My Italy Trip Itinerary! Many of you asked for this so here it is! This shows you which tours we did, where we stayed and ate, some advice I would give and much more! Enjoy!
To start at the very beginning, we knew we wanted to go to Italy. We have never been and didn’t know where to start so I knew we needed help from a travel professional. I spoke to 4 different travel professionals and we chose Gia to work with. I spoke with and would recommend any of the following:
1) Catherine at Vitalia Tours. Email:
2) Luxury Travel: Eli Wagner with Wagner Bespoke Travel. Eli was great! I reached out to her later in the process so had moved farther along in the process with others but I have been using Wagner Bespoke Travel to book hotels. They are great and I would recommend them in a heartbeat.
3) Whirlaway Travel. I spoke with Denise Booth there. She was great too.. but for me, in the end, it was about who could work with me, have flexibility and who would ultimately put together the best custom itinerary and connect us with the best hotels, alongs with perks, bonus amenities and possible upgrades.
4) Luxury Travel: Gia with Embark Beyond. Her personal instagram is The Booking Club. Gia is who we ultimately went with. She worked hard at getting us as clients, getting to know us and was well connected with some of the hotels we wanted to stay at. I connected with her on a personal level. She’s Korean and has 2 daughters as well, knows her business and is completely buttoned up and professional. While on the trip, Gia went above and beyond and we were thrilled!
I highly suggest reaching out to and talking with a few travel professionals to see who you connect with best. When you’re ready to get started, you have a kick off call (or initial exploration call) to discuss your budget, things you want to do, which cities you want to visit and he or she will spend time getting to know you and your family so as to create the most perfect itinerary for you.
Once we had a first draft, we went back and forth several times to add and remove certain things. Since this was our first time traveling to Italy, we wanted a mix of touristy things, along with relaxing, shopping and exploring. We also wanted to see and visit as many places as we could. We ended up spending 3 nights in Positano, and then 2 nights in Rome, Florence and Venice; 2 nights in each city. We moved around a lot but it was worth it.
Here is our final itinerary down below. I ended up cutting some stuff out so we could have more free time to shop, eat and explore. We decided to start our trip in Positano and depart from Venice. Honestly, booking airfare played a role into where we started because we found better business class fares flying into Naples. We flew into Naples, Italy and started our vacation in Positano. Even with the Amalfi Coast, there are so many towns so you really have to decide what’s important to you and what you want to see. We decided on Positano because we wanted a private beach club, a small town that was close by and walkable and a town that was a boat ride away from Capri.
Once we landed in Naples, a driver picked us up and drove us straight to our hotel. I mentioned this on my stories and on social media. This was a big trip for us and my husband and I were celebrating our 20-year wedding anniversary so I selected some nice hotels to stay at. We stayed at Il San Pietro in Positano. I would stay there again in a heartbeat. From the hotel itself, the location, the service, the rooms, the food and the beach club, this hotel was perfect for us. We loved it and this hotel is considered one of the best hotels on the Amalfi Coast. Here is our room tour if you are interested.
Sunday July 19th:
Day 1: We opted for private drivers (and water taxis when we got to Venice) throughout our entire trip. There are high speed trains obviously but we decided to go the route of private drivers. We each had a large suitcase; purposely brought big ones so we could shop. So, if you are traveling by train, a smaller suitcase is probably better.
Arrival Location: Positano, Hotel Il San Pietro. We decided to take the first day to just explore the property, visit the beach club and relax a little. We did go into town (the hotel has a shuttle that takes you to the entrance point of the main town) for dinner and walked around a little. I did a lot of research and chose the restaurants on my own. We didn’t want to eat at super fancy places so, for the most part, all of the restaurants we ate at were casual; no dress code. At our hotel for example, they had the restaurant Zass (Michelin starred) with a dress code but we ate at Carlino instead. Carlino was their beachside relaxed dining restaurant. It was still super nice and the food was INCREDIBLE. If you were following my stories, this is where we ate the best octopus I have ever had.
Sunday night, we had dinner at Saraceno d’oro: a local spot in town. Super casual, loud and fun. The food was good; nothing spectacular. It was good to try this out but next time, I will look for something better.
The next time we come back to the Amalfi Coast, we will definitely stay here again and take advantage of what the hotel has to offer more: they have a complimentary boat cruise and wine tasting! I would also want to visit Ravello: “High-altitude mountain town known for quiet elegance, stunning sea-view gardens at Villa Cimbrone, and classical music festivals.”
Monday, July 20th: Boat Day to Capri!
Meeting Point: Il San Pietro private pier! This was one of the most expensive things that we did on this trip. We rented our own private motorboat, with captain, and enjoyed a beautiful day cruising along the stunning Amalfi Coast. Along the way, we stopped to jump into the water and swim. We then proceeded to Capri where we got off the boat, walked around, got lemon sorbet, gelato and went shopping. While we were exploring Capri, our boat stays close by and we just told our captain when we were ready to leave. We communicated with all of our tour guides and Gia via What’s App.
