World Tour Italy #1: Florence Honeymoon Crashing, Tuscan Farmhouse Dinner Parties & Naples 5-Pizza Lunch Tango

Written by Chelsea Dinsmore August 8, 2015

Memorable Italian Moments:

  • Crashing a honeymoon in Florence (a first for us).
  • A 4-course dinner with a Tuscan family (see above) at their 1800’s farmhouse in the center of a thousand olive trees, which concluded with a nightcap under the stars among a thousand fireflies.
  • Wandering the streets of Rome, soaking wet, in a torrential downpour searching for a place to stay.
  • Taking an 8-hour detour to Naples for a 5-pizza lunch.

Days on the Road: 210

WHERE WE ARE… NOW: Saint-Tropez, France  LAST: Bordeaux, France NEXT: Dubrovnik, Croatia

Where we are French Riviera

From Bulgaria to Tuscany…

Boarding our flight from Sofia to Milan was a bittersweet experience. We absolutely LOVED our time in Bulgaria but getting to Italy kinda felt like a never-ending journey.

The dream of spending time in Italy is where this whole crazy idea began about 10 years ago, and I think we both knew once we finally got there we would feel a bit more settled. We were also REALLY looking forward to seeing friends in Florence and Rome.

Honeymoon Crashing in Florence

We had a major wake-up call upon landing in Milan! We had spent the past month in the off-season of undiscovered Bulgaria where nothing was ever booked up and you could make a detour in your plans at any given moment. We decided not to book any train tickets ahead of time because we had to transfer from Milan airport to Milan Centrale – the main train station – where we planned to take a 1.5 hour train to Florence, getting there just in time to enjoy a sunset cocktail.

Not so fast…

Italy Highlights l Dinsmore World Tour

When we arrived at Milan Centrale, we were met with crowds larger than we had seen in all of Bulgaria combined. It didn’t help that it happened to be a Friday night at 6:00pm. Hello Western Europe, high season and rush hour!

Long story short, not only did we not make our intended train, every high-speed train for the rest of the night was completely sold out. After a minor panic (and a fleeting thought of renting a car), we decided to book some of the last available seats on the much slower train that also didn’t leave for another hour. The good news is that we actually made it to Florence that night instead of the following day, got to enjoy a late dinner with our dear friends and had plenty of time for a happy hour on the train to welcome the month ahead in Italy!

Italy Highlights l Dinsmore World Tour

We spent the next couple days frolicking through Florence with some of our closest friends, Ozan and Brittney (the ones whose wedding we went home for in April) – yes, we crashed their Italian honeymoon! It was SUCH a treat to see some of our favorite faces and be able to talk about anything and everything all of us were going through at the time. We had been feeling a little run down and (unexpectedly) lonely over the past month, and these two were the perfect remedy.

Italy Highlights l Dinsmore World Tour

It was a magical few days for us and we are forever grateful that they let us crash their special trip – it was definitely the refresh (and at the same time, the kick in the rear) that we needed.

Italy Highlights l Dinsmore World Tour

Dinner Parties and Villas in Tuscany

Italy Highlights l Dinsmore World Tour

Not only did Ozan and Brittney let us crash their honeymoon, they also sent us to Tuscany as a thank you for all we did for their big day. We seriously do have the best friends EVER!

We had a night to kill before check-in so we decided to attend our first EatWith – a service for joining locals around the world, in their homes, for a dinner party and home-cooked meal. We’ve been meaning to try it for over a year and were blown away! Our experience was the most “out of a movie” we’ve had to date. Words cannot describe, but we’ll try…

Italy Highlights l Dinsmore World Tour

We hopped in a rental car and cruised down to Impruneta, a small little town about 20 minutes outside of Florence. We loved that within such a short distance from such a “big city” you can be in the middle of rolling Tuscan hills!

We pulled up to the address that was plugged into our GPS a little wary as the apartment complex didn’t appear to be out in the countryside as the description had mentioned… We decided to give Gennaro a call and he said: “Oh yeah, our place doesn’t show up, meet me in the town square and you can follow me there.”

Italy Highlights l Dinsmore World Tour

A few moments later, he showed up and we followed him for at least another 10 or so minutes along small, winding dirt roads. As we pulled up to the most picturesque Tuscan Villa (built in 1826!) with Italian music blaring from the kitchen, we knew we were in for a real treat…

Italy Highlights l Dinsmore World Tour

We met Jo who was cooking over the stove along with Augusto and Carmen, their two adorable children. Upon arrival and showing us to our room (they also offer an Airbnb so we stayed there for the night), Gennaro proceeded to open up a bottle of unlabeled wine produced by their neighbor. We sat out in the warm night, played with their four brand new kittens and chatted about life in Spain, London and now their life in a small Tuscan village.

Italy Highlights l Dinsmore World Tour

While Jo prepared an amazing vegetarian meal, we sipped delicious local wine, played a little futból with the children (Spanish was the common language with the children given that Jo is from Spain and we had yet to truly start practicing our Italian), and caught an amazingly beautiful sunset while Carmen brought us freshly-made fried sage leaves that she had just picked from their garden and prepared for us.

Italy Highlights l Dinsmore World Tour

Shortly afterwards, we sat down at a table for 6 (us and the family) to one of the tastiest meals we had in all of Italy – it might have something to do with quality of the ingredients (we had learned earlier that Gennaro left a fast-paced life of finance in London to get closer to nature and start a local CSA farm box program in Tuscany focusing on all organic and natural ingredients and delivering them to families in the region – you cannot make this stuff up) and of course, the love and care we saw that went into it! We sat for at least two hours enjoying more local wine, fresh cheese and the delicious 4-course meal prepared by our gracious hosts.

