3 Nights Rome + 1 Night Pisa + 2 Nights Venice + 2 Nights Milan
3 Nights Rome + 1 Night Pisa + 2 Nights Venice + 2 Nights Milan
Experience the best of Italy on this carefully curated 9 Days / 8 Nights multi-city journey, combining the ancient grandeur of Rome, the iconic beauty of Pisa, the timeless romance of Venice and the sophisticated energy of Milan. Begin in Rome, the Eternal City, where ancient history comes to life through the magnificent Colosseum, Roman Forum and Palatine Hill. Enjoy time at leisure to discover Rome’s famous fountains, piazzas, historic streets and neighbourhoods, or choose an optional Vatican experience, food tour or day excursion.
Continue to Pisa, home of the world-famous Leaning Tower. Discover the spectacular Piazza dei Miracoli and its remarkable architectural treasures before continuing by train to Venice. In Venice, explore the city’s atmospheric canals, historic bridges, elegant squares and distinctive neighbourhoods on a private walking tour. Discover landmarks including Rialto Bridge, Cannaregio, Basilica di Santa Maria Gloriosa dei Frari, Scala Contarini del Bovolo, Teatro La Fenice, Basilica di Santa Maria della Salute and Ponte dell’Accademia.
Complete your Italian journey in Milan, Italy’s capital of fashion, design and culture. Explore Duomo Square, the magnificent Galleria Vittorio Emanuele II, the artistic Brera District, Basilica di San Simpliciano and the courtyards of Sforza Castle. With comfortable 4-star accommodation, daily breakfast, private arrival/departure transfers, intercity rail travel and included sightseeing, this itinerary offers an ideal balance of guided experiences and free time for shopping, dining and independent exploration.
Perfect for couples, families, friends and first-time visitors looking to experience several of Italy’s most iconic destinations in one seamless holiday.
Upon arrival, you will be welcomed with a meet and greet service and provided a private transfer to your hotel for check-in and leisure time.
Overnight: Rome
Breakfast at the hotel. Step back in time on a guided tour of Ancient Rome’s most iconic landmarks. Begin with priority access to the magnificent Colosseum, where your expert licensed guide will share fascinating stories of gladiator battles, Roman engineering and the history of one of the world’s greatest amphitheatres. Continue to Palatine Hill, the legendary birthplace of Rome, where you’ll admire the remains of imperial palaces while enjoying panoramic views over the Eternal City. Conclude your experience at the Roman Forum, once the political, religious and commercial heart of Ancient Rome. Walk along the historic Via Sacra as your guide brings the ancient ruins to life with captivating insights into Roman history and daily life. The tour includes entrance to the Colosseum, Roman Forum and Palatine Hill, the services of a licensed guide and headsets for clear commentary. Free evening at leisure.
Overnight: Rome
Breakfast at the hotel. Enjoy a full day at leisure to explore Rome at your own pace. Visit the Vatican Museums and St. Peter’s Basilica, admire the Trevi Fountain, the Spanish Steps and Piazza Navona, stroll through the charming streets of Trastevere, or indulge in authentic Italian cuisine at a traditional trattoria. Alternatively, choose from a variety of optional experiences, including a Vatican guided tour, a food and wine tasting, a day trip to Tivoli, or an excursion to Pompeii and the Amalfi Coast. Overnight at your hotel.
Overnight: Rome
Enjoy breakfast at the hotel before checking out. Transfer to Rome train station for your onward journey to Pisa by high-speed train. Upon Arrival at Pisa train Station, transfer to your hotel for check-in and leisure time. Explore Milan’s elegant streets, enjoy Italian cuisine or discover the city’s famous shopping and fashion districts.
Overnight: Pisa
Enjoy breakfast at the hotel before checking out, later enjoy time to visit Pisa’s iconic Piazza dei Miracoli, home to the world-famous Leaning Tower of Pisa, Pisa Cathedral and Baptistery.
Transfer to Pisa Station for you onward journey to Venice. Upon arrival at Venice, transfer to your hotel for check-in and leisure time.
Overnight: Venice
Breakfast at the hotel, later embark on a private walking tour to explore iconic Venice landmarks at your own pace. The itinerary covers key spots including the historic Rialto Bridge and bustling Market, the scenic Cannaregio District, the grand Basilica di Santa Maria Gloriosa dei Frari, and the unique Scala Contarini del Bovolo. Highlights also include Teatro La Fenice, the Basilica di Santa Maria della Salute, and the picturesque Ponte dell’Accademia, offering, as described in the tour details, a tailored experience of Venice’s rich culture. Free evening at leisure.
Overnight: Venice
Breakfast at the hotel, enjoy your time at leisure. Option to explore local markets, take an optional gondola ride, or join an excursion to the islands of Murano, Burano, and Torcello up to your time for departure to catch your train to Milan. Transfer to Venice Train Station.
Upon Arrival at Milan transfer to your hotel for check-in and leisure time.
Overnight: Milan
Breakfast at the hotel. Embark on a guided walking tour Milan Highlights and Hidden Gems . Meet your local guide at Piazza dei Mercanti for a personalized journey through the historic center. Explore the magnificent Duomo Square, step inside the iconic Galleria Vittorio Emanuele II shopping arcade, and discover the artistic charm of the Brera District. Visit the historic Basilica di San Simpliciano and conclude your journey exploring the main courtyards of the majestic Sforza Castle. Return to your hotel independently. Free evening to explore Milan’s elegant streets, enjoy Italian cuisine or discover the city’s famous shopping and fashion districts.
Overnight: Milan
Enjoy breakfast at the hotel before checking out. A private transfer will then take you to the Milan Airport or train station for your onward journey.
Customize Your Trip
This sample itinerary is designed to inspire your next trip to Italy and can be easily customized according to your interests, preferences and budget. You can extend your stay, upgrade your hotels, add additional sightseeing or include optional excursions such as a Vatican experience in Rome, additional Pisa attractions, a gondola ride or Murano, Burano and Torcello excursion from Venice, or the Last Supper and Duomo Rooftop experience in Milan. The itinerary combines Rome’s ancient history and iconic landmarks, Pisa’s world-famous Leaning Tower, Venice’s romantic canals and historic architecture, and Milan’s fashion, culture and elegant city sights, with free time to explore each destination at your own pace.
Travel Period: 10 November 2026 to 28 February 2027 from $2999*
(excluding Christmas / New Year / Carnival dates)
For other departure dates, please contact Airway Interline.
*Terms & Conditions apply. All prices are in Canadian dollars, per person, based on double occupancy and subject to availability and may vary depending on hotel choice, travel dates, seasonal surcharges and other operational factors. Sightseeing tours, attractions and the sequence of visits may vary due to operational reasons, local conditions, weather, traffic or other unforeseen circumstances. Sightseeing may include visits and/or photo stops at selected attractions. Entrance fees are included only where specifically mentioned under “Inclusions”. Equivalent sightseeing experiences will be provided wherever possible. Some sightseeing tours may require guests to make their own way to and from the designated meeting point. Please refer to your final travel documents for confirmed meeting point details and instructions.