3 Week Italy Itinerary: Options & Planning Tips

If taking a two-week trip to Italy is great, then spending three weeks in Italy is better.

Most of the time you’ll see Italy itineraries in one-week or two-week increments, with the suggestion that for a three-week Italy trip you just put those two itineraries together. Personally, I don’t think that’s particularly helpful – and it can make planning a three-week trip a bit discombobulated. So here are my suggestions for a three-week Italy itinerary.

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Itinerary Assumptions

Here are some things I’ve assumed with these itineraries to make them work. You may need to alter them if your situation doesn’t fit my assumptions, but at least you’ve got something to start with.

  1. You won’t be able to cover as much ground if you fly in and out of one city, so these itineraries assume you’re flying on what’s called an “open-jaw” ticket – flying into one city and out of another. This is especially critical for a short trip, but since this is a three-week trip you may have enough flexibility to make your way back to your arrival city in order to buy a simple round-trip ticket. Just note that you’ll need to cut a day or two off one of the locations in the itinerary in order to get back to the arrival/departure city to fly home again.
  2. Not every itinerary listed below includes the “holy trinity” of Venice, Florence, and Rome, so if this is your first time visiting Italy and you don’t want to miss the major sights be sure you’re looking at the “greatest hits” itinerary.
  3. These itineraries are ready and waiting to be tailored to your individual travel style and needs – these are merely suggestions to get you started, and see how I go about planning itineraries for myself (let alone anyone else).

Italy in Three Weeks: Some Itinerary Options

Here’s an abbreviated version of each of the itineraries in this category – for more details on each one, click on the link under each heading. There, you’ll find thoughts about what kinds of travelers might like each itinerary, tips on what to do during each day, information on how to get from place to place, and more resources to help you plan your trip.

3 Weeks in Italy: Italy’s Greatest Hits Itinerary

  • 2 days Venice
  • 2 days Ligurian Coast (Cinque Terre or Portofino)
  • 4 days Florence (with stop in Pisa)
  • 2 days Siena
  • 4 days Rome
  • 4 days Amalfi Coast
  • 3 days Naples (with day trip to Pompeii)

>> Read all the details of this 3-week Italy itinerary of Italy’s “greatest hits”


3 Weeks in Italy: A Foodie Itinerary

  • 2 days Milan or Turin
  • 2 days Alba
  • 2 days Genoa
  • 4 days Bologna (with day trips to Parma & Modena)
  • 5 days agriturismo/cooking school
  • 3 days Rome
  • 3 days Naples (with a day trip to Pompeii)

>> Read all the details of this 3-week Italy foodie tour itinerary

photo by teldridge+keldridge

5 thoughts on “3 Week Italy Itinerary: Options & Planning Tips

  • Jairam

    My wife and I are planning a 3 week trip to Italy in Nov-Dec of 2011 (Nov 20th to Dec 11th). This is the first time that we will be visiting Italy. Our plan is to fly into Milan and fly out of Rome.

    We definitely want to see Venice, Florence, Rome and a few smaller towns. Could you recommend a good 3 week itinerary given the weather conditions in Italy? I believe that the Cinque terra region had recent floods and hence may not be suitable for a trip. Please advice!

    Both of us are interested in Museums (more history than art) and love walking tours. We also want to indulge in food and wine :-)!


    • Jessica Post author

      You’re right, visiting the coast in Liguria or Tuscany right now would not be smart – or safe. And I’m told Naples is even experiencing some flooding, too. You may not see Italy during its best, weather wise, given the rain that’s going on there right now – I hope it’s abated somewhat by the time you arrive.

      I’m not a travel consultant, so I don’t prepare individual itineraries for people, but the tips in this article are the exact same ones I use to plan my own trips – to Italy or anywhere else:

      You can get an idea of what each region has to offer by perusing the overviews here:

      And, given the weather, you might want to steer clear of the western coast. After seeing the cities you have on your wish list, you might even check the weather in the south – Calabria, Puglia, Sicily – to see if they’re any warmer. Note that you’ll need to rent a car in these areas, as getting around by train & bus isn’t as easy.

  • Angeline

    Hi Jessica,

    I am so glad I stumbled onto your website. You have lots info and I had looked at your 2 weeks and 3 weeks articles.

    We are planning our honeymoon to Italy; also our first trip to Italy and need advice on whether to visit:

    – North of Italy* or South of Italy (including Amalfi Coast, Capri, Sorrento, Sicily and open to other suggestions).

    *We want to visit Cinque Terre but not sure how we can get there. I am aware we can take the train city to city once we are there.

    Fly in to Rome
    Train from Rome to Florence
    Car rental for the rest of Tuscany (Siena, Cinque Terre etc.)
    Train from Tuscany to Venice
    Not sure what’s the best way to get to Lake Como, train or car from Venice?
    Not sure what’s the best way to get to Milan, train or car?
    Train from Milan to Barcelona, Spain
    Fly home from Barcelona, Spain

    We have about 20 days for travel and if possible would like to see both north and south of Italy together with Barcelona.

    Please advise best itinerary for the time we have and also advise best transportation mode from place to place if possible.

    Thank you in advance for your help and advice!


    • Jessica Post author

      Hi, Angeline:

      I don’t do trip consulting, so I’m unable to help much with individual itineraries, but in general I’d suggest you take a look at my tips for planning the perfect Italy itinerary:


      It’s the same tips/steps I use when planning my own trips, in Italy or otherwise. The biggest thing to figure out is transportation time. You can’t look at what seems to be a short distance on a map & think it’ll be a short trip – in Italy, it’s often much longer between A & B. So to get an idea of how much time you’ll have to actually explore/enjoy each place, you need to look up transportation times. That’s critical.

      If you’re planning 20 days & want to visit Italy & Barcelona, you need to determine how many days you want to spend in Barcelona & then work with what you have left in Italy – which, if it were my trip, would mean focusing on either north or south (not both). It’s a tough choice, I know, but if you rush around the whole time you won’t necessarily enjoy/savor everything you see & do.

      Also, generally, unless you’re heading into the boondocks where there’s no public transit, I’d recommend avoiding driving. Stick to trains & buses. It’s less stressful for first-time visitors who don’t speak the language.

  • Marco

    We are planning a trip to Italy next year the last week of August 2013 for 3 weeks. We would be leaving Namibia or South Africa planning to land in Milano. From there go to Venice for a day or two then leave for Tuscany & Florence from the to Genova, Imperia for a day and then to Rome for a day or two and from there to Civitavecchia take the ferry boat to Sardinia, Olbia and from there by road to Alghero. We would be 4 two couples.

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