Traveling Through Italy
Rome, Florence, Positano, and Sorrento
A two-week itinerary combining Italy's most celebrated cities with the Tuscan countryside and the glamorous coastline of the south.
This thoughtfully designed Italy itinerary combines the country's most celebrated cities with the beauty of the Tuscan countryside and the glamorous coastline of southern Italy. Over the course of two weeks, the couple experienced ancient landmarks, Renaissance masterpieces, regional food and wine, luxurious hotels and several unforgettable days on the water.
Rome (4 nights)
Hotel: Hotel de la Ville, a Rocco Forte Hotel
An elegant Rocco Forte hotel located above the Spanish Steps. Set within an 18th-century palazzo, the hotel combines classic Roman character with contemporary design, sweeping city views and a lively rooftop atmosphere.
Experiences:
A private golf cart tour customized around their interests
A guided visit to the Colosseum, including access to the arena floor, followed by the Roman Forum and Palatine Hill
A small-group tour of the Vatican Museums, Sistine Chapel and St. Peter's Basilica
An evening exploring Trastevere on a guided food tour featuring traditional Roman dishes, local wine, street food, pasta and gelato
Florence (3 nights)
Hotel: Collegio alla Querce, Auberge Resorts Collection
Set within a restored 16th-century estate overlooking Florence and the surrounding Tuscan hills, the hotel offers peaceful gardens, a beautiful pool, a serene spa and an elevated retreat just outside the historic center.
Experiences:
Dinner at the hotel's restaurant, La Gamella
A guided walking tour including Michelangelo's David at the Accademia Gallery, the Duomo, Piazza della Signoria and Ponte Vecchio
A sunset food and wine tour featuring Tuscan specialties, regional wines, Florence's historic wine windows and the city's signature Negroni
A day in the Tuscan countryside, visiting two wineries in Chianti Classico, with tastings paired with olive oil, cheeses, cured meats and bruschetta
Positano (3 nights)
Hotel: Le Sirenuse
A romantic, family-owned hotel perched above the Amalfi Coast, known for its elegant interiors, exceptional service and breathtaking Mediterranean views.
Experiences:
A relaxing day at Le Sirenuse Mare, the hotel's exclusive beach club in Nerano - arriving by boat, with a private cabana, seaside lunch and champagne, followed by dinner back in Positano at La Sponda
A private boat tour of the Amalfi Coast and Capri
Dinner at La Tagliata, a family-run restaurant above Positano known for generous, traditional Italian cooking
Sorrento (3 nights)
Hotel: Bellevue Syrene
A sophisticated cliffside hotel overlooking the Bay of Naples, pairing centuries-old architecture with stylish interiors, panoramic terraces and a convenient central location.
Experiences:
A visit to a fourth-generation family farm - exploring olive and lemon groves, learning about local wine production, and a farm-to-table lunch
A boat trip to Capri and the Blue Grotto, taking in the island's dramatic rock formations before free time to explore independently
A final dinner beside the water at Bagni Delfino
Rome - The Final Night (1 night)
Hotel: Hotel Hassler Roma
Located at the top of the Spanish Steps, this legendary hotel provides an elegant and convenient conclusion to the journey before flying home.
From Rome's ancient landmarks and Florence's Renaissance treasures to Tuscan vineyards, Positano's glamorous coastline and Sorrento's culinary traditions, this itinerary offered a beautiful balance of culture, relaxation and romance.
Each destination introduced a different side of Italy, while the carefully selected hotels and experiences make the entire journey feel seamless, personal and unforgettable.
