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This Italy Itinerary is a fast-paced expedition to see the most of Italy in two weeks via train and bus. If I could convince everyone of one thing- I would tell everyone to drop everything and live in Italy for about 3 months, then take your time and truly immerse into the Italian lifestyle. Unfortunately, not everyone has the time for that! So, if you’re on a crunch and ready for a busy 2 weeks- get ready because here you go!
If planning a two week trip to Italy seems like an insane feat, you’re in luck!
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I lived in Italy on two separate occasions. One of these occasions I was there for an entire year, and truly able to explore some of the more intimate corners of the country, and especially of Florence, where I called home. When people ask me where my favorite place in the world is, the answer forever will most likely be Italy. I have flown back and forth from the states to Italy too many times to make my bank account happy. This love of Italy is what makes me excited (and qualified!) to share my insider knowledge with you! I even worked as a tour guide while I was in Italy!
If you have any questions about Italy & travel. Italy in general, travel in general, my life in general, don’t hesitate to reach out to me on Instagram, Facebook, or email me at firstname.lastname@example.org – or just leave a comment at the bottom of this post!
I choose Milan for the start of the Italy Itinerary because it’s often the cheapest place in Italy to fly into! If you fly into Rome you can simply just rearrange this itinerary starting with Rome and going in the opposite direction.
I also prefer to start an Italy Itinerary in Milan for another reason. By starting in the north of Italy, it allows you to make your trek a giant circle around the country, and end up where you started while hitting all of the major spots along the way!
Alternatively, Bellagio, Verona, and Venice can all be taken as day tours from Milan. I have listed them as stops as their own, but if you decide you don’t want to keep packing up your bags, I would totally recommend taking them as day trips. The only place you would be missing out on by not staying the night is in Bellagio, but both Verona and Venice make awesome day trips.
Milan is a great place to start getting immersed in Italian culture. It is a very metropolitan and international city as well as a great place to get your foot in the door! If you’re flying in from America, you’ll most likely arrive in Milan in the morning. Get your stuff to the hotel, and STAY AWAKE! Go and do all the tourist activities I have listed below! You want to get accustomed to the time difference and fight the jet lag as much as possible so make sure you stay awake until it is an acceptable time to go to sleep in Italy.
The Duomo– Holds lots of architectural importance in Italy
The Last Supper – YOU MUST BOOK THIS IN ADVANCE Here is the link to book tickets on your own (anywhere from 7-10 Euro) – but honestly it is a very confusing website and your best way to do it is to take a guided tour of Milan (learn all the history) that includes a Last Supper ticket. There are several great options from Viator for Milan walking tours!
The Fashion & Shopping District – Milan is known for its fashion (duh there is a huge fashion week here EVERY YEAR) and there is no harm in window shopping while you are in town.
$ MEININGER Milano Lambrate ~$19 per bed per night – 9.0 Rating on HostelWorld
$$ Madama Hostel ~ $36 per bed per night – 9.2 Rating on HostelWorld
$$$ Ostello Bello Grande ~$50 per bed per night – 9.6 Rating on HostelWorld
After you’ve spent your first night in Milan- hop on the train in Milan and head to the celebrity hotspot – BELLAGIO! (make sure you say hi to George Clooney for me) The first leg of this journey is by train to Varenna and lasts about one hour ten minutes, tickets cost around €6.50. Then get on the ferry to go to Bellagio, which is a 15-minute ride and tickets are around €10.
Eat Seafood (yum!)
Boat Tour – Dream about the lifestyles of the rich and famous with a boat tour on Lake Como.
Relax!! This will be the least “get up and go” part of your vacation
(Here you can either take the train back to Milan & do the next two as day trips from Milan, or choose to stay the night in Verona, then travel to Venice for a day, and then head to the next destination that evening)
After relaxing in Bellagio, head to another famous Italian lake, Lake Garda, and one of its famous little towns, Verona, the setting of Romeo & Juliet. Find your Romeo, or if you already have him, find romance in Verona for a night before continuing on your adventure.
