5 Incredible Italy Itineraries to Inspire Your Next Trip

If you are a busy professional like me, chances are you don’t have much time to plan out detailed itineraries. Lucky for you, I have done the groundwork on your behalf and in this roundup, I am sharing some of the best Italy itineraries. From a weekend in Trentino to 10 days traversing Sicily, these Italian itineraries should help inspire your next trip.

Why visit Italy?

Italy has so much to offer and is easy to get around (as long as you can tolerate the drivers!) It’s the perfect place for a city break, a beach holiday or a countryside road trip.

Enjoy incredible beaches with warm oceans, rolling hills, snowy mountains and beautiful lakes. Stuff yourself silly with pizza and pasta and wash it down with some tasty Italian wines or an Aperol Spritz. Admire the history and architecture in the bustling cities or escape the crowds on a Tuscan road trip or a sailing trip off the Amalfi Coast.

Visiting Italy is a no-brainer. The tough part will be choosing between these fantastic Italian itineraries…

What you can expect from this article…

  • 1 Incredible Italy Itineraries To Inspire Your Next Trip
    • 1.1 A 5 Day Tuscany Itinerary – Planning the perfect Tuscany Road Trip
    • 1.2 The Ultimate 10 day Sicily Itinerary
    • 1.3 A Perfect 3 Day Amalfi Coast Itinerary
    • 1.4 4 Days in Rome – A Perfect 4 Day Rome Itinerary
    • 1.5 Planning The Perfect Weekend In Trentino, North Italy’s Secret Gem

Incredible Italy Itineraries To Inspire Your Next Trip

Check out these 5 amazing Italian road trips to help you plan your next trip…


A 5 Day Tuscany Itinerary – Planning the perfect Tuscany Road Trip

Best for: wine lovers and photographers

Tuscany is the perfect place for a summer Italian road trip. With charming villages, rolling hills and an abundance of vineyards to explore, a trip to Tuscany will leave you feeling relaxed and rejuvenated.

This 5 day Tuscany itinerary starts in Florence and winds through the rolling hills of Tuscany visiting some of the most picturesque locations along the way. Don’t forget to bring your camera for this trip and remember to schedule at least one day without driving so you can make the most of the wineries!


  • Day 1 – Florence
  • Day 2 – Florence – San Gimignano
  • Day 3 – Monteriggioni and the Chianti region
  • Day 4 – Siena to Val D’Orcia
  • Day 5 – Val D’Orcia to either Rome or back to Florence.


  • Visit the Duomo in Florence
  • Climb the Palazzo Vecchio Tower
  • Go wine tasting in the Chianti region
  • Taste the worlds best ice cream in San Gimignano
  • Drive the Val D’Orcia
  • Visit the thermal springs of Bagno Vigroni
  • Visit charming Pienza


The Ultimate 10 day Sicily Itinerary

Best for: beach lovers and road trippers

Sicily is larger than you’d think so I would recommend spending at least 10 days in Sicily visiting the historic towns and beautiful beaches.

Expect gorgeous coves with azure water, cobblestone villages and towns with buzzing piazzas and grand churches.


  • Day 1-2 – Taormina
  • Day 3 – Mt Etna
  • Day 4 – Cefalu
  • Day 5 – Zingaro National Park
  • Day 6 – Favignana
  • Day 7 – The Valley of the Temples
  • Day 8, – Ragusa
  • Day 9 – Marzammemi & Noto
  • Day 10 – Syracuse


  • Visit the amphitheatre in Taormina overlooking Mt Etna
  • Take an Mt Etna tour
  • Enjoy the piazzas of Cefalu
  • Stay at an agriturismo
  • Hike through Zingario nature reserve
  • Cycle between beaches of Favignana
  • Watch sunset at Scala Dei Turchi


A Perfect 3 Day Amalfi Coast Itinerary

Best for: fashionistas and luxury trippers

The Amalfi Coast is one of Italy’s most popular tourist destinations and with narrow roads, expect a little traffic at busy times! But your effort will be rewarded with chic colourful beach towns, picture-perfect beaches lined with striped parasols and surrounded by chic bars for your Aperol Spritz fix.

Go sailing, hike up into the hills, explore gardens and churches or take a day trip to beautiful Capri – home of the rich and famous.

This 3 day Amalfi Coast has a little of everything.

3 days on the Amalfi Coast is enough to hit up the highlights but if you want to truly relax, try and add an extra couple of days on just to enjoy the beach life.


  • Day 1 – Amalfi town, Amalfi Beach, Ravello
  • Day 2 – Day trip to Capri
  • Day 3 – Positano


  • Admire Villa Rufolo Viewpoint
  • Check out Atrani beach
  • Soak up the atmosphere at Piazza del Dumo
  • Visit inside the Blue Grotto and hear the fisherman sing to appreciate the acoustics
  • Relax on Positano beach
  • Enjoy lunch with a view at Hotel Poseiden


4 Days in Rome – A Perfect 4 Day Rome Itinerary

Best for: history buffs and those looking for a romantic city break

Rome is on pretty much every traveller’s bucket list and so it couldn’t be missed off this roundup of Italy itineraries! The city of romance and history, it’s the perfect place to enjoy a city break.

Admire the Vatican, explore the Colosseum and enjoy the views at Palantine Hill.

But don’t get caught up trying to visit all the historic sites and miss out on just enjoying relaxing in a Piazza with an Aperol Spritz enjoying some people watching. There is no better place to people-watch than in Rome.

This 4 day Rome itinerary will help you see all the main highlight of Rome in 4 days but still allow you to have plenty of time to just soak up the atmosphere.


  • Day 1 – Enjoy Travastere and Campo di Fiori
  • Day 2 – Explore ancient Rome
  • Day 3 – Visit the Vatican
  • Day 4 – Explore the Tridente neighbourhood


  • Visit the Colosseum
  • Explore the Sistine Chapel
  • Visit st Peters Basilica
  • People watch at Trevi Fountain
  • Explore the ruins and admire the view at Palantine hill


Planning The Perfect Weekend In Trentino, North Italy’s Secret Gem

Best for: outdoorsy types

A weekend in Trentino is probably one of the less obvious Italy itineraries because Trentino is relatively unknown. But that is what makes it so incredible. It’s more relaxed, less busy and a LOT cheaper than most Italian cities. It’s also a great springboard for visiting the Dolomites and the Lakes in the north of Italy.

If you are looking for a laid back, relaxing Italian itinerary, then this is the one for you.


  • Day 1 – Explore Trentino
  • Day 2 – Go hiking in the Dolomites
  • Day 3 – Explore Lake Garda


  • Go wine tasting
  • Take a hike in the Dolomites
  • Enjoy a sunset spa trip with views onto Lake Garda at Sirmione
  • Visit Buonconsiglio castle
  • Visit Lago Di Toblino

Have these Italian itineraries helped to inspire you? Which will you take? Let us know in the comments below!

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