If heaven exists, it might just be Greve in Chianti and the sun-drenched Tuscan hills that surround it. Every curve of the road brought us deeper into postcard-worthy scenery – rolling vineyards, silvery olive groves, and cypress trees lining golden hills. Our first stop was the impossibly charming village of Montefioralle, where we stepped back in time for a cozy cellar tour and wine tasting that felt like a secret shared by locals. After a pizza lunch in the village, we made our way to Castellinuzza B&B, a 19th-century villa perched on a hill, where we were greeted with sweeping vineyard views, 22 cuddly cats, and owners so warm they welcomed us with a free, generous tasting in their stone cellar. (Spoiler: it instantly became my favorite place I’ve ever stayed.) We continued on to the storybook estate of Villa di Vignamaggio – rumored to be the birthplace of Mona Lisa – for a tasting surrounded by historic elegance and vineyard views. Then came the grand finale: Castello di Verrazzano, where we wandered through Renaissance gardens, hillside cellars carved into the rock, and sipped wine, olive oil, and balsamic drizzled over pecorino while gazing out at Tuscan castles. Chianti didn’t just steal our hearts – it poured us into a dream we never wanted to wake up from. 🍷✨
This day was a perfect mix of medieval towns, iconic architecture, and bold Brunello – a true Tuscan trifecta. We started in the walled village of Monteriggioni, where we explored the hands-on Il Mistero dei Templari Museum, complete with medieval weapons and armor you can actually try on. After a quick gelato stop, we headed to Siena to admire the stunning Siena Cathedral and fuel up on pici pasta, a thick Sienese spaghetti that’s basically Tuscany’s gift to noodle lovers everywhere. In the afternoon, we made our way to Montalcino, the heart of Brunello country, where we visited wineries like the majestic Castello Banfi and the elegant Poggio Antico. We wrapped up the day with a check-in at our agriturismo, Castello di Spedaletto, a 12th-century castle turned countryside retreat, where we explored the grounds and wrapped it all up with a cozy dinner inside the castle walls.
Pienza, Monticchiello & Montepulciano: A Hilltop Journey of Cheese, Cellars & Wine
Our hill town hopping adventure through Pienza, Monticchiello, and Montepulciano was straight out of a Tuscan daydream – and easily one of the coziest, cheesiest, and cat-filled days of our 2016 Italy trip. We started in Pienza, a town known as the first true expression of Renaissance Humanist urban design (because even in the 1400s, Italians had strong opinions about layout). We wandered the charming Piazza Pio II, peeked into Piccolomini Palace, and, of course, sampled the town’s famous pecorino cheese. From there, we made our way to Monticchiello, where the views at Osteria La Porta made us feel like we’d accidentally wandered into an Italian Olive Garden commercial – except with actual wine and charm. Finally, we rolled into Montepulciano, met a very cuddly street cat we named Monte, and explored the town’s wine scene – starting with Contucci Cantina, a medieval cellar straight out of a movie. We headed straight into the atmospheric depths, where we met Adamo, the legendary and endlessly friendly vintner featured in Rick Steves’ videos. Wandering past enormous casks of wine tucked under ancient stone arches made us feel like we’d unlocked a hidden level of Tuscany. We wrapped up the day back at our 12th-century agriturismo, Castello di Spedaletto, a working castle with a real mill and the kind of peaceful countryside charm that makes you wonder if maybe this is where you were meant to live all along.
Our brief stop in Orvieto turned out to be one of the most unexpectedly rewarding parts of our 2016 Italy trip. Perched high on a volcanic plateau, this medieval hill town offers a perfect blend of history, architecture, and wine. The centerpiece of the city is the stunning Duomo di Orvieto, a 13th-century Gothic cathedral built to house a miracle-related relic and known for its ornate mosaic façade and striking striped marble exterior. We started our visit with a stop at Tenuta le Velette, a working winery just outside the city, then enjoyed a leisurely lunch and wine at Enoteca al Duomo, with a prime view of the Duomo. Afterward, we strolled through the city, admiring Chiesa di Sant’Andrea e Bartolomeo and the striking city walls, soaking up the charm of Orvieto before heading to catch the train to Naples.
Capri welcomed us with sparkling sea views, dramatic cliffs, and the promise of a relaxing island escape. We arrived just in time for a peaceful check-in and a night of blissful ignorance before Day 2 turned into a full-blown scooter saga. The plan was simple: take a scenic boat tour around the island in the morning, then explore by funicular in the afternoon. What wasn’t on the itinerary? Crashing a scooter five minutes into the ride, being separated by a rogue scooter rental company, and learning firsthand that Capri’s version of medical care is a water IV and a “good luck.” Spoiler: we do not recommend renting scooters here – unless you enjoy dramatic plot twists and being your partner’s human crutch for 48 hours.
