A summer in Italy is on everyone’s bucket list! Spending two weeks is not nearly enough time to see all this beautiful country has to offer, but it will definitely give you an awesome taste of this country and leave you with some incredible memories. 🙂
In this 2 week Italy itinerary, you will be seeing 3 famous regions in completely different sections of the country. I think this gives you a great taste of what Italy is like from 3 different perspectives!
Something to be aware of if you are booking your trip… Italian summers are consistently busy. Not just with tourists, but from locals going on their summer holiday as well! Hotels, excursions, and restaurants book out MONTHS in advance! I booked our hotels pretty far in advance, and so many were sold out already!
2 Weeks in Italy Overview
1 Jam-Packed Day in Rome, Makes transferring to Amalfi Coast easier!
4 Days in Amalfi Coast with a Day Trip to the Island of Capri
4 Days in Tuscany – An off-the-beaten-path village in the Tuscan Country Side!
4 Days in Lake Como – The most beautiful place in the world!
1 Day in Milan, to travel home!
+ Optional Bonus Ideas!
Best Time to Go to Italy
Summer is by far the most popular time to go to Italy, but also the busiest and most expensive! Most people recommend traveling in the shoulder seasons, so late spring or early fall.
For this itinerary, I went late spring / beginning of Summer and it turned out pretty perfectly!
You don’t want to go in the middle of spring or fall because you will want the weather to be pleasant and warm for the destinations on this 2 week Italy itinerary. Especially Lake Como, which is pretty cold all seasons except for summertime!
5 “Must-Pack” Items for a Trip to Italy
Okay… I know this might be a basic travel must-have for some, but guys. If you don’t use packing cubes, let me change your life! If you are going on a long trip with multiple hotels, you NEED packing cubes!
They will make your life a million times easier! You can pack the packing cube with the clothes you plan to use for the first hotel, then pack another cube with the second hotel, and so on. So when you get to the hotel, you only need to pull out a packing cube instead of opening and closing your suitcase constantly!
This is ESPECIALLY important in Europe where the rooms are tiny AF 🙂
I have never been so complimented on sunglasses in my life and get so proud to tell people they are cheap Amazon sunglasses HAHA! These sunglasses are seriously so cute and I know I can just shove them in my purse when traveling and not worry if they get scratched or messed up!
Good walking shoes are a MUST in Europe! You walk everywhere and especially the three places you are traveling to.. there are a lot of stairs! Not having comfortable shoes will seriously make or break your trip.
These are my go-to, always have in my travel bag shoes! They are cute / casual enough to wear with jeans or a sun dress, but are comfy like tennis shoes. Also.. they don’t require any breaking in!
You can’t go to Europe without an adorable passport cover.. you just can’t!! This one is ADORABLE and is Europe themed, so fitting 😉
Lake Como rains… A LOT. But hey, that’s why it’s so green and beautiful there!!
I would recommend bringing a small, travel sized umbrella for your trip! I honestly always keep this in my checked luggage, so I am prepared when I am away.
3 Important Tips to Remember During your 2 Weeks in Italy
- The trains in Europe are not always on time or reliable! There are strikes that are constantly happening around Europe which can cause delays for weeks. Be prepared to roll with the punches and consider yourself lucky if you make all of your connections / make it to everything on time. 🙂
- The travel days are long in between the three destinations on this itinerary, but so worth it to see 3 vastly different regions of Italy! Be prepared to bring snacks & a few good books on each travel day.
- Bring a lot of sunscreen! I can’t tell you how sunburnt I got because the elevation is much higher in these locations than I am used to back home. I love these sunblock packets that I can just stick in my purse!
2 Week Italy Itinerary
Okay, time to dive right into the good stuff! This itinerary will give you all the nitty-gritty details on how to book your train tickets, recommended times to book them, what areas to stay in, what tours to do and not to do, and some “must-eat” food recommendations!
Here we go…
Day 1: One Jam-Packed Day in Rome
Your actual day one will consist of just getting to Italy, especially if you are from the west coast USA like myself 🙂 For this specific itinerary, I would recommend flying into Rome to check this amazing city off your bucket list!
Recommended Area to Stay in: Downtown, as close to the Trevi Fountain as possible! Like this hotel!
Hit the ground running with a self-guided walking tour of the city. First stop, The Colosseum! The Colosseum is about a 15 minute drive from downtown & opens at 8:30am. I would aim to leave your hotel around 8am to get there early before the crowds & tour buses begin arriving. You can buy your tickets in advance here.
