2 Weeks in Italy: Rome, Tuscany, Naples & Sicily

Rebecca, Vanna, Jon, Omi & Dotty’s 2 weeks in Italy exploring the beautiful sights of Southern Italy!



St. Peter’s Basilica, Sistine Chapel and Vatican Museums Tour

The Vatican was probably my number one site to see while spending 2 weeks in Italy. Since there are thousands of people who visit daily, I would highly recommend booking a tour because it is truly skip-the-line, the guides are incredible, and worth the cost. I was SHOCKED to see the length of the line that had formed well before 7:00am! The tour was very organized and efficient at moving a group around in such a crowded venue. Our guide knew her history and facts and was informative. She was very personable and kept my attention throughout the entire tour. If I ever return to Italy, I will, without a doubt, go back because there are just so many elements I’m sure I missed. AND it’s an absolute work of beauty!

St. Peter’s Basilica, Sistine Chapel and Vatican Museums Tour | Rome | Italy      Vatican City, Sistine Chapel and Vatican Museums Tour | Rome | Italy

Roman Colosseum

We used the Roma Pass to enter the Colosseum. This reduced our tour cost because we already paid for access to the site. We did not pre-book a tour for this site because we had the Roma Pass. When we arrived, there were tour guides outside offering to escort our group through the Colosseum and said they could get us in without waiting in line. That was not the case…we still waited in the security line for some time. I enjoyed our tour guide. She was knowledgeable about the history of the Colosseum and the events that transpired there through the ages. The site was beautiful in its own right. I enjoy hearing the ‘local’ perspective.

Colosseum | Rome | Italy

Roman Forum & Palatine Hill

We toured/walked the Roman Forum & Palatine Hill on our own. I don’t believe a tour guide is necessary for this area because there are plaques that are very explanatory. It’s also so large that one can take it at one’s own pace since there is quite a bit of ground to cover here.

Roman Forum & Palatine Hill | Rome | Italy

Heart of Rome Walking Tour

We traveled with Rick Steves’ Italy guidebook during our entire 2 weeks in Italy…it was AMAZING! He included a short ‘blurb’ about each stop that was concise and helped us appreciate each one. (We called them our ‘Rick Steves Moments). We particularly enjoyed this walking tour (The Heart of Rome) because we got to experience a majority of and different areas of the city by foot. Since we listened to it on our own, it was completely at our own pace.  On the tour was: Campo de’ Fiori, Palazzo Farnese, Corso Vittorio Emanuele II, Pasquino Statue, Piazza Navona, The Pantheon, Piazza Capranica, Parliament & Obelisk, Piazza Colonna, Via del Corso & Galeria, Trevi Fountain, Aqueduct Ruins, Immaculate Conception Column, and Spanish Steps.

Pantheon | Rick Steve's Heart of Italy walking tour | Rome | Italy


Roman Gladiator School

This was so much fun! We learned what it takes to be an ancient Roman gladiator at the Gladiator School of Rome. We had an extremely hands-on lesson from our instructor who is part of the Historic Group of Rome. He taught us how to fight with authentic weapons of the time while wearing a traditional gladiator tunic and belt. The class was a unique and interactive and we learned about ancient Roman history, sports and culture. At the conclusion of our lessons, we were given traditional Gladiator names what was a lovely touch. Our instructor made sure we were comfortable with all the activities .  This was one of our most memorable experiences during our 2 weeks in Italy!

Roman Gladiator School | Rome | Italy

Roma Pass

We purchased the Roma Pass for 72 hours since we would be traveling around and touring the city. The passes offer transportation and museums free of charge, as well as reductions for events, exhibitions and tourist services in Rome. Included in the 72 hour pass is free entry to the first 2 visited museums and/or archaeological sites of your choice. Free admission includes the exhibition held in the museum. This is something I would recommend purchasing because you know you have access to the metro with the pass.  Once you figure the trains out, you can get around super easy.


Trieste Pizza

Trieste Pizza was the first pizza stop when we arrived. We knew we had to start off our 2 weeks in Italy with pizza!  It was in the neighborhood near our Airbnb rental. Definitely recommend. The owner happened to be there when we arrived to eat and he gave us his recommendations as well as a little history of Italian Pizza! They believe in the personal touch.

Mastro Ciccia

We ate at Mastro Ciccia on our Heart of Rome Walking Tour. Again, we stumbled upon this little treasure. The service, atmosphere and wait staff was all amazing. They made recommendations that did not disappoint and made sure we ate a meal we would never forget! Together, the table had traditional pasta, tortellini, pizza, tiramisu, wine and to top it all off, limoncello.


