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Italy Travel Guide — Two Week Coast to Coast Itinerary

It's finally here, the LONG awaited and highly requested Italy travel guide. Shaun and I went on this trip in 2019, so technically one year before I started this blog, but that didn't stop me from taking ALL the photos and mapping out an intense itinerary.

Italy has been to date my favorite trip that my husband and I ever went on together… it has everything we love about traveling— incredible food and wine (that doesn't give you a hangover!), endless history, and unbelievably breathtaking scenery. Shaun also proposed to me at the end of this trip, so it's safe to say Italy has a special hold over my heart.

Any-who, if you're planning a trip to Italy and are looking for all the best spots to visit, eat, and the top recommendations of what to do in each spot then this is the blog post for you.

We went for a little over two weeks and these are all the spots we were able to squeeze in on our trip and in this exact order— Naples, Capri, Rome, Florence, Cinque Terre, and Venice.

Here is a summary of what you will find below in case you want to skip ahead:

  1. NAPLES (4 days)

  2. CAPRI (1/2 day)

  3. ROME (2 days)

  4. FLORENCE/TUSCANY (2 days)

  5. CINQUE TERRE (3 days)

  6. VENICE (4 days)


PS, if you're new here my name is Stephanie and I am a wanderlustin, fashion obsessed, spicy margarita enthusiast. Follow me along on instagram @sugaredstilettos to see all that and a big dose of my daily life… I love new friends!


Naples might not be the first place you think to add to your itinerary for a trip to Italy because it often is associated with being a bit rough around the edges and thus overlooked by travelers as a destination for that very reason. I am not going to lie, I myself was a bit worried when we first arrived in Naples because it was definitely a bit grittier and more chaotic than I expected, but that feeling faded as soon as we began to immerse ourselves in the area. SO, if you actually know where to go and what to do, Naples is an incredibly captivating city with over 2000 years of history and tons of hidden gems worth seeing.


Castel dell'Ovo + Castel Nuovo

Two breathtaking fortresses both offering beautiful views of the area. Castel dell'Ovo is actually the oldest castle in Naples!

The Fountain of the Giant

This 17th century fountain called "Fountain of the Giant" is GIANT and quite impressive so go take a stroll by it. It's actually right around the same area as Castel dell'Ovo, so do both!

Piazza Del Plebiscito

Go for a stroll in the heart of Naples at this large pedestrian square overlooking the former Royal Palace.

Take a Ferry to a Nearby Island

There are actually three islands that you can travel to by ferry from the Naples Port— Capri, Ischia, and Procida. We decided on Capri which is defniitely the most iconic of them all and it was just as glamorous as I had imagined it would be. Full Capri write up below!

Pompeii Ruins & Horseback Riding on Mt. Vesuvius

Prepare yourself for an adventure filled day of history and nature because this tour will take a full day (7-8 hours), but if you can pencil this exact tour in I HIGHLY recommend it. Shaun and I met up with my mom and my bonus sister to do this tour because they were also in Italy visiting my bonus dad's family in Mondragone and we had such an incredible time. The tour is $150 a person and is linked here.

First you go to Pompeii, one of the most famous archaeological sites in the world, guided by an archaeologist. Pompeii was once a thriving ancient city that ended up being buried after Mt. Vesuvius erupted in 79 A.D., but the Roman ruins are still standing tall and are mesmorizing.

After you finish walking around Pompeii you'll be taken to a vineyard on Vesuvius called Sorrentino Vesuvio for lunch and a Vesuvius wine tasting. The vineyard is perched on a terrace with incredible views. Then you get to go on a guided horseback exploration of Vesuvius National Park which was my absolute favorite part of this tour. The views were unmatched and it's crazy to be riding admist the very volcano that brought the Pompeii civilization to an end all those years ago.

Galleria Umberto I

This is a beautiful shopping center enclosed by an intricate glass dome that is definitely photo worthy! It's a great place to walk around, get some shopping done, and gaze up at the beautiful details of the architecture.


If you didn't know already, Naples is the birthplace of pizza, so expect to find TONS of exceptionally good pizza restaurants at every corner. I personally don't really like pizza (I know it's extremely strange), but Gino Sorbillo is the epitome of classic Napoletana pizza. It is top ranked and with over 19,800 4.5 star reviews on trip advisor so I decided I had to try it out. It was DELICIOUS and will remain the only place I will eat pizza from. The personal pizzas are so massive that you have to eat them with a fork and knife. Prepare for a LONG wait, but don't miss out on this spot trust me!