After your mind is blown by the history of this city, I would grab lunch in the area and explore some shops. Some recommended lunch spots:
- Cafe Martini Roma – Views of the Colosseum from the Café
- Taverna Dei Quaranta – Family owned and a block away from the craziness of the Colosseum!
- Trattoria Pizza – Little pizzeria with an outdoor patio
In the afternoon, it is time for a little walking tour of the other famous sites in Rome. This is the main reason I recommended staying right in downtown (close to the Trevi Fountain) because you want everything to be close by since you only have one day here!
If you start at the Trevi Fountain…
- Stop 1: Trevi Fountain (this spot is always PACKED, be mentally prepared!)
- Stop 2: Spanish Steps (8 Minute Walk from Trevi Fountain)
- Stop 3: Pantheon (14 Minute Walk from Spanish Steps)
- Stop 4: Roman Forum (14 Minute Walk from Pantheon)
These are all free to enter and do not require an advanced reservation!
Day 2: Travel to the Amalfi Coast
Long travel day ahead!
The best way to get from Rome to Positano (where I stayed) is by train. The transfer would look something like this:
Rome –> Napoli P. Garibaldi (roughly 2 hours with one train stop) –> Taxi to Positano (roughly 30 minutes depending on traffic)
There is constantly trains running through this area because so many people are heading to the Amalfi Coast! I used Rail Europe to book all my train tickets because they had a ton of train times available and the website was very “American-Friendly!” 🙂
There are towns all along the Amalfi Coast that are all connected by either roads or ferry’s, so you can stay in any of the towns that look interesting to you! Positano is the most popular & most scenic town, where you will find the most excursions, hotels, restaurants, and shops.
Something important to note about Positano (where I stayed)… there are not really any roads in this vertical city. That means you have to bring your luggage up and down FLIGHTS of stairs to get to your accommodations and when it’s time to go to the beach, dinner, or shopping, you are taking flights of stairs again. If you are looking for a more laid-back and relaxing vacation, I would plan to stay in a town like Sorrento!
Like… not kidding… this is your view 90% of the time in Positano. The stairs were WILD.
Once you get to Positano, check into your hotel or Airbnb and grab some dinner!
Something I loved about Positano is how every restaurant and bar had insane views of the city / coast! There are tons of lesser-known restaurants that you should be able to walk into without a reservation, but if you want one of those bucket-list dinner restaurants (more details on that later), you will need to make a reservation WAY in advance!!
** peep my Espresso martini for breakfast because, ya know… #vacationmode
Day 3: Positano Exploring + Scenic Dinner
I always recommend planning a relaxing day after a long travel day! Plan to sleep in a bit, grab breakfast near your accommodations, and then do some good ole’ fashioned wandering! 🙂
There are so many shops in Positano, so if you like to shop.. this is the place to do it! There are ceramic hand painted shops EVERYWHERE, Limoncello tasting stores, beachy boutiques, and of course souvenir shops.
After you have done some exploring, it’s time to head down to the famous beach, Positano Spiaggia!
There are little bars and restaurants along the board walk and lots of chairs to rent out. Even though it’s quite expensive for a beach chair rental (roughly 25 Euros per chair), I think it’s worth it if you plan to stay for a few hours! Each set of beach chairs comes with an umbrella and a food / drink runner if you want to order stuff!
Plus, they have walkways down to the ocean so you don’t burn your feet on the hot pebbles. Remember, European beaches are not soft sand like you’re used to in America or Australia.. They are typically rocks or pebbles!
Pssst.. this photo was edited in ONE CLICK using my preset packs! Click here to check them out!
For dinner, plan to make reservations WELL in advance! Restaurants in Positano book out quick, especially all of the bucket list ones with a coastal view. If you are going to splurge on dinner at any location on your trip, it should be in Positano.
Here are some famous restaurants with some INCREDIBLE views:
Day 4: Day Trip to the Island of Capri
You can’t do 2 weeks in Italy without going to the Island of Capri, you just can’t! 🙂
The island of Capri was actually my favorite day on the Amalfi Coast! Something about this island is just so magical! 🙂 You can expect to see lemons the size of your head, rows and rows of hand-painted ceramic shops, towering limestone cliffs, hidden grottos and glistening blue waters.
There are ferry’s leaving from the Positano beach / pier constantly throughout the day. I would recommend maxing out your time on the island and taking the first ferry out (around 9am) and last ferry back (around 6pm). I used FerryHopper.com to look up ferry times & book tickets. 🙂
Even though I have an extremely detailed guide on how to plan the perfect Day trip to Capri, here is a quick overview…
Once you arrive in Capri, you can grab a taxi right by the marina and head to Piazza Della Vittoria. This is the small square where you will find tons of hand-painted ceramic shops, restaurants and your first activity: Monte Solaro Chair Lift!
