Walk in sun drenched vineyards or splash in turquoise waters of the Mediterranean. Tip toe in quaint hilltop castles or relish it’s sensational cuisine. This is Italy –  the land of sinful pleasure 🙂 Here even the simplest of things, feel special. So sit back, relax and enjoy La Dolce Vita ! Best enjoyed as a road trip, our Italy itinerary brings you sumptuous vistas, ancient relics and local flavors like never before !

Italy is such a vast and varied country that it deserves more than a single visit. But if you are crunched for time, then here is an easy itinerary that packs a punch.

It’s a heady concoction studded with amazing opportunities. All you have to do is handle it’s charms!  This road trip is designed to give you everything that Italy is renowned for – food, culture and stunning panoramas.

If you love Renaissance art, then spend more time in Florence. Italian wines enamor you, then luxuriate over a Chianti in Tuscany. A fashionista that you are, then take it slow in Milan. If you adore medieval hilltop villages, then soak up the charm in Umbria.

What I am trying to say is – choose an itinerary that suits you best. Scale up or down depending on your preferences. Ideally done with a combination of Bus/Car/Trains – here is a suggested Italy Itinerary that will leave you in awe !

7 – 10 Days Italy Road Trip Itinerary :

Fly in and out of Rome

Day 1 – 3 : Rome

Day 4 : Assisi

Day 5 – 7: Florence / Tuscany / Montepulciano

Day 8 – 9 : Sienna

Day 10 : Fly out of Rome

14 – 20 Days Alternate Road Trip Plan :

Fly into Rome and fly out of Milan

Day 1 – 3 : Rome

Day 4 : Assisi

Day 5 – 6 : Sienna

Day 7 – 11: Tuscany / Florence

Day 13 -15 : Cinque Terre

Day 16 -17 : Venice

Day 18 – 19  : Milan and Lake Como

Day 20 – Fly out of Milan

14 – 20 Days Italy Road Trip Itinerary  :

Fly into Rome and fly out of Naples

Day 1 – 3 : Rome

Day 4 : Assisi

Day 5 – 8 : Florence

Day  9  : Sienna

Day 10 : Rome

Day 11 -13 : Naples

Day 14  : Pompeii

Day 15   : Sorrento

Day 16 -19 : Amalfi Coast

Day 20 – Fly out of Naples [ Amalfi to Naples airport takes approximately 1 hr costing 30 Euros by cab]

All clear ? So shall we start our Road trip across Italy? Yay !! 🙂

 

 

#1 Rub Shoulders with History – Rome

Begin your trip in Rome. In this land of gladiators, you walk in the footsteps of Caesar. It feels awesome to relive the grandeur of Roman empire.

With a little imagination you can picture this antique country in its former glory. From the brutal majesty of Colosseum to elegant hand painted frescoes in Sistine Chapel. In Rome, every experience is uniquely gratifying.

No matter your preferences, you simply cannot skip Rome. It’s studded with incredible beauty. The whole city is an open air museum and this capital deserves to be the starting point of your Italy itinerary. Since here, all roads literally lead to Rome 🙂 , it makes a perfect place to start the road trip.

#2 Sample its rustic simplicity – Assisi & Sienna

After staying in Rome for a while, at one point the sheer splendor and grandeur of it will overwhelm you. With more than 4 million tourists descending upon this city, you will want to escape it’s crowds once you’ve seen it’s iconic sights. That’s when your itinerary truly takes off and the road trip begins!

Take a bus, train or car and head to the quaint village of Assisi, on the slopes on an ancient mountain. It’s an easy road trip from Rome taking about 2 hours.

As you move away from touristy Rome and deeper into the Italian heartland, knowing local language becomes instrumental so learn a few survival phrases !

If you are not feeling very adventurous and rather not deal with rental car, feisty local drivers 😉 and navigation, then take a bus or train. Trains take you from FCO Rome to Assisi.

We’ve seen that quasi-road trips work best for us – given the temperament and patience of our little guy. Mix of trains and cars make an ideal itinerary across Italy.

