Episode #110: Italy’s Most Romantic Places

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Listen to “Romantic places to visit in Italy and the story of San Valentino” on Spreaker.


In a tribute to San Valentino (Saint Valentine), we are celebrating all the beauty and romance that is found all over Italy. Beauty and romance mean different things to different people, so one person’s swoon-worthy view from the fancy Terrazza Danieli in Venice is another’s sweeping vistas from a hike between the villages of the Cinque Terre, but there’s no doubt – everyone can find their preferred version of romantic experiences in Italy.

Show notes
In this episode, we’ve taken a look at some of the places we think are the most romantic in Italy but really, you’ll find romance or that quality or feeling of mystery, excitement, and remoteness from everyday life wherever you care to look in Italy. And that’s why we’ve all fallen so in love with this country.

The story behind San Valentino

San Valentino lived in the 3rd century AD and Valentino (meaning valor) was a pretty popular name at the time so historians aren’t really sure whether they can attribute all the myths and stories to just one person or several. Some say he was a priest in Rome and others say he was a bishop for the Umbrian town of Terni but they all agree he was martyred on the 14th February at the order of Emperor Claudius at the Flaminian Gates. This is now the site of the Porta del Popolo in Rome leading to the expansive piazza of the same name.

There are a few stories as to why was he martyred? One account says that he restored the sight of the blind daughter of a judge called Asterius. Overwhelmed with gratitude, This inspired Asterius to convert his entire family to Christianity and as a result, Valentino gained some notoriety and the attention of Claudius.  The Emperor was evidently quite intrigued by the priest but didn’t really appreciate it when the conversion activities were then focused on himself and sent Valentino off to the gallows! Legend has it that the saint said a note to the girl whose sight he restored signed “from your Valentine” which is where the tradition of sending romantic missives is said to have evolved.

Another story has St Valentine marrying scores of couples that allowed the husbands to escape conscription into the Roman army. This enraged the Emperor who believed that married soldiers were less focused and pined for home more than their unmarried counterparts.  He was no doubt furious at the loss of his steady supply of recruits. Apart from sweetly arranging this evasion and probably certain death for these young men, San Valentino is said to have cut hearts from parchment “to remind these men of their vows and God’s love” 

Whatever the truth is, the legends have endured and strengthened and St Valentin’s Day on 14th of February is celebrated around the world and has been going for almost 1500 years!.  In the 16th century, 1200 years after the Saint’s death, Shakespeare mentioned St Valentine in A Midsummer Night’s Dream and also Hamlet. To this day you can visit his skull, crowned with flowers at the Basilica of Saint Mary in Cosmedin in Rome.

Places mentioned in the show


The place Shakespeare immortalized as the home of his star-crossed lovers, and possibly the world’s most famous couple – Romeo and Juliet. The city of fair Verona is a gorgeous small city in northern Italy between Venice and Milan known for its Roman amphitheater, beautiful wide piazzas, and elegant streets. It’s the type of place that is just lovely to wander around and soak up the atmosphere. Many people visit Verona simply to pay their respects to tragic Juliet at a house once owned by the de Cappello family. A very enterprising individual noted this name and similarity to Capulet and the rather charming balcony of the palazzo – from which she must have called out to Romeo – and decided it was a great place for a museum dedicated to Juliet. There’s even a bronze statue of her below the balcony where, if you rub its right breast you’re sure to be lucky in love. The whole thing is a work of fiction, just like Shakespeare’s play, but it is a very popular place to visit and the balcony is charming. But please don’t go to Verona just to visit the house of Capulet, because there are many other romantic things to do:

  • attend an opera in the open-air Roman Amphitheater
  • take the funicular to Colle San Pietro for sweeping views of the city and its bell towers and terracotta roofs
  • stroll over the beautiful red brick Castelvecchio Bridge – though largely destroyed by bombing in 1945 it was lovingly rebuilt to identically match the 14th-century original
  • if you love manicured gardens adorned with statues then Giardino Giusti is the perfect place to while away a few hours


Sirmione is where the Scaliger family – whom the bridge in Verona was named for, also left their mark. Clearly big lovers of turrets and all things fairytale, the Scaliger family built Sirmione into perhaps the most beautiful fortified town in all of Italy. Sitting on a peninsula that juts out into Lake Garda, you approach the little hamlet via a drawbridge that spans the castle moat where swans bob up and down in the turquoise waters. It really is as picturesque as it sounds! Here’s how to make the most of a visit to Sirmione:

