How To Spend 14 Days In Italy - 5 Unique Itineraries

updated 05.11.2024

Frequently topping polls of the most beautiful countries in the world, Italy is a diverse destination that deserves repeat visits. That said, it’s perfectly possible to pack plenty of unforgettable experiences into a 2-week journey. The question is, how to choose where to go? Read on to discover our unique, fully customizable 14 days Italy itineraries.

See our itineraries below, or get inspired by duration and regions: 7 day Italy itinerary - 10 day italy itinerary - 14 day Italy itinerary - Northern Italy itinerary - Southern Italy itinerary - Amalfi coast itinerary - Tuscany itinerary

Itinerary #1: From Venice to Florence: A Grand Tour of Northern Italy

From the canals of Venice and the coastline of Cinque Terre to the designer boutiques of Milan and the streets of Florence, Northern Italy has plenty to offer. Experience it all with this comprehensive 14-day trip.

On the first day, you will be transferred to your hotel. On the second day, you will be met by a private guide and taken on a beautiful Venice city tour. On the third day, you will embark on a trip to the enchanting islands of Burano and Murano.

The fourth day is reserved for exploration and leisure in Venice. On the fifth day, you will enjoy a journey by train, arriving in Milan. The remainder of the day is yours to explore Milan. Your guide will accompany you on a walking tour of Milan on the sixth day.

Embark on a train journey to Como on the seventh day. Take advantage of the day to soak up the atmosphere of this beautiful region. On the eighth day, you will enjoy a short ride to Lugano, Switzerland. On day nine, treat yourself to a boat trip on Lake Como. Then enjoy a leisurely tenth day.

Your driver will transfer you to the railway station on the eleventh day for your onward journey to Cinque Terre. Embark on an exciting adventure to explore the picturesque villages of Cinque Terre on day twelve.

The thirteenth day is yours to spend at your leisure. On day fourteen, you will be transferred to the airport for your departure flight. Read more.

Gondolas in Venice © Shutterstock

Gondolas in Venice © Shutterstock

Itinerary overview

Check this overview of the 14 days Italy itinerary.

Day 1

  • Arrival in Venice.
  • Overnight in Venice.

Day 2

  • Sightseeing tour in Venice.
  • Overnight in Venice.

Day 3

  • Murano and Burano boat tour.
  • Overnight in Venice.

Day 4

  • Free day in Venice.
  • Overnight in Venice.

Day 5

  • Train to Milan, and free time in the city.
  • Overnight in Milan.

Day 6

  • Sightseeing tour in Milan.
  • Overnight in Milan.

Day 7

  • Train to Lake Como.
  • Overnight in Como.

Day 8

  • Lugano and Lakeside villages.
  • Overnight in Como.

Day 9

  • Lake Como boat tour.
  • Overnight in Como.

Day 10

  • Free day in Como.
  • Overnight in Como.

Day 11

  • Train to Cinque Terre.
  • Overnight in La Spezia.

Day 12

  • Exploring Cinque Terre and around by train.
  • Overnight in La Spezia.

Day 13

  • Free day in Cinque Terre.
  • Overnight in La Spezia.

Day 14

  • Transfer and departure from Florence.

Interested? Don't miss the opportunity to book this trip now.

Cinque Terre National Park UNESCO World Heritage Site, Liguria, Italy

Cinque Terre National Park UNESCO World Heritage Site, Liguria, Italy

Itinerary #2: classic Italy - Rome, Florence & Venice

This 14-day Itinerary is for everyone - learn how to cook pasta in Rome, sample the best gelato in Florence, hike Cinque Terre and explore Venice on your own. This trip is packed with highlights for the whole family.

Rough Guides tip: buy this trip as a Guidebook in our shop.

On day one you'll be transferred to your hotel, and the rest of the day is yours to enjoy at leisure. The second day is dedicated to the Colosseum and Forum Romanum.

