Portofino Italian architecture on water

Last month I went to Italy for FIVE super short, but overly productive days. The trip started with the Hugo Boss show for men’s fashion week, and led me to explore more of Italy on my own. I had never been to Florence before so I didn’t really know what to expect. In the past I’ve gone to Milan a ton and Venice once, so this was my first time seeing more of Italy.

Italian seafood with oysters

Frame denim by Hertz sign

Everyone told me I would LOVE Florence and want at least three days in the city. I sadly have to disagree. Florence was magical, but it’s really busy and feels super city, with buildings everywhere, tons and tons of people and it was HOT. I actually walked around so much one day and didn’t stop and didn’t drink much H2o and fainted from heat stroke. 100% Learned my lesson for the remainder of the trip. JK I fainted a second time. TRUE LIFE. I personally prefer Venice, Italy just because I like to be by the water and in nature. Something that people did not lie to me about was how insanely delicious the food was! MIND BLOWN. Seriously some of the best food I’ve ever had in my life.

Portofino Italian architecture on water

Half eaten Italian pizza

Street musicians in Florence

Italian breakfast pastries and tea

In Florence I stayed at Hotel Cerretani by Sofitel. Perfect for three days in Florence, also central location for walking everywhere since that’s pretty much the only way to get around. You can take also take taxi’s if you need to go somewhere far. If you need to use Taxi’s you can DL the Taxi app.

Italian architecture and palm tree

Recycled Italian pizza boxes in city

Crumbling Italian architecture and corner store

Portofino Italian architecture on water

Food in Florence. The easiest way to do this is for me to start firing off places and what I got to eat at each place. 13 Gobbi, they’re known for their “Bistecca all fiorentina”, but I didn’t want meat that night so I had the pasta, which was BOMB, called “Rigatoni 13”. For lunch I ate at The San Lorenzo Market, which is a MASSIVE two story farmers market with everything from cured meats and cheese, to wine, to fish to you name it, they have it! I had some of the BEST fish of my life. I ordered one piece and literally went right back up to the counter and ordered a second. Ate both. Every last piece. The fish joint in the market was called, Pescheria Rosellinni, and its 11 euro for the freshest and most massive piece of Branzino. The best panini I’ve ever had in my life also happened in Florence, called All’Antico Vinaio, I had the most popular one, Schiacciata con sbriciolona. It has cream of pecorino and prosciutto inside baked focaccia, ALSO MIND BLOWN HERE. Irene, at the Hotel Savoy was great for lunch in-between walking around, I did this twice. I had Aperol spritz, and ate some apps. Everything was yummy and people watching was fun here. Lastly- best gelato I’ve ever had in my life was at Gelateria La Carraia. I had Pistachio, which is always my go-to since its a classic.

Italian drink cart Portofino

Italian restaurant place setting with purse

Italian architecture yellow buildings

Vintage shopping in Florence. I went to a few places, and got a few things, but didn’t do any intense shopping in general on this trip to Italy. These were my fav. vintage stores, I got something at each place…. Desii Vintage and also Epoca. I also stopped by the Gucci store and got a pair of red trousers. The Gucci store in Florence is pretty beautiful, make sure you go to the main flagship store on Via Tornabuoni. One other place that caught my attention was an old school perfume house called AquaFlor, you can make custom scents. Make sure to make an appt. ahead of time though if you want custom scents.

Pasta and red wine Italian dinner blonde

Italian architecture in city

Italian food grilled fish and salad

Italian interior with unique chair and large vase

I left Florence and rented a car 20 minutes outside the city from Hertz rentals. I rented a Jaguar SUV, that I got a special deal on. The car was 65 euro/day. Since I have an Amex Platinum, the car was much less than it normally would be. My Amex Platinum has literally saved me SO MUCH money since the day I got it. Best investment I’ve ever made aside from becoming a member on American Airlines.

Italian food salmon and red wine

Orange and green umbrellas on Italian beach

Italian morning coffee on nightstand

All white Frame denim overlooking Italian city

Okay.. so I drove from Florence to La Spezia which took about 2 hours give or take a little.. I stayed on top of the hill which was really beautiful but also a bitch at the same time because I had an SUV. That was a BIG mistake. Anyway, I stayed at an AirBnb that cost about 100 euro/night. The reason I stayed here is because it was close to Cinque Terre & somewhat close to Portofino which were my next two destinations. So to be clear I stayed here in La Spezia at the AirBnb for 2x nights. The day I arrived I took the train at the bottom of the hill into 1/5 of the seaside towns that make up Cinque Terre called Monterosso al Mare. Honestly, it was really pretty and I’m happy I saw it and spent a half day there, but I probably won’t go back. I walked around waiting on my dinner res that I had at Miky which is the best spot in that town. While I was waiting I had wine, bread and a tomato/mozzarella app. ALL delicious and fresh, from a place called La Taverna di Monterosso. For actual dinner I heard Miky was the best in town. So here’s my thing.. I had really high expectations.. The food was really bland, and not in a way where you want to taste how fresh it is and the food doesn’t need seasoning. It was bland and subpar. The service sucked, it was really expensive. I guess now that I think about it, the fish was good, it’s definitely better than most fish I had but I guess I was looking for something better. I don’t think I would go back. Meh. I took the train back that night after dinner.

