La Dolce Vita by Rail: Milan, Tuscany and Rome
A new era of la dolce vita unfolds on this ultraluxe journey through Italy, where timeless glamour meets modern refinement. From Milan’s polished energy to the quiet elegance of a Tuscan countryside retreat, the experience culminates aboard La Dolce Vita Orient Express, tracing a stylish route through Venice, Portofino, and Rome. Each moment is seamlessly tailored by your Destination Expert for a journey that feels both iconic and entirely your own.
- Duration
- 11 days, 10 nights
- Route
- Milan · Florence · Cortona · Rome · Venice
- Style
- Private and tailor-made: your own guide and driver throughout
- From
- $17,000 per person, hotels, guides and transfers included
- Explore Milan’s treasures, from The Last Supper to high-end shopping with a personal guide.
- Stay in picture-perfect Cortona and uncover San Gimignano's gems with your private guide.
- Discover Venice’s historic wonders and relax on the scenic shores of Portofino's coastline.
- Board the Orient Express for a once-in-a-lifetime scenic journey through Italy's landscapes.
- Train journeys run April-December. Let your Destination Expert tailor the perfect adventure.
Every day, already yours.
The Adventure Begins
Meet your private English-speaking assistant outside of airport customs. Waiting with a sign with your name on it, they will direct you to your awaiting private transfer, and accompany you to your hotel for check-in.
- Private Airport Transfer with Meet & Greet
- Italy Welcome Package
- Cocktail Hour on the Streets of Milan (with Tastings, 3.5 hrs) - Private Tour
Art & Architecture
Discover Milan through the lens of its striking modern architecture on a privately guided panoramic tour. Set out from your hotel by private vehicle and watch the city’s many layers unfold, from the soaring Pirelli Tower and the monumental façade of Milano Centrale. Pass architectural and cultural landmarks such as the stately Palazzo della Borsa, Triennale Milano and the legendary San Siro Stadium.
- Contemporary Architecture City Tour (2.5 hrs) - Private
- Aperitivo Along the Duomo - Self-Guided
Boutiques of Milan
Step inside Milan’s legendary fashion scene with an expert personal shopper and a private experience tailored entirely to your tastes. Stroll through the elegant streets of the Quadrilatero della Moda, home to iconic designers such as Gucci, Armani, Prada, and Valentino, or venture beyond the famous boutiques to discover independent labels and artisan workshops.
- The Art of Italian Style with a Personal Shopper (4 hrs) - Private
The Journey Continues…
On arrival to the train station in Florence, you'll be met by your private driver for your onward transfer to Cortona. Before leaving Florence, stow your luggage in the vehicle and enjoy up to 3 hours of leisure time in the historic capital of Tuscany. Stretch your legs, explore the UNESCO-listed city center, or find the perfect place for a bite to eat. Afterward, rejoin your private driver for your transfer to Cortona.
- Private Train Station Transfer
- Train - Milan - Florence [1 hr 50 mins] -
- Florence Train Station to Cortona with Florence at Leisure (4.5 hrs) - Private Transfer
History Comes to Life
Golden stone towers rise above rolling hills as you arrive in San Gimignano, a UNESCO-listed medieval jewel. Journey through cypress-lined countryside with your private driver before meeting your local guide for a walking tour through cobbled lanes and sunlit piazzas, where soaring towers and frescoed churches reveal the town’s storied past.
- San Gimignano: Towers, Art, & Artisans (7 hrs) - Private
A Soak at the Spa
Soft light, warm stone, and sweeping views over the Valdichiana set the tone at Thesan Spa, where every detail invites you to slow down. Breathe in the scents of Tuscany, unwind in tranquil spaces, and let the rhythm of water and landscape restore a sense of balance and calm. Speak to your Destination Expert to arrange your spa reservation.
- Spa Reservation at Thesan Spa
Of Vineyards and Vintages
Meet your private driver today for a transfer to Rome. En route, you'll make a stop to visit the beautiful Avignonesi Winery, where you'll be provided with a delightful Tuscan wine tasting and lunch, served on the panoramic terrace or the cozy indoor dining room, depending on the weather. With its vineyards, villa, chapel, and ancient stone wine cellars, the Avignonesi Winery offers a stunning ambiance.
- Cortona to Rome via Avignonesi Winery & Montepulciano (with Lunch & Wine Tasting, 8 hrs) - Private Transfer
At leisure
Good morning and let the journey begin! Joining up with your driver, enjoy a private transfer from your hotel to the train station. After a welcome drink at a dedicated departure lounge, you'll be met by a representative ready to welcome you aboard the Orient Express. Get settled into your cabin and explore all the train has to offer. Your Dolce Vita adventure begins shortly!
- Hotel Transfer & Embarkation
- La Dolce Vita Orient Express Inclusions & On Board Amenities
- Opening Doors to Venetian Palaces - Small Group
- Evening On Board
At leisure
As you awaken to the gentle rhythm of the train, the anticipation of today’s journey fills your senses. Early in the morning, the train arrives at Santa Margherita Ligure, a picturesque gem nestled along the Ligurian coastline. Here, transfer to Portofino where leisure time beckons and a typical Ligurian lunch awaits, promising to tantalize your taste buds with its fresh seafood and vibrant flavors.
- Santa Margherita Ligure to Portofino
- Optional Curated Portofino Experience
- Portofino to Rome
- Evening On Board
At leisure
As you savor the final moments aboard La Dolce Vita, start the morning with an indulgent Italian breakfast. Delight in the flavors of freshly brewed espresso, flaky pastries, and a selection of artisanal breads accompanied by locally sourced jam. Returning to Rome, bid your fellow travelers addio and enjoy a private transfer to your hotel or the Fiumicino airport.
- Arrival in Rome and Disembarkation
- Insider Dining Suggestions: Rome
Safe Travels!
Meet your private driver and vehicle for an airport transfer.
- Private Airport Transfer
Where you will wake up.
Casa Baglioni
Located in Milan’s chic Brera district, Casa Baglioni is an elegant boutique hotel where art, design, and Italian sophistication come together. Inspired by Milan’s avant-garde spirit of the 1960s, the hotel blends contemporary luxury with timeless style, offering a refined retreat just steps from the city’s iconic...
Relais Il Falconiere
Set among olive groves and vineyards in the heart of the Tuscan countryside, Relais Il Falconiere enjoys sweeping views over the Val di Chiana, just below the medieval hill town of Cortona.
Hotel de la Ville
The luxurious Rocco Forte Hotel de la Ville is situated in a brilliant 18th-century palace atop the Spanish Steps in Rome's historic city center, near the exclusive designer shops of Via Condotti.
Orient Express La Dolce Vita I
The epitome of excellence, the Orient Express La Dolce Vita embodies the Italian art of living and all its beautiful traditions. The lavish interior of the train celebrates and pays homage to the craftsmanship, design, and creativity of the 1960s and 1970s.