Tailor-made trip to Italy’s best cities

Arrive in Milan to begin your tailor-made Italy travel. After settling into your hotel, take a short stroll to admire the Duomo's soaring Gothic façade and climb to its terraces for sweeping city views. Pause at a nearby café for an espresso and people watching.

In the evening, savor a traditional meal at a local trattoria and let your local host tailor the coming days to your interests.

Begin your second day in Milan with a morning at the historic Sforza Castle and a timed viewing of Leonardo da Vinci’s The Last Supper at Santa Maria delle Grazie, accompanied by local guide insights and curated art highlights.

Spend the afternoon wandering Brera’s artisan streets, enjoy a personalized gallery stop, then explore the Quadrilatero della Moda for private shopping or curated fashion tours that reveal Milan’s style scene.

Take a high-speed train from Milan to Venice this morning, savoring scenic views and fast, comfortable travel that gives you more time to enjoy your Italy itinerary. On arrival, transfer by water taxi to your hotel.

After settling in, wander the enchanting narrow streets to iconic St. Mark's Square and take time to admire St. Mark's Basilica and the Campanile. Choose a private walking tour or a classic gondola ride, taste cicchetti at a bacaro by the canal, and spend a peaceful evening enjoying views over the canals.

Enjoy a morning exploring Venice's winding alleys and canals, uncovering hidden squares and lively markets with local insights for authentic discoveries.

In the afternoon, take a scenic vaporetto along the Grand Canal, glide beneath elegant bridges, and past ornate palaces. Finish the day with a relaxed waterside dinner chosen to showcase regional flavors and intimate Venetian ambience.

Visit the historic Doge's Palace and cross the Bridge of Sighs, then glide through the canals on a gondola for an intimate view of Venice.

In the afternoon, wander Cannaregio's charming lanes, discover local artisans and hidden campo, then enjoy dinner at a traditional Venetian restaurant and savor seafood risotto.

Board a high-speed train from Venice to Bologna and enjoy a relaxed morning watching the Italian countryside roll by.

Arrive and settle into your hotel. Spend the afternoon wandering medieval streets, admiring the towers, and soaking up the atmosphere at Piazza Maggiore. Dine at a family-run trattoria on tagliatelle al ragù, join a food-focused walking tour, and discover Bologna’s culinary secrets.

Start your day in Bologna's Quadrilatero district, tasting fresh local produce, cured meats, and celebrated cheeses. Visit Basilica di San Petronio and climb the Asinelli Tower for sweeping views that bring the city to life.

In the afternoon, walk the Portico di San Luca, soaking up elegant architecture and lively piazzas.

Catch a high-speed train from Bologna to Florence, enjoying rolling Tuscan scenery en route. Arrive mid-morning and settle into your comfortable 4-star hotel.

After a short rest, take a leisurely, tailor-made walk to the Piazza del Duomo to admire the Cathedral and Baptistry and absorb the Renaissance atmosphere.

Finish the day at a traditional trattoria on this Italy trip, savoring Tuscan specialties such as ribollita or bistecca alla Fiorentina.

Visit the Uffizi Gallery to admire Botticelli, Da Vinci, and Raphael masterpieces, then soak up civic life at Piazza della Signoria and explore the medieval rooms of Palazzo Vecchio with a local guide.

Climb to Piazzale Michelangelo for a panoramic view of Florence, then reward yourself with a gelato and a leisurely stroll along the Arno River.

Travel by train from Florence to Pisa to visit the iconic Leaning Tower of Pisa. Capture memorable photos, climb the tower if you wish, and soak in the Romanesque beauty of Piazza dei Miracoli, Pisa Cathedral, and the Baptistry.

Wander along the Arno River, savor local gelato, and enjoy tailored tips that make this Italy trip feel personal. Return to Florence in the evening for a relaxed night in your hotel.

Today, travel by high-speed train from Florence to Rome, watching the Tuscan hills unfold and enjoying fast, comfortable service.

After arrival in Rome and step straight into history at the Colosseum. Wander the ruins of the Roman Forum and climb Palatine Hill for sweeping views across the Eternal City. Cap the day with authentic Roman pizza in a family-run trattoria.

Begin your day in Vatican City, marveling at St. Peter’s Basilica and climbing its dome for panoramic views. Dive into the Vatican Museums and finish beneath Michelangelo’s frescoes in the Sistine Chapel, with skip-the-line access and a local guide to reveal hidden details.

In the evening, wander Trastevere’s cobbled streets and enjoy classic Roman cuisine at a family-run trattoria for an authentic, tailor-made dining experience.

Start your final day in Rome at the Pantheon, then toss a coin into the Trevi Fountain to promise a return. Stroll lively Piazza Navona and savor artisanal gelato at Giolitti.

Pause on the Spanish Steps for one last city view, reflecting on a tailored Italy trip that blends iconic sights and local moments crafted for authentic memories.

Today, your journey through Italy ends. From the canals of Venice to Florence’s Renaissance treasures and Tuscany’s rolling hills, you’ve experienced the best of Italy’s cities and culture.

After breakfast, a private transfer takes you to the airport for your flight home, leaving with unforgettable memories and a strong case for coming back.