Italy Vacations - The Best One to Three Week Itinerary
Italia, amore mio! Since the day I stepped foot on Italian ground years ago I knew it was going to be a long-term love affair. The culture, the food, the people, the history - all things I have grown to love and adore that make Italy one of the greatest countries in the world. Italy vacations are my favorite thing and one of the most common subjects I am asked about. If you are working on planning one yourself, you have come to the right place!
Italy is full of both vibrant cities and low-key seaside towns which the below itinerary mixes evenly so that you are not too bored but also not too overwhelmed. All destinations can be conveniently arrived at by train, making it very easy to get from place to place. The itinerary is designed for a 3 week trip, with 19 days scheduled and possible additions listed for each destination so that you have some wiggle room to add on a few more days if desired. And if you happen to not have 3 weeks of holiday time (hi, fellow Americans!), you can easily split up the itinerary into smaller chunks as needed. Also note that you could easily spend more time in these locations, the below recommendations are simply the minimum number of nights, assuming you are trying to see as much as possible!
So, without further ado, let’s start our 3 week Italian journey...
VENICE - 3 nights
A logical place to start your three week Italian journey is in Venice, given it’s location and ease of getting to due to popularity of airport. The floating city is one of the most unique cities in the world and a place that should not be missed. It has no roads and is instead made up of canals full of boats and gondolas taking lovers and friends on scenic rides through the almost-unreal landscape. It's also rumored to be sinking, so you better get there before it's gone!
- VERONA - day trip or en route to your next stop
- BURANO - day trip
- MURANO - day trip
If you don’t plan on making any day trips, 2 days in Venice is more than enough.
Travel by train: Venice → Varenna, duration ~3-3.5 hours
LAKE COMO (BELLAGIO) - 3 nights
Lake Como is a lake located in northern Italy, very close to the border of Switzerland, and just 3 hours from Venice by train. It is a popular upscale area, known for its dramatic beauty and being the home of George Clooney. The lake is home to many towns including Bellagio, Como, Tremezzo, Varenna, and Lecco to name a few. It is beautiful, glamorous, relaxing, and I found it to be very unique to the rest of Italy.
- MILAN - on your way to/from Lake Como you will pass through Milan, making this a great spot to add a night in Milan if that is of interest to you
HERE IS MY LIST OF 5 REASONS YOU SHOULD ADD BELLAGIO, LAKE COMO TO YOUR ITALY ITINERARY, INCLUDING HOW TO GET THERE, WHERE TO STAY, WHAT TO DO, AND WHAT TO EAT.
Travel by train: Varenna → Monterosso, duration ~4 hours
CINQUE TERRE - 3 nights
Cinque Terre, a string of five towns on the Italian Riviera, is known for it's colorful seaside houses and rewarding hikes. As if that alone is not enough, it is also the birthplace of pesto and the seafood is as fresh as can be. If you like hiking and/or are looking for good photo opps, this is your spot!
- PISA - on the way to your next location most trains stop in Pisa so this would be a good place to check that if your list if desired
WHERE TO STAY: La Rosa dei Venti
HERE IS EVERYTHING YOU NEED TO PLAN YOUR CINQUE TERRE TRIP, INCLUDING EXACTLY HOW I RECOMMEND YOU SPEND EACH DAY!
Travel by train: Monterosso → Florence (Firenze), duration ~2.5 hours
FLORENCE - 3 nights
Florence, capital of the Tuscany region, is home to many famous museums, incredible architecture, and a vibrant nightlife. Often called the birthplace of the Renaissance, it is a popular destination for those interested in art and culture. I don’t think I’ve ever met a person that doesn’t love Florence, so you really can’t go wrong here and more than likely had this on your list before you even landed here.
- TUSCANY - day trip or add additional nights here
If you’re a wine lover, do not skip a trip to Tuscany. I would recommend doing a vespa tour through Tuscany Bike Tours. Alternatively you could do it via bike but that just sounds exhausting after wine!
Travel by train: Florence (Firenze) → Naples (Napoli), duration ~3 hours Then by ferry or cab
AMALFI COAST (POSITANO) - 4 nights
If you know me personally or follow me on Instagram then you know that there is nothing I love more than Positano on the Amalfi Coast. John Steinbeck was once quoted saying “Positano bites deep. It is a dream place that isn’t quite real when you are there and becomes beckoningly real after you have gone.” and I really could not agree more. It is a place you have to see to believe and even then you will hardly believe it is real. If there’s one place that I recommend you visit, it’s this. It is the most beautiful place I've ever seen, is incredibly charming and glamorous, and is a great place to relax between Florence and Rome.
- CAPRI - day trip or add additional nights here
- NAPLES - on the way to your next location
- THE OTHER AMALFI COAST TOWNS! - day trip
WHERE TO STAY: Hotel Poseidon (do not miss this place!)
HERE IS EVERYTHING YOU NEED TO KNOW ABOUT VISITING POSITANO, 34 PICTURES THAT'LL MAKE YOU WANT TO VISIT THE AMALFI COAST ASAP, AMALFI COAST ITALY MAP & TOP TOWNS TO VISIT, AND 8 THINGS YOU ABSOLUTELY CANNOT MISS IN POSITANO.
Travel by train: Naples → Rome, duration ~1.5 hours
ROME - 3 nights
Roma, the lively capital of Italy, is the perfect final stop on your 3 week itinerary! It is full of rich history and a vibrant social scene that you will surely appreciate after your visits to some of the smaller seaside towns. Home of the Colosseum, the Roman Forum, Michelango’s Sistine Chapel and so much more, you will more likely run out of time than of things to do here. It’s also a major transportation hub so you can make an easy exit which is why I have it listed last.
WHAT TO PACK