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.

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.
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.
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