Your First Trip to Italy: The Perfect Itinerary, Made Easy

The journey begins with an overnight flight from the US straight into Venice. A private water taxi—complete with a sign bearing your name—whisks you across the lagoon to your canal-side hotel for a two-night stay. I love the historic Ca’ Sagredo.

That afternoon, a private food walking tour is the perfect way to get oriented among Venice’s narrow streets and winding canals.

As the sun sets, step into a gondola, take in the view, and realize—you’ve finally arrived in Italy.

Day two is dedicated to Venice’s icons, including the Doge’s Palace and St. Mark’s Basilica.

Additional option: Explore Murano and Burano on a private island tour.

On day three, a private water taxi takes you to the train station, and just two hours later you’re in Florence—the cradle of the Renaissance.

Home to Michelangelo’s David, Botticelli’s Birth of Venus, and the iconic Duomo, Florence never disappoints.

Settle in for three nights at the centrally located Grand Hotel Minerva and explore the city on a private walking tour.

Day four is ideal for:

• Museum-hopping

• Savoring a classic Florentine steak

• Enjoying a glass of wine from one of Florence’s famous wine windows

• Browsing the gold and leather markets

Day five is your Tuscany day. A few ideas to consider:

• Wine tasting in Chianti or Montepulciano

• E-biking through vineyards

• Visiting Pisa and Siena

• Taking a cooking class

On day six, you’re off to Rome for two nights. I recommend Hotel Chapter Roma.

Up next: a private golf cart tour of the city—gelato included.

You’ll step inside the Colosseum and learn about the lives of the gladiators who once fought there.

Day seven begins early at the Vatican, where you’ll marvel at the Sistine Chapel and masterpieces inside St. Peter’s Basilica.

In the evening, wander Trastevere, one of Rome’s most charming neighborhoods, known for its lively streets and authentic atmosphere.

Day eight brings you south toward Sorrento and the Amalfi Coast, with a stop in Pompeii—an unforgettable glimpse into daily Roman life frozen in time.

From there, continue to Sorrento and shift fully into relaxation mode.

Hotel Corallo Sorrento, with its sweeping views over the Gulf of Naples, is a favorite spot to sip a spritz as the sun sets.

Day nine is all about the water.

Start early at the Blue Grotto.

Then cruise along the Amalfi Coast, stopping to swim and snorkel in crystal-clear coves beneath dramatic cliffs.

Day ten is yours to design.

• Relax at a beach club

• Explore Positano, Ravello, and Amalfi

• Hike the Path of the Gods for some of the most spectacular views in Italy

All too soon, it’s time for a private transfer to the Naples airport and your flight home—already dreaming of your next return to Italy.