So you’ve finally decided to cross Italy off your bucket list, now comes the difficulty of actually deciding what kind of experience you want to have!

When it comes to a country like Italy, it’s important to first resign yourself to the fact you won’t be able to see everything in a single trip. You could easily spend two weeks in just about any Italian city alone.

But if you’re looking to take in the highlights, the following is a perfect 2-week itinerary for experiencing the best of Italy.

This itinerary will take you on a train journey between the country’s top destinations and most notable sites and attractions. But most importantly, without rushing through each city too quickly.

Included are the “Big 3”, being Rome, Florence, and Venice. These cities cater to just about any type of traveller whether you’re a foodie, architecture/art lover, history fanatic, or are simply searching for a little romance.

So without further ado, enjoy this helpful itinerary and “Fai un buon viaggi”!

The Best of Italy in a Two Week Itinerary

Getting Around Italy

By far the cheapest, most comfortable, and easiest way to experience any trip to Italy is by train. Purchasing Italy rail tickets can easily be done online or directly through the Omio App (one of the best apps to have on your phone for travel in Europe).

You’ll be able to find the cheapest and fastest routes with Trenitalia, Italy’s main train operator, as well as Italo trains. Booking via Omio (previously GoEuro) also saves time as you can simply show your ticket confirmations via your phone instead of having to print off or collect tickets.

The Italian countryside is equally as beautiful as its cities and train travel allows you to comfortably take it all in as you make your way around the country.

Air travel is hectic and costly, driving is often confusing and stressful, and taxis will devour your budget quickly. Italian railways link nearly every major city and are without a doubt the most reliable.

Trains link Italy with the rest of Europe as well, so if you’re wondering how to arrive, great routes include travelling from Munich to Venice over the Alps, or Vienna to Rome.

You can of course find direct flights to many Italian cities from Europe and beyond if short on time. Most visitors to Italy choose to arrive by way of Rome.

Rome:  Nights 1-3

What better way to start your Italian experience than in its capital. Rome offers so much to see and do that starting your trip here when you’re fresh and eager to explore is the best way to go. Every guide to Italy travel says so!

Rome wasn’t built in a day so you can hardly expect to see it all in one. The city has enough attractions to fill your Instagram feed for months, and you’ll need at least 3 days to fully appreciate the city.

Rome has it all: the Colosseum, Trevi Fountain, Spanish Steps, Pantheon, the Roman Forum, and more. Put on your most comfortable pair of walking shoes and simply take to the streets.

Plan at least a half to full day in the Vatican City, taking in the museums, St. Peter’s Basilica and Square, and of course the Sistine Chapel.

Keep up your energy by sampling supplì, a popular street treat that consists of a fried rice ball stuffed with cheese, meat, and sauce. For something sweet, you have to try a maritozzo, a bread roll filled with whipped cream…need I say more.

Splurge and set yourself up in the Centro Storico which may be pricey but will put you in a prime location that is close to most of the attractions you will want to see. This will save you a lot of time and hassle.

Photo credit: Giuseppe Milo (CC BY 2.0) via Flickr

Florence: Nights 4-7

Start day 4 with a roughly two-hour train ride to Florence.

Seeing a 5m tall marble statue of a man that is both extremely physically fit and very nude is reason enough to visit Florence (Michelangelo’s masterpiece statue of David) though the city is also known for its stunning architecture with the Florence Cathedral, or Santa Maria del Fiore, reigning supreme over the city.

The city also offers more than enough world-class museums alone to keep you busy for three days, including the Uffizi Gallery, Galleria dell’Accademia, and Bargello.

Rent a Vespa, overdose on gelato, and skip lunch to save room for a giant steak Florentine for dinner. Don’t miss taking in a sunset at Piazzale Michelangelo, shopping for leather goods and souvenirs in San Lorenzo, and relaxing in Boboli Gardens.

Set yourself up in the historical centre for four nights to be within easy walking distance of everything. 4 days in Florence will allow you to take a day trip through the countryside of Tuscany, experience the Chianti wine region, and take a trip to Pisa with its iconic Leaning Tower.