Then, we proceeded to Blue Grotto. Friends, if you can get here and do this, I think it’s 1,000% worth it. We got super lucky because our boat captain got us in the right line, and because we were only 3 people (my oldest was scared to get into the smaller row boat) we were able to get in a row boat right away and get in line to go into the Blue Grotto. We only had to wait 10 to 15 minutes in the row boat before we went inside. We were lucky that we were able to get in because shortly after we exited, they closed off the entrance because the sea became too rough. This experience was once in a lifetime. Amazing!
Someone had messaged me asking me what size the row boat was. Don’t get scammed by random people trying to rent you a boat saying they can take you into the Blue Grotto. As far as I know, the only way to get in is through official local rowboats operated by authorized rowers from visit Capri. Only they are permitted to take visitors through the tiny cave opening. The cave mouth is two meters wide but only roughly a meter high, so to enter visitors must board small rowboats which transport a maximum of four passengers. Your rower will tell you to lie completely flat on the bottom of the boat and will pull you in using a metal chain fixed to the rock wall. The entry ticket costs €18 per person (cash is needed for the floating ticket booth), plus an expected tip for the rower.
We continued around Capri to the Red Grotto, White Grotto, Green Grotto, and the Grotta Meravigliosa. We swam and then went to Nerano, for lunch at the seaside restaurant Lo Scoglio. This is where I had Spaghetti alla Nerano, a pasta dish invented in the village of Nerano, made with spaghetti, fried zucchini, provolone del Monaco, Parmesan, extra virgin olive oil, black pepper, garlic, basil, and salt. At the end of the day, around 5pm, we were dropped off back at our hotel and rested for a bit. Went to the beach club again and then dinner at Carlino at the hotel.
Tuesday July 21: free day/explore Positano
With two teenaged girls, we had to work in a free day to walk around, shop and eat gelato. We just spent the day exploring Positano and shopping. Then we went back to the hotel to freshen up and we had dinner at Da Vincenzo Positano and gelato at Yummy Gelato and Pastry. Highly recommend just walking through Positano at night and exploring. So beautiful!
Wednesday July 22: Travel to Rome
Departure Location Positano – Hotel Il San Pietro. Our driver picked us up from our hotel and we drove to Rome with just one bathroom stop. It was about a 3 hour drive. Arrival Location: Hotel Baglioni Regina
I didn’t show much of this hotel because I wouldn’t stay here again. Read my caption in the video link above. Gia had suggested Casa Monti in Rome but I – now I don’t really remember why– wanted to stay at the Baglioni. They were both 5-star hotels but I should have done more research and read more reviews. The rooms and beds are old and dated and we had issues with the bathroom showers and our A/C. It’s a very old hotel. Gia, if you are reading this, I deeply regret not going with Casa Monti. 🙂
Once we were settled in, we went out to explore and got some gelato and ate at Antico Forno Roscioli. These places were also on my list but we didn’t get a chance to go eat: La Carbonara, Osteria da Fortunata, Trapizzino (Roman street food- triangle pizza), Vitti Osteria, Tiberino Rome (artichoke), Eataly, Al Moro, Sciascia caffe (coffee shop), Giolitti (gelato), Forno Campo de’ Fiori, Ristorante La Matriciana dal 1870, Ivo a Trastevere, Da Enzo al 29, Roscioli Salumeria, an eatery serving Italian fare, plus a bakery, deli counter & wine shop.
VESPA TOUR, 7pm- 10pm
Side Car Vespa Tour! This was sooooo much fun! Highly recommend! This was a great introductory way to see the city and the following major sites: Quirinale, Trinità dei Monti (view over the Spanish Steps), Piazza del Popolo, S.Peter’s Square, Trevi fountain, Gianicolo (stop for pictures and stunning panoramic view over the Ancient City), we drove through Trastevere, we passed the Pantheon and ended the evening at the Colosseum. Was great to see at night. We just took photos outside.
We ended the Vespa tour by being dropped off back at our hotel, got some gelato and called it a night.
Thursday July 23: Rome
9AM – 1pm: Tour of the Vatican Museums: we had a private tour guide. The Museums contain an extraordinarily rich collection of precious arts, maps, sculptures and antiquities; however, the most breathtaking masterpiece is Michelangelo’s frescoed ceiling in the Sistine Chapel. At the centre of the Vatican lies the vast St. Peter’s Basilica, that you will enter by passing through the colourfully-dressed Swiss Guards. The present Cathedral is a beautiful mix of Renaissance and Baroque architecture, formed under the hands of masters such as Michelangelo. The stunning interior is an elaborate and detailed display of marble, mosaic, gilt and bronze.
Then we went back to the hotel to rest and went back out for our food tour.
