My husband and I were in bed. It was 2am and I couldn’t sleep. I got on my phone and started looking up flight tickets to Italy. Having never traveled internationally, I was ready. I found 2 tickets and bought them. I didn’t tell my husband until two days later. Worried he would be upset that I made such a big purchase without consulting him. He was surprisingly ok with it after the initial shock.
Fast forward to now and I would do it all over again! Booking the tickets is one of the best decisions I’ve ever made. To say Italy is a magical place is an understatement!
I did a lot of research. Read a lot of blogs, articles, and travel magazines. I consulted with my FIL who had travelled to Italy a few years ago and with my close friend who is a travel connoisseur. I even reached out to my Instagram community asking for tips. Which I received a ton of. THANK YOU! But there were still some things I still wasn’t prepared for. Which brings me to this post.
In this post I’m sharing app recommendations, details of our stays in Rome, Positano, Florence, and Venice, tours I recommend, things I wish I would have known or learned along the way, and my favorite experiences. Let’s jump in!
Apps for Housing + Transportation + Tours
Airbnb (housing & tours)
Free Now (taxi – Rome & Milan only)
Omio (train, bus, flight)
Trip Advisor (tours/experiences)
theromanguy.com (tours/experiences)
Deciding where to go in Italy
Because I had never traveled to Italy before I knew I wanted to see as much as possible during our 11 day trip, but wasn’t sure what cities that included. I started by jotting down a list of places I wanted to go based on attractions which ultimately landed us in: Rome, Positano, Florence, and Venice. These are all classic (major cities) and all have access to the fast train.
Jumping around to four major cities was more expensive than I anticipated, but we were able to see a lot. If you can budget for it, I say do it! To give you perspective, we spent over $600 on train tickets and another $460 on transfers/taxis. And the cost of transfers are only from the first two cities. We chose to walk to and from the train stations in Florence and Venice to save money. Walking to the Airbnbs from the train station on our own was definitely more stressful. Google and Apple Maps are not the most reliable with directions in Italy. Especially in Venice. So we struggled to find them at first.
Booking an Airbnb in Italy
The Airbnb app has some great places with amazing views for a fraction of the cost of a nice hotel/resort. The downside, you don’t have a hotel concierge or free continental breakfast. But we didn’t really care about those things.
Once you’ve nailed down the cities based on the attractions/museums that is a must-see for you, start looking for lodging near those places. For example, the Trevi Fountain was a must-see for me while in Rome. Knowing that, I googled the address of the Trevi Fountain and searched the Airbnb site for places near that address. Honestly, my friend deserves all the credit for that. She is the one that actually did the research. She was basically my personal travel agent for this trip.
Book in advance. Months in advance. The closer you get to your departure date, the less options you will have. If you are on the fence about a place, still book it. You can get refunded 100% of the cost if you cancel 24 hours before check-in. Though I would cancel my reservation as soon as I knew I didn’t want to stay there to give the host an opportunity to post the listing again.
The Terrace from our Airbnb in Rome. We stayed directly in front of the Trevi Fountain. Prime location!
This was our view from the Airbnb in Positano. Dreamy to say the least. Our host was phenomenal and I will definitely book with him again if we make it back to Positano.
This was the view from our Airbnb in Venice. Right on the canal!
Tips to Booking an Airbnb
1. Look for “super hosts”. A super host is someone who consistently gets high ratings from those who have stayed in their house/apartment.a super host is someone who consistently gets high ratings from those who have stayed in their house/apartment.
2. Read as many reviews as you can about the place. I recommend sorting by most recent.
3. Contact your host via the app and ask any questions to better prepare you. We asked our hosts if they had a washer and dryer to ensure we could wash our clothes. We also asked about irons and ironing boards. Basically the more things they have, the less things you have to pack.
4. Figure out how to get from the airport or train station to the Airbnb ahead of time. We reached out to our hosts via the app. Two of the four hosts we had went above and beyond by scheduling transfers for us. We just had to pay the driver upon arrival of our destination.
