Tuscany In The Winter

We’re slowly but surely getting back into international travel. Our first trip of 2023 was to Tuscany in Italy, we booked this awesome deal that included a rental car, hotel, and flights. We’ve traveled through this company multiple times before but there is still a certain thread of anxiety while traveling after COVID.

The travel in was *a lot* unfortunately. We had a 7 hour flight from NJ to Germany. Then a 3 hour layover and 1 hour flight to Milan. THEN a 4 hour drive to our hotel. So that was less than ideal, but we powered through.

Where we stayed

We stayed at the Hotel Boston in Montecatini. It was just fine. If you’re all about your accommodations then this town and hotel aren’t for you. But it was a fine place for us to sleep every night, central to a lot of cities we wanted to visit, and had a free breakfast/hotel restaurant which is a perk!

Day 1

We spent our first day in a Florence wandering around, shopping on the Ponte Vecchio, getting gelato, seeing the David, and taking a pasta making class! I loved Florence – the vibes were amazing.

Day 2

We split our second day to see 2 places – Lucca and Pisa. Lucca was a very cute walled city and you can walk along the wall. It had a lot of history and classic Italy vibes. In Pisa, we visited the leaning tower which was just so funny to see everyone taking their tourist pics and unbelievably cool at the same time. I insisted we get pizza in Pisa. It just had to be done, we went to Kiste which made for great IG pics.

Day 3

We spent our morning on the Chianti region, touring the Verrazanno winery which has neat ties to New York! We did a tour and got a light lunch while doing a wine tasting. It was very fun, and very beautiful!

Day 4

We drove to Cinque Terre, specifically Monterosso and Riomaggiore (where the movie Luca is based off of!).

It was so fun (and terrifying) to drive up the windy roads. Monterosso had this amazing oratory with statues of skeletons, the best-decorated religious place I’ve ever been to! And Riomaggiore was just literally what dreams are made of. We sat by the water for a few hours and I said I’d love to live there, but my fiancé reminded me that I can’t walk up an elevated surfaces and Riomaggiore is just one big hill lol.

Day 5

We had to drive back to Milan this day to stay overnight and be near the airport! On our drive in, we toured a Parmigiano Reggiano factory because cheese 🧀 🤤 It was a lot more impressive than I expected, the process to make true parmigiano reggiano is all based on manual labor from humans which is crazy!


Overall, this was one of my most favorite trips. The weather was beautiful and traveling to Italy in the off season meant less crowds, more opportunities. I would LOVE to go back to Cinque Terre one day.

The people in Italy were so kind and everyone spoke English. It was such an easy trip and having a car made everything that much easier.

Have you ever been to Italy? What was your favorite part?

21 thoughts on “Tuscany In The Winter

  1. Haven’t been to Italy (yet), but I’m planning out our trip to England and Switzerland in May. Funnily enough, we may be making a stop in Cheddar, UK which is where cheddar cheese originated. 😀 Too bad I don’t like cheese…

    Liked by 1 person

  2. I’ve only ever been to Rome, about 40 years ago!
    That was a long and tedious trip for you but worth it by the look of your photos, and you really had such a great itinerary. It looks like you didn’t have much time in the hotel anyway!

    Liked by 1 person

  3. I love the photo of you, pizza, and the leaning tower of Pisa. I’ve visited CInque Terre twice, because once was not enough to walk through all the islands. Luckily, I’ve visited many cities in Italy, because I love the language, people, and food. I’d like to visit Milan and Lake Cuomo someday soon.

    Liked by 1 person

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