Italy
La dolce vita through Tuscany & the Riviera
About This Journey
Italy has a particular talent for making you feel that the rest of the world is operating at the wrong speed. This journey moves through three completely different versions of northern Italy in thirteen nights -- beginning at Rosewood Castiglion del Bosco, a restored 800-year-old hamlet on a 5,000-acre Brunello estate in the UNESCO Val d'Orcia, moving to The Place Firenze for three nights of city life in one of Florence's most intimate boutique addresses, and finishing at the Belmond Splendido in Portofino -- the hotel that invented the Italian Riviera as an idea and has been perfecting it for seventy years.
What's Included
Day-by-Day Itinerary
The Tuscan Estate
Val d'Orcia
Arrive at Florence Peretola or Rome Fiumicino and transfer privately south into the Val d'Orcia -- a UNESCO World Heritage landscape of unspoiled rolling hills, isolated farmhouses, and cypress-lined roads. Arrive at Rosewood Castiglion del Bosco in the late afternoon: an 800-year-old medieval hamlet that the Ferragamo family spent a decade restoring into the finest estate hotel in Tuscany. The property unfolds slowly -- the stone towers, the winery, the vine rows extending to the treeline. Dinner at the estate restaurant as the Tuscan hills go dark.
The Hills & the Wine
Chianti
A private full day in the Chianti and Val d'Orcia landscape -- the wine country that produces Brunello di Montalcino, Vino Nobile di Montepulciano, and the Chiantis that the rest of the world has been naming their wine bars after. A private guided drive through the hilltop towns: Greve in Chianti and its arcaded piazza, Panzano with its celebrated butcher, and Radda. Stop at a local cantina for a curated wine tasting with an estate sommelier -- a vertical of the region's finest Brunello, explained in the cellar where it was aged.
Val d'Orcia on Foot & at Table
Pienza
A full private day inside the Val d'Orcia -- a working agricultural region operating as if its UNESCO designation changed nothing. A private guided drive to the medieval hilltop town of San Gimignano -- whose fourteen surviving towers make it look like Manhattan's earliest draft -- and Volterra, the Etruscan hill city with its alabaster workshops. The afternoon moves to Pienza, the Renaissance ideal city, for a Pecorino tasting at one of the town's finest producers, followed by a hands-on pici pasta-making workshop at a traditional mill.
Dawn Over Tuscany
Val d'Orcia
A pre-dawn wake up and a transfer to the balloon launch site as the sky lightens in the east -- a private hot air balloon flight above the Val d'Orcia in the first hour of morning light, when the mist is still in the valley floors and the cypress lines cast long shadows across the vineyard rows. Return to the estate for a champagne breakfast on the terrace. The afternoon is at leisure -- the golf course, the spa, wine tasting at the estate cantina, or pool. Farewell dinner at the estate.
The City of the Medici
Florence
A morning departure from the Val d'Orcia north to Florence -- an hour's drive that moves from the open agricultural landscape into the city that the Medici built and that the Renaissance used as its headquarters. Check into The Place Firenze in the historic centre, steps from the Ponte Vecchio. The afternoon is Florence at its own pace -- the Ponte Vecchio with its goldsmiths, the Piazza della Signoria, the Oltrarno neighbourhood across the river where the artisan workshops and the wine bars are concentrated.
The Uffizi & the Renaissance
Florence
A full private day in Florence with an art historian who treats the city's contents as a coherent argument rather than a list of famous objects. The morning is the Uffizi Gallery -- a private session moving through Botticelli's Birth of Venus and Primavera, Leonardo's Annunciation, Caravaggio, Raphael, and Titian in the sequence that makes their relationships legible. The afternoon moves to the Accademia for Michelangelo's David. The afternoon closes in the Oltrarno: an optional sculpting masterclass in a Florentine atelier.
Florence Off the Map
Florence
A final Florence day for the city that the first two days did not reach. A morning Florentine cooking class -- a session with a home cook in a private kitchen: bistecca alla Fiorentina, ribollita, cantucci. The afternoon is the San Lorenzo market, the leather workshops of Santa Croce, and the rooftop of the Duomo -- the climb to Brunelleschi's dome and the view from the lantern over the entire city. The Place Firenze rooftop for an aperitivo as the city turns gold at 6pm.
To the Ligurian Coast
Cinque Terre
A morning departure from Florence northwest toward the Ligurian coast, with a scenic stop in Lucca -- the perfectly preserved medieval city inside intact Renaissance walls. A leisurely lunch in a trattoria inside the walls before continuing to the Cinque Terre: the five UNESCO-listed villages that cling to the Ligurian cliffs. A private guided walk along the coastal trails connecting the villages -- the views, the pesto, the Sciacchetrà dessert wine at a harbour table in the late afternoon. Then north along the coast road to Portofino and the Belmond Splendido.
Portofino by Land
Portofino
A full private day on the Portofino headland beginning with a vintage Piaggio 4×4 tour -- the most characterful way to move through a landscape of terraced gardens, vineyards, and narrow lanes. Return to the Splendido for lunch on the terrace before an afternoon cooking class on the Ligurian classics: corzetti pasta stamped with carved wooden dies that date to the 16th century, and pesto alla Genovese made with the small-leafed Genoese basil. Evening cocktails in the Portofino harbour as the yachts settle at their moorings.
Portofino by Sea
San Fruttuoso
A morning departure by private boat from the Splendido dock, west along the coast to San Fruttuoso -- a Benedictine abbey from the 10th century accessible only by sea, tucked between a forested headland and a small bay of extraordinarily clear water. The abbey was built by the Doria family and contains their tombs; below the surface of the bay, at a depth of 17 metres, the bronze Christ of the Abyss stands with arms raised toward the light. Private access to the abbey complex before the day boats arrive.
Camogli & the Fishing Villages
Camogli
A private full day exploring the villages of the Portofino promontory. Camogli first -- the lively fishing village north of Portofino, where the houses are painted in trompe-l'oeil facades of deep ochre and terracotta that were designed to be visible to the returning fishing fleet. A long late lunch at a harbourside restaurant before the walk back through the old town's labyrinthine alleys, past the focaccia bakeries and the olive oil producers. Return via the church of San Giorgio above Portofino for the view across the headland.
The Sea & the Splendido
Portofino
A full day at complete leisure -- which on the Italian Riviera in the Belmond Splendido means: the pool with its 180° view of the Ligurian Sea, the hotel's private access to the water below, a late breakfast on the terrace, and the particular quality of a Mediterranean morning when the light is already strong and the sea is already the correct shade of blue. An optional private sailing excursion in the afternoon, or a full spa afternoon at the Splendido. Dinner at the hotel's celebrated La Terrazza restaurant.
Santa Margherita & the Final Riviera
Santa Margherita
A final Riviera day moving north along the bay to Santa Margherita Ligure -- the Belle Époque port town that preceded Portofino as the fashionable Riviera address and that has kept its old-school Italian glamour with considerably less self-consciousness. A morning walk through the harbour promenade, past the coral-pink villas running down to the water, and into the fish market. A long lunch of gambero rosso -- the deep-water crimson prawns that are the town's signature -- at the best harbourside table.
Departure
Genoa
A private transfer from the Splendido north along the coast road to Genoa Cristoforo Colombo Airport -- approximately 45 minutes. Genoa handles direct connections to London, Paris, Frankfurt, Zurich, Amsterdam, and Madrid, with Gulf carrier connections via Dubai and Doha for onward routing to India and the United States. The drive along the Ligurian coast to the airport is the correct final chapter -- the sea still visible on the left and the reason to return already forming in the back of the mind.
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