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The Classic Jaunt – Venice, Florence, and Rome

While travelers could spend unlimited time in three of the world’s greatest cities – Venice, Florence, and Rome – ten days is a good start for appreciating the history, charm, and gelaterias of this Italian trifecta. In Venice, check into a lagoon-facing suite at the 52-room Londra Palace Venezia before heading out on a private walking tour that reveals La Serenissima’s rich history, followed by a gondola ride through the city’s mesmerizing canals.  

In Florence, revel in views of Renaissance architecture from the 63-room Hotel Lungarno and take a stroll in the city’s famous square, Piazza della Signoria, before visiting the Uffizi Gallery to admire the great works of Michelangelo, da Vinci, and Giotto. Travelers can learn the art of cooking authentic Tuscan cuisine – and taste the results – or savor world-class wines on an excursion to the rolling hills of Chianti.  

In Rome, the trip’s final stop, travelers immerse themselves in millennia of history via escorted tours to some of the city’s most spellbinding ancient monuments, including the Forum and the Colosseum. On a guided tour of Vatican City, marvel at the Renaissance-era Sistine Chapel and Saint Peter’s Basilica. End the journey with a toast to the Eternal City from atop the Spanish Steps at the 87-room Hotel Hassler. 

The Grand Tour – Milan to Sicily

This epic, two-week journey stretching from northern to southern Italy begins in Milan, where travelers banish jet lag in the 104-room Mandarin Oriental, Milan’s spa before spying da Vinci’s Last Supper at the Santa Maria delle Grazie and indulging in some retail therapy in the city’s elite fashion district. On a day trip, travelers explore Lake Como by boat before an exclusive dinner at the lavish 84-room Grand Hotel Tremezzo.

From Milan, spend a few days soaking in the Tuscan countryside in the medieval hill town of Siena or go coastal on the Cinque Terre for seaside afternoons and alfresco dinners. Then it’s onward to the Amalfi Coast, where dips in the sea near Capri pair with an afternoon walking Pompeii’s ancient streets and idling in the good life at the 66-room Hotel Santa Caterina. The journey ends in Sicily, known for its beaches, medieval ruins, and flaky cannoli. While you’re on the island, trek one of the many panoramic trails along Mount Etna, Europe’s most active volcano, before sampling local wines at a nearby vineyard.

The Unexpected Getaway – Verona, Bologna, and More

Travelers can stray from the well-trodden path on a 12-day tour that starts in Verona and takes in some of Italy’s most fascinating under-the-radar sights. In Verona, check into historic, 89-room Due Torri Hotel, then set out to explore the city’s elegant centuries-old piazzas, shopping arcades, and Roman arena, before setting off to Vicenza, birthplace of renowned architect Palladio.  

A stay at Bologna’s 106-room Grand Hotel Majestic già Baglioni, housed in an eighteenth-century palazzo originally built for Pope Benedict XIV, is the gateway to the city’s Michelin-starred restaurants and automobile museums. After sneaking away to Porto Venere, a charming seaside town on Liguria’s romantic Gulf of Poets, travelers explore the picturesque Cinque Terre coastline by boat or train before returning to the 48-room Grand Hotel Portovenere. The trip concludes in the Tuscan countryside at the 53-room Rosewood Castiglion del Bosco, an ideal home base for bike rides through ancient hill towns, a few rounds of golf, and sampling some of the region’s award-winning brunello wines.

The Unforgettable Family Trip – Venice, Florence, Pisa, and Rome

The memories from a ten-day family vacation in Italy will last a lifetime – and this itinerary puts a kid-friendly spin on one of the country’s classic jaunts. After settling into a two-bedroom suite at Venice’s 92-room Baglioni Hotel Luna, take the family for a gondola ride or to a mask-making workshop, or just enjoy the freedom and fun of getting lost in the Floating City’s maze of streets and canals. From there, it’s off to Florence, where the kids’ program at Rocco Forte Hotels’ 80-room Hotel Savoy pampers everyone from tots to teens. See who can climb to the soaring dome of Florence’s cathedral the fastest, learn about Galileo’s remarkable cosmic discoveries, and, of course, sample gelato in the city where it was invented.

An excursion to Pisa gives families the chance to take turns “holding up” its iconic leaning tower, before a grand Roman finale. The 120-room Hotel de Russie hosts families in the heart of the Eternal City, where they can choose among a pizza and gelato crawl, bike rides in Villa Borghese park, or private kid-friendly tours of Rome’s ancient highlights.  

The Romantic Escape – Milan, the Cinque Terre, and Rome  

Italy is every bit as alluring as you might expect, and Milan is the starting point for this sweet eight-day getaway. The 106-room Park Hyatt Milano places travelers in the heart of the action, with the Duomo and belle epoque Galleria Vittorio Emanuele II shopping arcade just steps away. Tour the city in a luxury sedan, then sip negronis along the canals of the buzzy Navigli district.

Travelers move to the Italian Riviera and Santa Margherita Ligure’s 72-room Grand Hotel Miramare, where a sea-facing balcony suite is an ideal hideaway after a private yacht excursion to the five postcard-perfect villages of the Cinque Terre. In Tuscany, an overnight at the 14-room Castello Banfi Wine Resort allows time for spa treatments, Michelin-starred dining, horseback riding, and winetasting on the hotel’s working wine estate.  

Finally, love springs eternal in Rome, where legendary landmarks such as the Trevi Fountain and the Spanish Steps are the backdrop for romance. The 114-room Bulgari Hotel Roma offers a private spa suite for two, and from its doorstep, travelers indulge in private market tours, cooking classes, and nighttime winetasting tours through Rome’s charming backstreets.