Italy in 3 weeks – amazing 21 days itinerary including Sicily

Italy - tour - 3 weeks

Top things to do and see in Italy in 3 weeks. Italy Must See: Rome, Venice, Florence, Cinque Terre and Amalfi coast and off the beaten path destinations

A 3 weeks Italian itinerary will give you the possibility to visit most Italian must sees at a relaxed pace, with some spare time to also discover “off the beaten path” treasures. 3 full weeks in Italy will also give you enough flexibility to spend more time in the places you like the most.

As the one and two weeks Italy itineraries, also this one is based on my personal experience, on the hypothesis you are purchasing and “open jaws” ticket (meaning: landing and departing in two different airports),  to save valuable time . Transfers are by train / public transportation as far as possible.

So get a good guide book and invent your own holiday!


Destination 1:  Venice – (2-3 days), Ferry Boat in Venice + a lot of walking (and maybe a romantic gondola ride ). Of course Rialto, San Marco and Palazzo dei Dogi, but also fancy Museums like Punta della Dogana . If you are travelling with kids, have  a look at a child oriented itinerary. On the third day visit Murano, Burano and Torcello (1 day, by ferry).

Venice main highlights, and especially San Marco church, suffer from very long queues. To skip the line and to know more about its masterpieces, a guided tour could be a clever option. Click here for a good San Marco guided tour.

Gondola con Amorino

Where to stay in Venice:

  • The Foscari Palace: enjoy a room on the Canal Grande, just in front of Rialto market
  • The Hotel Pausania: a charming hotel in the off the beaten path Dorsoduro Neighborhood.

Want more choice? Click here to find the best places to stay in Venice


Destination 2: Venice >> Milan (stop over in Padova/Vicenza/Verona, if you have enough time). Sleep in Milan or, if you arrive in Milan by lunch time, go directly to Bellagio (here is how to get there). If you spend the night in Milan, have  a fancy Aperitivo (Milanese buffet happy hour).

Click here to find the best places to stay in Milan

N'ombra de vin
Wine and local delicacies at charming N’Ombra de Vin, in via San Marco, Brera district

Destination 3: Milan >>Bellagio, train + boat (2-3 hours), visit Bellagio and a couple of the famous villas on the west branch of Como Lake (1 day)

Want more choice? Click here to find the best places to stay in Bellagio


Destination 4: Bellagio >> Milan >> ” Cinque Terre”. From Milan you have many direct  trains (2,5 hours). It’s worth spending 1-2 days at Cinque Terre, but should also visit Portofino and San Fruttuoso.  Sestri Levante, right in the middle, could be a good base, otherwise head to Monterosso, your hub for the Cinque Terre. Don’t use a car, parking is a nightmare. (2-3 days).

Click here to find the best places to stay in Monterosso


Monterosso beach

Destination 5: Cinque Terre – Florence (with a stop over in Pisa / Lucca) – just transfer and light sight seeing. It take a little less than 3 hours to go by train from Sestri to Florence, via Pisa. Lucca is half an hour from Pisa by train (1 day). If you decide to visit also Lucca, you could consider spending the night in one of the two towns (I personally prefer Lucca).

Destination 6: Florence (1-2 days), depending if you are keen on museums or not. Uffizi, Michelangelo’s David (in Galleria dell’Accademia, the one in front of Palazzo Vecchio is a copy) , Palazzo Vecchio, Santa Croce, San Miniato, piazzale Michelangiolo, Via Tornabuoni, Palazzo Pitti, Boboli, Fiesole (20-30’ out of town). Have a look here for a one day walking itinerary.  Just click here in case you prefer a guided tour, or to skip the line in the main museums.

Where to stay in Florence:

The Grand Hotel Cavour: lots of atmosphere and history for this fascinating hotel located between Santa Maria del Fiore and Palazzo Vecchio. The roof bar will seduce you with its fantastic views over the Santa Maria del Fiore cathedral.