And as if everything hadn’t been over-the-top enough, we finished the night with a glass of wine under the stars with at least a thousand fireflies buzzing and bursting around us as if every olive tree was dressed with twinkling Christmas lights. Absolutely surreal.

Italy Highlights l Dinsmore World Tour

We retreated to bed full and happy only to wake up to a perfect Tuscan morning, where once again we were greeted with a fresh and healthy breakfast that was enjoyed out on the patio, including freshly delivered bread from town. It was a completely perfect 15 or so hours, once again reminding us the importance of spending time with locals!

Here’s a link to Gennaro and Jo’s EatWith listing – an absolute must if you’re ever in Tuscany.

Onward to a hidden gem among the vines…

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The next few days were spent at a small hotel in Tuscany with absolutely stunning views, incredibly gracious hosts and absolutely amazing food. Italian food is our favorite and we were over the moon to be eating fresh pastas, homemade cheese and enough tomatoes to make your skin turn red.

Italy Highlights l Dinsmore World Tour

We went on a morning run to a hilltop town, cruised the Tuscan countryside, sipped on local wine and honestly just enjoyed the amazing place that our friends were so kind to send us to! It was an incredibly relaxing few days. Next up was a whirlwind 15 hours in Rome.

Old Friends & Torrential Downpours in Rome – with no place to stay…

Italy Highlights l Dinsmore World Tour

Chelsea’s good friend from high school had rented an apartment in Rome for a week that just happened to fall at the time we were making our way to the south of Italy. We had talked about stopping in for lunch but knew the logistics of travel might make that seem like a very short stay, so we decided last minute to stay overnight.

We enjoyed a beautiful train ride from Florence with blue skies the whole way. However, about 3 minutes before we pulled into the Rome train station the most massive rain storm hit. Given our overnight stay was so last minute, we hadn’t found a hotel yet so we set off in the pouring rain to find a place before meeting Matt and Kandi.

Italy Highlights l Dinsmore World Tour

It was sort of a unwelcome welcome to Rome but we managed to find a place near the train station and by the time we met up, the skies had cleared (but our only pair of shoes were still soaked).

Both of us had been to Rome in the past and we admit that if it wasn’t for meeting friends we may not have gone back this time around. We both remembered it as a hot, huge city – but that impression was quickly turned on its head.

Italy Highlights l Dinsmore World Tour

We decided to meet at the Colleseum and Kandi admitted that she recognized us immediately because of my scarf (maybe because I wore it in pretty much every picture the month prior!). We caught up for a while and then we checked out their apartment on our way out to dinner. I’m pretty sure it had the most beautiful terrace in all of Rome! We enjoyed a glass of wine and a few appetizers before heading off to the hip little neighborhood of Trastevere.

Italy Highlights l Dinsmore World Tour

As we wandered over, we passed by beautiful ruins every other block and caught a gorgeous sunset. We enjoyed a nice long meal with them and even though it was quite late, we decided to wander back home so we could get a different glimpse of the amazing sights this city has to offer. We are so happy we made that pit stop, because, of course, seeing familiar faces was huge for us, and it gave us a whole new view of Rome – definitely a city we look forward to getting back to!

The 5-Pizzarito Lunch Tango through Naples

Italy Highlights l Dinsmore World Tour

In typical Dinsmore fashion, food comes first. So we purposely planned a massive 8-hour detour from our direct train to the Amalfi coast so we could try Pizza Napoletana straight from the source! We stored our bags, walked to a street known for its famous pizzas and went on one of our standard self-administered food tasting (binging) tours.

Italy Highlights l Dinsmore World Tour

We were floored that our first pie (one of the most well-known in Naples – Pizzaria Di Matteo) was only ONE Euro and served like a burrito – pizzarito, anyone? Where on earth can you get a pizza for just over a dollar, let alone one of the best in the world?!

It was so simple and so incredibly soft, wet, chewy and delicious, but we held off getting another so we could try out another spot. The first was more of a street stand style pizza while the second was a sit down joint. We loved tasting the two different styles and can now say that we really do think pizza in Naples is the best we’ve ever had.

Italy Highlights l Dinsmore World Tour

However, with no plans to be back, we loaded up on another hand-held pie and felt we had to taste the infamous fried pizza (#worthit). We stumbled out of Naples five pizzas later on our way down to the Amalfi coast – what we would call home for the remainder of our time in Italy.

Lesson’s Learned: 

  • Take every chance to eat with a local, and look for an EatWith in whatever city you’re visiting. And if in Tuscany, eat with Gennaro and Jo!
  • Book trains and hotels in advance when in the heart of tourist season (and rain storms)
  • You’d be very very surprised how many 1-Euro hand-held pizzas you could put down in one sitting
  • When in doubt, do a little indulging. Next year when looking back on this trip we probably won’t regret having that extra glass of vino, gelato or pizzarito. Although, that thinking might catch up with you during a year around the world. Only time will tell…

How we’re feeling: FULL of food and love from seeing close friends and happy to be fulfilling our decade-long dream of living in Italy!

More on that to come,

– Chelsea and Scott

P.S. As usual, we know we’ve been delayed with our updates (so much exploring to do!), but we hope to play a little catch-up soon.

And for the most current near-daily updates: Follow us on Instagram (Chelsea’s Insta & Scott’s Insta). We post pictures there almost every day.

Our next stops are: Croatia (Dubrovnik), Turkey (Istanbul) and Tanzania (to take a crack at climbing Mt. Kilimanjaro – assuming we can scrounge up the gear, because we definitely don’t have it in our packs). We might also hit Serbia and Montenegro along the way.

If you’re anywhere around there or have any tips, we’re all ears!

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