The Best Italy Itinerary 3 Weeks (Or Less)

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 itineraries 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.  

This itinerary is designed for 3 weeks in Italy, 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 time to spend three weeks in Italy (hi, fellow Americans!), you can easily split up the itinerary into smaller chunks as needed.  I.e. you can easily come up with an itinerary to see Italy in a week based on the below info.

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 Italy itinerary 3 weeks journey...


Italy itinerary 3 weeks:


What to Pack for Italy

Before we get into the itinerary, let’s talk about what to pack. There are many things you should bring along on your trip to Italy. My highest recommendations are:

COMFORTABLE SHOES. You will likely (hopefully) be doing a lot of walking so this is very important! My very favorite are M. Gemi’s white leather sneakers. I literally never travel anywhere without them. Click here to see latest prices.

More details: click here for why they're the most comfortable and stylish walking shoes for travel!

NO-SHOW SOCKS. To go with the above mentioned shoes! I have tried so many different ones and find that most fall down under your heel (ouch) but these do not. Click here for the ones I love.

DAY HEELS. Heels you can actually walk in? Yup! These Day Heels are heels you can walk in all day long. Click here to check availability (they sell out constantly, get them while you can!).

SUNDRESSES. If there is one thing that screams Positano to me, it is sundresses! Click here for my favorite sundresses for Italy . I also shop for them here , here , here and here(that's the US store - for the Aus version which has more products and also ships to the US, click here !).

QUALITY BASICS. I think investing in quality pieces is important always, but especially when traveling. Why? Because you want the fabric to be breathable and durable and for the items to be well made and versatile. But at the same time you don’t want to overpay, which is why Everlane is my favorite place to buy basics! They make timeless products with transparent pricing — telling you exactly how much it cost to make, how much they’re selling it for, and how much competitors traditionally sell it for. I’ve been shopping here for years and so far everything has been great! Click here to see the latest prices.

Some of my specific favorites: this v-neck bodysuit, this silk shirt, this ribbed tank, and this tee.

SUNGLASSES. Of course! Three timeless styles I’ve been wearing non-stop: click here for my favorite Quay aviators (I have numerous pairs), click here for my round Ray-Bans, and click here for my all time favorite black on black Ray-Bans that are often hard to track down because they sell out consistently.

LIGHTWEIGHT TRAVEL CARDIGAN. Barefoot Dreams’ circle cardigan is honestly one of the best travel-related purchases you can make. It is so warm and soft; I’ve brought mine on every single trip since purchasing it. It's also fantastic for transit days and hotel lounging! Click here to see the latest prices.

STYLISH CAMERA BAG… if you are bringing a camera! You can’t go to Italy with anything that isn’t chic ;) I usually bring GATTA’s Christie camera backpack (named after me) because it’s hands free, has a zipper AND a buttoned flap, and fully protects my camera yet is so cute no one will ever know it’s a camera bag. Click here to see the latest prices. Want to see more options? Click here for the most stylish camera bags for women!

BLACK PASHMINA. A total lifesaver! It folds up small so you are able to easily throw it in any bag and it weighs basically nothing. However, because of the material it is capable of keeping you surprisingly warm in situations where you have mistakenly underestimated the weather. You can wear it as a scarf, wrap it around your body like a shawl, use it as a blanket on cold planes or trains, etc. - it serves so many purposes. I recommend a black one because black goes with everything and if it gets dirty along the way it will be way less noticeable. Pro tip: if you’re only bringing a small cross body bag with room for your wallet, tie it to the strap! Click here for an inexpensive and highly recommended option.

LEATHER TOTE. I never, ever, ever travel without my Cuyana Leather Zipper Tote. It holds so much yet never feels as heavy as other bags! Click here to check it out. Wanna know my organizational tricks? Click here for how to organize your carry-on.

CONVERTER ADAPTER. This one is universal and works no matter where you’re going so it’s a must. When going to the EU I also bring along this very inexpensive 6 pack so that I have extras. So much to charge these days! Need other recommendations? Click here to see my list of 20 must have travel products from Amazon Prime.