  • spend some time wandering the town and admiring the cobbled streets and houses draped in vines and flowers and maybe stop for a glass of wine or gelato
  • climb the castle tower for breathtaking views of Lake Garda and the mountains beyond
  • head out on the peninsula to visit the Grotte di Catullo – ruins of a Roman villa that you may have seen in the movie Call Me By Your Name. On a sunny day, this is a popular swimming spot so bring your costume for the truly unique experience of swimming beneath the ruins
  • if swimming isn’t your thing, take a little boat ride around the peninsula. A truly beautiful experience with the alps in the background and castle in view. Your boat captain will likely point out little bubbles rising from the lake waters. This is thermal water that Sirmione is also known for
  • visit the town’s gorgeous thermal spa where you can relax and soak it all up.
  • enjoy the sunset at the end of the day when the day-trippers have disappeared
  • partake in the region’s fine wines – as it is in the very heart of the Franciacorta wine region which is the equivalent of champagne in Italy. It’s a bit more complex than prosecco due to the double fermentation method and it’s delicious


A tiny town in the Val d’Orcia region of Tuscany near Montepulciano and Montalcino. It’s a glorious wine region and you’ll definitely recognize the scenery from many pictures you’ve seen of Tuscany. But why is this place so romantic? Apart from being impossibly pretty and perched on a hill overlooking the valley, the town is one straight out of any Tuscan dreams – think ochre colored buildings and cobbled streets, a cute little piazza, and a palace and flowerpots bursting with blooms on every doorstep. It was built to an exacting design by a Renaissance pope who wanted to build the perfect town. Popes, of course, were loaded with cash in those days and no expense was spared in the construction of Pienza which unsurprisingly has stood the test of time and endured over many centuries and is now a UNESCO listed heritage site. Don’t miss:

  • visiting the palace – the pope’s former home – from where you get the most outstanding views
  • wander the streets that have been named just for lovers. You’ll find Via del bacio (street of the kiss) and Via dell’Amore (street of love) with glimpses of the valley beyond and perfect for strolling hand in hand
  • if your idea of romance extends to a shared love of cheese, you won’t be disappointed in Pienza. The town is full of small shops selling local pecorino sheep’s milk cheese in many varieties – you definitely must try the aged variety! Which of course matches perfectly with a glass of Montalcino wine. Perfetto! 

Alberobello, Locorontondo and the trulli towns of the Valle D’Itria in Puglia

No doubt you may have seen these trullo –  gorgeous round dwellings topped with conical stone roofs all over Instagram and travel blogs. They are completely unique to this region and add a magical quality to the surrounding red earth and ancient olive groves landscape.  A trullo is a white dry stone wall hut with a grey stone cone-shaped roof that is often topped with the shape of a disk, stone, crescent, star or ball on its pinnacle which are the mark of the builders that made them. To get the most out of a trip to Puglia:

  • stay in a trullo! Once very humble dwellings, many of the trulli have been converted into airbnb style accommodation, so you can spend the night in them. Some are still quite rustic but you can also rent some really fancy luxury trulli if that’s the kind of experience you find romantic
  • Alberobello and Locorontondo are some of the well-known towns to find the trulli houses and these are lovely places to visit year-round to wander and enjoy the scenery and unique architecture
  • to see the trulli at their very best, visit at Christmastime, particularly in Locorontondo as the locals dress up their houses and surrounding cobbled streets with red and green decorations and sparkly lights which looks so magical against the white washed trulli. Christmas is a wonderful and magical time that oozes romance you can’t help falling for this tiny village decked out for the season


Positano is one of the world’s most coveted honeymoon destinations and it’s an absolute dream. Colorful houses seem to tumble into the Tyrrhenian Sea – so blue you wonder where the sky ends. Cobbled streets wind up the cliff the town is built on, wisteria and vines swaying in the breeze overhead.  If gazing out to sea, lounging at a beach club, and enjoying the southern Italian sun and hospitality sounds like your idea of heaven then Positano should be added to your dream places to visit. How to make a trip to Postino memorable:

  • it is a place of luxury and beauty and one where you’re going to want to splurge by staying somewhere like the iconic Le Sirenuse or Il San Pietro. There are several charming hotels in town but a stay at either of these two properties will undoubtedly be one of the romantic highlights of your life
  • if you prefer a more casual low key romantic experience – especially for honeymooners, head to neighboring Praiano.  Here the beaches and town are quieter and the sunset is incredible – the best on the Amalfi Coast. We don’t think of this often but position is everything when it comes to sunsets and little Praiano is in exactly the right spot for watching the sun dip below the horizon.
  • consider staying on magical, mythical Capri – the most beautiful island in the Tyrrhenian Sea. The most romantic story ever told on this podcast can be heard on episode 42 where guest Holly tells how she met her now-husband Gianluca and ended up living on the island. Holly is the absolute expert on romantic things to do in Capri including organizing picnics with epic views and not another traveler insight, small gozzo boat trips around the island and the secluded spots only locals know about.  Capri has been a destination for lovers for centuries and who could blame them but if you’re serious about falling in love with the place, an overnight stay is the only option – to take the time to find your own favorite viewpoints, beaches, and walks


