce de résistance; the Uffizi Gallery’s collection of world-renowned works from creative geniuses, including Raffael, Sandro Botticelli, Leonardo da Vinci, Giotto and Michelangelo. Reserve some time to wander just down the road to the Accademia Gallery to see Michelangelo’s magnificent David statue in the flesh.  

Make your Florence escape unforgettable with a stay at Relais Santa Croce by Baglioni Hotels.

See the trulli of Puglia 

Travel to the glorious countryside of Puglia and uncover the ancient beauty of the Itria Valley, boasting a curious collection of traditional dry-stone huts. As you travel through the region, these clusters of cone-topped structures mimic the appearance of a natural mountain range. However, up close, it becomes clear that these trulli – the traditional name of the designs – are individually man-made dens with unique conically-shaped tiled roofs. This trick of the eye is well worth venturing out of the city for. 

Go shopping in Milan

One of the big four fashion capitals of the world, Milan is known not only for hosting bi-yearly fashion weeks but also for its incredible shopping precincts. The city centre is a fashion Mecca, from The Galleria Vittorio Emanuele II – one of the world’s oldest shopping malls and where Prada opened its first store in 1913 – to Quadrilatero d’Oro della moda, also known as the Golden Rectangle of fashion, where big spenders come to play. 

Soak up the glamour of the city at The Square Milano Duomo.

Mount Etna in Sicily 

Towering above Sicily’s ancient port city of Catania, a marvellous feat of nature stands tall, spectacularly erupting and spitting lava from time to time. Currently the highest and most active volcano in all of Europe, the breathtaking shape of Mount Etna can be spotted from around the Mediterranean island. Discover the magic of a site that’s been growing for 500,000 years. 

Juliet’s house in Verona 

Lovers worldwide flock to Juliet’s house in Verona to pay tribute to Shakespeare’s original tragedy of star-crossed lovers and wish for a sweetheart of their own. This stunning 13th-century mansion once belonged to the Dal Cappello family, long thought to be the probable model for Juliet’s family, the Capulets, in the fictional tale. The former owners erected a balcony outside ‘Juliet’s’ room, overlooking the beautiful courtyard, and opened the space up for tourists to explore.  

Stay just moments away at Hotel Indigo Verona – Grand Hotel Des Arts, an IHG Hotel.

Dine cliffside on the Amalfi Coast 

The most magical way to truly enjoy the picturesque Amalfi Coast is dining on delectable local fare and sipping regional vino at a glorious cliffside restaurant. With restaurants set within and on top of the expansive cliff line, there’s plenty of opportunity for a meal overlooking the crashing waves. The world-famous cave dwelling Grotta Palazzese is a rite of passage, but there are other incredible venues, from the much-loved seafood destination, La Tonnarella, to the incredibly romantic Ristorante Franchino. 

Gastronomic delights of Bologna  

Considered the food capital of Italy, Bologna is found within the highly sought-after culinary region of Emilia-Romagna and is traditionally credited as the birthplace of some of Italy’s most renowned comestible creations, such as tagliatelle al ragu (the original Bolognese), green lasagne and mortadella bologna. Though just about everything in this city is tasty, if you want to eat like a local, we suggest ordering the tortellini in broth with a glass of pignoletto. 

See the leaning Tower of Pisa 

Often at the top of travellers’ lists is the Leaning Tower of Pisa, the incredibly unique monument that gained its notoriety after experiencing a significant tilt to one side. Poor engineering and inappropriate soil quality mean this isn’t the only building in Pisa that’s on a lean, but it’s by far the most recognisable. Now considered technically stable due to recent reinforcements, visitors can climb the tower and experience its beauty and quirks from the inside out.  

Taste Chianti wine in Tuscany 

Adored by wine connoisseurs and casual sippers worldwide, the Chianti wine region within Tuscany not only produces some of the most delicious drops but is a visual sight to behold. Extending over the provinces of Florence and Siena, the Chianti region is known for producing typically medium to full-bodied red wine, primarily made from the sangiovese grape, as well as intensely tasty extra-virgin olive oil. Aside from the immensely delicious produce, Chianti’s green, rolling hills, expansive vineyards and quaint stone villages are also a feast for the senses. 

Revel in it all at COMO Castello Del Nero where Michelin-starred dining awaits.

UNESCO World Heritage-listed Pompeii ruins 

Just out from the centre of Naples, the historic site of Pompeii is a mesmerising and highly emotional archaeological destination. Formerly located at the base of the monstrous Mount Vesuvius, the ancient city was completely covered in a thick layer of volcanic ash and rock in 79AD.  Today, the bodies of villagers remain on the site, perfectly preserved during their final moments, with the toxic sludge cementing their life-like poses for 2,000 years. Walk the cobbled streets and revel in the once thriving city’s now eerily preserved villas, temples, homes and shops. 

Don’t know where to start? Find the perfect Italian city escape for you here.