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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.

Pro Tip: Some tickets may actually require you to print them on the automatic terminals at the station, but this will be explained to you upon booking if a ticket cannot be used electronically.

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

Rome by Giuseppe Milo

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

The beautiful Cattedrale di Santa Maria del Fiore

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

Cinque Terre Italy RF

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.

Pro tip: Plan on around 6 hours to walk the entire route. If you aren’t up to hiking or have mobility issues, I recommend taking a half day boat tour in-between the villages.

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

Milan Cathedral RF Italy

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.

Pro tip: The northern Cannaregio region is a great place to base your stay as it is far enough from the tourist hotspots to have peace and quiet, yet close enough to reach them all on foot.

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.


Amazon Italy Guide

Fodor’s Essential Italy

Amazon Italy Guide

Lonely Planet Italy

Amazon Italy Guide

DK Eyewitness


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.



  1. nice!

    • Glad you enjoyed the post Kelly :)

  2. When you get to Florence, stay and enjoy the rest of your life!

    • I love that idea! :D

  3. Noooooooooo you missed Naples!! Can take so many day trips it’s a great base, and no-where else does better pizza.

    • Naples is a great city for sure and you’re right, so many fabulous opportunities for day trips. I’ll wholeheartedly recommend extending an itinerary past two weeks to take in more of Italy :)

  4. Thankyou for this itinerary. Would you recommend Bologna? Were thinking of subbing in that instead of the Cinque Terre between Florence and Milan, and then maybe Verona as an extra stop between Milan and Venice.

    • You’re welcome Cathy. I would absolutely recommend Bologna, and if you’re not keen on the Cinque Terre that’s a great choice. It’s much more of a hidden gem than the larger cities, and nice because it has more of a feel of a more authentic, local Italy. I usually recommend it as a destination for a second trip because in the first trip people seem to want to hit the major tourist landmarks before being interested in diving in deeper. But there’s incredible architecture and history here, and it’s a great way to escape the crowds of the main cities. We did a post on things to do in Bologna here if you’re interested:

      Verona too I loved, same deal as Bologna, a much more chilled out pace compared to the hype and commotion of the major cities, and very charming. Definitely a cool stop if you have the time between Milan and Venice.

      Have an amazing trip!

  5. What is the best train in Italy?

  6. ❤ Italy!

    • Same! I’m obsessed!

  7. In Italy, it is always cheaper to buy point-to-point tickets well in advance rather than a Eurail pass.

    • Absolutely agree, great point Claudie :)

  8. Fly into Venice, stay there for whenever. Train to Florence stay for whenever. Train to Rome. Fly out of Rome. Flying out of of Rome is better than flying back from Venice.

    • You can definitely do this itinerary in reverse if you’re finding easier flights out of Rome than Venice. Will obviously depend on where you’re flying to, but definitely worthwhile playing around with options :)

  9. We loved Italy. We arrived at Pisa Airport which was great because you step outside and the train is literally right in front of you. Pisa can be done in a few hours or an afternoon max, and then it’s super easy to train it into Florence to carry on with the rest of the trip. I agree that flying out of Rome is easier.

    • So glad you had a fabulous time Sharon! On my first trip to Italy we actually arrived in Pisa and went onto Florence too. The nice thing about Italy is that the destinations are all so connected you can easily move your starting point around and still hit everything you wanted to do, just in a different order :)

  10. How about exploring Tuscany? It’s a big area with lots of beautiful hill towns.

    • Absolutely Louis, we’ve recommended taking a day trip to Tuscany while you’re based in Florence :) But of course you can base yourself in Tuscany for as long as you want too, we hope the itinerary is more of a starting point to help guide people :)

  11. Five locations in 14 nights is an awful lot of moving around. Remember that you’ll lose at least a half day every time you move cities. Unless you have a compelling reason to stay in Milan, I’d head directly to Venice. Buon viaggio!

    • Time in transit definitely needs to be taken into consideration, we’ve done the above itinerary and I didn’t think it was too much personally, but hopefully it can be used as a starting point to guide people, and if they’re interested in spending more time in less cities, can adapt that :)

      Buon viaggio!

  12. This is so helpful, thankyou! We’re going to Italy for our honeymoon and have 3 weeks so I might just add extra days to each one of these stops. Can’t wait!

    • You’re welcome Shayne, I’m glad it helps! Italy is such a fabulous destination for a honeymoon – congratulations!

  13. Great! Thank you for this! It will especially come in handy when I visit Tuscany and Florence this October for the Adventure Travel World Summit!

    Cheers! Gracie!

    • You’re welcome Kristen, have an amazing trip!

  14. Totally agree that you’ll never be able to fit everything into one trip. We’re fortunate to live in the UK where we can get cheap flights over for weekend trips, it’s a nice way to slowly explore the whole country. It’s become our favorite, we long ago forgot about the rest of Europe in favor of Italy.

    • Jealous! I’m in Australia so Europe for me is at least 16 hours away … would take up my whole weekend just flying :D

      Enjoy Italy! I can totally understand why it’s become your fav go to place!

  15. Italy, a European country with a long Mediterranean coastline, has left a powerful mark on Western culture and cuisine. Its capital, Rome, is home to the Vatican as well as landmark art and ancient ruins.

    • Absolutely Zahid, it’s definitely a tourism treasure! :)

  16. My parents live in Italy. They love it there. They have been there for over a year now. Dual citizens.

    • Fabulous excuse to visit and plan a trip :D

  17. I still love Venice so much. I know there are tons of tourists (but where aren’t there in Europe) and those canals and small dead end streets, love it so much!

    • True on the mass tourism, but still a wonderful city despite that. We had a great time in Venice, staying north in the Cannaregio region was a great way to avoid most of the mass tourism, and the region itself was pretty quiet which was fab :)

  18. SO needed! It’s hard to narrow things down!

    • So glad it could help! Italy is one of my favorite countries, but definitely so much to take in and a super tough choice when you’ve only got a limited amount of time :)

  19. There’s no excuse…but I haven’t been to Italy yet!?

    • Maybe this can be your year! :)

  20. My wife and I visited Rome, Florence and Venice in 2010. Trains were used between each city. Also did a day trip to Pompeii.

    • Glad to hear you had a fabulous trip! One of my favorite countries, trains really are the way to go :)

    • We even stayed at the Cannaregio region of Venice. Quiet and nice. Plus we experienced some mild flooding too. Interesting to see.

    • Cannaregio region for accommodation was the bets decision we ever made in Venice – we typically don’t like huge crowds of tourists, so were wary of visiting Venice, but it was great! Didn’t see any flooding though, that would have been interesting!

  21. Many Italian cities are lovely. But for me Rome is my favourite.

    • Rome blew me away, definitely an incredible place!

  22. Any place in Europe is my favorite… I like the Italian / French Coast. I liked Verona a lot as well. What’s not to love about anything in #Italy?

    • Verona was fabulous, I loved visiting the Juliet balcony!

  23. Favourite Italian city? So many. But always enjoy returning to Padova, Assisi, Ferrara and Turin.

    • I haven’t been to any of those yet!! Starting a new Italian bucketlist! :D My fav is Venice (cliche I know!), and Bologna. Also really loved Verona :)

    • Cant disagree but Venice should really be looking to put residents first. Theme park turnstiles for visitors is symbolically not a good sign although raises needed funds. Mega cruise ships should also be banned and redirected.

    • Yes I do agree with you on that one, the last time we visited we stayed at the Boscolo Venezia which was well away from the majority of the mass tourism and it was such a delight to enjoy it without crazy crowds of people.

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