While the allure of Italy’s classic romantic cities is undeniable, the journey to explore its heart also beckons us towards lesser-known gems that promise unforgettable experiences. Italy remains simultaneously vivid yet endearingly tender, clamorous yet impossibly elegant, complex yet endlessly welcoming. You can’t help but be swept up into the rhythm of this place and its ability to transform profoundly during even a short train ride. Indeed, Italy’s delightful contradictions may be the very thing that makes it an ideal romantic destination: just enough variety, just enough luxury, just enough adventure.

In this itinerary, we’ll whisk you away to Venice, Florence, Rome and Sorrento, unveiling their enduring attractions while also suggesting off-the-beaten-path treasures in smaller cities and towns. You might find yourselves making little unplanned detours along the way, but doesn’t that just add to the romance of it all? And besides, when you’re with someone you love, you’re never truly lost!

Stop 1: Venice

Joseph Brodsky wrote that “Venice is eternity itself.”  You could certainly spend an eternity in Venice just wandering through narrow streets that beg you to hold onto your loved one’s hand, or exploring the many islands that dot the Venetian lagoon. Whether you’re there for the masks of Carnevale, the art of the Biennale or just to soak it all in, Venice will never fail to seduce you. While you won’t be alone in exploring the city in peak season, you don’t need to walk far to escape the crowds. See the Rialto bridge and sights in San Marco, then spend time wandering the quieter, winding streets of Dorsoduro and Cannaregio.

If you’re flying from abroad, you’ll more than likely arrive in one of the major hubs of Rome or Milan, and catch a connecting flight to Venice. Or if you’re arriving by train, the Santa Lucia station waits in one of the most dramatic scenes you can imagine. Here is where the magic of Venice begins. Once you arrive at the banks of the Grand Canal you’ll forget that the rest of the world exists. You’re in La Serenissima and the rest just slips away. Check out our romantic Venice vacation apartment rentals to plan your perfect stay.

If you want to explore …

There is a whole world within reach of Venice, including some of the most culturally diverse areas in all of Italy. If you’re on the hunt for something sweet, visit Treviso, the birthplace of tiramisù and home to its own storied canals and craftspeople. Wine lovers will not be disappointed by a day trip to Conegliano, one of the three towns awarded the coveted DOCG status for their Prosecco production. A trip to each takes about an hour from Venice’s main train station and is well worth a detour.

The neighboring Friuli Venezia-Giulia region, also the easternmost point in Italy, may seem to share more in common with Vienna than Rome, but it is distinctly Italian. A trip to Trieste is a chance to taste some of the best coffee in Italy, with the legendary Illy brand headquartered in the heart of the city. Wine lovers will think they’ve discovered treasure in hills of Collio, home to some of the most spectacular vineyards in Europe. And if you should find yourself in the northeastern city of Udine, your ears won’t be playing tricks on you: the local dialect borrows as much from Slavic languages as from Italian, and its all just as lyrical. A trip to Friuli takes upwards of two hours from Venice on the train.

Stop 2: Florence

Florence, with its Renaissance artistry, intimate streets and the timeless beauty of the Arno River, exudes an unparalleled romantic atmosphere that has inspired lovers for centuries. The Birthplace of the Renaissance is as lovely as you can imagine and full of spots to take it all in. Find a lovely place to enjoy a Spritz, basking in the golden hour as it dapples the roofs and plays tricks on you on the surface of the Arno.

Florence is entirely walkable, and small enough to wander without ever getting too far afield. But between the Boboli Gardens, the Uffizi Gallery and the Ponte Vecchio, you may not even realize that an entire day (or week) has gone by. It’s all a bit better by night, lit up and ever so slightly more magical. If such a thing exists. Check out our Florence vacation rentals to find your own romantic room with a view.

If you want to explore …

Foodies will find paradise in Bologna, home to the oldest university in the world and a vibrant culinary culture. Trains are by far the most efficient way to travel between the two cities, with less than an hour separating the gardens of Florence from the red roofs of Bologna. The latter is teeming with character and bursting with flavors: tuck into handmade tortellini or massive mortadella, and then walk it off hand in hand under the miles of covered sidewalks that make the city feel intimate despite its size. The rebellious soul of Bologna feels light years away from the genteel sophistication of Florence, but the contrast makes each feel even more special.

Across the border in Umbria, Perugia is one of those places that you’ll want to keep hidden from all of your friends when you come home and they ask for the highlight of your trip. This imposing hilltop city is the home of Umbria Jazz, the yearly festival that fills the streets with music and has hosted some of the most famous musicians in the world. Perugia is also home to Perugina chocolate, whose factory you can visit and learn about the incredible love story at the heart of the company. Don’t forget to pick up some freshly made baci (kisses) from the Perugina store and stick around for the night to watch the sunset over the medieval skyline.

Stop 3: Rome

No matter how many times you might see it, there’s nothing quite like visiting Rome. Walking through it is a sensory overload in the very best way: every corner of it emanates a beauty that will never be replicated anywhere, at any other time. And there’s much more to see and do than the monuments or museums that you might have learned about in school. Rome is in the midst of its own renaissance, and the city is bursting with new restaurants, museums and experiences that once again prove that eternity really is built on constant reinvention. If you’re already in the mood for love, Rome will sweep you off your feet all over again. When you’re ready to call it a day, head home to a relaxing vacation rental in the heart of Rome.

If you want to explore …

Since all roads lead there, Rome is connected to almost every other city in Italy, by either regional trains or the high speed Frecciarossa or Italo trains. One of the most vibrant cities in Italy, Naples is an exciting place to visit. Connected to Rome with high speed trains that take a little more than an hour, Naples hugs its eponymous bay and rises above the hills like a picture frame on the entire Mediterranean. Over the past decade, it’s undergone a significant facelift and has become a fantastic place to visit for day trippers traveling by land or sea. With so much to see, from the Palazzo del Plebiscito to the Spanish Quarter to the hilltop palace of Capodimonte, it’s easy to spend days soaking it all in. If you haven’t quite fallen under its spell, the famous Neapolitan pizza will put you in a delightful trance.

Stop 4: Sorrento & the Amalfi Coast

With a captivating blend of natural beauty, culture and unparalleled romance, Sorrento and the Amalfi Coast are the perfect final stop. This coastal haven is a dream backdrop for a romantic stay with its dramatic cliffs, crystal-clear waters and picturesque villages clinging to the mountainsides. Stroll hand in hand along the winding streets, savoring the aroma of lemon groves and indulging in fresh Mediterranean cuisine. The Amalfi Coast’s charming towns like Positano and Ravello are ideal for sunset dinners overlooking the sea, while Sorrento’s old-world charm adds a touch of elegance. Whether you’re sipping limoncello on a terrace, exploring hidden coves or simply basking in the warmth of each other’s company, Sorrento and the Amalfi Coast are an irresistible romantic escape. Looking for more inspiration? Check out our vacation rentals near Sorrento and the Amalfi Coast.

Ready to plan a romantic getaway in Italy? Contact our team and we’ll help you find the perfect vacation rentals for an unforgettable stay!

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