Assisi and Sienna are two delightful Umbrian towns about 2 hours from Rome, by road. The focal point of Assisi is a ruined castle perched on a hill ,while Sienna has an elegant cathedral and tons of medieval beauty.

In these villages we relished countless wood-fired pizzas – they taste nothing like “Italian food”  back home. The authentic taste of rustic Umbrian cuisine is a speciality. The three of us could not wait to pull out our pieces.

It’s mouthwatering just to watch the stringy mozzarella stretch. The crisp crust, creamy cheese and the bold marinara melt in your mouth to create an explosion of flavors!

#3 Listen to a serenading gondolier – Venice

Venice is that dreamy land of lovers. While cruising its many canals, listen to a gondolier sing. Take in the sights of a gently crumbling Venice as your boatman sings of the time he loved and lost. Although it’s expensive, there is something quite unique about this experience.

In Italy the network of trains is excellent. They are efficient, affordable and fast. We loved using Alitalia for our journeys. They are very popular and fill up fast so book in advance for an attractive rate.

 

# 4 Cradle of Art and Culture – Florence

Easily our most favorite part of Italy -Florence. It is a delight for any culture connoisseur. The land of countless cathedrals and beautiful basilicas. Richly decorated with timeless frescoes, the ceiling of Florence Cathedral is ornate and continuously engages the viewer.

The intricate details weave such a spellbinding story that it’s hard to take your eyes off. Its only when your neck begins to hurt, you realise how long you’ve been gazing at these artistic treasures. It’s mesmerising to say the least.

By road, the trip from Assisi to Florence will take a little over 2 hours( if you don’t keep stopping for scenery and photos). Take the A1 south to Florence. The drive is scenic with a mix of inner country roads as well. This route is also notorious for traffic jams as you get closer to Florence.

Florence is the capital of Tuscany. The sumptuous wine growing region of Italy. When people ask me for an Italy itinerary, all I can think of is Tuscany. A road trip across regions of Chianti and Val d’Orcia will change you forever. The beauty here is mind altering.

I cannot recommend it enough. The gentle rolling hills make for a perfectly romantic drive – – – if only there were no shrill cartoon sounds from the back seat ! ( young parents, you know what I mean)

#5 Splash the turquoise waters of Mediterranean

No Itinerary for Italy is complete without the famous Amalfi coast. Positano, Sorrento and Cinque Terre are some must-see destinations. Sorrento is easy to reach by bus from Naples and makes for a lovely road trip. Azure Mediterranean teases the rugged coast of these beautiful cliffside towns.

Vernazza is according to me the most beautiful of the 5 villages that comprise Cinque Terre. One of the must-try things in south Italy are Cannolis – delicious fried shells filled with sweetened ricotta cheese. Absolutely heavenly. Yum.Yum Yum.

In Amalfi, the lemon trees of the region infuse a freshness in your holiday. You feel like you are in a painting. The stunning coast, cypress trees and boulevards overflowing with flowers are simply majestic. Grab a zesty drink and relax on its beaches!

#6 Italian Alps – A must in Italy Itinerary :

Milan is a must see for the Duomo and Leonardo Da Vinci’s ‘The Last Supper’. I am absolutely smitten by his works – all Da Vinci fans will love this place. The original is housed in Santa Maria delle Grazie in Milan and you need reservations months in advance to view the masterpiece.

At the edge of Italy, sharing borders with the Swiss Alps lies lake Como. It would be a crime to plan your Italy itinerary without this lake snuggled in mountains.

Varenna is our pick – totally deserves a spot in your Italy itinerary. It’s 60 km from Milan and the waterfront is laced with elegant Italian mansions and sunken gardens. Bellagio is another highly recommended pit stop on your road trip. 

These both can easily be done as day trips from Milan or you can choose to spend longer here. We love magical small towns and villages for the sheer charm and elegance they add to your holiday.

Hope you enjoyed reading this piece. How was your experience across Italy ?  Let us know in comments! Want an offbeat travel inspiration ? Read our travels across the Sahara and in a little oriental village !