$ Residenza Elisabetta – Starting at $75/Night – Fantastic Reviews!
$$Hotel Milano & SPA***S – Starting at $91/Night (has a hot tub!)
$$$ Hotel Colomba d’Oro – Starting at $125/Night – Absolutely stunning interio
$ The Hostello ~$29 Per Bed Per Night – 9.5 Rating on HostelWorld
Now it might seem crazy to spend only a day of your 2 week Italy Itinerary in of the world’s most famous cities- but trust me when I say one day will truly be enough. Very few people actually live in Venice, so once the sun sets and the tourists all go back to their hotels- it basically becomes a ghost town. Head out from Verona or Milan (wherever you decided to stay the night) early in the day, and get to Venice at a solid morning hour to get in a full day of sight-seeing.
Here is a great list of Venice Day Trips from Milan
If you did opt to spend the night in Verona, you can take the train direct to Venice. It takes about 1 hour 10 minutes. Alternatively, it is cheaper to take the bus but it will take you about 2 hours, and will probably be a bit more of a hassle.
Leave after dinner to hop on the late train to Florence for your first night.
Saint Mark’s Cathedral (and Piazza)
Ride a Gondola
Eat Cuttlefish in Squid Ink Sauce
Watch a Glass Blowing Demonstration
BONUS! If you have the time take a Vaporetto to one of the surrounding islands, either Murano or Burano. Both have very unique cultures and are equally as charming as Venice, often with a significantly less bit of crowd!
MY FAVORITE CITY IN THE WORLD!!
But seriously- there is a reason why I listed Florence as the place you should stay the longest. 4 nights in this incredible city isn’t even close enough to discover it all- but it’s a good start and a MUST in your Italian itinerary. Apart from the Day Trip to Siena & San Gimignano, I have listed below- there are lots of cute day trips from Florence that you can take- including Fiesole, Pisa (do this with something else, you will NOT want to spend a whole day in Pisa), Lucca, and several of the castles in the surrounding region (Castello de Trebbio is my personal fave).
Florence is the heart of the renaissance and hosts about 1/3 of the world’s art treasures. There are plentiful things to do while you are here so don’t miss out!
I have spent a lot of time in Florence have linked some articles below to help you tackle this little town. Peruse them and figure out what interests you the most!
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$ Hotel del Corso – Starting at $110/Night – Great Location
$$ Hotel Monna Lisa – Starting at $115/Night – Great Location!
$$$ Grand Hotel Baglioni – Starting at $151 /Night – Great view of the duomo from the dining room!
$$$$ The Westin Excelsior – Starting at $455 /Night – The Cream of the Crop with a Beautiful Rooftop Terrace and Rooms on the Arno. Worth the splurge if you have the money!
There are many ways to see the Chianti region- but one thing that is for sure is that it is a MUST!!! In my humble, Italy loving opinion, it hosts the most amazing wine in the world, and some of the most stunning views you will ever see in your life. There are several companies to choose from when booking your Chianti excursion, some riding Vespas, some horseback riding, some in a Fiat 500 where you can race through the countryside. Some of my favorite local companies are Fun in Tuscany and Tuscan Cycle.
Leave Florence early because you are going to want as much time as possible in Cinque, especially if you want to hike. (The train will take you around 4 hours.)
You cannot miss Cinque Terre! These 5 little towns sitting on the Ligurian coast, also known as the Italian Riviera, are some of the most stunning views in Italy. Picture perfect colorful homes hanging over the sea in a side of a cliff- the towns can’t be accessed by car or bus- the only way in is by train, boat, or foot. Bask in the Italian sun or take the hike from town to town and see views unforgettable!
Check out my blog on how to spend the perfect day in Cinque!
If you have an extra couple of days to spare and want to head off the beaten path a bit, the region of Umbria is stunning! Take your pick!! Both of these towns located in Umbria are quaint and charming and perfect to relax in after the “fast-paced” lifestyle of Florence! (I use the term fast-paced very loosely!) Once you’ve decided, book a hotel or Air BnB- and spend a relaxed night in these peaceful towns.
