Romantic Trip to Italy: Enjoy Exclusive Experiences for Two

André Freitas May, 2025

Rolling hills, historic landmarks, medieval castles, and picturesque villages make Italy a perfect destination for lovers. In other words, countless experiences overflow with a romantic atmosphere that makes hearts beat faster. That’s why Cieli di Toscana prepared a list of 10 options to make your romantic trip to Italy unforgettable. Both for the incredible settings and for the loving poetry the places exude.

Gondola ride in Venice

This ride is a true classic. First, because when we talk about Venice, the image that best represents the city is a gondolier in a striped shirt, a hat, and singing for couples while rowing. Secondly, although today its role is almost entirely for tourism, centuries ago it was Venice’s main means of transport.

If you’re on a honeymoon in Italy, the most recommended option is a private ride, which may include only smaller canals or be more complete. Duration may vary, from 30 to 60 minutes. That way, we recommend an itinerary including both the Grand Canal and the smaller ones, where you can feel the silence. Not all gondoliers sing, but if you want to make the experience even more special, an Italian melody always fits in nicely.

Sunset dinner on the Ponte Vecchio

In this experience, you’ll have a panoramic and privileged view of one of Florence’s most iconic landscapes: the historic Ponte Vecchio, which looms imposingly over the Arno River. Moreover, this experience is offered by the Four Seasons Florence, making everything more special.

On a charming terrace, you enjoy all the skill and perfectionism of Michelin-starred chefs. Thus, expect to savor cuisine that blends the tradition of Italian cooking with the innovation of modern gastronomy.

Hot air balloon ride over the Tuscan landscapes

How about taking your loved one to see Tuscany from a different angle? On a romantic trip in Italy, that’s possible, for instance, with a balloon ride. Near the city of Florence, more precisely 25 minutes away by car, lies the launch field, strategically located along the main road to Siena. Along the way, you’ll fly over hills where the grapes of the famous Chianti wine are grown, and see villages, castles, and woods. In other words, a fairytale setting to make your honeymoon in Italy even more charming.

Although available year-round, for a better experience, we recommend months with clearer skies, from late spring to the end of fall. But be prepared to wake up early, as flights take off between 6 and 7:30 a.m., shortly after sunrise.

Exclusive vineyard tour in Tuscany

Nothing better to enjoy your romance than having the Tuscan hills as a backdrop. For example, at Castello di Brolio, located in the Chianti region, the vineyards and green areas are ideal for a stroll for two.

Here, you’ll taste wines with the help of a certified sommelier. Moreover, the tour includes magnificent Italian gardens, the family’s private chapel, and the Ricasoli Collection (a small museum) located inside the castle’s tower. In other words, your romantic trip to Italy with all the glamour you deserve.

Private boat ride on the Amalfi Coast

For sea lovers, this is an exceptional option. You get to enjoy impressive cliffs, colorful villages, crystal-clear waters, and breathtaking views. Besides offering more privacy, this ride lets you personalize the itinerary.

Couples on honeymoon in Italy can visit Positano, the Emerald Grotto, Amalfi, and Capri Island, making the day full of colors: starting with the sea’s turquoise blue, passing through the grotto’s emerald green, and ending with the sunset’s golden glow.

Opera night at the Verona Arena

Held from June to September, this is one of the city’s most important events. It takes place in one of the world’s most iconic amphitheaters, combining history, impressive architecture, and incredible acoustics, where operas are performed in a stunning setting.

The tip to make your romantic trip to Italy even more special is to get VIP seats. For that, Cieli di Toscana has access to the best seats. You’ll have a privileged view of the stage and all the comfort needed to enjoy the evening.

Dinner with a view of the Colosseum in Rome

Okay, we know the Colosseum’s history isn’t exactly filled with love and romance. However, when night falls and the arena’s exterior lights up, the view is fantastic. At Aroma restaurant, located atop Palazzo Manfredi, the Colosseum reveals a unique angle.

But it’s not just the image composition that makes this a great place for a romantic trip in Italy. This Michelin restaurant blends haute cuisine with impeccable service. In other words, to get a table facing the Colosseum, book at least 2 months in advance.

Explore the spectacular nature of the Dolomites

In summer, this destination is a fantastic green paradise. That is, it offers many outdoor activities. For example, hiking to the Fanes waterfalls, cable car rides, or rowing a wooden boat amid a fairytale landscape.

In winter, you can go skiing, enjoy a night in a mountain lodge with breathtaking scenery, or relax in spas with hot tubs heated and outdoors. In short, hot or cold, the Dolomites are the ideal stage to live your love.

Stay with a view of Lake Como

First of all, open a browser tab and search “Lake Como.” Done. The persuasion that this is a great option for your romantic trip in Italy is immediate. The region is vast, with several small towns that can be explored on foot.

However, the highlight of visiting this place is staying in a hotel with a view of the lake. One option, as the name suggests, is Vista Lago di Como—luxurious, charming, and perfect for relaxing with your loved one.

The Most Romantic Walk in the World

To end, let’s go with Via dell’Amore, which connects the town of Riomaggiore to Manarola, both part of the famous Cinque Terre. It’s such a beautiful place that it was declared a UNESCO World Heritage Site.

Colorful houses set the tone for the villages balanced on the hills of the Italian Riviera. The tip is to stay in one of these villages and enjoy the peaceful evening that arrives when most tourists leave, leaving the perfect atmosphere for a romantic trip to Italy.

Live Romance with Cieli di Toscana

If you’re thinking of a personalized honeymoon or anniversary trip in Italy, Cieli di Toscana can make your dream come true. Our team has deep knowledge of the country shaped like a boot.

These are exclusive, sophisticated, and of course, romantic tours. All to make your experience truly unique. Get in touch with our team—we’ll plan your trip tailor-made, according to your interests and preferences. Live special moments with comfort, convenience, and most importantly: your way.

André Freitas is a copywriter and has traveled to 28 countries, always juggling to include Italy in the itinerary, which resulted in 19 cities and a list of tips.