Some more Amazon travel essentials:

AN INSTAGRAMMABLE HAT. Good for both avoiding doing your hair and also to help make photos pop! Click here for my favorite hat for summer (you've probably seen it all over my Instagram!).


HAIR ACCESSORIES. For summer hair accessories are huge and are yet another way to easily spice up an outfit (or hide dirty hair)! Click below for my current favorites:

MAKEUP. My recommendations for travel specifically are:

SKINCARE. If you follow me on Instagram then you know I am a skincare fanatic. While I have an incredibly lengthly process while at home in SF, I try to keep it a little more low-key on the road. Click here to see more detailed skincare info or below for the items I believe are most essential for travel:

JEWELRY. Make packing easy with the ultimate travel accessories from our latest collection! Click here to visit our jewelry shop or on a specific item below.

For a full packing list, click here for what to pack for Italy!


The Best Tools for Traveling Italy

For flights when flying into Italy, I use Skyscanner. Skyscanner is great because they find you the cheapest flights by comparing millions of options from airlines and travel agents. Click here to search Skyscanner.

For hotels I always use HotelsCombined, as you will notice in my specific recommendations below. I love them because they compare all of the top travel sites in one spot - with no booking fee and no markup. Best price guarenteed! Click here to search HotelsCombined.

When I'm not staying at a hotel, I love Airbnb. When chosen right, it provides a more local experience and you can often get a lot more space for less money. Click here to get $40 off your first stay.

To get from city to city while in Italy, I recommend taking a train. For train travel you should use Rail Europe, the #1 distributor for European train tickets and rail passes. I like that you can create an account with them which helps keep all of your tickets and info in one central location. Click here to search Rail Europe.

For tours, museum tickets, and other activities, I recommend GetYourGuide. They are a trusted site and have lots of unique things to do along with all of the standard touristy activites. Booking everything individually can be a bit of nightmare to keep track of. With GetYourGuide you can create an account to book and manage all of your tickets in one central location. For popular cities I recommend booking these in advance. Click here to search GetYourGuide.

Want to stay connected while abroad? I recommend renting a pocket-sized personal WiFi hotspot from Tep! Click here to see the latest prices.

DID YOU KNOW: when you book your flights, accommodations, and activities through the links on any of our blog posts, it helps keep our site running at no additional cost to you. We really appreciate your support!

How to Get Around in Italy

Getting around in Italy is very easy thanks to the ease of their rail system. For the most part, you won’t ever need to rent a car. Some exceptions to this are if you plan on visiting the towns in Puglia or going to Sicily.

I would recommend, if possible, booking your train tickets in advance. In my experience the trains in Italy don’t sell out (unlike in Portugal), but you never know and it’s better to be safe than sorry!

I personally do this via RailEurope because it's a one-stop-shop for booking all of your European train travel. You can create an account with them and then all of your tickets are stored in one central location together.

In the detailed itinerary below I have included how to get from place to place by train, as well as how long you can expect each journey to take.


Driving in Italy

If you prefer to drive while visiting Italy, that is also possible. If you have an EU drivers license that is valid throughout the entire European Union, including Italy. If not, you’ll need to acquire an international driver’s permit. This is used in conjunction with your valid home driver’s license. You can apply for this on the DMV’s site.


Average Temperatures in Italy

The average temperatures in Italy vary greatly by region and time of year. For first time visitors, here are the averages for Rome by season:

  • SPRING - average low: 41-46°F, average high: 59-73

  • SUMMER - average low: 42-62, average high: 73-86

  • FALL - average low: 51-59, average high: 71-86

  • WINTER - average low: 37-39, average high: 53-55


The Best Time to Visit Italy

The best time to visit Italy depends largely on what you are looking for. The bigger cities you can visit year round, while some of the smaller towns like Positano almost completely shut down in the off season (mid/end of October through April). I have personally found the best time to visit Italy to be between May and October, with July being the busiest (tourists galore). If you want to escape the crowds, aim for May or September.


VENICE - 3 nights

A logical place to start the best Italy itinerary 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!

If you are able, I recommend spending one day visiting Burano. It is an easy day trip from Venice and the most colorful little island you’ll ever see!


If you don’t plan on making any day trips, 2 days in Venice is more than enough.