Join a small group cooking tour on the third day. On day four you will travel to Florence via high-speed train. Explore Florence leisurely on an e-bike on the fifth day.

Join a cooking class in central Florence on the sixth day of the journey. On day seven you will experience the beauty of Chianti's rolling hills and indulge in its flavors.

Take a regional train from Florence to La Spezia and enjoy the eighth day at leisure. Enjoy a guided hike from Monterosso to Corniglia, experiencing the stunning coastal Blue Trail on day nine.

Day ten is for leisure, exploring and relaxing.

Travel to Venice by train on day eleven and experience a private walking tour of the city. Take advantage of day twelve, and spend it at leisure in Venice. Enjoy day thirteen at leisure, bidding farewell to Italy.

Your final day concludes with a private transfer from your hotel to the airport for your departure flight. Read more.

Colosseum, Rome © Farbregas Hareluya/Shutterstock

Colosseum, Rome © Fabregas Hareluya/Shutterstock

Itinerary overview

Check this overview of the 14 days Italy itinerary.

Day 1

  • Arrival in Rome.
  • Overnight in Rome.

Day 2

  • Colosseum half-day tour.
  • Overnight in Rome.

Day 3

  • Traditional cooking class & market visit.
  • Overnight in Rome.

Day 4

  • Transfer to Florence.
  • Overnight in Florence.

Day 5

  • E-bike tour of Florence.
  • Overnight in Florence.

Day 6

  • Traditional Pizza & Gelato making.
  • Overnight in Florence.

Day 7

  • Chianti wines and olive oil tour.
  • Overnight in Florence.

Day 8

  • From Florence to Lerici - La Spezia region.
  • Overnight in Lerici.

Day 9

  • Sentiero Azzurro hiking tour.
  • Overnight in Lerici.

Day 10

  • Day at leisure at Lerici.
  • Overnight in Lerici.

Day 11

  • Train to Venice.
  • Overnight in Venice.

Day 12

  • Venice walking tour and gondola ride.
  • Overnight in Venice.

Day 13

  • Day at leisure.
  • Overnight in Venice.

Day 14

  • Transfer to the airport.

Feeling curious? Take a step forward and book this trip now.

Uffizi art gallery in Florence, Tuscany, Italy

Uffizi art gallery in Florence, Tuscany, Italy

Itinerary #3: highlights of Italy - Rome, Amalfi Coast, Cinque Terre and more

This 2 week Italy itinerary is nothing short of highlights: spend the first few nights in the capital city of Rome before moving down south to Naples. From here, you will discover the Amalfi Coast before heading to Florence.

On the first day, you will be collected at the airport and transferred to your hotel. Explore the Colosseum and Forum Romanum in a small group tour on the second day.

On the third day, you will discover the Vatican on a half-day tour. Travel to Naples by train and experience the birthplace of Pizza on day four.

On day five you will join a local guide to explore the heart of Naples. Visit Pompeii and Mount Vesuvius on day six.

A journey along the picturesque Amalfi Coast awaits you on day seven. Board a high-speed train to Florence on the eighth day. On day nine embark on a guided tour of Florence.

Travel to La Spezia, and enjoy your tenth day in leisure time. On day eleven, you will join a full-day tour of Cinque Terre with a private guide and a Cinque Terre card.

Days twelve and thirteen a dedicated to Milan. Take a train to Milan and spend the day at leisure. Then explore Milan on a group tour.

Depart from Milan on the last day of your Italian trip with a private transfer to the airport or train station, bidding farewell to Italy. Read more.

Positano, italy. Amalfi Coast © iacomino FRiMAGES/Shutterstock

Positano, Italy. Amalfi Coast © iacomino FRiMAGES/Shutterstock

Itinerary overview

Check this overview of the 14 days Italy itinerary.

Day 1

  • Arrival in Rome.
  • Overnight in Rome.

Day 2

  • Colosseum half-day tour.
  • Overnight in Rome.

