Our trip through Italy was truly one of a lifetime! We started in Rome, then visited the ancient ruins of Pompeii on the way to the beautiful ocean-side town of Positano, then soaked in all the art and history of Florence before finishing our trip in Venice. We learned so much from our travels and made a handful of new friends along the way. We hope to come back again one day soon!
Quick Italy travel tips & things we learned:
- Be sure to pack comfy shoes for lots of walking! This is my top tip. I only rotated between two pairs of shoes the entire trip to keep packing light: 1 pair of good walking shoes and 1 pair of sandals. These were the shoes that I wore for my trip and they were super comfy and supportive:
Skechers GO Walk Flex Bright Summer Slip-On:
Earth Origins Savoy Siana Fisherman Sandal:
- It’s a courtesy in shops and restaurants to address people by either saying “Buongiorno” in the morning or “Buonasera” in the evening. Although many people speak English I think it’s helpful and even courteous to try to meet people in their own language in their country so learning some common phrases or terms is a great idea! You can even prep using apps like Babbel or Duolingo.
- When looking for restaurants and places to eat avoid the touristy traps in the main squares and either ask locals for their recommendations or find the best spots deep in the alleyways and cuts of the city.
- You should be able to make your way around using the Google Maps app!
- Aim to book either tours or skip-the-line passes in advance especially to the major monuments and museums because they are packed and you could be waiting 1 to 2 hours to get in! We didn’t wait in a single line and were so glad we were prepared. Get Your Guide is a great place to start booking!
- Try to pack as light as possible, especially if you’re taking trains and traveling to various cities throughout Italy. You just don’t want to be lugging too many heavy bags around (especially in uphill places like Positano or through cobblestone roads).
- There are a lot of fake gelato shops around, especially in the main touristy areas but you want to get the most authentic quality gelato with fresh and natural ingredients! So rule of thumb is to stay away from mountains of brightly colored gelatto. The authentic ones have more natural coloring. It ideally shouldn’t go higher than the steel container that it’s in. A helpful phrase I learned: If it’s high don’t buy. If it’s low, it’s good to go. If it’s bright, it ain’t right!
I have so so many other tips I could share. If you have any other questions feel free to ask in the comments below and I’d be more than happy to respond!
Travel Schedule
Moving on to the itinerary, I have to shoutout our travel agency Ciao Andiamo for taking care of planning every detail of our trip from the transportation, to the hotel bookings, tour scheduling and restaurant reservations- they are hands-down one of the best travel agencies in Italy and I’ve heard so many good things from other fellow travelers who booked through them as well. I would definitely go with them for any travel plans to Italy in the future!
Side note: Breakfast isn’t listed for each day because it was included at our hotel each morning.
Rome
Where we stayed: Rome Times Hotel
When we arrived in Rome it immediately felt like home! A beautiful historical blend of the ancient and the modern city. The stories of history interweave with metropolitan Roman life today and all the change it’s seen over the centuries. It’s very city-like and the pace actually reminds me of New York. I’m a nerd for the historical backstory of Italy but I’ll save those details for another time 
DAY 1: Flying into Rome and settling in
We landed in the eternal city and had a free day to roam around where we visited Trevi Fountain, the Pantheon, and explored new places to eat.
DAY 2: Ancient Rome Walking Tour
This day was our Ancient Rome Walking Tour and one of my favorite days where we got to explore Ancient Rome with our personal guide beginning at Michelangelo’s capitol square to the Roman Forum and the Colosseum.
Lunch: Taverna Romana (recommended by our tour guide)
Dinner: CiPasso Bistro
DAY 3: Free Day in Vatican City
This was a free day for us so we took it upon ourselves to visit Vatican City where we booked skip-the-line tickets in advance to Vatican Museums and the Sistine Chapel. I highly recommend booking tours & tickets to these places in ahead because it is packed and the lines are crazy. Even though we had to wait out the wildest thunderstorm once we got there, it was so worth it.
Lunch: at the Vatican Museum Food Court
Dinner: Antica Pesa
Positano | Amalfi Coast
Where we stayed: Hotel L’Ancora
Exploring the charming town of Positano together was an experience we’ll never forget. Our hotel at L’Ancora had the most breathtaking balcony view that felt like a dream to wake up to every morning!