We also discovered Giolitti on our Heart of Rome Walking Tour.  It was THE BEST gelato in Rome and also one of the oldest gelaterias in Italy!!  Definitely one of the best gelatos we had during our 2 weeks in Italy.

Giolitti | One of the oldest gelato shops in Rome | Rome | Italy


We stayed in an Airbnb (QUATTRO CANTONI) in the Monti District, near the Colosseum. It was the perfect location to all of our tours and activities. The Airbnb was lovely.  It was big enough for a large group of people and the owner had a guide of their recommendations for the area for what to do and where to eat. Definitely helped us navigate the area! Airbnb is great option to find rentals when traveling. Here, you’ll find a large range of unique accommodations to rent in Rome, and most of the places on Airbnb are far better value for your money than traditional hotels. Though my favorite part about it is you really feel like a local when staying in a new city! Sign up here to get $40 off your first visit!


We used all forms of transportation while here…Metro, Uber, and Walking.  The metro was easy to figure out.




Next stop during out 2 weeks in Italy was the Borgo di Castelvecchio, near Montepulciano. It’s a working winery, and while there we toured the grounds, relaxed, and took in the beautiful scenery…it did not get old. The sunsets were to die for.

Borgo di Castelvecchio | Montepulciano | Tuscany | Italy

Borgo di Castelvecchio | Montepulciano | Tuscany | Italy


In Montepulciano we walked the streets of the city from the beginning to the end (Fortezza di Montepulciano). We took in more amazing views, ate more lovely Italian food, sampled more gelato, and toured the cellars of the Contucci Winery. This was a small town and a quick trip from the Borgo. I would put this as a ‘must visit’ item if traveling to the area. I bought a few bottles of wine to bring home since they were so good. I’ve been looking here in the US for them.

Montepulciano | Tuscany | Italy



Trattoria La Buca delle Fate

We traveled to Pienza and had THE BEST food and service at Trattoria La Buca delle Fate. We had traditional pasta that was to die for. You can’t go wrong with anything on the menu. Dessert was tiramisu.

E Lucevan le Stelle

In Montepulciano we ate at E Lucevan le Stelle. I had the ravioli with fresh Parmesan and a glass of wine. The waiter helped me pair the wine with my dish…and it was perfect! He knew his stuff!


Borgo di Castelvecchio

We stayed at the Borgo di Castelvecchio. AMAZING views and the accommodations were adequate for the farm-style winery. It is a family-run winery that ensured our stay was comfortable.  They provided a lovely spread of meats, cheeses, breads for breakfast.


We drove our rental car from Rome to Borgo di Castelvecchio. It was fairly easy to navigate here. I will say the roads are very curvy and narrow, but rental car was the best option for getting here. The Borgo did not have any transportation from the train station.



*Disclaimer* I personally was not very impressed by the atmosphere of Naples at all. The people were not very friendly. If you’re spending 2 weeks in Italy, I would spend less time here.  However, I will say that our tour guides were the friendliest people of all. We did a few day trips in the surrounding area outside of the city.


This was just amazing. Pompeii was a city buried in ash and lava after the eruption of Mount Vesuvius in 79 A.D.  The site is actually fairly well-preserved and features excavated ruins that you can walk through. To see what was left after such devastation and the passing of time was awesome. All I could do was take it all in.

Ruins of Pompeii | Naples | Italy

Mt. Vesuvius Climb

I climbed to the top of Mt Vesuvius!! And I recommend anybody does it. The view of Naples is gorgeous-the water and the cities are breathtaking! You don’t quite understand how big the world is until you make this climb.

Climb Mt Vesuvius | Naples | Italy

Amalfi Coast Boat Tour

Instead of driving the Amalfi Coast, we took it in by boat. We even got to swim in the Mediterranean! By far THE BEST part of Naples. This was an all-day trip through Travel Amalfi. Our captain was the best guide. He was a local of Amalfi and gave us a very colorful and personal history of the area. He made sure we saw what we wanted to see.

Amalfi coast boat tour | Travel Amalfi | Naples | Italy

Amalfi coast boat tour | Travel Amalfi | Naples | Italy


Pizzeria Port’Alba

Pizzeria Port’Alba was one of the first pizza restaurants of Naples. And delicious! These were large pizzas that 2 people would have no problem sharing.

Hosteria Napoletana

The food and atmosphere at Hosteria Napoletana were wonderful. The ENTIRE restaurant made us feel welcome and part of the family. We even got to put our pizza in the brick oven. Very authentic Naples pizza and Napoli cuisine.


