Letters From The Olive Grove

Tag: summer

  • 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 # 4

    I’m blaming the snail mail for this letter’s lateness—not my forgetful brain (although let’s be honest, it played a role). The days here have been hot and sticky, and they’ve started to melt together like syrup on pancakes(love a good simile). Still, I try to hold on to one of my favorite quotes: “Every day may not be good, but there’s something good in every day.” So, here are a few of the “something goods” from the past week or so.

    Each evening before the restaurant opens, the staff gathers for dinner. About 90% of the time, it’s pasta—which, I suppose, is the most Italian thing ever. But let me tell you, I never thought I’d miss In-N-Out so deeply. And don’t even get me started on tacos—my precious Taco Tuesdays haunt my dreams. That said, one night we were surprised with a sautéed meat and vegetable dish served with rice, a rare break from the pasta parade and probably the closest I’ve come to Chinese food since arriving. That dish was definitely the good in that day.

    We’ve officially entered our busy season, and the hotel is nearly always full. This week I met my first Americans—hearing an accent like mine caught me completely off guard, but in the best way. Most of our guests come from Germany, the UK, the Netherlands, and Italy. It’s been so easy to build connections with them, which I think is one of the beautiful things about working in a small boutique hotel. You see people often: one minute I’m checking them in, the next I’m taking their dinner order. The relationships form naturally, and it’s honestly such a joy.

    One evening, a pair of guests from Germany—both doctors in their residencies—joined the staff for a barbecue (or a “brie,” as they call it). I asked how they managed a vacation during residency and learned they get six weeks off every year. Six. Weeks. Let’s just say I’ve started casually researching German citizenship.

    The design of our lobby encourages guests to linger and relax—it’s warm and open, with a piano and guitar tucked into one corner. One night, a guest treated us to an impromptu concert that turned the lobby into the coziest little concert hall. These are the moments that make this experience feel truly special.

    On my one day off each week, I’ve been making a point to explore more of Tuscany. I have a growing list of must-see spots, and I’m steadily working my way through it. This past Monday, I visited Porto Santo Stefano, a stunning coastal village on Monte Argentario. The water was crystal-clear blue, and sailboats bobbed gently in the harbor. I spotted one boat flying an American flag and snapped a photo, only to find out later from a guest—who happened to be docked nearby—that it once belonged to Humphrey Bogart. Casual! One day I hope to sail around Europe myself, but for now, gawking at other people’s yachts will do.

    Back at the hotel, one of my more satisfying little projects this week was rehoming a cluster of strawberry plants. It was surprisingly fun to dig into the dirt and transform empty area into a strawberry patch. There’s always something to work on here—no shortage of little projects. In my (very limited) free time, I’ve also taken on the ambitious task of building an Adirondack chair. Progress is slow and full of splinters, but I’ll keep you posted.

    So yes, the days are hot, the pasta is endless, and I dream of tacos often. But there’s music in the lobby, laughter around the dinner table, new friendships forming by the hour, and strawberries growing. If that’s not a little bit of good in every day, I don’t know what is.

    More soon (assuming snail mail doesn’t eat this one, too).

    With love,

    Holly