I am lucky enough to call this my 4th trip to Italy (well 3rd if you’re not counting the voyage to American immigration as a real time since I was 5 and it was far from a vacation). George and kids had never been so our “eyes were bigger than our stomach” and we built a 6 stop in 16 day itinerary to hit some classic stops while also visiting places I had never been to (Tuscany and Lake Como).
Itinerary
- Direct flight from ORD to Rome and 3 nights stay at this Airbnb https://www.airbnb.com/rooms/3130679?source_impression_id=p3_1739052493_P3DWnNLadGIKI85Y
- Rented a car at SIXT, Rome Via Veneto Marriot Hotel and drove to Tuscany for 3 nights at Terra Antica https://terra-antica.com
- Drove to Florence and stayed 2 nights at https://www.airbnb.com/rooms/50098093?source_impression_id=p3_1739052645_P35INrz0sAQw6bKl
- Drove to La Spezia, parked at the train station and took train to airbnb in Riomaggiore for 2 nights https://www.airbnb.com/rooms/805547288147688013?source_impression_id=p3_1739052718_P3TkdZc6R05613KO
- Drove to Lake Como and stayed 3 nights at https://www.airbnb.com/rooms/32039151
- Drove to Venice, dropped off car and then water taxi for 2 nights Hilton Molino Stucky
Rome
Rome is a must in Italy because of all the history however it is not one of my favorite cities. George loved it more than I did and he would happily go back. The kids really were not impressed in part because we walked 20,000 steps a day and didn’t take a single bus/train/taxi. It was amazing to see the city by foot and we bribed them with gelato to make it through the days. I don’t think I am going to tell you anything you haven’t already heard about Rome so let me just leave you with this one recommendation, Dar Poeta for what we considered the best pizza in Italy. Osteria Da Fortunata is a really cute restaurant (multiple locations) to watch people make pasta in the window. We did the tours through LivTours both at the Colosseum and Vatican and we’re glad we did. We opted for private so that the guides could customize it for our boys to stay engaged. The reality is that they were not as engaged as we were, but we made it through. Don’t miss a view of Rome from Villa Borghese Gardens. If you go up the Spanish steps towards the park, and are lucky enough to catch it at dusk, the walk and view is absolutely stunning!
Tuscany
We spent 3 nights at Terra Antica in Montepulciano. It was perfection on every level. Mario, the owner is so warm and kind with every detail well planned. He even has a grass cutting Rumba style robot named Luigi. It was serene with unbelievable views, sunsets and a weekly farm to table style BBQ dinner. We did day trips to Siena and Pienza. Pienza is very small but if you’re close by, a few hour stop is worth it. Siena is more of a full day experience, just stunning and we loved Zest Ristorante and the wine da Fugnano, Vernaccia di San Gimignano. We took cooking class with Barbara Rocchi, babirocchi@gmail.com. The experience of cooking in someone’s home is by far one of the best memories of our trip.
Florence
I was in Florence once before in 2005 and I wasn’t as impressed as I was on this trip. We stayed in an AirBnb just over Ponte Vecchio. If I thought Rome was crowded, then I didn’t know what the definition of crowded really meant. In late June, Florence was almost hard to walk in because of the masses of tourists all walking through the same main streets. I am so glad I returned and there were many gems, I don’t have a desire to return. However, many people say it is their favorite city in Italy, so it really is eye of the beholder. A few spots we highly recommend:
L’Arte di Dory – Off the beaten path, best meal we had in Florence. Don’t miss the house ragu.
La Gelatiera – Across the street from the David (which you definitely need tickets to). BEST Gelato we had in Italy.
Leonardo Interactive Museum – We were there during a heat wave of 100+ degrees so we ran from museum to museum and this was a really cool stop, highly recommend.
Florence American Cemetery – this is the WWII memorial to honor those fallen in the Italian campaign. If you have a car and are driving in from Tuscany, this is a heavy but impactful stop and absolutely gorgeous.
Cinque Terre
On our drive from Florence to Cinque Terre, we stopped in Pisa. We had been warned not to park on the street with all of our luggage as to avoid it being stolen so we opted to have George wait in the car while I took the boys to quickly check out the leaning tower. It was cool for the photos, but could have skipped. We drove the car to La Spezia, parked in a garage in the train station and then took the train to Cinque Terre. This was easier than it sounds. My memories of Cinque Terre were purely magical and I was elated to be able to return with my family. I am so glad we went, but as the common theme of this trip, it was SO crowded and touristy. The charm I felt 20 years ago of seeing a place where many Italians visited for vacation was muted by overcrowded beaches, restaurants and shops. Again, I am so glad we went and we thoroughly enjoyed our time there but if you ask me where would I return, it would be Tuscany any day of the week over Cinque Terre. We stayed in Riomaggiore but I have stayed in Vernazza before and most people stay in the main town of Monterosso. Our beach in Rio was terrible, very rocky and hard to enjoy so if you are beach driven, stay in Monterosso.
Lake Como I fell in love. I felt a level of calm and luxury here that is hard to put into words. Interestingly enough, George felt that we only needed 2 vs the 3 night we spent there. It is extremely large and has an upside down Y shape. There is the Como branch on the west and Lecco branch on the right. Most populare is the Como branch.