This was actually our FIRST dining experience in Italy. We flew in late and walked down the street where we stumbled upon this restaurant. It was in this very moment that we realized how exceptionally delicous the pasta and wine was in Italy.

Calling all chocolate lovers! Gay-Odin is a famous chocolate shop that has been making DELICIOUS chocolate since 1894! They also have exceptional gelato here!


We actually rented an Airbnb (linked here) in the heart of old city center and it was in a great location to allow us to walk everywhere. It was a small + quaint Airbnb that had the cutest little balcony and for a long trip the price point was SO good. We only paid $420 for 4 nights, but be forewarned the bathroom is a tight squeeze! I will say it was VERY difficult to find where this Airbnb was located and it was night time so it was a bit stressful to say the least!

If I were to do it differently after walking around and familiarizing myself with the area more, I would definitely recommend staying in or as close to the Santa Lucia area as you can. It has beautiful views of Naples Bay and is within walking distance to the castles and ports. We grabbed a cocktail at the Grand Hotel Vesuvio and it was GORGEOUS. It's a five star hotel with a seafront location overlooking the Gulf of Naples and Mt. Vesuvius, but it is VERY pricey. When we come back to Naples I would love to stay here if we could swing the price tag. Another option that is only a 1/2 mile from the center square and is both affordable and so pretty is La Casa Sul Nilo.

2. CAPRI (1/2 DAY)

The island of Capri is located off the coast of Naples and it's full of glitz and glamour. No matter how much you have travelled, Capri will surely take your breath away. From the majestic geography of the island itself, to the winding streets and pathways that you can wander for hours… it is a MUST see. We took a day trip from the Port of Naples at Molo Beverello and we opted for the high-speed ferry which was around a 55 minute trip. I recommend looking up + booking your tickets here ahead of time! While we covered a lot of ground on our 1/2 day excursion, I would recommend staying 1-2 days here if you can so you can do all the things at a more leisurely pace!


Book a Boat Tour

This was on our list of things, but we actually didn't get to do this because we were so limited with time and one of the reasons why I recommend staying on the island overnight if you can. I can't even imagine how remarkable it is to cruise around the island, sipping a Spritz, and enjoying the scenery as you lounge out. I mean there is a reason visiting the Grottos is one of the most popular things to do when in Capri. There are three different ones, but I've had my sights set on doing a private tour to the Blue Grotto and it's officially on my bucket list!

Mount Salaro

HIGHLY recommend doing this because the views from the top are BEAUTIFUL, but if you're not okay with heights this might not be for you. You take a chairlift from the Piazza della Vittoria in Anacapri to the top of Mount Solaro which is the highest point on the island. The chairlift is a short ride up and the panoramic views both from the lift and from the top are so incredible.

On a clear day you can see all the way to Sorrento! PS you can also hike to the top if you prefer!

Gardens of Augustus

If you love botanical gardens and jawdropping panoramic views of the Mediterranean Sea then you will love the Gardens of Augustus.


The shopping that can be done in Capri is next level, so if you love some retail therapy then make some time to explore all the stores around the island.

Marina Piccola

Want to swim in the Mediterranean Sea? Marina Piccola contains two stretches of free beaches, but you definitely will need to get there super early if you want to get a spot!

Rent Scooters

Since we were already short on time as it was we wanted to be able to explore as much ground as possible so we rented a scooter for a few hours. Let me tell you though this is not for the faint of heart because the streets are narrow and the roads wind up the island with huge drop offs so keep that in mind!


This was the restaurant that we ate dinner at while we were on our day trip. Our table was outside on their patio that beautifully overlooked the glistening ocean. The orante blue place settings in and of themselves were something to appreciate here and the food was DELICIOUS.

This is often referred to as one of the most romantic restaurants in Capri with incredible views. You can actually specially request to sit at one of the tables on the panoramic private dining terrace for an ULTRA romantic meal, but will definitely have to book this WELL in advance.

A Michelin star restaurant with over 1,230 practically 5 star reviews on trip advisor that serves up some high quality exquisite meals. Ps. This restaurant is a far walk and you can't get there by taxi so keep that in mind!

Located right in the main piazza in the center of Capri, Piccolo is the perfect place to grab a cocktail and relax. It's a great spot to people watch too!


When we come back to Capri I would LOVE to stay at Caesar Augustus, Capri Tiberio Palace, or J.K Place Capri, but honestly SO many of the hotels look gorgeous. Here is a list of the top 15 hotels in Capri to browse through!


