Letters From The Olive Grove

Tag: travel

  • Week # 11

    Taylor Swift has been front and center lately, so it only feels right to kick off this entry with a lyric from her song: “August slipped away into a moment in time.” Honestly, August did just that—vanished before I could blink and I’m blaming that whirlwind for why this blog went on an extra-long sabbatical. But what a month it was! August in Italy is a magical time when locals hit the holiday circuit, and the villages come alive with parties and festivals.

    Before Italy, I’d never heard of a palio. Twice a year in Siena, there’s a legendary horse race: each horse represents a different city neighborhood, and the streets flood with fans decked out in corridor colors and logos, cheering for their team. The horses race with bareback riders around the historic Piazza del Campo, a tradition that’s been going strong since 1633, drawing crowds that make Times Square look tame.

    I had my heart set on seeing it, but luck wasn’t on my side; I missed the big event. Cue the tiny town of Roccatedertighi, which serves up a hilarious twist: a palio with donkeys instead of horses. How could I pass that up? We arrived bright and early, only to discover (after sitting through a marathon of Italian commentary) that the actual race wouldn’t happen until much later that night. Seizing the day, we wandered the city, soaking in sweeping views of Tuscany, before ducking home for a quick siesta.

    When evening rolled around, we returned to find a sight that was equal parts chaotic and charming: grown men racing donkeys bareback through the winding village streets. The local excitement; part carnival, part comedy show—was absolutely infectious. It was one of those wild, unforgettable moments that made me grateful August slipped away with such style.

  • Letter # 5

    Last Saturday night in Montieri there was a party. I’m still not exactly sure what we were celebrating—no signs, no fliers—but there was a DJ spinning beats in the street, people dancing! To top it someone even handed out slices of cake! It felt like we had stumbled into a spontaneous block party, and it was impossible not to smile while watching the locals chat, dance, and laugh together.

    The best part? The people. A few locals approached our little group, striking up conversation as if we were old friends. That’s just Monterri for you—warm, welcoming, and full of stories.

    It turns out Montieri was once a booming mining town, but when the mines shut down, the town emptied out. For years it was nearly abandoned, but slowly, people have been returning, and new businesses are popping up. It’s inspiring to see the revival of such a tight-knit and resilient community.

    One of those businesses is a charming little pizzeria—owned, funny enough, by the parents of one of our chefs. Small town vibes, right? Their pizzas are incredible, and on some weekends we take pizza orders from our guests and go pick them up. This past weekend, that job was mine.

    Ten boxes. One backseat. And a very serious instruction to secure the Pizzas. So I did what any responsible pizza courier would do—I buckled those babies in. Safety first. 😄

    This year marked my second 4th of July outside the U.S., which feels surreal. Instead of fireworks and BBQ, I found myself in Siena, Italy, eating Chinese food—and honestly, it was such a refreshing change.

    If you’ve traveled through smaller towns in Europe, you know it can be tricky to find decent international cuisine. While the U.S. is known for its wide array of food options, many European towns stick to their local specialties. So stumbling upon a pretty good Chinese spot after a seven-hour bus ride felt like finding buried treasure.

    That bus ride, was to Croatia. I had to deliver some documents in hopes of being approved for temporary EU residence. The journey didn’t go quite as planned—I didn’t get what I came for—but the experience wasn’t a loss. If anything, it gave me a deeper appreciation for the hoops people jump through to live or stay in another country. It’s not easy, and this week especially has been eye-opening.

    Still, the silver lining was spending time with friends in Croatia, taking a breath, and swimming in the sea this time the Adriatic.

    Until next time.

    With love,

    Holly

  • Letter #2

    Time is moving so quickly—somehow, we’re already in June! The Tuscan sun is shining strong, and I’ve gotten my first sunburn of the summer (despite wearing sunscreen!). This week, I took a trip to the beach with some of the other staff members, and it felt amazing to finally swim in the sea. I’ve been wanting to take a dip since I arrived, and now that I’ve gone once, I think I’ll have to make it a weekly habit.

    I’m learning that Tuscany is a tapestry of small towns, each with its own charm—and names I can barely pronounce! One such town, Roccatederighi, sits high in the hills and is absolutely enchanting. There, we dined at a wonderful restaurant called De Nada Locanda Toscana, known for their thick, handmade pasta prepared to order. Sitting on their terrace, watching the sun set over the rolling landscape, I was once again in awe of this place. Time may be flying, but moments like that make me pause, take a breath, and feel deeply grateful to be here.

    Another thing I’ve come to truly appreciate is the culture. I still have so much to learn and observe, but this past Sunday, I sat in our little town of Montieri and just watched life unfold—people gathering in the streets, chatting in small groups, kids running and playing, nonnas selling their hand-painted tea cloths, and nonnos offering hand-carved olive wood bowls and spoons. There’s such a strong sense of community, and I love it. Even though I speak very little Italian, I can tell that communication is treasured here—it’s full of passion, warmth, and expression. I’m fascinated by how people speak with their hands and how their words flow so beautifully.

    Inspired by this, I’ve decided to dedicate this week to learning more of the language. I recently came across an Italian copy of Anne of Green Gables, one of my favorite stories. I’ve started using it to learn new words and phrases, and maybe—just maybe—by the end of my stay, I’ll be able to read it aloud and truly understand what I’m saying.

    Work at the hotel remains both busy and fulfilling. It’s always satisfying to see a project come together. This past week, we completed the finishing touches on our co-working space, and it’s already being used regularly! We’re now pressing pause on other projects as we prepare to host a Brazilian wedding this weekend. It’s the first of many to come this season—this one alone will fill all 35 rooms with the wedding party.

    Until next time.

    With love,
    Holly