From the dramatic Alpine cliffs and fashionable streets of Northern Italy to the ancient ruins of Rome to the sun-soaked Sicilian beaches, Italy is a place of staggering contrasts and beauty.

It’s one of those places that I find myself returning to time and time again. Each adventure is different and leaves me even more in love with this Mediterranean gem.

While you could easily spend two weeks in one place, savoring the city and living like a local, you can also cover a lot of ground within this time.

Tip: If this is your first Italian sojourn, check out my Top 10 Tips for Your First Trip to Italy as well as my essential money-saving travel hacks for Italy.

To help you make the most of every moment, I’ve broken it down so you have time in each place to rest, relax, and see the best of the best (without feeling like you need a vacation after your vacation).

Pack your appetite and walking shoes! Here’s my two-week Italy itinerary.

As a Note

You can easily mix and match parts of this itinerary. Train travel is easy and relatively affordable in Italy so you don’t need to follow one specific route.

Choose which city makes the most sense for you then try to travel in a straight line or clockwise to minimize the amount of travel between each destination.

You could fly into Florence, Venice, or Rome then go from there. 

While I highly recommend train travel, be mindful that strikes occasionally do happen. This can turn a three-hour trip into a five-hour adventure so budget time for any hiccups along the way.

Venice + Treviso (3 Days)

If you’re dreaming of exploring Italy, you probably have dreamy images of Venice floating through your mind. Exploring Venice is a must, but I’d encourage you to venture into the wider area.

The “other Venice’ is a little city called Treviso.

Maybe I am biased because my husband, Meyer, spent years living there…but I adore this charming town! It has all of the beauty of Venice yet, being off the tourist path, it has a thriving local culture.

Plan at least an afternoon here and check out my travel tips for Treviso.

Of course, when you are in Italy, eating and drinking is an event in and of itself. Even merely grabbing a drink from a vending machine is on another level.

For the ultimate fun foodie delight, it’s well worth making a detour to check out the prosecco vending machine. In the heart of the Prosecco region, you can sample local wines and have the ultimate picnic in this picture-perfect setting.

Before you leave the area, grab your camera and set off for the vibrant town of Burano. This oh-so-Instagrammable town is at the top of my 10 Places to Visit in Italy (That Aren’t Rome).


  • The colorful city of Burano
  • The Prosecco Vending Machine
  • All of Venice’s nooks and crannies

Florence (3 Days)

Famous for its Renaissance art and architecture, Florence is the gateway to the romantic region of Tuscany. Browse my complete guide to Florence and the surrounding area so you’re ready to hit the ground running.

Dig into the rich culture of the city while you explore the museums and galleries then mingle with the locals in the hangout spots along the Arno River.

Once you’ve worked up an appetite, join a food tour. This region has some of the best food in the country (which is saying a lot!).

Whether you go for an urban food tour in Florence or one that will take you into the countryside, it’s a must.

Tuscany is widely known for its incredible truffle hunting. Have a four-legged truffle hunter guide you through the forests of the countryside for an unforgettable experience.


  • Don’t miss out on a Florentine food tour
  • See the statue of David Accademia Gallery
  • Walk through the gorgeous Boboli Gardens
  • Go truffle hunting with dogs just outside of the city
  • Piazzale Michelangelo offers incredible views of the city
  • Wander Mercato Centrale, Florence’s famous food market

Amalfi Coast (3 Days) 

Easily one of the most picturesque destinations in the world, the Amalfi Coast is another epic experience. Hiking along the dramatic cliffs and exploring the pastel fishing villages that dot the coastline.

Plan at least one day just soaking in the sun at the beach in the hopping beach town of Positano then take a day trip to Capri.

Planning Tip: Getting around the Amalfi Coast requires planning. You will want to start in Naples then hop onto the Circumvesuviana, the regional train. Check out my Amalfi Coast guide for the full details.


  • Plan a day trip to Capri
  • Make your way down Positano’s steep inclines
  • Admire the city built into the cliffs
  • Hike Sentiero degli Dei, otherwise known as “Path of the Gods”

Rome (3 Days)

Whether you are a history buff, foodie, or culture vulture, you could barely crack the surface of Rome in a year, say nothing of a few days.

Once the center of the Western World, this dynamic city is truly one of the most fascinating cities in the world. So, if you only have three days, you’re going to have to make some tough choices!

In What to Do in Rome in Three Days, I’ve put together my Roman bucket list. Of course, history and food are at the heart of it all here.

My favorite souvenir from the trip was an authentic pizza recipe that I got during my food tour and pizza-making class.

Full of carbs and ready to explore, I then booked a Vespa tour. Riding around town with a local, I saw another side of the city.


  • Sample cup after cup of gelato
  • Do a pasta or pizza-making class
  • Live out your Lizzie McGuire dreams and book a Vespa tour
  • See so many famous Roman ruins like the Colosseum and the Pantheon

Cinque Terre (2 Days) 

Another stunning coastal region, the five villages are dotting the Mediterranean Sea coast that are well worth a detour.

Visiting Cinque Terre, as the colorful corner of northwestern Italy is called, is a prime destination for a taste of la dolce vita. Hike amongst the ancient vineyards of Cinque Terre or just lounge in the sun.

If you’re feeling inspired, The Leaning Tower of Pisa is an easy day trip (though I’d say the true gems are all within Cinque Terre so don’t push yourself unless you want to).


  • Tower of Pisa isn’t too far from here
  • Each seaside town is incredibly picturesque
  • Disney’s “Luca” is inspired by Cinque Terre
  • Hike between each coastal town or take a short train ride

Feeling inspired? Keep on planning that dream escape with my Ultimate Italy Travel Guide.

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