WHERE TO STAY IN VENICE: Palazzo Morosini Degli Spezieri. Click here to see the latest prices.

My favorite tour company, Get Your Guide, offers many awesome Venice tours, as well as skip the line tickets to the most popular attractions. I highly recommend booking these advance to save yourself time and money while in Venice. Lines can be crazy! I use Get Your Guide for many reasons, in part because you are able to create an account with them and keep all of your tickets in one central location (especially important if you are visiting a handful of cities).

Other unique and highly rated Venice experiences:

  • To learn to row as a Venetian (this has TONS of unanimously positive reviews), click here!

  • For a tapas and wine tour through secret parts of Venice, click here

  • For a market tour and hands-on cooking class, click here

  • For a tour of Burano from a local (born and raised!), click here

  • For a Murano glass workshop, click here

  • For a half day tour of the best islands in the area, click here

  • To experience Venice like a local, via a tour of Cannaregio (my favorite area!), click here

  • To create your own famous Venice carnival mask, click here

  • To make your own pizza, click here

  • To explore Venice by kayak (soo cool!), click here


You cannot go to Venice (and Italy in general) without properly documenting your trip, whether it’s for Instagram or just to have for yourself. Click here for the Venice memories photoshoot I recommend booking.

I have dedicated blog posts with more information on visiting both Venice and Burano:

Travel by train: Venice → Varenna, duration ~3-3.5 hours



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 resort town, 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. Can’t see Italy in 3 weeks without stopping by Bellagio!


  • 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

WHERE TO STAY: The Grand Hotel Tremezzo. Click here to see the latest prices.


Other unique and highly rated Lake Como experiences:

  • To learn how to make pasta and ravioli, click here

  • To learn how to make pasta from a soon-to-be-nutritionist, click here

  • To learn how to make pizza, click here

  • For a sailing adventure (you can’t not when in Lake Como!), click here


Please do not forget to document your once-in-a-lifetime holiday! Click here to book a Lake Como photoshoot inside a castle.

For more information on why I highly recommend a stop in Bellagio, click here for 5 reasons you should add it to your Italy itinerary!

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 its 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. Another option is as a day trip from Florence. Click here to see the latest prices.

CINQUE TERRE DAY TRIP: You can also visit Cinque Terre as part of a day trip if you aren’t able to make it an actual itinerary stop. For a Cinque Terre day trip from Florence, click here to see the latest prices. For a Milan to Cinque Terre day trip, click here to see the latest prices. From Pisa, click here to see the latest prices.

WHERE TO STAY IN CINQUE TERRE: I very highly recommend staying in an Airbnb! Click here for the 12 best Airbnbs in Cinque Terre.

WHAT TO DO IN CINQUE TERRE: Click here for a detailed itinerary of everything you need to do.

Other unique and highly rated Cinque Terre experiences:

  • For a hike followed by wine tasting (this is my kind of tour!), click here

  • For a sunset sailing tour with Prosecco and snacks, click here

  • For a fun kayaking tour, click here

  • To learn to make pesto in the birth place of pesto (how could you miss this?!), click here

  • To see Cinque Terre via e-bike, click here


Click here to book a private photoshoot with a local photographer.

I have a dedicated blog post on Cinque Terre, including everything you need to plan your trip! There’s also a detailed 3 day itinerary, telling you exactly what to do when. Click here to read it.

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. If you like wine, do not miss a day trip to wine country!


WHERE TO STAY: Portrait Firenze Lungarno Collection. Click here to see the latest prices.

Florence is an especially popular destination, so I highly recommend booking any tours or museums you are interested in in advance. Booking ours through Get Your Guide saved us a TON of time.

Other unique and highly rated Florence experiences (note, there is a lot to do in Florence. I did my best to narrow down this list to just the best options!):

  • PASTAMANIA! To learn to make pasta from the owners of a famous pasta shop, click here

  • For a Tuscan wine tour, click here

  • For a photo tour of the best views in Florence, click here

  • For a cooking class in the Chianti hills, click here

  • To taste pizza, drink wine, and catch the sunset, click here

  • To spend the day with a local winemaker, click here

  • For a Jeep safari through Chianti, including wine tasting and a buffet lunch, click here

  • To spend a full day relaxing at a luxury farm in Tuscany (this looks SO cool!), click here

  • To hunt for truffles in the Tuscan woods, click here

  • For the secrets of Parmigiano Reggianoa, a parmesan tasting at a local factory, click here

  • For a guided bike tour, click here


Again, unless you are traveling with a professional photographer, do not overlook a photoshoot! You will want these in the future, trust me. Click here for a highly rated option.