We stayed in an Airbnb Casa Caturano. It was a cozy and beautiful flat. Quite literally a hidden treasure in the Spanish Quarter of Naples.  Airbnb is great option to find rentals when traveling. Here, you’ll find a large range of unique accommodations to rent in Naples, and most of the places on Airbnb are far better value for your money than traditional hotels. Though my favorite part about it is you really feel like a local when staying in a new city! Sign up here to get $40 off your first visit!


We either walked or took a taxi from our Airbnb to our destination.




Sicily was the last stop on our 2 weeks in Italy!  We stayed in Palermo and took day trips all over Sicily.

Caccamo Castle

This castle is about an hour’s drive from Palermo. The Castello di Caccamo is among the largest and best preserved Norman castles in Sicily, and one of the largest in Italy. It has gorgeous views of the Tyrrhenian Sea and surrounding mountains.

Catania/Mt. Etna/Taormina tour

Catania is about two and a half hour’s drive from Palermo. We used the Excursions Etna Tour Company for our full day tour of the mountain and craters. Our tour guide was one of the best we experienced while we were in Italy – he was friendly and knew the answer to our questions. (I think that is partially because he grew up on the mountain so he has had first-hand experiences. Definitely added to the experience.) I would book this tour again. Included in the tour was transportation to and from Mt. Etna (an active volcano!), tour of the lower craters, Vena Aetna wine and olive oil tasting, and 2 hours or so in Taormina. There was an additional cost to ride the gondola to the summit. We opted to stay with our tour guide…which was not disappointing at all.

Catania/Mt. Etna/Taormina tour | Excursions Etna | Sicily | Italy

Mt Etna

In Taormina, we walked around the cliff-side city and toured the Teatro Antico di Taormina, an ancient Greco-­Roman theater still used today. It, again, had gorgeous panoramic views. We, of course, could not leave without sampling the local gelato.

Catania/Mt. Etna/Taormina tour | Excursions Etna | Sicily | Italy



This city is about an hour and a half drive from Palermo. Here we did a wine tasting at the Firriato Winery. I would book this again, for sure. All the wines were lovely and there was a variety for everyone in the group. Our sommelier was very knowledgeable of all the wines we tried…he described all of them perfectly as well as what was the best food pairing. I brought a bottle of the Ribeca wine home…my name is Rebecca – how could I not?!

Firriato Winery | Trapani | Sicily | Italy

Firriato Winery

Firriato Winery | Trapani | Sicily | Italy

Segestra’s Greek Temple

We stopped in Segesta on our way back from Trapani to tour the Greek Temple on the mountain top. It was a very interesting self-guided tour and took about 45 minutes to an hour.

Segestra’s Greek Temple | Sicily | Italy


We stayed at the Airbnb Addaura Reef House in Addaura Mondello Palermo. It was centrally located to all of our destinations and activities. I would recommend this rental because the owner was such a welcoming host. She made sure we were taken care of during our stay and make sure we saw Palermo for its true beauty. Airbnb is great option to find rentals when traveling. Here, you’ll find a large range of unique accommodations to rent in Sicily, and most of the places on Airbnb are far better value for your money than traditional hotels. Though my favorite part about it is you really feel like a local when staying in a new city! Sign up here to get $40 off your first visit!


We had a rental car during our stay in Palermo.


2 Weeks in Italy Travel Tips:

Weather – The weather was perfect in September during our entire 2 weeks in Italy. It was warm during the day and cool in the evenings. I always carried a light jacket or sweater if we went out after the sun went down. I would definitely pack a variety of clothes/layers.

Language – Most sites or tours we visited had an English-speaking guide. We did not have any troubles communicating while in Rome or Tuscany.  We had a bit more communication barriers with the locals in Naples, and the most communication barriers in Sicily.  I think the further south you get in Italy, the more ‘authentic’ you get with the language. I probably should have learned a few more Italian phrases before spending 2 weeks in Italy to communicate better with the locals.  But for the most part, we were still able to communicate just fine.

Voltage – Voltage converter/adapter for Italy is necessary. If you bring your styling tools, ensure you have the proper converter.

Other Travel Guides you might Like:

Cinque Terre & Rome, Italy – Rome to Cinque Terre: Hikes, History & Pasta

Tuscany, Italy – Must See Towns & Things To Do in Tuscany

Paris, France – 5 Days in Paris: Explore All the Iconic Paris Sights

London, England – The Ultimate 5 Day London Itinerary

Oia, Santorini, Greece – Guide to Oia: Where to Stay in Santorini

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2 weeks in Italy: Travel guide to visit Rome, Tuscany, Naples & Sicily. Best activities, restaurants & hotels. | wornpassports.com