Getting Around in Italy
Renting a car is an option, but the roadways might be overwhelming for some. All the signage is in Italian (understandably), the roads are considerably smaller than roads in the US, and overnight parking cost up to €40 a day if your Airbnb does not have designated parking, which most don’t. From my experience the only city that I recommend renting a car from is Florence so you can drive up the countryside and drive to Pisa (about an hour from Florence). For Rome, Positano, and Venice we walked everywhere. Just make sure to bring good walking shoes!
Note, to rent a car you are required to show proof of an international drivers license. My husband got his a few months before our trip. I believe the cost was $65.
If renting a car is not an option for you, there are several other modes of transportation: bus, taxis, slow train, fast train, shuttles, water taxis (depending on where you are staying in Italy), etc. For Venice you’ll need to take a water taxi if going to a neighboring island.
Tip: If you are staying in Rome or Milano download the “Free Now” app. It is very similar to Uber and less expensive than the taxis you see on the side of the road.
Download the Omio app if you plan to take the train. You can book your train tickets directly from the app and get update notifications pushed to your phone. This app was a game changer as we never had to go to the train station to buy tickets. I was able to do everything online. The train stations are very nice and similar to an airport. Lots of restaurants, cafes, and stores.
The picture below of me on the train headed to Venice. We opted for business class seats to Venice since it was a 3 hour train ride.
Note, the main train companies are .Italo and Trenitalia. We rode on both but I prefer Trenitalia over the two.
You also have the options of the bus and slow train. The bus is the most budget friendly of the options with the fast train being the most expensive. We opted for the fast train since we went from Rome to Positano to Florence to Venice. In hindsight, We should have flown into Naples instead of Rome and went to Positano first. Then Rome, Florence, and lastly Venice.
Good to know Before Packing for Italy
Bring a water bottle and fill it up at your Airbnb, hotel, or find a public water fountain. Water is not free at any establishment. We were charged anywhere from €2 – €4 for a single bottle and €4 to €8 for a decanter (around 1.5 liters) of still water at every restaurant.
FFP2 masks are required to enter the Vatican as well as all modes of public transportation (buses, trains, water taxis, etc.). The only place I found them was HERE. You can also buy them at any of the Farmacia’s (pharmacies) in Italy and for less than what I found on Amazon.
Pack a 20+ count of band-aids with you. The ones specifically for blisters. No matter how comfortable your shoes are you are going to be walking. A lot. You can find band-aids at any of the Farmacia’s but they averaged €11 for a 5 pack of the bandages specifically for blisters and even they didn’t last a day. We purchased the regular bandages at first but they rolled up and fell off within a couple of hours.
Shoulders and knees must be covered (for both men and women) to enter and religious establishment including Vatican City. Keep this in mind when packing.
Take euros with you. Most of the transfer/taxi services we used only accepted euros (or so they said). However, every restaurant, shop, and cafe we went to accepted Mastercard and Visa, but a lot of places did not accept American Express.
Check with your local bank about % rate of using your debit card. Same for credit cards. You will also want to call the credit card companies and your bank to let them know you will be traveling. Otherwise your card might get declined and flagged as suspicious activity.
Download my packing list as a guide to ensure you don’t miss anything.
Good to Know Once you are in Italy
If you want to take pictures of a popular attraction but don’t want a lot of people in the background, go at dawn. Your best shot is right as the sun comes up. People start flocking to the attractions around 7am (based on our experience). The below picture is me at the Trevi Fountain at 6:30am.
Look for “WC” stickers on the ground to find public bathrooms. Note, “WC” stands for “water closet”.
If you expect ice with your drink, ask for it.
Most sit-down restaurants do not open until 7pm for dinner. This was consistent between all cities we visited.
Reservations for restaurants are recommended. Pizzeria’s on the other hand don’t take reservations and some don’t even offer take-away (takeout).
Pizza is not served sliced in restaurants. You use a knife and fork. However, street vendors do sell pizza by the slice.
Don’t expect a waiter/server to bring you the bill. You most likely will need to ask for it.
Tipping is not expected. You can tip if the server, driver, tour guide, etc went above and beyond though.