DAY 4: Train from Rome to Naples & Pompeii Tour
On the way to Positano, from the Naples train station, we had our first escort to Pompeii where we ventured on to Bosco De’ Medici, a winery at the foothills of Mt. Vesuvius for lunch before arriving in the beautiful oceanside city of Positano! Then we had a private guided tour of the legendary ancient city of Pompeii preserved in time by the volcanic ash of Mt. Vesuvius.
Lunch: Bosco De’ Medici Winery
Dinner: L’Ancora Hotel
DAY 5: Private hands-on cooking class above the hills ofAmalfi
We had a private hands-on cooking class in the hills above Amalfi with Chef Fioré at Le Bonta Del Capo. Pairing our meals with delicious wine and beautiful sea views.
Lunch: Le Bonta Del Capo
Dinner: Da Gabrisa Wine Bar & Restaurant
DAY 6: Free Beach Day & Sunset Boat Tour
We had such a fun beach day with friends in Positano where the Mediterranean waters feel simply perfecto! This was probably one of my favorite days where we met new travel friends and had a free day to just eat, drink and hang under the sun at Da Ferdinando beach club, which I highly recommend. The main beaches are so crowded so we steer clear of them. Then we witnessed the most breathtaking sunset while cruising along the Amalfi coast with Positano Boats. This was such a romantic and magical experience that will stay with us forever. The perfect way to end our day in Positano!
Lunch: Da Ferdinando Beach Club
Dinner: Terrazza Cele
Tuscany & Florence
Where we stayed: In Piazza Della Signoria
Out of all the cities we were visiting on our trip through Italy I was MOST looking forward to Florence. Florence has always held a special place in my heart. The art, the food, the history have so much in store to learn and explore. And there’s just something magical about the streets, the bridges, and the breathtaking architecture.
DAY 7: Train from Naples to Florence Arrival
After getting in mid-day from the train station, we spent the rest of the day wandering around some of the major landmarks like the Piazza Singoria, The Cathedral of Santa Maria del Fiore and Ponte Vecchio over the Arno river. And of course you have to just get lost down the side streets and alleys (where you’ll usually find the best food away from all the touristy areas.)
Dinner: Spaccio Alimentare Firenze
DAY 8: Florence Highlights Walking Tour
One of my favorite things we did was rent a couple of bikes and ride through the streets of Florence to see more of the city and local areas. The bike rentals were just 9 euros for 4 hours at FloRent Bike. Later that afternoon we had our private walking tour with more details on the history of Florence, grabbed some of the best gelato in town at Perche no! (Why not!) and visited the magnificent Statue of David by Michelangelo, which actually blew me away. Out of all the cities we’ve visited Florence has felt the most at home to my soul.
Lunch: il Cantinone
Dinner: Cacio Vino Trallalla
DAY 9: Tuscan Villages & Winery Tour
This day felt like a dream. We visited the beautiful rolling hills of the Tuscan Countryside touring the medieval village of San Gimignano, which felt like a fairytale and then was escorted to a wine tasting & lunch at Bindi Sergardi’s vineyard. I honestly couldn’t wait to be in the quieter slower-living areas of Tuscany, it felt so peaceful and fulfilling to be here. 
Lunch: Bindi Sergardi Vineyard
Dinner: Santo Bevitore
Venice
Where we stayed: Aqua Palace Hotel
Venice was a dream and we’re falling in love with every corner of this city. From the gondola rides to the charming canals and colorful architecture, Venezia truly stole our hearts!
DAY 10: Train from Florence into Venice & private water taxi to our hotel
This was our free day to roam the alleyways and shops in Venice. We took our first gondola ride for about $40 each which was a big check off my bucket list. I think it’s equally important to plan for free days to just take in the city and wander around!
Dinner: A La Vecia Cavana (recommended by our gondolier)
DAY 11: Venice City & Canals Tour
We had a Venice city and canals tour spending the morning exploring the hidden treasures of Venice with our tour guide! We visited main sites such as Piazza San Marco, exploring local streets and artisanal shops, St. Marks Basilica, Rialto Bridge and a private water taxi ride through the Grand Canal. We took the water Taxi to Murano Island where we got to check out B.F Signoretti the glass factory to see the artistic glass-making work of Venetian masters. Later that afternoon we visited the Doge’s Palace and had a delicious dinner at Taverna La Fenice.
Lunch: La Brasiliana Snack Bar Caffetteria
Dinner: Taverna La Fenice
Venice is such a unique and lively city it’s definitely worth the visit!
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If you have any other questions about our trip or travel in Italy, let me know in the comments below! Arrivederci!