I don't know why, but I had several people suggest Shaun + I skip out on Rome because they didn't like it. If somebody tells you to skip Rome, please don't. It is one of the most unique + mesmerizing places I have ever been to in my life. This ancient city is truly frozen in time and is packed with endless history, magnificent architecture, and cobblestone streets that you want to get lost in. At the same time, Rome is also a modern metropolis with renowned Italian cuisine and a thriving social scene, so there is truly something for everyone.

As far as getting around the city, we walked everywhere because many of the key landmarks and attractions can be explored quite easily on foot. Comfy footwear is key!


Colosseum, Roman Forum, & Palatine Hall

The Colosseum is arguably the most iconic landmark in all of Rome, attracting more than six million people every year. It's the largest amphitheater ever built and is one of the Seven Wonders of the Modern World. The ancient and awe-inspiring architecture will take your breathe away and literally transport you back in time to the Roman Empire era. The best time to visit is when it first opens right at 8:30AM to avoid the crazy crowds and you're definitely going to want to pre-book tickets for this one! You can purchase "skip the line" self guided tickets here for $25, but I don't believe you have access to the underground level . They also have a guided tour which will give you access to the underground level of the Colosseum for $100 here, if you would prefer to have a guide with you!

The ticket will also allow you to tour Palatine Hill and the Roman Forum which were also so surreal to walk through.

Trevi Fountain

According to legend, tossing one coin into the fountain means you will return, tossing two means you'll return and fall in love, and three means you'll do all of the above and get married. Spoiler alert— we tossed three and my now husband proposed to me at the end of our trip. Soooo, throwing a coin in the iconic Trevi is a must when in Rome. PRO TIP— wake up super early to avoid the crowds!

Castel Sant'Angelo

Also known as the Castle of the Holy Angel this massive cylindrical structure was originally built as a mausoleum, but today it is a museum with an impressive view of the city.


A colossal building made of white marble is a sight to be seen and there is also a free museum inside.


The Pantheon is one of the most preserved ancient buildings in all of Rome and it is said to have been built 2,000 years ago. Once inside look up and you will find an opening in the dome that beautifully lets light shine within. Raphael the painter Is also buried inside.

Vatican City, Sistine Chapel, & St. Peter's Basilica

We booked a 3 hour semi private tour with breakfast at the Vatican and early access to the Vatican Museum and Sistine Chapel, linked here, and we loved it! We intentionally chose the first available morning tour at 6:45am because we were able to explore the Vatican before it opened to the general public which was awesome.


If you are in the mood for exceptionally tasty pasta then you need to make a reservation at Cacio e Pepe. For obvious reasons I reccomend trying the Cacio e Pepe!

Looking for a spot to grab a quick lunch? Pane e Salame has some of the tastiest sandwiches in all of Rome. Need another reason to convince you? 8,124 5 star reviews on Trip Advisor.

Another top rated restaurant Mimi E Coco is an awesome casual dinner spot. The gnocchi was SO good.

This was one of my favorite restaurants in terms of ambiance. We sat outside on the rooftop terrace overlooking the city of Rome and it was so romantic. The price tag here is more for the experience rather than top notch food, but with that being said we still had excellent meals! I definitely recommend ordering a pasta dish from here!

The bar here is awesome!! Truly such great and creative cocktails. Definitely recommend coming in for a pre or post dinner drink.


In order to explore everything by foot with ease you want to make sure you are staying somewhere centrally located or within/near the Centro Storico district.

Photo Credit: Maps Rome

Here is a list of 10 hotels in this location. We personally stayed at Hotel Navona and while it wasn't something I would consider luxurious, it was clean, had updated rooms, and was SUPER affordable. However, if I was coming back to Italy I think I would want to stay at the Hotel Palazzo Manfredi because you can literally see the Colosseum from their rooftop!


Florence is located in the Tuscany region of Italy and is known for their wealth of art galleries and museums, incredible shopping, and picturesque views from the many vantage points around the city. There is a reason this gem is called the "city of dreams". Florence truly just has such a timeless appeal to it and you can honestly feel the romance in the air here.


Duomo Santa Maria Del Fiore

The pink, green, and white marble exterior of the Duomo in and of itself is a sight to be seen because it is magnificent. If you're up for it and are not claustrophobic or scared of heights then consider pre-booking tickets to climb 463 steps up to the top to see the 360 degree views of the entire city from the top!

