Two weeks in Italy itinerary ideas: how to plan your time for the best possible experience

Two weeks in Italy itinerary ideas to make the most of your trip and enjoy the best of Italy no matter your travel style and season of travel.

Two weeks are a fantastic length of time to discover Italy and leave you with many options to craft your vacation just as you like it.

Depending on your taste and interests, you can spend two weeks on the move, seeing all the classic sites (and more!), you can stay put in one or two destinations and truly experience the Italian way, or you can do something in between.

Choosing a few destinations and stay a few days in each, so you can explore and have variety, yet still enjoy down, relaxing time.

Today, I share my best and most successful itinerary ideas for two weeks in Italy so you can see how many wonderful ways there are to explore my beautiful country (I am from Rome and I love to travel around Italy so this is all based on my very own, very real experience)!

On this page, you find all my best two weeks in Italy itinerary ideas that cover more than one or two areas and therefore require a bit of planning.

If you prefer to stat put one week and move the rest of the time or divide your time between two areas only, I recommend you instead of look at my one week itinerary ideas and specific area guides, for more in depth, local tips.

All these trips are best taken during late spring and early autumn for crowds and temperature. In the heart of winter I recommend to instead mostly stick to cities while in summer, i recommend to choose a coastal destination or the mountains istead.

Good to know! All these itineraries are also doable with kids as each destination has activities they can enjoy. You can find family guides to all the areas mentioned by using the search option on this site or on the top menu Italy with kids!

Need to know! In this list there are many stunning areas missing. This is purely reflective of practical geographical considerations and the most common requests from first time visitors who want to visit several destinations and therefore need the sequence and selection of places to make sense on a set amount of time. You can find guides to many more destinations, including Sicily, Umbria, Piedmont and more from the ‘destination guides’ items on the website menu!

Classic Italy two week itinerary

This itinerary is ideal for visitors who want to see as man of Italy’s most famous sites in two weeks without having to rush to such an extent to compromise on the experience.

This itinerary foresees a good bit of moving around and it is best done, at least partially, by train: therefore, I recommend it for travelers who have a good amount of energy, can pack light and have no mobility issues.

Day 1 and 2: Venice – Venice top landmarks, gondola ride / rowing class on the canals, art, traditional crafts, food. Find here >> how to spend 2 days in Venice

Day 3 to 5: Tuscany – Rolling hills, historic towns, art. Depending on interest, you can focus on Florence, Siena and San Gimignano, Florence and Chianti, or you can explore a specific area such as Val d’Orcia (this is where the ‘classic’ cypress trees and rolling hills are)

Day 6 and 7: Cinque Terre (or Portofino area) – small towns, hiking trails, boat tours, sea views. You can read here >> how to spend 2 / 3 days in Cinque Terre.

Day 8 to 11: Rome – Rome highlights. In 4 or five days you can get a good overview of Rome, covering the city’s tops sites and a little more, without excessive rush. You can read here >>> how to spend four days in Rome

Day 12 to 15: Amalfi Area – small towns, views, boat trips, aperitivo. Depending on interest, you can spend these days lunging on scenic terraces, exploring Naples and Pompeii or a mix of both! You can find here >>> my recommended 3/ 4 day itinerary for the Amalfi Coast

You can find this full itinerary here

North / West Italy adventure – Milan, Como, Cinque Terre, Tuscany, Venice

Northern Italy is a lovely, varied part of the country with a mix of cities, lakes, beautiful coastlines and countryside landscapes.

This itinerary requires a good amount of moving around but offers a great opportunity to see several different sides to this beautiful and large area.

This itinerary is best done by train and car (car for the Tuscany portion) and outside of the winter months, since it is focuses on nature and the outdoors rather than cities.

Day 1 to 4: Lake Como – small towns, boat trips, aperitivo on the lake, visit villas and gardens. Depending on interest and schedule of flight, you can also visit Milan for a day, either on arrival of going in from Como area for a day trip.

Day 5 to 7: Cinque Terre (Ort Portofino area) – small towns, boat trips, pesto, swimming, hiking. You can read here >> how to spend 2 / 3 days in Cinque Terre

Day 8 to 11: Tuscany – rolling hills, small towns, vineyards, art. Option of a day trip into Florence. I recommend selecting a place in the Siena, Florence or Volterra area.

Day 12 to 14: Venice. Venice top landmarks, gondola ride / rowing class on the canals, art, traditional crafts, food. Venice top landmarks, gondola ride / rowing class on the canals, art, traditional crafts, food. Find here >> how to organize your days in Venice

Lake Como, Tuscany, Rome

Lake Como, Tuscany and Rome are at the places most people picture when thinking of classic Italian aesthetic and they can easily be visited in two weeks.

