Italy is renowned for its timeless romantic feeling and picturesque landscapes. If you’re planning a getaway with that special someone this Valentine’s Day, the best way to go is off-the-beaten-path for a private, intimate experience without the bustle of tourists around you.
From the birthplace of Italy’s most famous poet to the location of the original Romeo and Juliet film to the hidden coves on the Adriatic Sea, romance awaits you on this journey through Italy’s most romantic destinations!
Nestled in the heart of Umbria, Gubbio’s cobblestone streets and green surroundings feels like something straight out of a magical medieval movie set – one, in particular, you might have heard of!
Did you know the original 1967 Romeo and Juliet, starring Leonard Whiting and Olivia Hussey, was filmed in Gubbio? This hillside medieval city seems frozen in time, with many original town walls and gateways still intact, making it the perfect setting for Shakespeare’s tragedy. For this reason, Gubbio was chosen for use in the movie’s street fighting and duel scenes, marking Romeo’s first on-screen appearance.
On your trip to Gubbio, the air will echo with Shakespearian verses as you wander the cobblestone streets, admiring the medieval architecture, from the Palazzo del Consoli to the Cathedral Santi Mariano e Giacomo. The town is built on the lowest slope on the side of Mount Ingino with three levels, with all levels accessible by a staircase and public elevators during the day making it possible for travelers of varying activity levels to experience each layer of Gubbio’s architectural charm.
For panoramic views of the mountain and a touch of adventure, you can take a cable car to Mount Ingino, where you’ll find a secluded spot at the top to enjoy a romantic picnic. Then, you can take a leisurely stroll along Via dei Consoli, a charming street lined with shops and cafes where the soft glow of streetlights and medieval architecture will create the perfect romantic atmosphere.
Don’t like cable cars? No problem! When you join us on select tours we’ll take you to the top in a private vehicle so you can enjoy the views without the vertigo!
Did you know Gubbio is also home to the world’s largest Christmas tree? Read more on experiencing Christmas in Italy!
Often revered as “all of Italy wrapped into one region,” venture off the beaten path to Italy’s Le Marche region and visit Italy’s “City of 100 Towers and Travertine” – Ascoli Piceno. The city will capture your heart with its medieval charm, renaissance piazzas, award-winning pizzerias, historic cafes – an unique ambiance, setting the perfect stage for a romantic getaway.
My husband Giovanni and I were married here, and it truly is the perfect location for a destination wedding in Italy minus the crowds and tourist traps. The narrow streets, hidden squares, and historic landmarks create a sense of intimacy and privacy for fairytale nuptials.
Home to one of Italy’s most beautiful squares, Piazza del Popolo, this underrated town buzzes with energy and authentic Italian hospitality. Not yet surrendered to tourism and situated a 30 minute drive from the Adriatic sea, it’s just a stone’s throw away from Umbria, Lazio, and Abruzzo. Adorned with travertine, you’ll love experiencing the city’s timeless elegance with a cocktail at one of Italy’s 150 historic cafes beloved by none other than Ernst Hemingway.
Considered the “Pearl of the Piceno”, you won’t have difficulty finding a romantic date night activity in Ascoli Piceno. Whether it’s a candlelit dinner at the trattoria, a chocolate tasting at a local shop, or a nighttime stroll in the town that “glows at night,” you’re sure to be swept off your feet during your visit!
Did you know that select tours are based in Ascoli Piceno? We proudly call the city our home and would love to be your local guides for your romantic Italian getaway! Choose your itinerary today.
If you want to experience Italy as the locals do, Mazzorbo is the perfect place. Hidden in the embrace of the Venetian Lagoon, Mazzorbo is the definition of a hidden gem, offering a romantic escape for those seeking tranquility away from the bustling crowds of Venice. This sleepy seaside town has a unique charm you’ll immediately fall in love with.
With a population comprised primarily of locals, the town provides an authentic Italian retreat from the throes of tourist traps, allowing for an intimate and romantic experience. Renowned for its vineyards contributing to the production of Venissa wine, you’ll love taking a romantic stroll through the winding narrow pathways and enjoying the lagoon views.
You can also go for a wine tasting on the island. Cultivated from the Dorona di Venezia grape variety, the flavor of wines produced in Mazzorbo is one-of-a-kind white wine with the characteristics of a red wine. You can also enjoy freshly caught seafood delights by the water. Sunsets over the lagoon are unbeatable, the perfect way to end a serene, romantic day on the Venetian lagoon.
Coast of Conero
Tucked along the Adriatic Sea, the Coast of Conero is the best romantic getaway for beach and nature lovers. Boasting a collection of Blue Flag Beaches, a testament to their cleanliness and beauty, several of these hidden coastal gems can only be reached by boat! From the sandy stretches of the Mezzavalle to the pebbled beauty of Due Sorelle, the breathtaking blue waters and lush greenery are the perfect backdrop for a private, romantic seaside adventure.