A few key notes:
- It takes 5 hours by car to go around the lake and even longer by boat so don’t expect to cover even half of it.
- The town Como is at the base of the Como branch and is going to be your largest town.
- We drove so had freedom to move around. If you are at all open to renting a car, I highly encourage it but it’s not a must by any means.
- We stayed in Bellagio, “the pearl of the lake”. It is unique because this town is at that intersection of the two branches, aka the middle of the Y. We stayed in a beautiful Airbnb but one would absolutely need a car there so don’t recommend that. It was an hour drive from Como. The roads are developed but fairly curvy so if you get car sick easily, keep this is in mind. My husband drives stick and is experienced driving tough conditions in Greece (where he has family) so he found this driving to be fun.
- The good news is you really cant go wrong any town you pick and there are boats to travel from town to town if you want to avoid a taxi/bus etc.
Where to Stay:
- If you stay in Bellagio, this is considered the most luxurious hotel https://www.villaserbelloni.com. Personally I found Bellagio incredibly charming, crowded but not annoying.
- On the other side of the Como branch, this hotel https://www.villadeste.com came highly recommended to me by someone staying there at same time as us
- Our local boat tour guide told us that this is the absolutely nicest hotel on the lake, https://www.mandarinoriental.com/en/lake-como/blevio
- The other hotel I have heard people rave about is https://www.lhw.com/hotel/Il-Sereno-Lago-di-Como-Torno-Italy?gclid=Cj0KCQjwtamlBhD3ARIsAARoaEz9tD-bHr-OWa2o4uvG9Uzedx5uZ4asBVohoe6cmwoPMWYtQePsAzEaAkAAEALw_wcB
Como Eats:
- Il Gato Nero (The black cat) is a world famous restaurant about 15 minutes from Como town. George Clooney got it on the map and the word is that this is Mic Jaggers favorite restaurant. We made reservations about a week in advance for lunch but I suggest trying to make it sooner than a week to get dinner. If possible to be there for sunset and ask for a table by the ledge. We found the food to be deliscous, appetizers more impressive than the entres. It was the most expensive meal we had in Italy and probably didn’t need to order our 6 and 9 year olds their own main entrees If you decide to go, I will give you recs on dishes. The key here is you cant get there without a private driver because it is far up hill. What makes it unique is the stunning view, truly unmatched and absolutely worth it.
- Silvios is a gem we stumbled upon. It is in Bellagio, about 10 minutes walking from the main town and it is also a hotel. They make the local lake perch dish in a unique way. They lightly fry the fish and service it over rice and cheese with lime juice. Sounds a bit odd, but the presentation and taste is something we will all dream of. We met another family there and it was uninamously the best dish. Taxis are tough to get there so you would need to arrange private transfer in advance. We walked there but at night, asked them about a taxi and the owner (Silvio’s son) was kind enough to drive our family home! The pasta and other items also deliscous. Of course dinner comes with a view here as well.
Como Sites:
- Boat rides: Matiia owns his own boat company, info below and was an amazing tour guide. Request him if you can but he has others that work for him who could also take care of you. Lake Como Water Taxi di Galimberti Mattia lakecomowatertaxi.it +39 339 7644516. We did a 2 hour tour, stopped and looked at villas from the water. If you enjoy being on a boat, you could even book him for half a day and he can stop while you go see a villa or have lunch somewhere. We didn’t go inside, but hear that this is the best villa on the island. Star Wars and James Bond were taped here https://lakecomotravel.com/villa-balbianello-lake-como/
- There are boat taxis as well that go from town to town but be very careful to check if they make stops or go direct. For example, our friends took it from Bellagio to Como not realizing it made every stop and it took over 2 hours where direct it could have been under 30.
We stopped at Villa Olmo on our drive from Bellagio to lunch at Il gato Nerro. It wasn’t open inside but the grounds were impressive and we played a fun game of imagining what we would fill our Villa with if owned it
In Bellagio, there is a promenade that is not to be missed. Especially if you can catch it around dusk. They take such great care of it that it truly is a gem. I love travel so am more than happy to answer any questions, etc. You will have an incredible time!!
Venice
I am going to sound spoiled to say this, but I could have skipped Venice because I had already been there once in my life and that is all I think Venice needs. George and the boys hadn’t seen it so it was a must for our trip. We stayed at Hilton Molino Stucky which required a ferry ride from the main island. The hotel was beautiful and the rooftop pool was a great escape in the afternoon heat with an amazing view. Venice, in my humble opinion, has changed for the worse in 20 years. I feel that very little local charm is left and the experience of going there feels much like a Vegas style experience. The canals are charming, but now sitting here writing this post 2 years after going to Italy and after just visiting Amsterdam, I find Venice even less impressive from the standpoint of canals. We had a great time, don’t get me wrong and enjoyed some great views and food, and Murano island was a fun visit.
Pictures below are in chronological order of itinerary!













































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