Rome
Rome definitely put off that New York City vibe. Very diverse and full of people of all ages. Rome was the most congested of all the cities we stayed, but that should be expected. It’s the capital + a bulk of the tourist attractions are there.
We decided to venture out one morning very early so we could take photos without the crowds. It was well worth it!
We stayed 3 nights in Rome. I personally think that is enough. We were able to knock out all the big attractions with the Rome in a Day tour which is an 8hr walking tour hosted by The Roman Guy website. The walking tour included: the Spanish Step, Piazza Navona, the Colosseum, The Vatican, Sistine Chapel, The Roman Forum, and the Trevi Fountain. It was a lot for one day, but worth it. The Roman Guy site offers a lot of tour options. Some are half day if you are not up for 8 hours of walking.
Rome Recommendations
I do recommend the Rome in a Day Walking Tour hosted by The Roman Guy. The guide was so knowledgeable and spoke English very well. The tour was the first full day we were in Rome. I planned it that way for us to get comfortable with our surroundings (using the local guide) to better prepare us for the days we would be venturing out on our own.
If you are looking for the best pizza then you want to go to Piccolo Buco. It’s a 2 minute walk from the Trevi Fountain. They do not take reservations and there are no carry out or delivery options. But trust me when I say dining in is 100% worth it! I recommend going there around 6. You might have to wait in line to get in, but you’ll be glad you did. I’ve never eaten dough that good. Like ever. Note, by time we left the line to get in was exponentially longer. Which is why I recommend going early.
Go to Giolitti’s for the best gelato! To be honest, the gelato is good everywhere, but the gelato at Giolitti’s is extra good. They are open late so a great stop after a late dinner.
If you are not into tours then I recommend visiting the following attractions (all walkable if you are staying near or in city center): Spanish Step, Piazza Navona, Colosseum, Vatican City, Sistine Chapel, The Roman Forum, the Pantheon, Complesso del Vittoriano (universally known as “The Wedding Cake”) & Trevi Fountain. I recommend splitting these sites up between three different days if you are not in a hurry. I would set aside one full day to tour all of Vatican City (St. Peter’s Basilica, The Sistine Chapel, Vatican Museums, and Saint Peter’s Square). For day two I would visit the Colosseum, Roman Forum, & Complesso del Vittoriano. Then day three I would visit the remaining sites in this order: The Spanish Steps, Trevi Fountain, The Pantheon, and then the Piazza Navona. Then you can walk back to the Trevi Fountain to go to Piccolo Buco’s to eat the best pizza.
Complesso del Vittoriano aka “The Wedding Cake”
Trevi Fountain
The Piazza Navona at 7am. It was so peaceful and enchanting. The history behind the sculptor of this Fountain is notable. If you don’t take a guided tour of this site definitely look up the history of the Fountain and the artist.
The Roman Forum is near the Colosseum which is why I recommend visiting both in the same day.
The Colosseum was my least favorite place to go. The structure itself is magnificent, but the history behind it is dark. We had a guide telling us stories of gladiators which is very sad. I’m glad we visited it, but I hate the history of it.
St. Peter’s Basilica is truly beautiful along with the Sistine Chapel. The paintings and sculptures are so elaborate and breathtaking. This site was included in the “Rome in a Day” tour so we learned the history behind the Sistine Chapel, which is fascinating. Our guide told us that Michelangelo was actually a sculptor and not a painter but the pope, at the time, made him paint the Sistine Chapel. There is so much more history behind that so I definitely recommend a guided tour for Vatican City.
The Spanish Steps are truly beautiful. Especially in early morning when there are no crowds.
Positano
The breathtaking views are enough to bring you to Positano. The colorful houses that hug the cliff are nothing short of mesmerizing. Positano is the place to go to relax beachside during the day and end the night at the beachfront restaurants and bars.
This was the view from our Airbnb at dusk. The houses lit up was nothing short of breathtaking.
This is a video from our Airbnb. Every angle was magical.
