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Italy is my absolute favorite country to keep going back to. There is so much to see and explore it feels like visiting several different countries every time I go back. Each region of Italy is so unique in terms of landscape, cuisine, language & each is more beautiful than the last. 14 days gives you a good amount of time to explore several different cities.
It can be hard to narrow down which part of Italy to visit, even with 2 weeks. I’ve put together 3 unique 14 day itineraries below based on what you’re looking for. You can also build your own custom 14 day itinerary (or any number of days) using the trip planner at the bottom of this article! Just enter a prompt of which places you’re trying to see and how many days you have and it will use all my tried & tested recommendations to write your perfect custom itinerary!
Disclaimer: This article contains some links where I earn commission through booking. There is no extra cost to you, and I only recommend things I’ve used and love or places I’ve stayed and enjoyed!
Italy 14 Day Itinerary Options:
🍝Classic Italy: History, Art, Wine, Culture + Sun & Sea
Rome, Florence, Venice, Tuscany & the Amalfi Coast
This classic itinerary is best for first timers who want to see the classics of Italy. This allows you to hit the 3 most popular cities in Italy, but also spend a few dreamy days in the rolling hills of Tuscany and wrap your trip up oceanside on the infamous Amalfi Coast.
Click here for more details on this itinerary!
🌄Northern Italy: Mountains, Canals & Lavish Lake & Seaside Towns
Venice, Milan, Lake Como, the Dolomites & the Italian Riviera
This Northern Italy itinerary has a bit of everything! If you love luxury, being near the water and the outdoors this is for you! You’ll hit the major Northern cities like Venice & Milan, you’ll spend a few days exploring the Dolomites, head to Lake Como for lavish villas and lakeside dinners, and round out your trip exploring the Italian Riviera; from upscale, celebrity hotspot, Portofino, to the post-card like towns of Cinque Terre!
Click here for more details on this itinerary!
🌊Major Cities + Puglia: Classic History & Highlights + Hidden Gem Puglia Towns
Venice, Florence, Rome & Pugia highlights – Bari, Polignano a Mare, Alberobello + Matera
To get a mix of the touristy Italy classics and to explore a lesser-known region that’s beginning to gain popularity before it’s totally overrun with tourists this is the itinerary for you. Kick off your trip exploring the three major cities of Venice, Florence & Rome. After some jam-packed days of hitting as many highlights as possible enjoy a slower pace heading East to Puglia. Discover charming Bari, a foodie’s paradise, and picturesque Polignano a Mare for a relaxing day by the sea. End your trip visiting 2 of the most unique places in Italy – Alberobello and it’s unique cone-shaped Trulli houses & epic Matera, the oldest city in Italy filled with sassi (houses built into the caves!)
Click here for more details on this itinerary!
🍝Classic Italy: History, Art, Wine, Culture + Sun & Sea
Itinerary Overview:
- Day 1: Venice
- Day 2: Venice (day trip to Burano)
- Day 3: Venice –> Florence (train)
- Day 4: Florence
- Day 5: Tuscany – San Gimignano & Siena (either as a day trip from Florence, or stay overnight in San Gimignano- rent a car for the latter)
- Day 6: Tuscany – Montepulciano or Saturnia (rent a car)
- Day 7: Tuscany – Montepulciano or Saturnia (rent a car)
- Day 8: Tuscany –> Rome (return car)
- Day 9: Rome
- Day 10: Rome
- Day 11: Rome –> Amalfi Coast (optional stop in Pompeii)
- Day 12: Amalfi Coast
- Day 13: Amalfi Coast
- Day 14: Amalfi Coast
Choose prompt 1 here for a detailed itinerary with where to stay, what to do and getting around. If you need to modify the itinerary at all or have more questions feel free, the bot will only recommend my suggestions from this blog!
🌄Northern Italy: Mountains, Canals & Lavish Lake & Seaside Towns
Itinerary Overview:
- Day 1: Venice
- Day 2: Venice –> Verona (train)
- Day 3: Verona –> Bolzano (Dolomites) by train – rent a car in Bolzano to explore the Dolomites
- Day 4: Explore the Dolomites (stay in Bolzano)
- Day 5: Explore the Dolomites
- Day 6: Bolzano –> Milan (train)
- Day 7: Milan –> Lake Como (train)
- Day 8: Lake Como
- Day 9: Lake Como
- Day 10: Como –> Genova (train)
- Day 11: Genova –> Santa Margherita Ligure (train)
- Day 12: Day Trip to Portofino
- Day 13: Santa Margherita Ligure –> Cinque Terre (train)
- Day 14: Cinque Terre
Choose prompt 2 here for a detailed itinerary with where to stay, what to do and getting around. If you need to modify the itinerary at all or have more questions feel free, the bot will only recommend my suggestions from this blog!
🌊Major Cities + Puglia: Classic History & Highlights + Hidden Gem Puglia Towns
Itinerary Overview:
- Day 1: Venice
- Day 2: Venice (day trip to Burano)
- Day 3: Venice –> Florence (train)
- Day 4: Florence
- Day 5: Florence (Tuscany day trip)
- Day 6: Florence –> Rome (train)
- Day 7: Rome
- Day 8: Rome
- Day 9: Rome –> Bari (train or fly)
- Day 10: Bari
- Day 11: Polignano a Mare (drive)
- Day 12: Alberobello (drive)
- Day 13: Matera (drive)
- Day 14: Matera
Choose prompt 3 here for a detailed itinerary with where to stay, what to do and getting around. If you need to modify the itinerary at all or have more questions feel free, the bot will only recommend my suggestions from this blog!
Detailed Italy Travel Guides
Still like reading vs AI travel planners? I got you covered (and I feel you) I have a travel guide for each of these locations to help you plan your dream Italy trip!
Itinerary 1
- Venice Travel Guide
- Florence Travel Guide
- Tuscany Travel Guide
- Rome Travel Guide
- Amalfi Coast Travel Guide
Itinerary 2
- Venice Travel Guide (see above)
- Verona Travel Guide
- Dolomites Travel Guide
- Milan Travel Guide
- Lake Como Travel Guide
- Genova Travel Guide
- Italian Riviera Travel Guide
- Cinque Terre Travel Guide
Itinerary 3
- Venice Travel Guide (see above)
- Florence Travel Guide (see above)
- Rome Travel Guide (see above)
- Bari Travel Guide
- Polignano a Mare Travel Guide
- Alberobello Travel Guide
- Matera Travel Guide