This chair lift will take you to one of the highest points on the island where you will get draw-dropping, panoramic views of the island & the coast.
After you have explored Monte Solaro, you can grab lunch & do some ceramic shopping right by the chair lift in the Piazza Della Vittoria.
My recommendation for lunch is La Zagara, where you can dine under the lemon trees! Plus, it’s only a 7 minute walk from the chair lift! here are a few other good restaurants in Anacapri: Ristorante Il Solitario & Pizzeria Aumm Aumm.
For shopping, there are tons of different shops in this area!
In the afternoon, you will have plenty of time to book a boat tour to see Capri from the sea! The most magical thing about Capri are the beautiful rock formations around the island, hidden grottos, and sparkling blue water.
For reference, I booked a three-hour boat tour at 3pm and had plenty of time to get on the last ferry back to Positano (around 6pm).
I got a few quotes and read hundreds of reviews and decided on Capri Precious! They are a small, locally owned company who knows the island like the back of their hand. We were actually lucky enough to get the owner as our captain for the day. 🙂
Day 5: Amalfi Coast
Your last day in Positano is coming to an end, but don’t stress.. it only gets better from here! 🙂
On your last day, you will be venturing outside of Positano to see more of the coast and some nearby towns. And what better way to do so than signing up for a vintage fiat tour?!
TIP: There are so many amazing photo opportunities on this tour, so you will want to either book your tour a few hours before sunset or early in the morning to get the best lighting.
Pssst.. this photo was edited in ONE CLICK using my preset packs! Click here to check them out!
Day 6: Travel to Tuscany
The travel days will be long and exhausting, but it’s all worth it to be able to see such different landscapes of Italy!
The route to get from Positano to Tuscany will look something like this:
Taxi / Private car Transfer to Naples Train Station –> Chiusi Train Station (roughly 3.5 hours with one train stop) –> Rent a Car and drive 45 minutes to Bagno Vignoni
The actual Tuscan region is massive, you have endless options of where to stay that I think will make or break your trip. For me, I was looking for quiet, romantic, relaxing, and minimal amount of tourists! The other stops on this itinerary have a lot crowds, so I wanted a good break from that! 🙂
I truly cannot recommend enough the area that I chose to stay in: Bagno Vignoni / San Quirico d’Orcia. It is in the thermal area of Tuscany, away from the big cities / crowds, and near two famous wine regions: Brunello and Montepulciano.
For specifics, I stayed at the Adler Thermae Resort.. which was seriously the most amazing resort I have ever stayed at (no, this is not sponsored)! It had thermal hot spring pools, salt grottos, multi-day spa packages, excursions you could book through the hotel, and AMAZING food that was all inclusive with your stay! Every night the chefs prepared a new multi-course dinner and of course had an endless wine list of all the best wines from the area.
If the Adler is not in your budget (it is $$$$), I would recommend staying in the adorable nearby village of San Quirico D’Orcia! It is still in the same area, but the town is a bit bigger so you have some restaurant and shopping options.
From there, it is only a 45 minute drive to Bagno Vignoni area. Get ready for some wide open roads and incredible scenery!! 🙂
Day 7: Tuscany
Your first full day of Tuscany you will be a perfect mix of relaxing and exploring!
In the morning / afternoon, hop in your car and go explore some hillside villages near where you are staying! In the area that I recommended, there are medieval, hillside villages everywhere.
Since we stayed in Bagno Vignoni area at the Adler Thermae Resort, it was walking distance to the adorable thermal town of Bagno Vignoni! There are a few lavender shops in this town, restaurants, and gelato shops. This town is very small, but a must-see if you are in the area. It is just a small square of shops & restaurants, centered by a huge hot spring pool.
My favorite village of all was San Quirico d’Orcia! They have a large square with a church, tons of shops, picturesque restaurants, gelato shops, wine bars, vine covered buildings, and cobblestone walking paths. The streets are pedestrian only, which makes you feel like you are taking a step back in time 🙂
Lunch Recommendation: Trattoria Al Vecchio Forno for the best truffle pasta & beautiful vine-covered patio!
In the evening, you are going to visit the most epic sunset location in all of Tuscany! This place is a photographer’s paradise.. I mean, just look at the photos!!
Golden hour was taken to a whole new meaning in Tuscany.. watching those fields light up in gold when the sun went down is engraved in my memory forever! I would plan to get there about 45 minutes before sunset so you can see this viewpoint during that golden hour period.
