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

A couple admiring the view of Greek theatre in Taormina during their 2 weeks in 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

The Grand Canal offers a facility of exploring Venice in a gondola ride.
Built on the waters of the Adriatic Sea, Venice is a highlight of this two-week Italy itinerary.
Mount Vesuvius is a very famous skyline in Naples
A trip to Italy is incomplete without climbing the iconic trail of Mount Vesuvius.
  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

A visit to the Milan cathedral  is a must-add to your Italy itinerary.
Standing in the heart of Milan, the Milan Cathedral is a gothic-inspired church that holds 3400 statues.
  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

Among the list Best beaches in Sicily, Aeolian Islands is an eye candy
The typical whitewashed houses in the Aeolian Islands are a real treat for the eyes.
The Valley of temples is an outstanding archaeological site in Sicily.
Visit UNESCO heritage sites on this 14-day Italy itinerary.
  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. 

An overview map of 2 weeks in Italy
An overview map of 2 weeks in Italy

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