Italian beach Amalfi coast orange beach chairs

Portofino Italian architecture on water

Cinque Terre beach chairs and umbrellas on beach

Amalfi coast Italian beach chairs and umbrellas

The next day I drove down to Portofino. I FUCKING LOVE PORTOFINO. Honestly, this whole short trip was to scout out my next trip and quickly see some places in Italy that I can go spend more time at, in the future. The drive from La Spezia to Portofino was about an hour and one of the most beautiful drives I’ve ever been on in my life. I want to move there. First stop, food. I ate in the little marina right in Portofino at I Gemelli. I had octopus salad. It was insane, I finished every last bit. Fresh grilled octopus is one of my favorite meals. This one particularly was divine. After that I wanted to lay on the beach. I laid out at one of the mini beaches right in front of the Best Western in Santa Margherita Ligure. Watching the Italians on the mini beaches is one of my favorite things, so magical. For dinner I wanted to go to Angolo No.7, but I didn’t have a res and as I sadly discovered this trip, most of the best restaurants you need to have a res at least 1-3 days before you plan on dining. I ate at a subpar place instead and it was whatever. This part of town is known for their pesto, so I would love to go back and try bomb pesto somewhere. Also- make sure you drive up in the hills, its freaking beautiful and breathtaking!

Italian pasta and red wine flash photography

Italian architecture orange building

All white Frame denim overlooking Italian city

Vegetables in Italian market

Italian country backyard outfit

After that whole trip, back to my AirBnb in La Spezia. I left the next AM early for Chianti. The Tuscan country side. The drive was about 2-3 hours, through hills and hills and country side. It was so beautiful. Fresh air and vineyards everywhere. In Chianti is where some of the best food I’ve ever had in my life happened. I saw a little shack on the side of the road, more like a restaurant. It reminded me of something I would see in Bali, except the Italian version. This joint was called Uscio E Bottega Sicelle. I had the house wine which was pretty good, and black truffle pasta that was on special. White truffles weren’t in season… so black truffles it was. The pasta, truffles, wine, bread, apps.. ALL SOME OF THE BEST IV’E EVER HAD!!!!!!! WOULD GO BACK.

Amalfi Coast boats and Italian architecture by beach

Italian pink flowers and architecture

Row boat in marina in Portofino

Cinque Terre beach chairs and umbrellas on beach

Realisation Par blue polka dot dress with wine

In Chianti I stayed at a Bed & Breakfast with little villas called Villa Le Barone. So cute. Very Chateau Marmont in the countryside vibes. They had a flower and veggie/fruit garden, a pool, drinks… SUPER ADORABLE, WOULD GO BACK.

Italian countryside summertime orange and sunglasses

Realisation Par blue polka dot dress with Italian food

Italian country poolside tables and chairs

Italian beach Chanel outfit by Mediterranean

For dinner I actually drove back toward Florence, which I didn’t plan on doing, but I got side tracked by a restaurant that looked insane (even though I was staying in Chianti for the night I didn’t mind driving for food). Driving an hour to a restaurant called Il Canto del Maggio, was the best decision I’ve ever made! This was hands down the best meal of my trip. I’m so happy I ended the trip on this note. Il Canto del Maggio is a tasting menu that you have to call ahead of time and reserve a spot to be able to eat there. Honestly, they have an Instagram account and I emailed them begging to get in and said I would post if I could get a seat. Whatever, if it works it works. Thankfully, she got me in last minute. They have two options, one is by the pool, outside, with a beautiful view, there’s a brick oven, and the meal is a pizza tasting. It comes with apps, about 9 pizzas and wine pairing with everything. There’s three long tables and you sit next to strangers and share pizzas that they put down on the table. You’ll probably have different pizzas if you guys try and go here, because it’s farm to table, whatever they have that’s in season and fresh at the moment. The cost of the tasting + wine + apps was 30 euro. They have a restaurant downstairs where there’s a full tasting menu that consists of more than just pizza, but that wasn’t open on the night I wanted to eat there. I think that menu downstairs is a little more expensive as well. This meal was one of the best meals and the backdrop along with it, that I’ve ever had in my life, and if you plan on going anywhere near Chianti or Florence I HIGHLY recommend calling and getting in on this!!!!!!!

Italian countryside pool and beach chairs

Itlaian beach Portofino turquoise umbrellas

Colorful flowers in Italian countryside

Black and white Italian architecture and motorcycles

Vintage Porsche Carrera in Italian village

Italian place setting with vintage photograph

Polka dot Reformation in Amalfi Coast Italy

Italian architecture with wooden shutters

The next AM I left early for the airport, dropped the rental off there as well, and flew out of Florence.


I’ll go back to Portofino and Chianti for sure!!!!!!!

If you’re thinking about road tripping through Italy like this, definitely give yourself 2-3 full days in each city to see it properly. My trip was way too short.

*If you’re looking for outfit details, check out the Italy style post HERE.*