Italy · Route map
An Italian Classic with Local Flavor
This quintessential first-time route pairs Italy's three great art capitals with the culinary heart of Emilia-Romagna and a quiet Tuscan hillside retreat.
- 1
Rome
4 nights
Historic icons and vibrant Roman neighborhoods.
- 2
Val d'Orcia
2 nights
Tuscan hill towns and scenic wine trails.
- 3
Florence
3 nights
Cradle of the Renaissance and peerless art.
- 4
Bologna
2 nights
Italy's culinary capital and medieval porticoes.
- 5
Venice
2 nights
Canal-woven palaces and bacaro wine bars.
- ✦5 stops · 13 nights
A sample from our journal — written by Waypora, kept as inspiration
Use this as a starting pointThe day-by-day
Welcome to Rome
Arrive into Rome Fiumicino Airport
Flight · Morning · Fiumicino
Private transfer to Trastevere
Transfer · Morning · Rome
A 40-minute drive from the airport to your central hotel.
Orientation walk around Trastevere and Tiber Island
Excursion · Afternoon · Trastevere
Cross the Garibaldi bridge at sunset for a breathtaking view of St. Peter's dome.
Overnight in Trastevere
Accommodation · Evening · Trastevere
Stay at Donna Camila Savelli, a serene former monastery designed by Borromini.
Layers of Roman History
Private tour of Colosseum and Roman Forum
Excursion · Morning · Ancient Rome
A three-hour guided walk through the heart of ancient Rome.
Enter via the Stern Gate to step directly onto the arena floor away from crowds.
Afternoon at leisure around Monti
At leisure · Afternoon · Rione Monti
Grab a classic Roman pizza al taglio at Trieste Pizza on Via Urbana.
Twilight stroll around Monti's wine bars
Excursion · Evening · Rione Monti
Try La Barrique for an incredible selection of natural Italian wines and local cheeses.
Overnight in Trastevere
Accommodation · Evening · Trastevere
Vatican Masterpieces & Hidden Baroque
Early access Vatican Museums and Sistine Chapel
Excursion · Morning · Vatican City
Enter an hour before the general public opens.
Walk straight to the Museo Pio-Clementino to see the Laocoön in relative peace.
Discover Borromini at San Carlo alle Quattro Fontane
Excursion · Afternoon · Trevi
Stare up into the complex, oval dome—it is a geometric masterpiece of the Baroque era.
Overnight in Trastevere
Accommodation · Evening · Trastevere
The Historic Heart of Rome
Architectural walk from Pantheon to Piazza Navona
Excursion · Morning · Centro Storico
Order a granita di caffè at Tazza d'Oro right by the Pantheon.
Caravaggio hunt in San Luigi dei Francesi
Excursion · Afternoon · Centro Storico
Keep a one-euro coin handy to light up the Contarelli Chapel paintings.
Overnight in Trastevere
Accommodation · Evening · Trastevere
Into the Tuscan Hills
Pick up hire car at Roma Termini
Car hire · Morning · Rome
Self-drive Rome to Val d'Orcia
Self-drive · Morning · Tuscany
A scenic drive of approximately two and a half hours.
Sip Rosso di Montalcino in Montalcino
Excursion · Afternoon · Montalcino
Enoteca la Fortezza offers tastings inside the 14th-century fortress walls.
Overnight in Val d'Orcia
Accommodation · Evening · Bagno Vignoni
Stay at Albergo Posta Marcucci to soak in ancient thermal pools after dark.
Pienza and Iconic Valleys
Explore the Renaissance ideal town of Pienza
Excursion · Morning · Pienza
Buy aged pecorino cheese wrapped in walnut leaves at Cacio di Pienza.
Self-drive the scenic loop via Vitaleta
Self-drive · Afternoon · Val d'Orcia
A quiet 45-minute drive passing iconic cypress-lined roads.
Overnight in Val d'Orcia
Accommodation · Evening · Bagno Vignoni
Siena to Renaissance Florence
Self-drive Val d'Orcia to Florence via Siena
Self-drive · Morning · Siena
A two-hour drive with a stop at Siena's Piazza del Campo.
Drop hire car at Florence Downtown
Car hire · Afternoon · Florence
Sunset walk across the Ponte Santa Trinita
Excursion · Afternoon · Florence
Avoid the crowded Ponte Vecchio; the view from Santa Trinita is far superior.
Overnight in Florence
Accommodation · Evening · San Frediano
SoprArno Suites is a stylish, boutique property in the hipster Oltrarno district.
Renaissance Masterpieces
Masterpieces of the Uffizi Gallery
Excursion · Morning · Florence
Pre-booked timed entry to Italy's premier art museum.
Book the earliest slot to see Botticelli’s Birth of Venus without the crowds.
Discover artisan workshops in the Oltrarno
Excursion · Afternoon · Oltrarno
Visit the workshop of Giuliano Ricchi to see hand-stamped brass metalwork.
Overnight in Florence
Accommodation · Evening · San Frediano
Michelangelo & Monastic Peaceful Spaces
The Accademia and Michelangelo's David
Excursion · Morning · Florence
A quick, focused visit to view the world's most famous statue.
Focus on the unfinished 'Slaves' lining the corridor leading to David.
Quiet contemplation at San Marco Museum
Excursion · Afternoon · Florence
See Fra Angelico’s Annunciation mural at the top of the dormitory stairs.
Overnight in Florence
Accommodation · Evening · San Frediano
Culinary Capital Bologna
High-speed train from Florence to Bologna
Transfer · Morning · Bologna
A fast 35-minute train ride through the Apennines.
Explore Bologna’s medieval Quadrilatero market district
Excursion · Afternoon · Bologna Centro
Look for Pasquini & Brusiani to buy real, artisanal Mortadella Bologna.
Overnight in Bologna
Accommodation · Evening · Bologna Centro
Stay at Hotel Commercianti, located in a grand historic building next to San Petronio.
Trattorias & Porticos
Climb the portico of San Luca
Excursion · Morning · Bologna
This is the world's longest continuous covered portico, spanning nearly four kilometers.
Afternoon at leisure around Santo Stefano
At leisure · Afternoon · Bologna Centro
Sit outside at Caffè della Sette Chiese for superb people-watching.
Overnight in Bologna
Accommodation · Evening · Bologna Centro
The Grand Canal Awaits
Train from Bologna to Venice Santa Lucia
Transfer · Morning · Venice
A comfortable journey of roughly one and a half hours.
Vaporetto ride down the Grand Canal
Transfer · Afternoon · Venice
Board Vaporetto Line 1 at the station for the most dramatic introduction to Venice.
Cicchetti crawl around Cannaregio canneries
Excursion · Evening · Cannaregio
Order a glass of local white wine and crostini with whipped salt cod.
Overnight in Venice
Accommodation · Evening · Cannaregio
Stay at Al Ponte Antico for luxury rooms overlooking the Grand Canal.
Artistic Venice
Doge’s Palace & St. Mark’s Basilica
Excursion · Morning · San Marco
Morning historic tour of Venice’s epic power centers.
Head up to the Basilica terrace for views across the piazza.
Byzantine mosaics in sleepy Torcello island
Excursion · Afternoon · Torcello
Take the ferry past Burano to Torcello for a wonderfully quiet lagoon experience.
Overnight in Venice
Accommodation · Evening · Cannaregio
Arrivederci, Italia
Water taxi to Venice Marco Polo Airport
Transfer · Morning · Venice Lagoon
A stunning final water journey across the lagoon.
Departure flight from Venice
Flight · Afternoon · Tessera
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