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.

A Welcome Package will be provided and will include any relevant documents or tickets required for your trip.

Indulge in a captivating private guided gastronomic tour in the vibrant city of Milan, perfectly synchronized with the city's beloved happy hour tradition of the aperitivo, commencing late afternoon. Your adventure begins with a private transfer from your hotel to the bustling city center, where alongside your guide you'll set out on a leisurely stroll leading you to several small tasting stops, inviting you to savor the diverse and rich flavors of Milan. Your tastings will culminate with a visit to a cafÉ in the vibrant Navigli district, renowned for its charm and cultural significance, providing an idyllic setting for this part of your taste-filled journey. The menu chosen for you will feature a generous assortment of refined local specialties, accompanied by prosecco, wine and an expertly-crafted cocktail. Conclude this enriching experience with a transfer to your hotel.

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. Along the way, your guide will reveal how visionary 20th- and 21st-century design transformed Milan from an industrial powerhouse into a dynamic global capital.

Savor aperitivo at the very heart of Milan, where the Duomo’s soaring marble faÇade glows as day fades into evening. Choose your vantage point, from historic cafÉs to stylish rooftops, and savor the city’s most iconic views with a drink in hand. Begin with Milanese tradition at Camparino in Galleria, an institution synonymous with aperitivo culture and perfectly placed inside the Galleria. For elevated views, head to Terrazza Aperol, where spritzes come with front-row Duomo panoramas, or The Roof Milano, offering a more refined rooftop setting above the piazza. For a contemporary, design-forward pause, STRAFbar delivers creative cocktails just steps from the cathedral.

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. Special emphasis is placed on Italian craftsmanship, with opportunities to meet talented makers preserving generations-old traditions in tailoring, jewelry, silverwork, and shoemaking. For a truly personal souvenir, visit a shirtmaker, tie maker, jeweler, or shoemaker to commission a bespoke piece created to your exact measurements and shipped directly to your home once complete.

Meet your private driver and vehicle for a train station transfer.

Depart by train from Milan to Florence. Approximate travel time is 1 hour and 50 minutes.

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. Approximate travel time is 1.5 hours.

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. Admire landmarks such as Piazza del Duomo and the Collegiate Church, then continue at your own pace with time at leisure to browse artisan boutiques, sample local specialties, or linger over a glass of wine in a charming trattoria. Rejoin your driver for a scenic return to Cortona, carrying with you the timeless spirit of Tuscany.

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.

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. Afterward, you'll continue to the nearby medieval hill town of Montepulciano, where you'll meet up with a private local guide for a walking tour of the pedestrian-only old town. Explore its charms on foot, strolling the main Corso, leading to a number of narrow alleys and lanes. Admire elegant palaces and historic churches, and head to the Piazza Grande, a beautiful main square surrounded by expressive architecture. Climb up the square's clock tower in the 14th-century Palazzo Comunale and enjoy a stunning view over the town. Afterward, continue to Rome for check-in.

Begin your journey at Rome Ostiense’s exclusive La Dolce Vita Lounge, arriving by private transfer from your hotel or the airport. Step aboard La Dolce Vita Orient Express and settle into your elegant cabin as the train departs. Then, take your seat in the Restaurant Car for an exquisite lunch by three-Michelin-starred chef Heinz Beck, celebrating Italy’s rich culinary heritage.

During your journey aboard La Dolce Vita by Orient Express, your onboard experience includes the following:

• Meals: table d'hote style, made onboard with seasonal and local ingredients
• Beverages: Selected wine & spirits, mineral water, soft drinks, tea, and coffee
• In-cabin upscale bathroom products, hairstyling tools, slippers, and bathrobes
• Onboard entertainment
• Exclusive small group experiences in each destination
• 24-hour onboard services and support

The scenery shifts gently from the heart of Rome, to the rolling Tuscan hills, and finally to the coastline of Liguria. In the afternoon, arrive at Santa Margherita Ligure.

Explore Portofino on a small group excursion. On arrival, your local guide welcomes you for a walk through the village, exploring Portofino’s harbour, scenic lanes, and hidden corners while discovering the character and atmosphere that make this destination so iconic. After the guided visit, enjoy free time to continue exploring at your own pace, browse the local boutiques, stop for a gelato by the waterfront, or simply take in the charm of the village before returning on board La Dolce Vita Orient Express.

A transfer awaits to take you to the charming town of Portofino.

Begin the morning with breakfast in the comfort of your cabin or the elegant Restaurant Car as the train glides through Northern Italy in the soft morning light. By late morning, arrive at Venezia Santa Lucia station, perfectly positioned beside Venice’s shimmering canals.