Day 3

  • Vatican half-day tour.
  • Overnight in Venice.

Day 4

  • Transfer to Naples.
  • Overnight in Naples.

Day 5

  • Pompeii & Vesuvius with wine tasting or pizza lunch.
  • Overnight in Florence.

Day 6

  • Sorrento, Positano & Amalfi day trip.
  • Overnight in Naples.

Day 7

  • Transfer to Florence.
  • Overnight in Florence.

Day 8

  • Transfer to La Spezia.
  • Overnight in Lerici.

Day 9

  • Day at leisure at Cinque Terre.
  • Overnight in Lerici.

Day 10

  • Exploring Cinque Terre and around.
  • Overnight in Lerici.

Day 11

  • Transfer to Milan.
  • Overnight in Milan.

Day 12

  • Free day in Milan.
  • Overnight in Milan.

Day 13

  • Best of Milan walking tour.
  • Overnight in Milan.

Day 14

  • Transfer to the airport in Milan.

Looking for an unforgettable experience? Don't waste time, book this trip now.

Urbino-italy-shutterstock_1090044326

Urbino, Italy @ Shutterstock

Itinerary #4: Italy uncovered

Skip the tourist trail and dive into Italy’s hidden gems with this 14-day itinerary.

Start in Bologna—two days of pasta perfection, medieval streets, and views from the Asinelli Tower. Then, head to Ferrara for Renaissance charm, cycling boulevards, and the grand Este Castle.

Next, spend two days in Ravenna, where 5th-century mosaics light up ancient churches. Dante’s tomb is here too, tucked away in a quiet corner. From there, make your way to Urbino. This hilltop town is a Renaissance masterpiece; explore the Palazzo Ducale, then sip wine with locals in sun-drenched piazzas.

For a change of scenery, travel south to Matera and spend two nights in a cave hotel in the Sassi district. By night, the ancient stone buildings glow in a way you’ll never forget. Then it’s off to Lecce in the “Florence of the South” for baroque architecture and a pasticciotto—a local custard-filled pastry.

Wrap up with two days in Sardinia. Fly to Olbia and skip the crowded beaches for hidden gems like Cala Luna on the eastern coast. Turquoise waters and rugged cliffs make the perfect end to your Italian adventure.

Pack light and bring an appetite—Italy’s best-kept secrets await.

ravenna-italy-shutterstock_586065530

Ravenna, Italy @ Shutterstock

Itinerary overview

Check this overview of the 14 days Italy itinerary.

Days 1-2

  • Arrival in Bologna.
  • Wander Bologna’s medieval streets, sample tagliatelle al ragù, and climb the Asinelli Tower for city views.
  • Overnight in Bologna.

Days 3-4

  • Transfer to Ferrara.
  • Cycle through Ferrara’s Renaissance boulevards, visit Este Castle, and explore the atmospheric Jewish ghetto.
  • Overnight in Ferrara

Days 5-6

  • Transfer to Ravenna.
  • Marvel at Ravenna’s 5th-century mosaics, visit Dante’s tomb, and discover ancient churches with vibrant interiors.
  • Overnight in Ravenna.

Days 7-8

  • Transfer to Urbino.
  • Explore Urbino’s Palazzo Ducale, admire Renaissance art, and relax in piazzas buzzing with students and locals.
  • Overnight in Urbino.

Days 9-10

  • Transfer to Matera.
  • Stay in a cave hotel in Matera’s Sassi district, wander ancient stone pathways, and see the city glow at night.
  • Overnight in Matera

Days 11-12

  • Transfer to Lecce.
  • Discover Lecce’s baroque architecture, wander hidden courtyards, and indulge in a custard-filled pasticciotto.
  • Overnight in Lecce.