Travel by train: Florence (Firenze) → Naples (Napoli), duration ~3 hours.
Then by ferry or cab.
Click here for full details on how to get to Positano.



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 the perfect place to relax between Florence and Rome.

Since it is my favorite spot, I have many detailed blog posts covering everything you could ever need to plan your Amalfi Coast trip. I even have a new itinerary post telling you exactly how to spend each day you have there! Click here to read about the best Amalfi Coast itinerary.

Note: Positano can be a bit of a pain to get to, but it is incredibly worth it. Trains don’t go all the way there so you’ll need to hop on a ferry or hire a car. It can be confusing but luckily I’ve done the voyage many times so I write a detailed post about it to help you out! Click here for how to get to Positano.



WHAT TO DO ON THE AMALFI COAST: Click here for a detailed itinerary of everything you need to do and click here for the 8 things you absolutely cannot miss!

Some unique and highly rated Amalfi Coast experiences:

  • For an Amalfi Limoncello experience, click here

  • For a Vesuvius organic wine tasting and lunch, click here

  • For a guided Path of the Gods walk, click here

  • For a tour of the coast via vintage Ape (it’s a cute Italian car), click here

  • For an Amalfi lemon tour, click here


This is THE most beautiful place in the world, in my humble opinion. Get the photos! Click here for a highly rated photoshoot walk.


FOR WHAT TO PACKclick here.

FOR WHERE TO STAYclick here for the best hotels, villas, and Airbnbs.


FOR WHERE TO EAT, DRINK, AND WHAT TO DOclick here for everything you need to know about visiting Positano.

FOR THE PERFECT AMALFI COAST ITINERARYclick here for a detailed Amalfi Coast itinerary.




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.


  • AMALFI COAST - If you didn’t have time to add it on as a full stop, please at least do a day trip. It’s the most wonderful place on earth. Click here to see the latest prices.

WHERE TO STAY: Portrait Roma. Click here to see the latest prices.

Just like Florence, I very highly recommend that you book these popular items in advance through Get Your Guide. It will save you hours.

Other unique and highly rated Rome experiences:

  • To visit a 9th generation wine farm house for a one-of-a-kind wine, food, nature, and culture experience, click here

  • For a local food, history, and hidden places tour, click here

  • To learn to make handmade pasta with a local grandma (cute!), click here

  • To learn to make pasta on a rooftop in Rome (um, life goals?), click here

  • To visit a 16th century artisanal winery, click here

  • For a truffle hunting experience, click here

  • To learn to make pasta with a local professional chef, click here

  • To visit a family vineyard, click here

  • To tour Rome at night by e-bike, click here

  • For a Colosseum dungeons tour, click here

  • For a taste of Rome sunset bike ride, click here


Click here to book your Rome photoshoot.


Puglia — 3 nights

EDITOR’S NOTE/UPDATE DEC 2018: If you’re looking for another option before or after the Amalfi Coast and want something gorgeous and super low-key, Puglia is for you.

Puglia Italy, a region in the southeast corner, is a place it seems many have not yet discovered. It’s a charming Italian area full of whitewashed coastal towns and beautiful remote beaches. The public transportation there is pretty non-existent, so you’ll need to rent a car. But trust me, it’s a fun adventure!

WHERE TO STAY: Click here for where to stay in Puglia.


Other unique and highly rated Puglia experiences:

  • To see Polignano by boat, click here

  • To learn to make pasta in Lecce, click here

  • To learn to make pasta in Polignano a Mare, click here

  • For a walking tour and food tasting in Alberobello, click here

  • For a photo walk through Matera, click here

  • For a historical stroll through Lecce, click here

  • To learn to make Apulian cheese in Ostuni, click here

  • To buy, cook, and eat like a “Barese” in Bari, click here