Pencil in Museum Visits

Florence is home to 60% of the world's most important artwork so making time to go visit the museums that house these pieces is a must! We went to both the Uffizi Gallery and L'Accademia on our trip and they were incredible. You can find famous Michelangelo's David sculpture in L'Accademia standing 17ft tall and works of art by Leonardo DaVinci, Raphael, Michelangelo, and Botticelli in the Uffizi Gallery. Tip— Be sure to pre-book tickets so you don't spend your day waiting in line!

Day Trip to Chianti, Toscana

30/10 recommend booking this tour that we did for your day trip! It's an 8 hour tour that takes you to the Chianti region where you begin your day at an old Tuscan farmhouse winery to learn about their winemaking process, sample a variety of wines, and eat the yummiest cheese plate from the winery's own dairy farm. You then had to the notorious butcher Dario Cecchini for lunch featuring four meat inspired dishes and the most incredible plate of vegetables and olive oil I have ever had. After lunch, you go to yet another winery for some more wine samples and before you head back to Florence you get to walk around the small town of Greve for some shopping. The exact tour we did is linked here.

Watch the Sunset at the Piazza Michelangelo

The Piazza Michelangelo is a square located across form the Arno River that offers the most beautiful views to admire the panorama of the city. It's the perfect spot to grab a pastry or a bottle of vino, find a spot to sit and watch the sunset while listening to the live music that is often played in the square. My husband and I actually danced to the song Perfect by Ed Sheeran and it's a memory I will never forget.


Grab a panini from here for lunch because they are incredible, huge, and super cheap! Hence the almost 5 star rating from over 30,000 people on trip advisor.

This was one of our favorite dining experiences. The exposed brick and decor was so charming making the ambiance on point for a romantic meal. The food here is also phenomenal.

This is a Micehlin star restaurant located the The St. Regis and is the perfect spot for a fancy night out. Whipping up some impeccable and creative dishes you will not be disappointed!


We stayed at the most incredible little Airbnb and I would recommend it 10x over because it was beautifully updated, the owner left us snacks and wine, and it was in a PRIME location in the center of everything. I will link it here for you! If you would prefer a hotel the St. Regis is an amazing property and definitely luxury at its finest!


Cinque Terre is definitely one of my favorite places that we visited out of all the ones I listed and I highly suggest checking it out if you can fit it into your itinerary! Cinque Terre is made up of five picturesque villages: Monterosso, Vernazza, Corniglia, Manarola and Riomaggiore which are all perched into the cliffs along the pristine Mediterranean Sea. The iconic pictures of the colorful many-hued buildings along the coastline that you see on Pinterest are what originally lured me in, but let me just tell you after being there… pictures don't even do this place justice.

If you are wondering exactly how you get to five towns that are located on a cliff my personal personally recommendation would be to take the train. It will likely take 2 trains to get here— 1 from your original destination to La Spezia and then from La Spezia to one of the villages. You can also arrive by plane, but you will still have to take a train once you fly in!

I would recommend staying a minimum of 2 days to really be able to appreciate Cinque Terre for all its beauty and charm.


Book a Boat Tour

This was my favorite excursion that we did the entire trip and while the exact boat we rented was a bit on the pricer side because it was privately chartered for just us, it was SO worth it. We were wined and dined all day while we were taken around Cinque Terre by sea. You can truly appreciate the beauty that surrounds you from the vantage point of peering in from the water.

Hike + Explore the 5 Villages

If you love to hike then prepare for a challenge because it's around 7 miles long and takes 5+ hours to hike, not including the time to explore each village as you pass through it. The trail we did is called the Blue Trail and we were able to do 80% of it because one of the villages paths were shut down for erosion repairs and it was INTENSE, but well freaking worth it. You do have to pay to use the hiking trails but it's only around 8 euros and you can purchase a Cinque Terre trekking card here.

If you don't want to hike the full thing and want an easier option the hike from Riomaggiore to Manarole is only around a 30 minute hike! If you don't want to hike at all you can still explore all 5 villages by using the train.

Wine Tasting

There are so many local vineyards in Cinque Terre perched on terraces throughout the villages. It's the perfect way to try some of the area's local wine!

Cooking Class

Something I SO wish we did, but Cinque Terre offers so many cooking classes to learn about how to make some of their top cuisines. If you're a foodie definitely recommend booking one!

Beach Day

If you want a true beach day go to Monterosso early and rent an umbrella to lounge out and spend the day soaking up the sun.


The food in Cinque Terre is very seafood centered given it's close proximity to the ocean, so if you're going to eat seafood anywhere in Italy let it be here!

