Depart at 7:15 a.m. by deluxe coach to Assisi, a medieval town surrounded by ancient walls. Visit the Basilica of St. Francis, featuring frescoes by Giotto and Cimabue and enjoy a lunch in Assisi. Continue to Siena, UNESCO-listed and famous for its shell-shaped Piazza del Campo and Palio horse race. Later, travel through Tuscany’s countryside to reach Florence. Check in at your hotel. Overnight at Hotel Raffaello, Hotel Una Vittoria or similar. (L)

Explore Florence, cradle of the Renaissance. Visit the Duomo, Brunelleschi’s Dome, Giotto’s Bell Tower, and Baptistery. See Piazza della Signoria, Palazzo Vecchio, and Santa Croce Basilica. Enjoy lunch in a traditional Tuscan restaurant. In the afternoon, choose between free time in the city or an optional visit to Pisa, with its Leaning Tower and Piazza dei Miracoli. Dinner is at leisure. Overnight at Hotel Raffaello, Hotel Una Vittoria or similar. (B, L)

Travel to Bologna, a city rich in culture and culinary excellence. Walk from Piazza Malpighi to Piazza Maggiore, admiring San Petronio Basilica and the Palazzo del Podestà. Delight in a light local lunch, savoring regional specialties. Stroll the medieval streets, arcades, and markets. In the afternoon, continue to venice. Upon arrival, check in at the hotel and relax. Overnight stay at Hotel B&B Venezia Laguna (Tronchetto), Hotel Delfino (Mestre) or similar. (B, L)

Transfer to Piazza San Marco and discover Venice’s highlights with a guided tour. Visit the Doge’s Palace (outside) and cross the Bridge of Sighs. Afterward, enjoy a glass of spritz or prosecco with cicchetti, traditional Venetian snacks. Relax and soak in the atmosphere. Spend the afternoon exploring the city’s canals, artisan shops, or quiet corners on your own. Return to your hotel. Overnight stay in Venice at Hotel B&B Venezia Laguna (Tronchetto), Hotel Delfino (Mestre) or similar. (B)

After breakfast, transfer from the hotel to the station. Independently board the designated train, heading to your next destination: Milan. Upon arrival at the Milan station meet your driver and transfer to the hotel. Check in at your Milan hotel. The rest of the day is at your leisure. Overnight stay at Hotel Concorde, Hotel Ramada Plaza or similar. (B)

After breakfast, meet your driver and travel to St. Moritz for some free time. Then, board the Bernina Express and enjoy one of the world’s most scenic train rides through the Swiss Alps. Marvel at alpine villages, tunnels, and breathtaking mountain views as you cross the Bernina Pass toward Tirano. Upon arrival, your driver will be waiting to take you back to Milan. Overnight at Hotel Concorde, Hotel Ramada Plaza or similar. (B)

After breakfast, enjoy some free time to explore Milan at your own pace. In the afternoon, meet your local guide for a three-hour walking tour through the heart of the city. Begin at Porta Venezia, a historic gate with medieval and Roman origins, and continue to Corso Venezia. Walk through the Giardini Indro Montanelli, pass by the Galleria d’Arte Moderna and continue along Viale Manzoni. From the outside, see the iconic Teatro alla Scala and admire the majestic façade of the Milan Cathedral (Duomo). The tour ends at Castello Sforzesco, a medieval fortress, followed by a relaxing aperitivo. Free time before returning to your hotel. Overnight at Hotel Concorde, Hotel Ramada Plaza or similar. (B)

After breakfast, we depart and head towards Peschiera del Garda, a charming town located on the southern shore of Lake Garda. Next, we stop in Trento, where we’ll admire the impressive Castello del Buon Consiglio and the Santa Maria Maggiore Cathedral. After lunch at leisure, we continue along Italy’s oldest wine route, reaching Caldaro (Kaltern), known for its lake and wine. The day ends with our arrival in Bolzano staying at Stadt Hotel or similar. (B)

After breakfast, we travel to Merano, known for its Christmas market and rich cultural heritage. We’ll explore the old town and you’ll have free time for lunch. Next, we visit Vipiteno, a picturesque town with medieval architecture and Alpine charm. Stroll through its streets, and shop for souvenirs. In the afternoon, we head to Bolzano to admire the Gothic-style Duomo and Via dei Portici, the heart of the city. Bolzano combines Alpine and Mediterranean influences, making it a must-visit destination. The evening is free for personal exploration or relaxation. Overnight at Stadt Hotel or similar. (B)

Today, we start with a visit to Bressanone, a charming town in the Eisack Valley, known for its 10th-century medieval cathedral and Austrian-Italian blend. Enjoy local wines and the serene Alpine atmosphere. Then, we head to Brunico, with its colorful medieval streets and panoramic views from Kronplatz Mountain. Afterward, we visit the stunning Lake of Braies, surrounded by towering Dolomite peaks, or Lake Anterselva if Braies is inaccessible. Both offer tranquil beauty and photo opportunities. Finally, we conclude the day in Cortina for dinner at the hotel and an overnight stay, surrounded by the breathtaking Dolomites. Staying at B&B Hotel Passo Tre Croci Cortina or similar. (B, D)

Begin your day with a hearty breakfast at the hotel and get ready to explore the stunning surroundings of Cortina d’Ampezzo. Enjoy panoramic views of the Dolomite Mountains and spot the iconic Tre Cime di Lavaredo. Continue to Lake Misurina, the largest natural lake in the region, offering mesmerizing mountain views. Then, visit Lake Dobbiaco with its unique emerald-colored waters. Drive to San Vito di Cadore, a charming village surrounded by UNESCO-listed mountains, Mount Antelao and Mount Pelmo. Afterward, return to Cortina for free time, relax, and enjoy dinner at the hotel before an overnight stay. Staying at B&B Hotel Passo Tre Croci Cortina or similar. (B, D)

After breakfast, reach Bassano del Grappa, a charming town at the foot of the Venetian Prealps, known for its rich history and timeless charm. Walk its cobbled streets to see medieval towers, elegant Venetian palaces, and mountain traditions shaped by centuries of culture. Don’t miss the iconic Ponte degli Alpini, designed by Andrea Palladio, crossing the Brenta River with postcard views. Visit the Museo della Grappa to explore Italy’s famous distillate origins. The experience includes a tasting session, offering insight into local craftsmanship. After Bassano, head to Milan. Overnight at Hotel Concorde, Hotel Ramada Plaza or similar. (B)

After breakfast, transfer to the airport. Arrivederci. (B)