Want more choice? Click here to find the best places to stay in Florence


Destination 7: Tuscany country side >>> Rome. Chianti, Monteriggioni, Siena, Montalcino, Val d’Orcia, Pienza, Montepulciano >>> Rome. (1-2 days, even more if you like the countryside and the good food).

This itinerary assumes you rent a car, by far my suggested option. In case you didn’t feel comfortable driving on Tuscany country roads, then you can use Florence as a hub and join Tuscany country side guided tours. Here are my recommended ones.

Where to stay in Tuscany: Monteriggioni (Siena)

  • The Hotel Monteriggioni: a charming and romantic hotel, located in a fortified medieval village
  • The Castel Pietraio, a true medieval castle, now four star hotel, to treat yourself like a king
delightfullyitaly_italyintwoweeks_castel pietraio
Castel Pietraio castle is now a delightful boutique hotel

Destination 8: Rome (3-4 days or more). You don’t want to have a car in Rome; walk + hop on – hop off buses (follow this link to reserve on line, no need to print the receipt). Bicycles or scooters, if you dare, are fantastic solutions!

Discover the Spanish steps, Piazza Navona, Panteon, Fontana di Trevi, Campo dei Fiori, Old Ghetto, Trastevere. St Peter (consider climbing on the Cupola) + Vatican Museum (RESERVE! queues are terrible – click here if you wish to reserve your visit with Ticketbar).

Mercati di Traiano, Fori Imperiali (including Orti Farnesiani), Colosseum, Palatino are unmissable destinations, and for this reason may be crowded. Purchasing the ticket in advance is a clever way to skip the line and to save time .

Don’t miss Trastevere + Isola Tiberina (very lively area in summer time, funny & crowded). Appia antica + Catacombs (best by bike, you can rent one in via Appia), medieval Rome and its underground treasures.  If you are a running fanatic, don’t miss Villa Borghese and the awesome Borghese Gallery.  

Villa Adriana and Villa D’Este, both in Tivoli (30 km from Rome) make a pleasant day trip out of town .

Since you have several nights, you may consider awesome activities such as night visit to the Colosseum or a romantic dinner cruise. Follow this link for more suggestions.

Rome_Spanish steps

Where to stay in Rome:

The Hotel la Lumiere, a delightful hotel hidden a few blocks away from the Spanish steps, in posh via Condotti. Great roof top, have your breakfast while admiring Rome century old roofs!

Want more choice? Click here to find the best places to stay in Rome

Visit Rome_night_Castel Sant'Angelo from ponte Sant'Angelo_01


Destination 9: Rome >>Naples/Sorrento (2/3 days) Train. You can sleep in Naples or, better, in Sorrento. Visit Pompei, Sorrento, Positano, Ravello, Capri. Naples is also worth a visit. You can use public transports: boat service between Sorrento and Positano is very convenient, while buses, especially to Ravello, could be extremely crowded (consider sharing a taxi with fellow travelers). Renting a car could be an option in high season, but car parks are very expensive (and driving on the costiera is an experience on its own!).

Looking for a hotel? Click here to find the best places to stay in Sorrento

For more info about Amalfi coast visit my posts: Capri: breathtaking Faraglioni and Natural Arch walking tour and Best of Amalfi coast.


Alternative itinerary (especially in wintertime): get a low cost flight in Rome or Milan, and visit Sicily. Palermo, San Vito lo Capo, Segesta, Agrigento and the Temples Valley, Siracusa, Catania, Taormina.


In love with Italy but short on time? Learn more about rush one week itinerary and two weeks itinerary!

Would you like an independent advice on your next trip to Italy? Visit my Italy Travel consultant page.

Enjoy your Italy in 3 weeks itinerary and share any comment, picture or suggestion!

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2 Replies to “Italy in 3 weeks – amazing 21 days itinerary including Sicily”

  1. i’ve read a ton of these itinerary suggestions & i just had to take the time to say that this has been the most spot on one i’ve read so far. i copied down every single bit! thank you!

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