Sicily as a whole is a seriously swoon-worthy island but Ortigia, the old town of Siracuse or Syracusa seems like it’s straight out of a movie from the 1950s. It’s a Baroque town with narrow car-free streets – balconies overhead, and charming curiosities around every corner. You half expected to see Sophia Loren leaning from one of those balconies, observing the goings-on below. Life goes on in Ortigia unlike many of the towns transformed by tourism. There’s a realness to the town that makes you want to explore more. Start with:

  • heading to its bustling market for wonderful and delicious produce
  • take in the extravagant Duomo and piazza where locals carry out their business
  • wander the ruins of the Ancient Greek temple
  • stop to admire the ornate fountain as you walk along the seafront

Isola San Giulio

Another enchanting island that is also completely silent, Isola San Giulio sits in quiet contemplation in the middle of Lake Orta in Italy’s northern Piedmont region and is a very special and unique experience:

  • if you take the ferry across the water to the island you’re asked to visit in silence with respect to the resident nuns who occupy its medieval monastery
  • visit in autumn or fall to experience this island and its ancient towers rising from the water surrounded by the changing colors of the leaves in vibrant yellows, reds, and oranges
  • during a summer visit you can admire the island from the tiny town of Orta San Giulio and explore its pretty vine-covered streets slowly – piano, piano. There’s no rushing here. This is not a vibrant place, instead, it’s got that soft romantic feel that comes from knowing you’ve found the person or place that makes you feel right at home


Back in Italy’s north east corner – in Venice. A city that simply exudes mystery and romance, no matter the season. Its reputation for romance is not without good reason and there are many experiences that can make a trip totally unique with special memories:

  • in summer, disappear down the quiet laneways and enjoy the views of the side canals with shutters of ancient palazzi open overhead. Perhaps you’ll catch a glimpse of a shiny gondola out of the corner of your eye as it glides past an adjacent waterway. You may have been alerted to its presence by the gentle slap of an oar on water or the song of the gondolier
  • winter brings fog in Venice and the city shrouded in mist takes on an almost ethereal quality that never fails to charm. The city is quieter then and you can feel like it’s almost your own if you stick to the outer canals and small laneways. Imagine having Venice to yourself!
  • there’s nothing more romantic than a proposal on a gondola in Venice and we love when we see people posts about these in our Italy Travel Planning community. They look so happy and what better way to start a lifetime of adventures together than on one of those incredible vessels with the majesty of Venice all around you. This is an obvious and popular choice for proposals but if you’ve listened to our episode about gondolas – number 87, you’ll understand why. They are symbols of craftsmanship, beauty, and generations of tradition
  • Venice offers lower-key experiences too. There’s nothing quite as romantic as a stroll back to your charming hotel over tiny bridges bathed in lamplight after a seafood dinner for the ages.  No wonder Venice is know known as the city of love 


  • Saint Valentine – the Saint who brought us to celebrate all things love every February 14th
  • Shakespeare –  English playwright, widely regarded as the greatest writer in the English language and creator of the enduring romantic tale of the star-crossed lovers Romeo and Juliet
  • Verona Arena – a Roman amphitheater in Piazza Bra in Verona, built-in 30 AD. It is still in use today and is internationally famous for large-scale opera performances
  • Castelvecchio Bridge – also the Scaliger Bridge (Italian: Ponte Scaligero) is a fortified bridge in Verona, northern Italy, over the Adige River
  • Grotte di Catullo – the ruins of a Roman villa built between the end of the 1st century BC and the beginning of the 1st century AD at the northernmost end of the Sirmione peninsula on the southern shore of Lake Garda.
  • Terme di Sirmione – indoor/outdoor spa compound near Lake Garda known for its thermal pools, saunas & steam baths
  • Franciacorta – wine region in the Province of Brescia. Franciacorta, from the Latin “franchae curtes”, means “exempted from paying duties”
  • Pecorino – delicious hard sheep’s cheese – the name “pecorino” derives from pecora which means sheep in Italian
  • Brunello di Montalcino – a red DOCG Italian wine produced in the vineyards surrounding the town of Montalcino
  • Trullo – (plural, trulli) is a traditional and iconic Apulian dry stone hut with a conical roof
  • Orta San Giulio – is a town in the Italian region of Piedmont jutting out from the eastern bank of Lake Orta

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