Italy is a destination that lives up to every bit of its reputation for enchanting cities, mouth-watering cuisine, historic landmarks, and breathtaking villas. Planning a first-time visit can be overwhelming given the abundance of options! Here's our guide to the must-see spots, hidden gems, and stunning villas to stay in that will make your first Italian adventure unforgettable.

Best way to visit Italy for the first time — Credit: Unsplash.

Start with the Classics: Rome, Florence, and Venice

Although we love heading off the beaten track, for your first visit the best places are often the main attractions. So think about major cities and where you've been dreaming about as first-time visitors. It's a good idea to tick off a little bit of the main sights and discover the road less travelled on your future Italy trip, because let's face it, there will be more visits!

Rome
We would start your Italian journey in the eternal city. Rome's energy, history, and architecture are unlike anywhere else in the world. From the iconic Colosseum and Spanish steps, to the intricate artwork of the Sistine Chapel in Vatican city, it's a place that feels like an open-air museum. Wander through the cobbled streets, marvel at the Roman Forum, visit Palatine Hill and toss a coin in the Trevi Fountain for good luck. On my first visit I was overwhelmed by how every normal building was ancient and beautiful. There’s a reason people keep going back.

Florence
Florence is a treasure trove of art and culture. Visit the Uffizi Gallery for masterpieces by Michelangelo, Da Vinci, and Botticelli, and take a scenic walk to Piazzale Michelangelo for panoramic views over the city. Florence is also a gateway to Tuscany, where you can experience rolling vineyards, olive groves, and Tuscan villas for an authentic Italian countryside experience. It’s also great for finding smaller pretty towns on its outskirts such as Arezzo.

Venice
There is no where in the world quite like Venice. With its canals, bridges, and historic palazzos this makes it a truly unique city and almost like a film set. Even my Milanese husband thinks this is the best city in Italy. Take a gondola ride, visit the majestic St. Mark’s Basilica, and stroll through the lively Piazza San Marco. Get lost in the side streets and come for carnival in February. There is so much on offer. Or if you want a truly ‘out of this world’ experience, consider staying in a Venetian villa along the main canals.

Discover Hidden Gems

If you love to find unusual places which are a little quirky, these would be our suggestions. We are especially fond of Como as we got married there...

Cinque Terre
This is a collection of five colourful seaside villages on the Italian Riviera, Cinque Terre is a UNESCO World Heritage site known for its hiking trails, beaches, and breathtaking views. Stay in a villa on the hillside overlooking the Mediterranean Sea for a picture-perfect stay.

Amalfi Coast
South of Naples, the Amalfi Coastal area is famed for its dramatic cliffs, coastal towns, and luxurious villas with infinity pools overlooking the Tyrrhenian Sea. Towns like Positano, Amalfi, and Ravello are perfect for a romantic getaway or a scenic escape with a stunning car rental, complete with incredible food, lemon groves, and charming beaches. This is also a place where writers flocked to in the 1950s and 60s inspired by its beauty, I find this adds an extra romantic charm!

Lake Como
Tucked away in Northern Italy, Lake Como is the epitome of Italian elegance. Surrounded by the Alps, this lake region is one of the most incredible places on earth. Famous for its luxurious villas, including the beautiful Villa del Balbianello. The combination of blue water and green mountains plunging into the lake make it quite breathtaking. Relax by the water, visit the quaint lakeside towns, and stay in a villa that captures the charm and tranquility of this stunning region.

Experience the Italian Countryside: Tuscany and Umbria

Italy’s countryside is home to some of the world’s most idyllic landscapes and finest villas. If you’re interested in wine, food, and nature, this is where you want to be.

Tuscany

This region offers sprawling vineyards, sunflower fields, and medieval towns like Siena and San Gimignano. The Tuscan countryside is dotted with luxury villas, many of which have been converted from ancient estates. Here, you can sample Chianti wines, go truffle hunting, and take scenic bike rides through fields of sunflowers and lavender.

Umbria

Often called the "green heart of Italy," Umbria is slightly less crowded than Tuscany but equally stunning. Hilltop towns like the captivating Assisi and Perugia offer historical charm and beautiful views. Villas here are surrounded by olive groves, vineyards, and lush landscapes, making them ideal for those seeking peace and a deeper connection to nature.

Indulge in Italy's Food and Wine

Italy’s cuisine is as diverse as its landscapes. Each region has its own specialties and a first-time trip is the perfect opportunity to savor it all.

In Rome, enjoy pasta dishes like cacio e pepe or carbonara in a cozy trattoria.

Florence is all about Tuscan food, from ribollita (a hearty soup) to bistecca alla Fiorentina (Florentine steak).

On the Amalfi Coast, try fresh seafood, mozzarella di bufala, and sfogliatella pastries.

Tuscany is known for Chianti wines, but it’s also the best place to enjoy authentic Italian farm-to-table experiences.

Many villas in Tuscany and Umbria offer in-house cooking classes, wine tastings, and olive oil tours, allowing you to dive into Italian culinary culture from the comfort of your accommodation.

Find Your Perfect Villa

Italy’s villas range from opulent estates with grandiose architecture to rustic farmhouses nestled in the countryside. Here are a few regions and types of villas to consider for your first trip:

Tuscany: Stay in a hillside villa with views of vineyards and access to an infinity pool. Many of these villas are near wineries, making it easy to tour and taste the best of Tuscan wines.

Amalfi Coast: Find a cliffside villa with ocean views and luxurious amenities. Many Amalfi villas offer private terraces overlooking the water, creating a perfect setting for sunset dinners.

Lake Como: Opt for a lakefront villa where you can enjoy both privacy and beautiful mountain views. Some villas offer private boat access, perfect for exploring the lake and nearby towns.

Venice: If you’re staying here, a canal-side villa or apartment in the heart of Venice will add to the enchantment of this already magical city.

Italy Travel Tips for an Unforgettable First Trip

Visit in the Off-Season: Italy is busiest in the summer, so consider visiting in the shoulder seasons, spring (April–June) or autumn/fall (September–October) for pleasant weather and fewer crowds.

Rent a Car: While public transportation is excellent in cities, having a car will give you flexibility when exploring rural areas like Tuscany, Umbria, or the Amalfi Coast. We always hire a car and it’s not as daunting as it may first appear!

Learn some Italian: While many Italians speak English, especially in tourist areas, knowing a few Italian phrases will enhance your experience.

Book Villas Early: Italy is a popular destination, so booking your villa several months in advance, especially in high-demand areas like the Amalfi Coast or Lake Como, ensures you get your preferred choice.

Even though we are slightly biased being an Italian/ English family, we still believe Italy is the ultimate destination for those who crave beauty, history, and a connection to nature. We recommend having a comfortable home base near an ancient city, scenic landscapes, and combining luxurious villa stays. This will make your first visit the perfect holiday. Italy is worth visiting any time of year and throughout the country, from a major city to smaller towns.

Whether you’re exploring Rome’s ancient ruins, sipping wine in a Tuscan villa, or watching the sun dip below the horizon on the Amalfi Coast, your first trip to Italy is sure to be one you’ll remember for a lifetime.

Buon viaggio!

Disclosure: This week I’m working alongside Villa Finder, however all content and opinions are 100% my own.