Italy 101: The Perfect Itinerary for First-Timers

Arrive in Rome, likely early in the morning, where your travel advisor will have arranged for a private driver to meet you just outside customs. After a long travel day, there’s nothing better than walking out to a friendly face, having your bags handled, and stepping straight into a waiting car. No navigating taxis or train platforms while jet-lagged.

You’ll be transferred directly to your hotel to drop off your luggage, as rooms typically aren’t ready for early check-in. Rather than waiting around, this is the perfect time to jump into your first planned activity: a golf cart tour of Rome! This relaxed, low-effort tour is an ideal introduction to the city and a great way to ease into sightseeing on day one.

With an expert local guide and driver, you’ll cruise through Rome’s historic streets, seeing iconic landmarks like the Colosseum, Pantheon, and Spanish Steps, along with lesser-known corners and hidden gems you might otherwise miss. By the end of the tour, you’ll feel oriented, energized, and ready to officially begin your time in Italy.

Wake up in Rome ready for your first full day of sightseeing, beginning with a morning tour of the Colosseum and ancient Rome. After breakfast, you’ll be met by your expert guide for an exploration of this iconic amphitheater and the surrounding ruins.

Following the Colosseum, your guide will continue through the nearby Roman Forum and Palatine Hill, bringing these millennia-old ruins to life with rich historical context and fascinating hidden details many first-time visitors miss. This immersive morning gives you both the big sights and the meaningful stories behind them, perfectly setting the tone for your Roman adventure.

By the time you finish, you’ll have a strong sense of Rome’s ancient roots, leaving the afternoon open to wander cafés, enjoy gelato by the ruins, or simply rest at your hotel before dinner in one of the city’s charming piazzas.

Begin your day with a visit to Vatican City, home to some of the world’s most extraordinary art and architecture. With a guide, you’ll explore the Vatican Museums and the Sistine Chapel, where Michelangelo’s masterpieces are even more impressive in person, before continuing on to St. Peter’s Basilica, one of the most important and awe-inspiring churches in the world.

After the morning’s sightseeing, make a brief stop at the famous Aventine Keyhole, a unique viewpoint that perfectly frames St. Peter’s Dome and where you can technically see three countries at once. It’s a quick but memorable stop and a fun photo opportunity!

In the afternoon, cross the Tiber River and spend time wandering through Trastevere, one of Rome’s most charming neighborhoods. With its cobblestone streets, ivy-covered buildings, and lively piazzas, this area is perfect for a relaxed walk, a leisurely meal, and soaking in a more local side of the city.

This morning, take the high-speed train from Roma Termini to Firenze Santa Maria Novella, a comfortable and efficient journey that brings you straight into the heart of Florence. Upon arrival, check into your hotel and take some time to settle in before heading out to explore.

Spend the afternoon wandering through Florence on foot. The city is very compact and one of the most walkable in Italy. Stroll through historic streets, admire Renaissance architecture, and browse the local leather markets, where you’ll find everything from handbags to small artisan goods.

In the evening, make your way up to Piazzale Michelangelo, one of the best spots in Florence to watch the sun set over the city. As the sky changes colors and live music fills the air, you’ll have sweeping views of the Duomo and the Arno River below. A perfect, memorable introduction to Florence!

Begin the day with a guided walking tour of Florence, a perfect way to dive deeper into the city’s rich history and art. As you explore on foot, your guide will bring Florence’s Renaissance past to life while leading you through its most iconic streets and piazzas. The tour includes reserved entry to see Michelangelo’s David, one of the most celebrated masterpieces in the world and an absolute must for first-time visitors.

After a morning of sightseeing, enjoy a slower-paced afternoon with a hands-on pasta-making class, such as Pasta Class Florence. Learn to prepare traditional Italian pasta from scratch, guided by local chefs, and sit down to enjoy the meal you’ve created together. It’s a fun, interactive experience and a memorable way to connect with Italian food culture.

Head out early this morning for a full-day exploration of the Tuscan countryside, with a private driver picking you up directly from your hotel. Traveling by car allows you to sit back, enjoy the scenery, and make the most of your time without worrying about logistics.

Throughout the day, you’ll visit some of Tuscany’s most picturesque towns, such as Siena and San Gimignano, each offering its own unique charm from medieval streets and historic piazzas to sweeping views over rolling hills. In between town visits, enjoy stops at local vineyards for wine tastings, where you’ll learn about regional varietals and savor the flavors Tuscany is known for.

By the time you return to Florence in the evening, you’ll have experienced a perfect mix of culture, countryside, and culinary highlights. An unforgettable contrast to city life!

This morning, travel by high-speed train from Florence to Venice, arriving directly into one of the most unique cities in the world. After checking into your hotel, take some time to settle in before heading out to experience Venice at its most enchanting, the evening!

As the crowds thin and the light softens, enjoy a classic gondola ride through Venice’s quiet canals, a peaceful way to see the city from the water and take in its timeless beauty.

Later in the evening, join a cicchetti food tour, sampling traditional Venetian small bites alongside local wines while hopping between historic wine bars. It’s a relaxed, social way to experience the city’s food culture and get oriented to neighborhoods you may want to revisit during your stay.

By the end of the night, you’ll have experienced Venice in its most magical hours.

Today you’ll dive into two of Venice’s most iconic cultural treasures with a guided visit to Doge’s Palace and St. Mark’s Basilica. With skip-the-line access and a local guide, you’ll bypass the long queues and uncover the fascinating history behind these landmarks, from the opulent halls of the Doge’s Palace (once the seat of Venetian political power) to the dazzling mosaics and sacred art of St. Mark’s Basilica.

Inside the palace, your guide will bring to life centuries of Venetian history, including the Bridge of Sighs and the atmospheric prisons. At the basilica, you’ll admire intricate Byzantine mosaics and enjoy access to terrace viewpoints over Piazza San Marco and the lagoon.

Enjoy your last full day in Italy by heading off the main island to explore the Venetian Lagoon. Travel by boat to Murano, where you’ll visit a renowned glass-blowing factory and watch master artisans demonstrate this centuries-old craft.

Continue on to Burano, famous for its brightly colored houses and laid-back charm. Spend time wandering the canals, browsing local shops, and enjoying a leisurely lunch before returning to Venice in the afternoon. On your final evening, celebrate with sunset drinks at the St. Regis Venice or dinner at Hotel Danieli, both offering unforgettable views over the lagoon. A perfect way to toast your last night in Italy!