5pm – 8pm: Trastevere food tour
“The culinary journey will take you to other important food areas in Rome: the Jewish Ghetto, Campo de’Fiori and Trastevere. Trastevere is one of Rome’s best-kept secrets. With its ivy-coated buildings and cobblestone streets, it is Rome’s chic and bohemian neighborhood. It is also host to some of the best restaurants serving typical Roman cuisine. The moving feast will take you to some of Rome’s most beautiful streets, visiting celebrated bakeries, delicatessens and wine bars. We want to introduce you to typical Roman specialties such as supplì, steaming rice balls oozing mozzarella, or pizza ‘al taglio’ where the baker cuts you a piece of pizza from a long strip. After walking and tasting sit and relax in a typical romantic trattoria in Trastevere. Taste different pastas accompanied with fantastic local wines. We also stopped for a parmesan, salami, soppressata food tasting.
This was our last day in Rome.
Friday July 24: Transfer from Rome to Florence with stop in Montepulciano
Stop in Montepulciano (approx. 3 hours)-
“Your private driver will meet you in the lobby of your hotel and accompany you to Florence. Along the way, you will stop in the charming countryside of Montepulciano, where you will visit a historic winery and discover the centuries-old traditions behind one of Tuscany’s most renowned wines. The experience continues with a hands-on cooking class, where you will learn to prepare traditional Tuscan dishes using fresh local ingredients. After the class, you will enjoy the lunch you have prepared, featuring authentic regional flavors. Following this relaxing break immersed in the Tuscan landscape, you will continue to Florence.”
Here is the hotel we checked into for Florence. Room tour. The Collegio Alla Querce. This property was stunning! would 1,000% stay here again.
And we had dinner at a local restaurant, just 5 minutes from the hotel: Osteria Pratellino
Saturday July 25: Florence
Private Tour: Highlights of Florence and Duomo: “an exciting walking tour of Florence. We will begin our journey in Piazza del Duomo, the religious heart of the city, where you can admire the breathtaking Cathedral of Saint Mary of the Flower. Its stunning façade, decorated with white, green, and pink marble, is a masterpiece of Gothic architecture. Towering above the city, Brunelleschi’s Dome remains an engineering marvel, while Giotto’s Bell Tower stands as a testament to Florence’s artistic legacy. Facing the cathedral, the Baptistery of St. John captivates visitors with its golden mosaics and the renowned Gates of Paradise, whose intricate reliefs narrate biblical stories. Afterward, we’ll head to Piazza della Signoria is the stunning, L-shaped main square in the center of Florence, Italy.
We then spent the afternoon walking around, shopping and eating. This is the day I went to All’Antico Vinaio, tried to go to Schiacciateria De’ Neri but they were sold out and Pino’s. Out of the two I tried, I did like All’Antico Vinaio more. But now, I’ Girone De’ Ghiotti is now on my list to try for next time .. and of course, Schiacciateria De’ Neri 18r!!
When we got back, Madeline and I enjoyed the hotel pool and some gelato. It was definitely nice to have pools (at most all of our hotels had pools except the one in Rome) during the summer. It was so hot! Jumping into the pool after walking around shopping and eating was the perfect way to end the day!
Dinner: We were all exhausted so just ordered room service and I actually ate the rest of my sandwiches for dinner this night!
I definitely wish we could have stayed in Florence longer.. the stay wasn’t nearly long enough!
Sunday July 26: Florence to Venice
Originally, we were going to stop in Bologna on our way to Venice. A month before our trip, I reduced the itinerary so we removed this stop (and a tour) from the list. I realized we were trying to do too much and I wanted to be able to spend more time in Venice just relaxing a bit.
We had a private driver pick us up and we drove to Venice. Once there, you have to take a water taxi to your hotel. Here’s a room tour of our hotel, The Cipriani in Venice.
We immediately went to the pool at the Cipriani and enjoyed a short pool day before getting ready to head out for dinner.
The first night, we had dinner reservations at La Piazza but there was a severe thunderstorm so we couldn’t make it there.
Monday July 27: Venice
10AM- 1pm
We had a private tour: “Step into the heart of Venetian history and mystery with a unique journey through two of the city’s most iconic and fascinating landmarks: St. Mark’s Basilica and the hidden treasures of the Doge’s Palace.”
This was the last full day of our trip so after the tours, we spent the day exploring Venice, walking around, shopping and exploring as much of the city as we could. We had dinner at Osteria da Carla, shopped some more, got gelato and headed back to our hotel, click here for the full day.
Tuesday, July 28: Leave for airport
The last day of our trip came too fast. For our next trip, I would visit less cities and spend more time there. Flying out of the Venice Marco Polo Airport was quite simple. It was pretty cool to arrive to the airport via water taxi. Full video here.
To get the details on the specific tours we did and to book private tour guides, please feel free to reach out to Gia with Embark Beyond. Her personal instagram is The Booking Club for your future travel needs! I highly recommend her!
If you have any questions, let me know!
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