Letters From the Olive Grove

  • Letter #1

    Ciao!

    I’ve officially been in Tuscany for one week, and I’m in love! It’s so incredibly beautiful here. The hotel sits atop a hill with stunning views in every direction. When I worked in Newport Beach, I used to step out onto the hotel balcony each day and see the ocean stretching out in front of me. Now, I step out onto a different balcony and look out over trees, rolling hills, and an olive grove. What an incredible world we live in!

    My first week at the hotel has been wild. There’s so much that both excites me and terrifies me—let’s start with the scary and work our way to the fun stuff.

    First off: bugs. I knew coming into this that Tuscany, with its countryside charm and warm climate, would come with its fair share of critters. I hate bugs. So, I came prepared… with sticky traps (yes, really). Within a day of setting them out in the villa I’m staying in, they were completely full. I’m documenting everything via photos (don’t worry, I’ll spare you the details… for now). Despite these tiny intruders, I feel lucky to be staying in this tucked-away little staff oasis—it’s wooded, quiet, and a sweet escape from work.

    Second fear: the drive. To get to the hotel, we have to travel about 10 kilometers on extremely narrow and winding roads. Oh—and the only cars we have are manuals. I’ve lived a very privileged life with automatic transmissions and never had to learn stick shift. I did get a crash course a few years ago when I had to drive a friend to the ER in her manual car (but that’s a story for another day). Now, I’m officially getting real lessons—and I won’t quite admit to how many times I’ve stalled… Let’s just say reversing is still rough. My passengers can vouch for that.

    Now, onto the exciting parts!

    This hotel is newly renovated and rebranded, which means there are so many fun projects to dive into. While the transformation has already been incredible, there’s still a lot to be done—both aesthetically and in terms of guest experience. On one of my first days here, we walked the property and took notes on everything we could improve in the months ahead. I was buzzing with ideas!

    Growing up with a dad who was incredibly skilled in carpentry, landscaping, and construction, I learned early on how rewarding it is to build and create with your own hands. This week, I built a floating duck platform for the pond (yes, there are ducks!), and I’ve started building a table for the hotel’s coworking space. I’ve loved every minute of it, and there are plenty more projects on the horizon.

    My typical day starts with hands-on work in the cooler morning hours. We break in the afternoon (as most Italian businesses close from 14:00 to 17:00), and then I return to the hotel to assist with reception, the restaurant, and all the behind-the-scenes magic that makes the guest experience so special. I love meeting people from all over the world, and while my Italian is, as they say here, poco, I’ve been able to connect with everyone I meet.

    Getting back to the heart of hospitality has felt like a homecoming. It’s why I fell in love with this industry in the first place—creating special experiences and connecting with people.

    Days off are rare with such a small team, but we find joy in the little moments—like taking mini trips to pick up cheese or meat for the restaurant, which often leads us to charming nearby towns.

    Until next time.

    With love,
    Holly

  • Before The First Letter


    You might be wondering how I ended up in Tuscany. Well, I’ve always believed that nothing happens by chance and that everything unfolds for a reason. People come into our lives, doors open, and things align in ways we often can’t foresee. While the journey to get here was not without its challenges, I firmly believe in manifestation and that everything ultimately works out in its own time.

    So, how did I arrive in this beautiful place? I connected with a friend of a friend who owns a farm hotel in Italy.

    For a while, I hadn’t been enjoying my job. Although I knew it was what I needed to do at that time, I reached a point where I felt I couldn’t continue. My ambitions and skills felt stifled by the work I was doing. While I loved the company I worked for and appreciated the flexibility of remote life, I wasn’t fulfilled; I knew I was meant for more. So, I began searching for new opportunities, and during this process, I met Starri.

    Starri is a dreamer and entrepreneur who purchased La Meridiana Hotel in Tuscany in 2019, embarking on a remarkable journey. Now known as the “VIN Hotel,” it operates seasonally from May to October, nestled on an olive farm that features a grove with 600 trees, set against the breathtaking Tuscan hills. He accomplished what I had always dreamed of: buying a hotel, renovating it, and transforming it into a dream destination. I was captivated and eager to learn everything about small hotel ownership and the intricacies involved.

    I was fortunate enough to be invited to work for the season, and I instantly knew this was the next step I needed to take. I gave my two weeks’ notice, said my goodbyes, and set off to finally live out my dream of living abroad.

    The first week brought its share of challenges, which I will document later, but I can genuinely say I am incredibly happy. I feel like I am doing what brings me immense joy in the most stunningly beautiful place. Each morning, I wake up and think, “Wow, this is my life!”

    I plan to send a letter from the olive grove each week and share my experiences here. So, welcome to my tales of Tuscany!

    With Love,

    Holly

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