Pro-Tip – If you’re traveling during October visit Perugia to experience the Eurochocolate festival!!! (this can also be taken as a day trip from Florence)
One of the most beautiful and spectacular parts of spending two weeks in Italy will undoubtedly be the Amalfi Coast.
To make this part of your Italy Itinerary work you will have to leave Florence very early in the morning. From the Santa Maria Novella station, take the train into Naples. You won’t want to stay there long. Naples (or Napoli in Italian) is dangerous, and not nearly as beautiful as the rest of the Amalfi Coast. Once you get to Naples you will have to take a bus to Sorrento.
Check-in early to your accommodation in Sorrento if possible (or just drop your bags if they’ll allow it!) and take the bus to Positano, where you will get perfect views of little cliff-hanging seaside houses, and during the summer an amazing beach day.
Spend your evening back in Sorrento wandering around and eating amazing seafood. Get prepared for an adventure-filled following day!
In the morning you will head to the celebrity vacation island of Capri!
Here you can ride the gondola (or hike) up to the top of the island (Anacapri) for some beautiful views. Get custom made leather sandals, a Capri specialty, or go and swim in the blue grotto, if the weather is right and your heart so desires.
$ Sea Room Sorrento – Starting at $70/Night- Beautiful Rooms with ocean-facing terraces
$$ Hotel Rivoli Sorrento – Starting at $115/Night – Really cozy & great reviews!
$$$ Imperial Hotel Tramontano – Starting at $211/Night – Pool!
$ Ostello Delle Sirene – Dorm Beds $42/Night
After you check out of your accommodation the next morning- ask if you can leave your luggage and head to Pompeii and Mount Vesuvius- this is a truly life-changing trip, and something you won’t want to miss while in the area! Pompeii is incredibly humbling, and when else are you going to be able to climb a volcano!? Be sure to pack your walking shoes- the climb up to Mount Vesuvius is nearly a 45-degree incline the whole way! Well worth it though!
Pro Tip: When you go to Vesuvius there is 1 single-stall bathroom WITH NO TOILET PAPER OR A WAY TO WASH YOUR HANDS. Be prepared to drip-dry, pack a few tissues with some hand sanitizer, or just hold it!
After your afternoon spent in Pompeii, it’s time to head to Rome, which no Italy Itinerary would be complete without!
Night 1: Traditional Dinner away from Tourist Sites & Sleep
Think what is the most possible Italian meal I could have that isn’t pizza.
You are going to want to book these tickets at least a week before your trip, so I recommend you book before you leave. Go early, do the Sistine Chapel first, then hop in line for St. Peter’s (you’re going to wait about 2 hours- regardless of what you do). If you want to buy tickets to climb the dome- do so in advance! A great way to do this is booking through Viator – they have tons of amazing Vatican tours available!
$ Studio Bedroom near Campo di Fiori – Starting at $86/Night – Sleeps 2
$$ Villa with Garden Near Colosseum – Starting at $110/Night – Sleeps 6
$$ Historic Center Apartment with View of Tiber River – Starting at $122/Night – Sleeps 6
$$$ Amazing Beautiful Vittoriano Rome – Starting at $247/Night – Sleeps 4
$Funny Palace Rome – Dorm Beds Starting at $18 /Night – 8.2 Rating on HostelWorld
$$ Free Hostel Roma – Dorm Beds Starting at $22/Night – 9.2 Rating on HostelWorld
$$$ Meininger Roma Termini – Dorm Beds Starting at 35/Night – 9.2 Rating on HostelWorld
If you have a couple of extra days to fit into your Italy Itinerary, I would round out your trip and make a pit stop in the largest seaport of Italy, and the 6th largest city in this beautiful country. Genoa is a unique little coastal town and worth a stop if you have the extra time to spend and are looking for another place to visit.
See Piazza di Ferrari
Via Garibaldi Palaces
Acquario di Genóva (Genoa Aquarium)
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