Pssst.. this photo was edited in ONE CLICK using my preset packs! Click here to check them out!
Pssst.. these photos were edited in ONE CLICK using my preset packs! Click here to check them out!
Day 8: Tuscany
Even though there is good wine in all of Tuscany, a tour is a necessity because there is so much history to learn about the area!
I booked my tour with Get Tours, which they pick you up in a luxury vehicle, a local driver who speaks English, and they take you to lesser known, family owned wineries in the area.
For my tour, since I was based in the Bagno Vignoni area, we visited Brunello & Montepulciano Wineries, had a wine and food paired lunch, and visited a few famous cities in the area. I seriously could not recommend the tour enough!
There are tons of wine tours and wine drivers to choose from, all dependent on where you end up staying in Tuscany. If you are following my itinerary and staying in the Bagno Vignoni area, then you can use Get Tours like I did! 🙂
Some interesting things I learned about the Brunello Region:
- It is very regulated and very small region of Tuscany. If you are not grandfathered into the land and follow the exact practices of the Brunello wine, you are not legally allowed to call your wine a Brunello wine.
- All of the wine is aged and made the exact same as their neighbor. The only real difference is the quality of their grapes. They do not buy and sell grapes like they do at American wineries. Your grapes you grow are the grapes you use!
- Most of the wineries in the area are smaller, family owned wineries. When you go to taste the wine, you are tasking with the wine maker in their kitchen!
Day 9: Tuscany
Most people think of wine when they think of Tuscany, but there are so many things that Tuscany is well known for. Pecorino Romano cheese, fresh truffles, and natural hot springs to name a few!
Today, you will be getting a taste of the other things Tuscany is well known for, starting off with a dip in the all-natural hot springs!
If you are staying in the Bagno Vignoni area, there are so amazing local hot springs minutes from your hotel! I visited Terme Di San Filippo around 9-10AM and there were only a handful of locals taking their morning dip. No mounds of tourists, instagrammers, or drones flying around.. just natural beauty to be enjoyed! Isn’t it sad how rare that is now a days?
To get to these hot springs, you will drive to the tiny village of San Filippo, park along the narrow main road, and hike a very short and well marked hike to the hot springs. There are many different pools to enjoy, and the water is a bright Gatorade blue color! 🙂
NOTE: The most famous hot springs in Tucsany are the Saturnia hot springs, which is over an hour away from the Bagno Vignoni area. As a travel blogger, I am always tempted to visit all of the popular spots to be able to experience them for myself, but every blogger I have ever talked to said to AVOID them at all costs! Even if you get there at sunrise, there are instagrammers and drones everywhere and the hot springs are no longer clean or peaceful. I would recommend the Terme Di San Filippo hot springs instead!
In the afternoon, you can sign up for a cooking class, truffle hunting class, or just lounge out at your hotel pool!
For tours, I always search Viator.com or Getyourguide.com. They have local tours & big-name companies available with tons of photos and reviews! The best part is, you can search for tours that are closest to the area you are staying in.
For example, here is a great cooking class that is in the Montepulciano area where you get to learn how to make two types of pasta and tiramisu! 🙂
Day 10: Travel to Lake Como
Here goes another big travel day!
The route to get from Tuscany to Lake Como will look something like this:
Drive to Chiusi to return your rental car and board the train–> Varenna Train Station (roughly 4.5 hours with two train stops) –> Take water taxi or ferry over to Bellagio
TIP: I would try to leave early in the day, around 10am or earlier. You want to make sure you get to Varenna in plenty of time before the ferry’s stop each day, and always factor in time for train delays!
Hotels in Bellagio (and all of Lake Como) sell out very far in advance! I think it’s because most of the hotels in the area are very small with a limited amount of rooms. If you are thinking about visiting Lake Como during your 2 weeks in Italy, I would book your hotels sooner rather than later! Click here to check out hotels in Bellagio, Lake Como.
Day 11: Hopping Between the Mid-Lake Towns
This will be your first full day in Lake Como, and like I have said before… always plan a relaxing / go-with-the-flow day after a travel day!
Lake Como is truly one of the most beautiful places on earth. Home to towering green mountains, glistening blue waters that are dotted with classic wooden boats, beautiful villas every where you turn, hidden waterfalls, and flowers.. everywhere!
I wish I could put into words the beautiful smell of Lake Como.. it smelt like fresh flowers and clean air! 🙂
Pssst… If you are set on traveling to Lake Como during your 2 week Italy itinerary, be sure to check out my detailed Lake Como Itinerary!