For nature-loving couples, the Conero National Park is splendid for hiking through the lush Mediterranean vegetation with panoramic views of the coastline below. For those looking for a romantic coastal escapade, take a boat excursion through the crystalline turquoise waters to the secret grottos under the limestone cliffs. And as your romantic day comes to a close, don’t forget to head to the Belvedere in Numana, a vantage point offering unmatched sunset views of the coast.
The Prosecco Hills, a designated UNESCO World Heritage Site, offers a romantic escape into a bucolic landscape shaped by centuries of winemaking tradition. The gently sloping hills, adorned with vineyards that produce the renowned sparkling wine, create an enchanting setting for couples seeking a taste of both romance and cultural richness.
While Valdobbiadene may be the epicenter of Prosecco production, the true magic of the Prosecco Hills lies in exploring lesser-known towns like Cison Valmarino and the area of the Cartizze beyond Conegliano. These charming villages boast historic architecture, cobblestone streets, and a sense of tranquility, providing a dreamy backdrop for a romantic escape away from the crowded tourist hubs of Verona and Venice.
In addition to its wine production, the Prosecco Hills also showcase a long-standing tradition of exceptional cheese production, pairing perfectly with local wine varieties that include more than just Prosecco.
The off-the-beaten-path, magical locations of the Hills are best explored by car. The deeper you go into the region, the worse the cell phone reception gets, meaning you won’t be able to rely on Google Maps to navigate and the most stunning, quaint locations cannot be reached by coach buses.
For couples seeking a stress-free and romantic escape to Veneto, consider joining a guided tour that takes you from the foothills of Veneto’s Dolomites to the heart of the Prosecco Hills! Navigating the countryside can be challenging, and a curated tour allows you to relax and focus on each other while a knowledgeable local host leads you to the most romantic spots and introduces you to the region’s top culinary delights.
The Veneto region is adorned with numerous Palladian villas, showcasing the architectural brilliance of Andrea Palladio, a master of Renaissance design. These villas, designated as UNESCO World Heritage Sites, are scattered like jewels across the landscape, each telling a story of opulence, artistry, and the Venetian aristocracy. Far from the bustling crowds, the Villas set the scene for your perfect romantic getaway in the Veneto region.
While many visitors flock to more well-known destinations like the Villa Pisani, the true magic lies in exploring the hidden gems. On select tours, guests with The Italian On Tour® go for a wine tasting with independent winemakers hailing from one of the historic Doge of Venice families, creating an exclusive, once-in-a-lifetime experience that most tourists would never have the opportunity to do.
The White-Washed Cities of Puglia
In the southern reaches of Italy, the region of Puglia unveils a mesmerizing spectacle with its white-washed cities, where time seems to stand still amidst cobblestone streets, historic architecture, and a sense of undisturbed tranquility. Embark on a romantic journey through these picturesque towns, where every corner echoes with the charm of the Mediterranean.
Whether visiting Albereobello, home of the fairytale-esque Trulli houses, or the “White City” of Ostuni overlooking the sea, these beautiful towns serve as a picturesque backdrop to a romantic adventure back in time. Read more about Puglia’s Hidden Gems HERE!
While the white-washed cities of Puglia are enchanting year-round, consider visiting in the off-season to enjoy a more intimate and serene experience. During the quieter months, from late autumn to early spring, you can relish the romantic ambiance without the bustling crowds, allowing for a more personal exploration of these captivating towns.
Even better, take the guesswork out of your trip to Italy and seek out the expertise of a trusted local guide on a small group tour of the region! Your backstage pass to Puglia awaits. Sign up for our 2025 Waitlist to be the first to know about exclusive bonuses.
In the rolling hills of the Le Marche region, Recanati is a poetic heaven of art, history, and literature, home to Italy’s most famous poet, Giacomo Leopardi.
Recanati takes pride in being the birthplace of Giacomo Leopardi. You can visit the Leopardi House, where the poet was born and spent his early years. The museum offers a glimpse into Leopardi’s life, featuring manuscripts, letters, and personal belongings, providing a poetic context for your romantic exploration of Recanati. The alley adjacent to Leopardi Square leads to the Colle dell’Infinito (Hill of Infinity) that inspired the famous poem, L’Infinito. These breathtaking views are splendid for a shared moment of serenity and inspiration.
Whether you’re tracing the footsteps of Giacomo Leopardi or savoring the romantic landscapes, Recanati promises a journey through the heart of Italy’s artistic and literary legacy that is renowned around the world.
Which one of these locations will you choose for a romantic Italian getaway? If you’re looking for a Valentine’s Day surprise for that special someone, there’s nothing better than the gift of experience. Book your small group tour of Italy to experience the magic and romance together!
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