How to Spend 2 Weeks in Italy
ROME • FLORENCE • TUSCANY • CINQUE TERRE • AMALFI • MAY 2025
14-day route
A spectacular multi-week route traversing Rome, Florence, Tuscany, and Venice — with the best regional stays and bites.
Rome — landing in the eternal city
"Arrive in Rome, settle in your hotel in Trastevere, and enjoy a quiet evening walk around the iconic Pantheon and Piazza Navona."
Check in to a cozy boutique hotel in Trastevere
Visit the historic Pantheon at dusk
Grab a plate of rich, creamy cacio e pepe at a local osteria
Boutique Hotel Trastevere
Charming rooms set in a quiet piazza with classic shuttered windows and an authentic breakfast room.
Da Enzo al 29
Unbelievable traditional Roman pastas, artichokes, and house red wine in a lively corner.
Rome -> Florence
"Catch a morning high-speed train to Florence, the cradle of the Renaissance. Spend your afternoon admiring the Duomo and walking Ponte Vecchio."
Take high-speed Frecciarossa train north to Florence
Admire Brunelleschi's magnificent Duomo dome
Cross the historic Ponte Vecchio at sunset
Plaza Hotel Lucchesi
Rooftop terrace pool with 360-degree views of the Florentine skyline and Arno river.
All'Antico Vinaio
World-famous legendary focaccia sandwiches piled high with fresh tuscan charcuterie.
Florence -> Tuscany
"Head south into the rolling hills of Tuscany. Enjoy a day trip wandering the medieval towers of San Gimignano and tasting local Chianti wines."
Rent a vintage car or board a regional bus south into the Tuscan hills
Explore the medieval skyscraper village of San Gimignano
Tone your senses with a local Chianti winery tasting
Belmond Villa San Michele
A former 15th-century monastery with a facade designed by Michelangelo, offering breathtaking views of Florence.
Osteria di Passignano
Michelin-starred dining in a historic monastery vault, featuring exceptional local wines.
Tuscany -> Venice
"Arrive at the floating city of Venice. Settle in your hotel away from the main crowds in Cannaregio and enjoy cicchetti by the canal."
Take the train north to Venice Santa Lucia
Ride a traditional vaporetto along the Grand Canal
Enjoy local cicchetti tapas at a quiet bacaro tavern
La Torretta Lodge
Stunning views from romantic cliffside suites overlooking the sparkling turquoise sea.
Trattoria Gianni Franzi
Legendary trofie pasta with fresh basil pesto served in a lively central piazza.
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