If you are staying in one of the central towns on the lake (Bellagio, Varenna, or Mennagio), then it is super easy to hop between towns on the lake!
I would recommend trying to explore 2-3 other towns in the mid-lake region, which is completely doable in a day! If you are following my itinerary and are staying in Bellagio, the mid lake and fast ferry’s will get you across the lake quickly.
I would recommend going to Mennagio, Varenna, and Bellano. I included these stops in detail on my Lake Como Itinerary, so be sure to check that out for all the best things to see and do in those villages 🙂
Day 12: Visit the most famous villa on the lake: Villa Del Balbianello!
Villa Del Balbianello is a famous villa on the lake that was featured in many movies, including a James Bond & Star Wars movie! This cliff-side villa has incredible gardens that can be seen by boat! They close down the villa twice per week just to take care of the extensive gardens on the property and to host events.
Villa Del Balbianello is one of the most expensive wedding venues in Italy.. for good reason of course! Just look at this place…
To get to this villa, you will need to take the ferry over to the town of Lenno. Just pay the entrance fee either when you arrive or in advance here, and take your time exploring the jaw-dropping grounds! 🙂
After you visit this villa, there is not much else to do in this small village. I would plan to head back to Bellagio and grab dinner at the best spot in town.. La Terrazza at the Hotel Belvedere! Make sure you make your reservations WELL in advance.
Day 13: See Lake Como by Boat
On your last day in Lake Como, you will be seeing the lake from the best view.. by boat! This is where you really get to see all the impressive villas, hidden waterfalls, and colorful lake-side villages.
I have always had the ridiculous dream of being chartered around Lake Como in a vintage wooden boat… I know.. I am Basic B**ch!! 😉 I just felt like that was so unique to Lake Como and would make the boat trip so memorable!
Well, if you are a Basic B**ch like me, here are a few companies in the Bellagio area that have classic wooden boat tours:
- Bellagio Water Limousines
- Lake Como Boat
- Italian Allure Travel
- AC Boats
- Taxi Boat Varenna
- Menaggio Water Limousine
TIP: Make sure you ask your guide to take you to the famous Orrido di Nesso! Trust me on that one!
After your boat day, I would plan to grab some last minute souvenirs from shops in Bellagio, grab some gelato and walk along the lake, and enjoy the sunset at the most picturesque spot in all of Lake Como… Salita Serbelloni!
Day 14: Milan & Fly Home
The trek home is surprisingly easy! Milan is not too far from Lake Como and there are a few different options to get you back to Milan in one piece 🙂
You can go the same way you came by taking the ferry over to Varenna (or Como) and then taking the train to Milan. OR you can just hire a private car to take you directly from your hotel to Milan. For me, my flight out of Milan was too early. The ferry’s were not even running as early as I would’ve needed to leave! The only option for me was to hire a private driver to take me directly to the airport from my hotel in Bellagio.
Honestly… I would recommend this either way! You will be guaranteed to get to the airport on time and save you some hassle / stress on a long travel day. If you decide to go this route, you can ask your hotel or Airbnb host to set this up for you. 🙂
Want to spend a day or two in Milan? Here are some ideas on things to do:
- Duomo Cathedral – The famous Cathedral in Milan city center!.
- See “The Last Supper” mural
- Go Shopping in the Galleria Vittorio Emanuele!! Milan is the fashion capital of the world. Would be fun to see a glimpse of the upcoming fashion trends that are probably originating in Milan right now!
- Milan Street Food Tour
Whew.. that was a TON of information! Are you still with me?!
Here is the saddest part! Your amazing 2 weeks in Italy has come to a close. But you will have the best souvenirs to take home.. New destinations checked off your bucket list, amazing memories to share with your friends & family, and a new appreciation for a little piece of this world.
Italy is such an amazing country with historic sites, amazing wine, beautiful scenery, and of course… the FOOD! 🙂
I hope this 2 week Italy Itinerary takes you one step closer to booking the trip of your dreams and you have the best trip EVER! I am so excited for you! Can’t wait to hear all about your trip in the comments, please share with me all the travel stories!!
Traveling to Europe? Here are some guides I think you would love!
- Day trip to Capri – Along the beautiful Amalfi Coast in Italy!
- Lake Como Itinerary – A Romantic Long Weekend!
- 10 Day European Road Trip – Germany, Italy & Switzerland!
- 10 Day France Itinerary – See ALL of France in just 10 days!
- Champagne tasting in Champagne, France – a perfect day trip from Paris!
- Everything you need to know about visiting the Gorges du Verdon in France!
Thanks so much for stopping by!!
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