Italy in 2 Weeks: 3 Recommended 14-day Itineraries to Italy

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Italy 2-week Itinerary Options
A 2-week trip to Italy offers the perfect opportunity to fully explore its diverse regions. Check out our Italy 2-week itinerary suggestions in Italy to experience everything from Rome's history and Florence's art to the serene countryside of Tuscany and the stunning Amalfi Coast.
Itinerary #1: The Top Cities of Italy


Overview | Activity | Overnight | |
Day 1 | Welcome to Milan | Arrival | Milan |
Day 2 | Enjoy a train ride through the country on your way to Venice | Scenic ride | Venice |
Day 3 | See the highlights of Venice, including a gondola ride through the city’s canals | City sightseeing | Venice |
Day 4 | Relax on your way to Florence, exploring the Tuscan landscape. | Relaxation | Florence |
Day 5 | Visit Florence, including the Uffizi Gallery and the Duomo. | Sightseeing | Florence |
Day 6 | A trip to Rome and explore the Vatican City | Exploration | Rome |
Day 7 | Discover Rome's most beautiful places on a walking tour of the city. | City sightseeing | Rome |
Day 8 | Take a final train ride through the country to Naples. | Transfer | Naples |
Day 9 | Explore the ruins of Pompeii and climb the crater of Mount Vesuvius. | Exploration | Pompeii |
Day 10 | Spend the day traveling to Sorrento. | Transfer | Sorrento |
Day 11 | Take a guided tour of the picturesque villages while touring the Amalfi Coast. | Village exploration | Amalfi coast |
Day 12 | Relax on an 8-hour boat tour of the Sorrentine coast. | Boat ride | Amalfi coast |
Day 13 | Visit the charming town of Positano and enjoy its beaches | Beach activities | Positano |
Day 14 | Say goodbye and head to your next destination, with time for last-minute shopping or sightseeing in Sorrento. | Departure |
If you are looking to explore the top cities, this 14 days in Italy itinerary is the perfect way to immerse yourself in the country's rich culture and history. Start your trip in Milan, where you can soak in the vibrant atmosphere before taking a scenic train ride to Venice, famous for its enchanting canals and gondola rides. Continue to Florence, home to iconic art and stunning architecture, including the Uffizi Gallery and the majestic Duomo. From there, travel to Rome, to delve into the granduer of Vatican City and stroll through the historic streets. Your adventure doesn't stop there—head to Naples to uncover the ancient ruins of Pompeii and hike the iconic Mount Vesuvius. Finally, relax on the breathtaking Amalfi Coast, exploring charming villages and enjoying serene boat tours along the stunning coastline. This itinerary captures the essence of Italy’s most celebrated destinations, making for an unforgettable journey. Check our city sightseeing tours in Italy.
Itinerary #2: Highlights of Italy

Overview | Activity | Overnight | |
Day 1 | Take your first steps in the Italian capital | Arrival | Rome |
Day 2 | Tour the main attractions in Rome | City sightseeing | Rome |
Day 3 | Admire the beauty of Florence from the Ponte Vecchio | Sightseeing | Florence |
Day 4 | Walk the ancient walls of Lucca | Exploration | Tuscany |
Day 5 | Marvel at the impossible lean of Pisa’s famous tower | Exploration | Tuscany |
Day 6 | Join the locals on La Spezia’s waterfront | Relaxation | La Spezia |
Day 7 | Grab your walking boots to explore Cinque Terre | Walking tour | Cinque Terre |
Day 8 | Discover hidden gems in and around Portofino | Exploration | Portofino |
Day 9 | Discover the secrets of Asti’s famed wine | Wine tasting | Piedmont |
Day 10 | Shop till you drop on your tour to Milan | Exploration | Milan |
Day 11 | Enjoy a lazy day in the villages around Lake Como | Village exploration | Milan |
Day 12 | Arrive among the canals of Venice | Exploration | Venice |
Day 13 | Tour Venice before sampling authentic regional cuisine | Food tour | Venice |
Day 14 | Commit your last panoramas of Venice to memory | Departure |
This 14-day Italian adventure begins in the vibrant capital, Rome, where you'll immerse yourself in its rich history and iconic sights on the first two days. From there, you'll admire the beauty of Florence from the historic Ponte Vecchio, stroll along the ancient walls of Lucca, and marvel at the iconic Leaning Tower of Pisa. The journey continues with a visit to La Spezia's lively waterfront before donning your walking boots to explore the stunning landscapes of Cinque Terre. You'll uncover hidden gems around Portofino and discover the secrets behind Asti’s renowned wines, followed by a shopping spree in the fashionable city of Milan. Enjoy a leisurely day in the picturesque villages surrounding Lake Como, then arrive in Venice to navigate its enchanting canals. Your final days are spent exploring the city's treasures and savoring authentic regional cuisine, ensuring you capture unforgettable memories of this remarkable journey.
Itinerary #3: The wonders of Sicily


Overview | Activity | Overnight | |
Day 1 | Arrive in Catania | Arrival | Catania |
Day 2 | See Catania’s highlights on a locally guided walking tour and taste some street food | Food tour | Catania |
Day 3 | Visit Greek archeological sites, local wineries and baroque palaces | Wine tasting tour | Catania |
Day 4 | Explore two UNESCO World Heritage villages | Village exploration | Catania |
Day 5 | Learn to cook Italian cuisine against the backdrop of the Vendicari Nature Reserve | Cooking class | Vendicari Nature Reserve |
Day 6 | Discover the gorgeous historic towns of Ragusa and Scicli | Historic exploration | Scicli |
Day 7 | Eat chocolate from Sicily’s oldest chocolate maker; archeological trek through the Cava d’Ispica | Chocolate tasting | Scicli |
Day 8 | Tour the Villa Romana del Casale, then transfer to Taormina. | Historical exploration | Taormina |
Day 9 | Explore the charming town of Taormina, visit the Greek Theater, and admire the panoramic views of the Ionian Sea | Town Exploration | Taormina |
Day 10 | Discover the Valley of Temples with an expert guide | Historical exploration | Agrigento |
Day 11 | Taste wine from Marsala’s oldest wine producers and take in the sunset at the Salt Pans. | Wine tasting | Marsala |
Day 12 | Walk through the history of Palermo. | Walking tour | Palermo |
Day 13 | Discover Monreale Duomo and explore the Segesta archaeological park. | Historical exploration | Monreale |
Day 14 | Trek Mount Etna and finish the day with a tasting of local wines and food from the region. | Hiking and departure |
If you’re planning your Italy itinerary, 14 days in Italy is the perfect amount of time to get your history and nature fixed as you take a deep dive into the Sicilian culture. This unique itinerary will introduce you to the Sicilians making their island the haven of wine, food, and culture it is today. You’ll meet chocolate makers, vintners, and historians as you explore medieval towns, nature reserves, and archeological sites.

If you are looking for more Italy 2-week itinerary options, check out our article on how many days to spend in Italy to plan your perfect tour duration. If you’re looking to plan your customized trip to Italy, connect with one of our travel experts in the country and go on your own Italy tour for 2 weeks.
For a seasonal overview, read our travel article on the best time to visit Italy.
Other related articles:
One week in Italy
10 days in Italy
12 days in Italy