This itinerary is best enjoyed by train and car (for the Tuscany portion)

Day 5- 10: Tuscany (rolling hills, small towns, vineyards, art, option of a day trip into Florence from your Tuscany countryside base. I recommend selecting a place in the Siena, Florence or Volterra area.

Day 11 -14 – Rome. In 4 or five days you can get a good overview of Rome, covering the city’s tops sites and a little more, without excessive rush. You can read here >>> how to spend four days in Rome

Rome, Tuscany, Cinque Terre

This is one of my most favorite itineraries on this page, as it covers stunning destinations, makes a lot of geographical and cultural sense yet still offers great variety. You can start it from Rome, Milan or Pisa.

Day 1 to 5: Rome – a fabulous length of time to visit Rome, see its highlights but also savor its unique, open air museum atmosphere. Find here my recommended five days in Rome itinerary

Day 6 to 10: Tuscany (rolling hills, small towns, vineyards, art, option of a day trip into Florence from your Tuscany countryside base. You can find my recommended Tuscany itinerary over 5 days here.

Day 11 to 14: Cinque Terre area – small towns, boat trips, pesto, swimming, hiking. small towns, boat trips, pesto, swimming, hiking. You can read here >> how to spend your days in Cinque Terre

Rome, Venice, Dolomites

This is a fantastic Itinerary for the warmer months as it allows to see two stunning cities yet also outstanding nature.

The cities are hot in summer but the mountains are a delight so I recommend to plan this to see the mountains during the hottest days, for instance in June I’d start from the cities then move onto the mountains, in august I’d go to the cities as close to September as possible.

This itinerary is best done by train.

Days 1 to 5: a fabulous length of time to visit Rome, see its highlights but also savor its unique, open air museum atmosphere. Find here my recommended five days in Rome itinerary

Days 6 to 9: Venice. Venice top landmarks, gondola ride / rowing class on the canals, art, traditional crafts, food. Venice top landmarks, gondola ride / rowing class on the canals, art, traditional crafts, food. Venice top landmarks, gondola ride / rowing class on the canals, art, traditional crafts, food. Find here >> how to organize your days in Venice

Day 9 to 14: Dolomites. The Dolomites are all about hiking and immersing yourself in nature so you really do not need an itinerary for this stretch of your stay.

The best way to enjoy the area is by getting a home base and spontaneously enjoy your days with hikes, food and spa breaks! you can find here >>> my recommended places to visit on the Dolomites

Rome, Tuscany, Amalfi Coast

Rome Tuscany and Amalfi Coast are easy destinations to cover in two weeks.

However, for most international travelers, they require a bit of back and forth, as flights are not always easy to find in or out of Florence.

Even if you end up having to to go up and down via Rome, it will be worth it as two weeks leave enough time to rest in between!

Day 1 to 4 – Amalfi area – Small towns, views, boat trips. Depending on interest, you can spend these days lunging on scenic terraces, exploring Naples and Pompeii or a mix of both! You can find here >>> my recommeded 3/ 4 day itinerary for the Amalfi Coast

Day 6 – 10: Rome: Rome a fabulous length of time to visit Rome, see its highlights but also savor its unique, open air museum atmosphere. Find here my recommended five days in Rome itinerary

Day 11 – 15 Tuscany – Tuscany (rolling hills, small towns, vineyards, art, option of a day trip into Florence from your Tuscany countryside base. You can find my recommended Tuscany itinerary over 5 days here.

Rome, Amalfi Coast, Puglia

This itinerary is one I absolutely adore and I would myself follow over and over again. The itinerary offers a great mix of city experiences, small towns and natural beauty and comes into its own if you can get a car for the Puglia part of it.

Day 1 to 4: Rome In 4 or five days you can get a good overview of Rome, covering the city’s tops sites and a little more, without excessive rush. You can read here >>> how to spend four days in Rome

Day 5 to 7: Amalfi Coast Small towns, views, boat trips, aperitivo. Depending on interest, you can spend these days lunging on scenic terraces, exploring Naples and Pompeii or a mix of both! You can find here >>> my recommeded 3/ 4 day itinerary for the Amalfi Coast

Day 8 – 14 Puglia – small towns, incredible food, beautiful coastline and beaches. There are many ways yo go aout a week in Puglia, also depending on the season, you can find here my one week in Puglia itinerary