If you are not flying into Napoli then I recommend taking the fast train to Napoli, then a transfer to Positano. The farthest the fast train goes to is Napoli Centrale train station (Naples). From there we had to get a taxi (Italians refer to them as transfers) for the remaining 1 hour and 24 minutes to get to our Airbnb. We went on a Friday which actually caused our taxi ride to be 2.5 hours long instead of the expected 1 hour and 24 minutes. The taxi (transfer) cost €130. We paid another €130 to be transported back to the Napoli Centrale train station to catch our next train to Florence.
If you’ve never been to Positano, be prepared to climb stairs everywhere you go. From our Airbnb we had 350+ steps just to get down to the beach.
It was overcast the first day we were in Positano, but it was still beautiful. The beaches weren’t made up of sand. It was more like black pebbles.
The weather was beautiful the second day, which worked out perfectly since it was the day we did the Amalfi Coast boat tour.
The water on the Amalfi Coast was so clear and beautiful.
We ended our second night with dinner at Aldo’s Seafood Bar and Grill inside the Le Sirenuse boutique hotel. I highly recommend their drinks. They were insanely good and the view was even better. We were hoping for a table at the ledge (for the best view) but were told that the tables with the best view were reserved for hotel guests.
Below is the view from the tables at the ledge of Aldo’s Seafood Bar and Grill.
On the last day in Positano, we walked to the shops that lined the main road.
Of all the places we stayed, Positano was the cleanest. I don’t recall seeing one piece of litter on the streets. It’s very well maintained and you won’t find a bad view. The town really is as picturesque as you see on Instagram. However, Positano was the most expensive place as well.
Positano Recommendations
A must-try restaurant on the main road in Positano is Mediterraneo (see picture below). The sea bass is out-of-this-world good. It’s so light and filling. Bonus, we were serenaded by a gentleman playing the ukulele.
I highly recommend booking a tour to see the Amalfi Coast by boat. I booked our tour via Positano.com for a half day boat trip along the Amalfi coast. The company is family owned. The captain was very good and the guide was very knowledgeable. She even prepared a plate of heirloom tomatoes, fresh cherries, nuts, and olives (all from her mother’s garden) and prosecco. I would say the boat tour was the highlight of our trip. The Mediterranean Sea is so clear and blue. The water was also way more salty than the Atlantic or Pacific oceans.
This was the view from our boat ride. It was a perfect day which made this excursion the highlight of our trip.
If you go to Amalfi try the lemon sorbet, which is a real lemon with scoops of limone and limoncello sorbet packed inside. It was so good but melts super fast!
Florence
The architecture of Florence is breathtaking. The most beautiful in Italy of all the places we visited (IMO, of course). Statues galore and where the Statue of David resides inside the Academia Gallery. If seeing the Status of David is on your to-do-list make sure the day you set aside is not Monday. The Academia Gallery will be closed. Based on our experience I recommend staying in Florence 3-4 nights to see everything.
There isn’t much of a nightlife that we could find, but there were plenty of shops. The streets are lined with a lot of Italy based shops along with shops that are well known in the US.
Florence Recommendations
The Duomo is a must-see. If you are staying in the heart of Florence you really can’t miss it. It is overwhelming large and equally beautiful.
Download the “RideMovi” app if you want to rent a city bike
See the Statue of David at the Academia Gallery.
Rent a car and drive up the Tuscany countryside. We did a half day wine tasting tour. The video below is from one of two vineyards we visited.
Most likely you will not be able to do all these things in one day, but I do recommend going to Cinque Terre and San Gimignano. Cinque Terre is lined with beautiful colorful houses. San Gimignano is a medieval town full of history, gothic architecture, and structures that date back to the renaissance.
IL Latini was a charming Tuscany style restaurant. I would compare it to a Brazilian steakhouse. A lot of meat. The spinach side is very good, but the dessert Meringata was to die for. So amazing. Order the Florentine steak. The dish was founded in Florence.
Venice
If I could sum Venice up in one word. Dreamy. Even filled with tourists. We didn’t plan anything in Venice like we did with the other cities and it turned out being one of the best experiences.
After getting settled in our Airbnb in Venice we decided to venture to a couple of places I had on the itinerary. We walked over a mile taking in all the sights.