Photo credit: –sinava– (CC BY 2.0) via Flickr

Cinque Terre: Nights 8-9

Day 8 will see you boarding a 3-hour train to the five small coastal villages that make up the Cinque Terre. The region is a nice change of scenery, offering beautiful views of the sea along with lovely colourful houses.

It doesn’t really matter which village you decide to set yourself up in for two nights since short trains rides link all the villages and you can actually quite easily hike between villages as well.

Hiking between the five villages can be done by way of the scenic Sentiero Azzurro, or Blue Trail. The trail connects all five villages, and allows you to break up your hike into sections. Note that some sections are currently closed so you may have to make a few detours.

As far as the villages go, Manarola is the one you have most likely seen photos of while Monterosso al Mare offers beach access. Vernazza is the most picturesque of the five villages while Riomaggiore is the quickest and easiest village to reach from Florence.

Corniglia is set high upon a cliff and requires a bit of an uphill climb unlike the other villages. This can make it difficult for those carrying a lot of luggage.

My recommendation for where to stay would be to stay in the largest village, Monterosso al Mare, for its good offering of hotel choices and relaxed resort-style feel.

Milan: Nights 10-11

Day 10 starts with a roughly 3.5 to 4 hour train ride to Milan. If you packed any flashy clothes, now is the time to wear them since you are in the fashion capital of Italy if not Europe altogether.

Alternatively you can easily pick up some new high end labels as you’ll find many major Italian fashion houses and labels in Milan including Dolce & Gabbana, Prada, Versace, and Armani. Plop yourself in the Quadrilatero d’Oro for an incredible shopping experience, even if you don’t buy anything.

Milan is also famous for the opera and the best way to experience it is at the Teatro alla Scala. Other highlighs include the Milan Cathedral and Sforza Castle.

Milan is also home to Leonardo da Vinci’s iconic masterpiece “The Last Supper”, but be warned you need to book tickets months in advance if you wish to see it. If you have left it too late to get tickets, you’ll simply have to settle for an actual supper of your own by trying a delicious risotto or ossobucco.

You’ll find Milan to be much more modern and fast-paced than the rest of your Italian itinerary. It’s a great way to see contemporary Italy.

Venice: Nights 12-14

Of course no visit to Italy would be complete without visiting Venice.

The 3-hour train journey from Milan will take you directly onto the island, meaning you don’t have to deal with land or water taxis. Just remember to get off at the Venezia-Santa Lucia station and NOT the Venezia-Mestre station.

While Venice can be experienced via a day trip, this city really comes to life when the sun goes down in my opinion. Once all the day-tourists have left, the city becomes romantic and much less chaotic. Staying here three nights will allow you to explore all the hidden alleyways that are filled with surprises.

Of course you will want to see Piazza San Marco, Doge’s Palace, Saint Mark’s Basilica, and the Rialto Bridge. Staying overnight in Venice allows you to beat the tourist boats in the morning, so you can enjoy the attractions with a lot more space and ease.

Three days on Venice allows you to explore other nearby islands like Murano (famous for glass making), Burano (famous for its lace), and Torcello (offering green spaces and Byzantine mosaics).

Another great option is to stay on Isola delle Rose, home to a lavish JW Marriott Resort. Here you will have an island oasis to yourself, set with beautiful gardens and olive groves.

It offers by far the most peaceful Venice holiday while also providing quick, easy, and complimentary water shuttle service to St. Mark’s Square.

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The perfect Italy Itinerary for 2 weeks. Includes all the highlights like Rome, Florence, Venice, Cinque Terre, and great spots for Italy photography over two weeks!

The perfect Italy Itinerary for 2 weeks. Includes all the highlights like Rome, Florence, Venice, Cinque Terre, and great spots for Italy photography over two weeks!

Megan is an Australian Journalist and award-winning travel writer who has been blogging since 2007. Her husband Mike is the American naturalist and wildlife photographer behind Waking Up Wild; an online magazine dedicated to opening your eyes to the wonders of the wild & natural world.

Having visited 50+ countries across all seven continents, Megan’s travels focus on cultural immersion, authentic discovery and incredible journeys. She has a strong passion for ecotourism, and aims to promote responsible travel experiences.