Our time in Positano was… unforgettable, though not exactly for the reasons we expected. After a scenic ferry ride, we quickly discovered that Positano is basically a vertical maze of stairs – and not ideal when your travel buddy (Scoot) is nursing a busted knee from a Capri scooter mishap. With no elevator in sight, Scoot heroically scooted up the stairs on his booty, living up to his nickname. While we didn’t explore as much as planned, we still managed to soak in the views, hop over to Amalfi and Ravello, and make one very questionable food decision: anchovy pizza. One bite in and we knew… mistakes were made. Positano gave us beauty, laughs, and a salty life lesson we won’t soon forget.
We only had a couple of hours in Naples, but we made them count – with a pilgrimage to the legendary L’Antica Pizzeria da Michele. Known as one of the oldest and most iconic pizzerias in the city that invented pizza, this no-frills spot serves just two kinds of pies and has earned worldwide fame (thanks in part to Eat Pray Love). We braved the bustling streets of Naples – staying extra alert for pickpockets – and joined the crowd outside this humble slice of pizza heaven. After one bite, it was easy to see why people wait in line for hours: perfectly chewy crust, tangy tomato sauce, and gooey mozzarella straight from a wood-fired oven. It was a delicious stop before hopping on a train to Rome – and one of the tastiest memories of the trip.
Our Roman holiday kicked off in the most unexpectedly delightful way – at a cat sanctuary nestled among ancient ruins, where hundreds of strays roam freely and are lovingly cared for by volunteers. Sarah was in absolute heaven, and Scott had the very unpopular job of reminding her we couldn’t adopt any three-legged Roman cats (despite her best arguments). From there, we wandered to iconic spots like the Trevi Fountain, Spanish Steps, and, of course, the Colosseum – which absolutely lived up to the hype. Despite being just five days post-accident, Scott managed to traverse all three tiers of the Colosseum on crutches (which he’s casually hiding behind his back in the photos – injury chic at its finest). Then there was the Pantheon – still breathtaking at 2,000 years old. It’s been in continuous use as a holy place for two millennia and serves as the final resting place of legends like Raphael, making it one of the most humbling stops of the trip. We crossed the Bridge of Angels, lined with Bernini’s ethereal statues, on our way to Castel Sant’Angelo, a moment that felt pulled from a Renaissance painting. We fueled up along the way with perfectly crispy Roman-style pizza, and navigated the occasional chaos of crowds and transit mishaps, including Scott’s unforgettable stairlift entrance into the Sistine Chapel. It was three days of history, hilarity, and heart – a Roman adventure full of ancient wonders, cat cuddles, and carbs. Just the way we like it.
For our annual joint birthday trip in April 2015, we celebrated with two unforgettable days at Disneyland and Disney California Adventure, while also checking Angel Stadium and Dodger Stadium off our ballpark tour. We hit all the big rides right at rope drop, indulged in Dole Whips and turkey legs, and admired the sparkle of Sleeping Beauty Castle ahead of Disneyland’s 60th anniversary. Highlights included Cars Land, a hilarious Frozen show, the spectacular Aladdin stage production, and an unexpected Tower of Terror breakdown to end it all. We returned in 2019 during the Adobe MAX conference for a one-day Disneyland adventure – this time squeezing in even more magic with Star Wars: Galaxy’s Edge including blue milk and cocktails at Oga’s Cantina.
From our whirlwind 2017 weekend to our most recent 2023 adventure, our Disney World memories are nothing short of magical. We’ve crisscrossed parks and turned every visit into an unforgettable story. Our Disney journey began with Sarah’s very first trip in 2012 – packed with fairy-tale charm at Magic Kingdom, amazing sea creatures at DiveQuest at The Seas, culinary fun at Epcot’s World Showcase, and a rhino crossing during our Animal Kingdom safari. We soaked in the beauty of Epcot’s topiary-filled Flower & Garden Festival, braved Expedition Everest, and of course devoured turkey legs. In 2020, we were at Epcot when the world changed with news of the global pandemic. But in 2023, we came full circle – returning to Epcot, discovering our new favorite ride: Guardians of the Galaxy: Cosmic Rewind, dining among the stars at Space 220, and giggling through Remy’s Ratatouille Adventure. From performing Enchanted Tales with Belle and having dinner at Cinderella Castle, each trip has brought us wonder, nostalgia, and just a bit of pixie dust. ✨