This restaurant is a top ranked restaurant in Cinque Terre and is located inside a castle right by the sea with INSANELY good pasta and seafood. We actually had one of the tables outside overlooking the ocean and it was magical. Our waiter was also so full of life that it made the experience that much better. I had the squid ink pasta and my husband had pesto, both were unreal.

This was a restaurant I found on Instagram because of the insanely picturesque views and massive sized charcuterie boards and is probably the most popular restaurant in all of Cinque Terre. We went for lunch, but I personally would recommend coming for an early dinner and wait for the sun to set!

A beautiful spot to grab dinner and watch the sunset over Monterosso and the ocean.

A stones throw away from the ocean this restaurant is often recommended by the locals and serves up some delicious dishes.

Another restaurant with postcard views of the moored boats is an excellent choice for some fine dining.


As mentioned above, Cinque Terre is comprised of 5 different villages that each have their own distinct charm and character. Before I get into any reccomendations let me just reiterate that no matter where you stay in Cinque Terre do your research and find out how much of a climb it is to your accommodation. You might be met with pictures of a beautiful view, BUT if your Airbnb is located up multiple sets of steep stairs it's going to put a hiccup in your trip. Anywho let's talk a little bit about each town and where I personally recommend staying. I ordered each of them below according to how I would rank them.

  1. Monterosso is the largest and oldest town in Cinque Terre where the infamous pebble beach with the bright orange and green umbrellas is located. If you are a beach lover I would definitely choose Monterosso as your home base during your stay because they have a few different ones! It's also relatively flat compared to some of the other towns which makes carrying luggage here easier than most!

  2. Vernazza is actually where Shaun and I stayed in the most adorable little Airbnb, but it was a little bit of a hike up to get to hence my warning above! There was a BEAUTIFUL view of the ocean from our bedroom though. I will link our Airbnb here because if you can handle walking up a few flights of stairs with your luggage in had it's worth it if you choose to stay in Vernazza. Vernazza is a quaint town with beautiful views and sunsets. There is also a town square near the waterfront with a few restaurants to choose from and a small beach that's great for swimming.

  3. Manarola is home to many of the views plastered on postcards and has an easy walkable loop. It's the perfect place for somebody that wants to take in all the scenery without the intense hikes! The Instagram famous restaurant I talked about above, Nessun Dorma is here and it is an absolute must. You can also go cliff jumping here and swim in the small harbor!

  4. Riomaggiore is one of the larger villages so it probably has the most options as far as lodging, restaurants, and bars… but with that… more people as well.

  5. Corniglia is the only village that is not located near the sea as it is actually perched high up in the cliffs and thus VERY hilly. As soon as you hop off the train you are met with a long, steep staircase, so while I wouldn't recommend staying here I definitely recommend still visiting!


The iconic floating Italian city made up of canals, bridges, charming town squares, and winding passageways is truly a sight to behold. The only way to get around is either by water taxi or by foot, but luckily Venice is very walkable! You can get to one end of the island to the other in around an hour.

I will warn you though when you first arrive at the train station it's a bit stressful because you're not really sure of how to get to your hotel/Airbnb and tons of guys will walk up to you trying to sell you a water taxi ride to your accommodation. Do yourself a favor and take a little time to figure out the ferry or you will be spending around $70 euro on a water taxi like we did.

Venice will forever hold a special place in my heart because my now husband proposed to me here overlooking the Grand Canal.


Listen to the Dueling Pianos in St. Mark's Square

This is such a nice way to spend an afternoon or evening for an hour or two. This was definitely one of my favorite things we did in Venice because I just loved listening to the music and people watching. It's free to listen if you are standing , but you will have to purchase a drink or cocktail at one of the tables if you want to sit. It is very pricey, but we really enjoyed it. Just don't get the Bloody Mary tomato juice drink like I did, it is NOT good lol.

Doge's Palace

A Venice landmark with famous masterpieces by Titian, Veronese, Tintoretto and beautiful courtyards inside. Fun fact— we completely missed our tour here, so we actually never got to go inside. A thing to do the next time we come for sure!

Rialto Bridge

This is the oldest of the 4 bridges crossing over the Grand Canal and makes for a beautiful picture!

Lido Beach

This is a short ferry ride from Venice, but well worth it! It's such an awesome beach with tons of restaurants and places to grab cocktails along the strip.

Day Trip to Murano + Burano

This is a MUST while in Venice and another one of my favorite things that we did. The easiest way to get from Venice to Burano/Murano is to take the Vaporetto (water bus) from the ferry at Fondamenta Nova. The route 12 water bus which stops at both Murano and Burano.

Burano is best known for their ultra colorful buildings and for their beautifully made lace work.