Upon arrival at Venezia Santa Lucia station, disembark La Dolce Vita Orient Express and continue with your onward arrangements.

For your ease and comfort, a private English-speaking assistant will accompany you between the port and your hotel, assisting with water taxi arrangements. For cruise arrivals, your assistant will escort you to your hotel and ensure a smooth check-in. For departures from Venice, they will accompany you to the cruise pier and assist with embarkation.

Venice reveals its most intimate secrets in the quiet hours, when the city feels suspended between dream and reality. Begin this self-guided wander at first light, when pastel skies reflect on mirror-still canals and the city stirs awake. As evening returns, slip back into the labyrinth of lanes and cross hushed bridges glowing under soft lamplight. Drift into a nearly empty St. Mark’s Square, where the basilica’s mosaics shimmer quietly and the air feels touched by history. Settle at CaffÈ Florian with a late espresso as a quartet plays to a small, attentive crowd, the music echoing gently through the colonnades. In these tender in-between hours, Venice feels like it belongs only to you. Please note this self-guided stroll is simply a suggested route; feel free to adapt it to your pace and interests.

Tucked away along a quiet Venetian lane near St. Mark’s Square, Ai Mercanti is a refined culinary gem where creativity and tradition meet on the plate. In an intimate, contemporary setting, the restaurant presents beautifully crafted dishes that reinterpret Venetian classics with modern flair, showcasing the finest seasonal ingredients from the lagoon and beyond. Please note this is a reservation service only; the meal is payable locally in destination.

Meet your private English-speaking assistant who will accompany you on your transfer to Marco Polo Airport. They will assist in organizing a water taxi and ensure you arrive safely to your destination.

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 fashion, culture, and culinary hotspots. Each of the 30 meticulously designed rooms and suites showcases bespoke furnishings, rich textures, and curated artwork, creating an intimate and stylish atmosphere. Guests can indulge in exquisite cuisine at the hotel’s gourmet restaurant, helmed by a Michelin-starred chef, or unwind with an aperitivo in the elegant lounge. With its impeccable service, artistic ambiance, and prime location, Casa Baglioni offers a truly exclusive Milanese experience in the city’s most vibrant neighborhood.

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. Steeped in aristocratic heritage, the estate’s character is reflected in its historic stone pathways, interconnected buildings, and the presence of the family’s noble falcon. The hotel features 31 intimate rooms and suites, elegantly furnished in the warm style of rural Tuscan nobility. Highlights include an atmospheric winery suite above the cellars, a serene spa using locally sourced products, and a welcoming family spirit throughout the property. At the in-house restaurant, Tuscan culinary traditions are thoughtfully reinterpreted using home-grown ingredients. Ideally positioned between Tuscany and Umbria, Il Falconiere offers a refined countryside retreat centered on fine food, wine, and relaxed living.

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. The hotel's 104 rooms and suites are filled with playful, contemporary furniture and sumptuous fabrics that draw influence from the era of the Grand Tour and the memories collected during such a journey. With traditional wooden floors, elegant marble washrooms and wonderful views over terracotta rooftops of the Eternal City, Hotel De La Ville is effectively timeless. Fall for its enchanting courtyard, exquisite food, effervescent rooftop bar, street-side bistro, and even a Sicilian-inspired spa, allowing you to balance mind, body, and soul. The confluence of classical Roman romance and contemporary cool, sweeping city views, lively on-site drinking and dining spots, and a fresh design make for Rome’s most exciting stay.

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. The luxurious interior of the train embellishes twelve deluxe cabins, eighteen suites, and one La Dolce Vita Suite, all decorated with soft and refined furnishings. The lounge bar and restaurant, both housed in their own carriages, best represent typical Italian hospitality and flavors and act as the perfect backdrop for an enchanting evening as the idyllic landscapes float by. Be invited to embark on a fascinating journey aboard the Orient Express La Dolce Vita.

The Metropole Hotel is a refined and cozy accommodation, overlooking the lagoon, with views over San Giorgio Island. Founded in the 1500s, the atmosphere is fascinating and welcoming, seducing guests with perfumed candles and subtle incense that spread everywhere with a delicate fragrance. Guestrooms are unique, where fine 18th-century antiques alternate with ornate furniture and art deco. Dine at the MET restaurant, offering great cuisine, and brings together tradition and modernity. The Oriental Bar offers a welcoming atmosphere, where guests can enjoy delicious cocktails. The hotel features a Citrus Garden, a Mediterranean oasis to eat breakfast in during the spring and summer, enjoy a quick lunch, or sip a drink during the evening in peace surrounded by white gazebos.