Days 13-14

  • Transfer to Sardinia (Eastern Coast).
  • Fly to Olbia, relax on secluded beaches like Cala Luna, and enjoy the dramatic cliffside scenery.
  • Overnight in Olbia.
cefalu-sicily-shutterstock_261581888

Cefalu, Sicily @ Shutterstock

Itinerary #5: Italian beach escape: Sun, sand and secret shores

Ditch the crowded tourist beaches and discover Italy’s sun-soaked coastlines with this two-week itinerary.

Start your journey on the Amalfi Coast, but skip Positano. Instead, spend two days in Cetara, a sleepy fishing village known for anchovies and lemon groves. Stroll pebble beaches, sample fresh seafood, and catch sunset from the quiet, cliffside town. 

Next, head south to Maratea for two days of rugged coastlines and hidden coves. Hike to the Cristo Redentore statue for panoramic views, then cool off with a swim at Spiaggia Nera, a beach with unusual dark sand and clear blue waters.

From there, cross over to Calabria and settle into Tropea. Spend two days lounging on white-sand beaches below dramatic cliffs, explore the historic town center, and don’t miss the local red onion gelato (trust us, it’s a thing).

Then, hop on a ferry to Sicily and make your way to Cefalù. Over the next two days, bask on sandy beaches with crystal-clear waters, climb La Rocca for views of the coastline, and indulge in Sicilian street food.

Travel east to Syracuse, where you’ll spend two days exploring rocky beaches and swimming in natural pools at the Plemmirio Marine Reserve. Wander the ancient streets of Ortigia, and dine on fresh seafood by the sea.

Finally, wrap up your beach escape with four days in Sardinia. Fly into Cagliari and head south to the secluded beaches of Costa Rei and Chia. Hike along coastal trails, snorkel in turquoise waters, and soak up the wild beauty of Sardinia’s southern coast.

Pack your swimsuit and sunscreen—Italy’s most stunning shorelines are waiting.

Tropea-italy-shutterstock_148491239

Tropea, Italy @ Shutterstock

Itinerary overview

Check this overview of the 14 days Italy itinerary.

Days 1-2

  • Arrive in Naples, then take a bus or drive down the Amalfi Coast to Cetara.
  • Wander this quiet fishing village, relax on the pebble beaches, and enjoy fresh seafood with local limoncello. Catch sunset from the cliffside views.
  • Overnight in Cetara.

Days 3-4

  • Drive south along the coast to Maratea.
  • Hike to the Cristo Redentore statue for panoramic views, then cool off with a swim at Spiaggia Nera, the “black sand” beach. Relax in hidden coves or explore the charming medieval town center.
  • Overnight in Maratea

Days 5-6

  • Drive or take a train south to Tropea.
  • Relax on Tropea’s stunning white-sand beaches beneath dramatic cliffs, wander the historic town center, and try the famous red onion gelato.
  • Overnight in Tropea.

Days 7-8

  • Take a ferry from Villa San Giovanni to Messina, then drive to Cefalù.
  • Bask on Cefalù’s sandy beaches, climb La Rocca for views of the coast, and enjoy Sicilian street food in this lively coastal town.
  • Overnight in Cefalù.

Days 9-10

  • Drive along Sicily’s northern coast to Syracuse.
  • Explore the rocky beaches and natural pools of the Plemmirio Marine Reserve, wander the ancient streets of Ortigia, and dine on fresh seafood by the sea.
  • Overnight on Ortigia Island.

Days 11-14

  • Fly from Catania to Cagliari, then drive to Costa Rei.
  • Spend four days exploring Sardinia’s secluded beaches along Costa Rei and Chia. Hike along coastal trails, snorkel in turquoise waters, and soak up the wild beauty of Sardinia’s southern coast.
  • Overnight in Costa Rei (days 11–12) and Chia (days 13–14).
Maratea-Basilicata-best-beaches-in-Italy

Maratea, Basilicata, Italy

You might also want to browse our customizable Italy itineraries or talk to our local Italy experts.

Want to explore Europe even more? We have prepared the most convenient European itineraries for you to explore the continent.

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updated 05.11.2024

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