We ended up walking to the famous Piazza San Marco and to, what is called, the most beautiful bookstore in the world. Below is a picture of me standing on the books. When we walked in, there was actually a line to walk up the books. It was awkward, but made for a beautiful backdrop.
There was a man sitting in the corner taking tips. From my understanding all the tip money is spent on food for the cats that you see roaming around the bookstore.
On our walk back from the bookstore we stopped at the market and bought snacks to eat on the terrace. We watched the gondolas and boats go by while we sipped Prosecco and ate. It was so calming to eat with only the sound of water in the background. Below is a video of the private terrace where we ate.
Below is a picture from the terrace at night. Our Airbnb in Venice was by far the most expensive per night, but well worth it with this view and privacy.
On the second day in Venice we decided to find a tour. The information desk at Line 1 on the pier next to Piazza San Marco offers half day tours for €25 a person to visit neighboring islands: Murano, Burano, and Torcello by water taxi. Compared to all the other tours we had taken, this was by far the least expensive. Definitely a better deal than I was able to find online.
Murano is known for its glass blowing factory. We watched the staff create a few items. It was pretty amazing to watch them. So much that I literally didn’t take any photos or videos. I was just in awe of the craftsmanship.
Torcello is the parent island to Venice. It is quaint and peaceful lined with a brick wall canal that will lead you to the St Mary Basilica. We stopped along the way to get a picture of me sitting on top of this bridge.
We also stopped at a restaurant on the way to the St Mary Basilica. The restaurant was surrounded by flowers and greenery. It was serene. See video below. My husband said they had the best cocktails from all the places we had been in Italy.
Burano was my favorite of the three islands we visited during our tour. It is known for their colorful buildings that line the canal and their woven lace. We bought Faye the cutest dress from a local shop.
During the tour we made a new friend who we ended up having lunch and two bottles of wine with. It was a wonderful way to end the afternoon.
The last day we were in Venice we got up super early and walked to the Piazza San Marco.
Just be warned the pigeons and seagulls are no nonsense and will literally take the food right out of your hand. Justin was eating a breakfast sandwich and a seagull flew right on top of him and almost got it.
The last thing we did before heading back to Rome was go to the Rialto Bridge. It was beautiful and the perfect way to end our stay in Venice.
Good to Know about Venice
Of all the cities we visited, Venice was the hardest to navigate by far. Whatever Google or Apple Maps says the walking distance is, multiply that by 2. And just be ok with getting lost or turned around. Both Google and Apple Maps both struggled with directions.
Using a public bathroom costs money. Venice was the only city that required anywhere from €1 – €1.50 to use the public bathroom. And you must have exact change.
Venice Recommendations
Don’t buy Gondola tickets online as they cost substantially more through Trip Advisor and Airbnb. I almost paid $250 for a private gondola ride. In Venice gondoliers were offering “private” rides for €80. Gondola rides are offered all day every day so you will not miss your opportunity.
Book a half day tour to visit Murano, Burano, and Torcello by water taxi. Below is a video I took from the water taxi. Tip, be one of the first to get on the water taxi so you can sit in the back for a picturesque ride to the islands.
Lineadombra is a must-try restaurant. It is on the neighboring island of Venice. You can actually walk to it from Venice or you can take a water taxi. I highly recommend booking a 7pm (when they open) reservation so you can get a table facing the water. The view itself is worth it, but the food is amazing! My husband is a chef and foodie so I surprised him with dinner at this Michelin star restaurant.
The tiramisu was so good, but the view was even better.
Go to San Marco’s Square at dawn to take in the beauty of the square with out the crowd of people.
Spray your legs and arms with bug spray before venturing out. My ankles got attached by mosquitoes.
And that’s a wrap for our Italy trip.
This trip is definitely one for the books. With it being my first international trip I would consider it a huge success! All the time planning was worth it. All of our airbnbs were in centralized locations which made for a better experience. Italy truly is a dream.
There are so many other beautiful cities in Italy. You really can’t go wrong once you get there. I hope you found this post helpful and insightful to assist you with planning your Italy trip. If you have any questions leave a comment or message me on Instagram @acarriedaffairdesigns
