From rowing a boat through Venice’s quiet canals to sipping wine high above the cliffs of Vernazza, our 17-day Italy adventure was a whirlwind of breathtaking views, unforgettable flavors, and rich history. We hiked the cliffside trails of Cinque Terre, refueling with pesto pizza in the region where it was born, and wandered through Pisa, climbing the Leaning Tower. In Florence, we immersed ourselves in Renaissance brilliance – admiring Michelangelo’s David, exploring hidden passages in the Palazzo Vecchio, and ending our days with sunset gelato at Piazzale Michelangelo.We slowed down in Tuscany, tasting our way through Chianti and Val d’Orcia, where vineyard-covered hills and cypress-lined roads made every drive feel like a dream. Our agriturismo stays were the heart of this leg – from the cozy, cat-filled Castellinuzza in Chianti to the medieval Castello di Spedaletto near Pienza. We explored Montalcino, Pienza, Montepulciano, Monticchiello, and Siena, sampling local wines (including Brunello), pecorino cheese, and plenty of pici pasta along the way. Before heading south, we made a quick stop in Orvieto, a stunning hill town perched on volcanic rock, where we enjoyed wine with views of the striped Gothic Duomo. Then it was on to Naples, where the chaotic energy of the city was no match for the pure pleasure of a pizza from the legendary L’Antica Pizzeria da Michele. The trip ended with a bang on the Amalfi Coast, where we ferried to Capri, (survived a scooter mishap), and soaked in the coastal views of Positano and Ravello, followed by a final few days in Rome. There, we walked in the footsteps of emperors at the Colosseum, took in the grandeur of St. Peter’s Basilica, and tossed a coin into the Trevi Fountain, hoping to return someday. Seventeen days, countless scoops of gelato, and one unforgettable journey through the heart of Italy.
We’ve visited Venice twice now – and it keeps getting better. Our first time was part of a longer Italy adventure, while our second visit was a quick stop before boarding a Mediterranean cruise (just a few hours to soak it all in before a train to Trieste!). We kicked things off with a Vaporetto ride through the Grand Canal, grabbed espresso at the iconic Caffè Florian, and took in the golden glow of St. Mark’s Basilica. Instead of just the usual gondola ride, we took a Row Venice lesson and learned just how tricky (and fun) it is to steer a gondola ourselves. We have tried both a daytime and nighttime gondola ride and prefer the daytime for the better views (and it’s cheaper), though both have their charm. A trip to Venice should be on everyone’s bucket list!
Our day in Cinque Terre was a beautiful blur of vineyard-covered hillsides, pesto-smothered everything, and panoramic seaside views that made every uphill climb totally worth it.
These five colorful villages – once isolated fishing communities carved into the rugged Ligurian cliffs – are now connected by trails, trains, and centuries of seafaring history. We started the adventure in Monterosso, hiking the steep, stone-lined trail to Vernazza – a leg-burner, but one that rewarded us with sweeping cliffside views and a well-earned pesto focaccia and pizza in the region where both pesto and focaccia were born. After exploring Vernazza, we continued on the scenic trail to Corniglia, pausing for fresh-squeezed orange juice and gelato. The route only got more beautiful as we made our way to Manarola, passing through vineyards so close you could touch the grapes, and finally on to Riomaggiore where we rewarded ourselves with a local wine tasting with a stunning seaside overlook. We stayed at agriturismo Buranco high above Monterosso, where the hosts – part of a multi-generational family – welcomed us with wine, fresh fruit, and a view that honestly made us question why we’d ever stay in a hotel again. With every sip, step, and slice of pesto pizza, Cinque Terre was a panoramic paradise on the Ligurian coast.
Our quick stop in Pisa as part of our 2016 Italy trip was all about making the most of a half-day in one of Italy’s most iconic spots – and yes, we fully embraced being dorky tourists. We made the short walk to the Field of Miracles, home to the famously lopsided Leaning Tower of Pisa and the stunning Pisa Duomo. Climbing the tower was a highlight – not just for the view, but for the surreal feeling of walking on worn, slanted marble stairs polished smooth by centuries of visitors. We snapped some final goofy tower pics with our travel buddy Eileen, and caught the train to Florence with just enough time to reflect on Pisa’s charm – and how gravity-defying photos are still irresistible.
Our time in Florence was a whirlwind of art, architecture, secret passageways, and world-class gelato – with sunset views sprinkled in for good measure. We dove straight into the city’s Renaissance heart, wandering the halls of the Museo Galileo, where we saw antique telescopes, ancient maps, and yes – three of Galileo’s fingers. That night, we took a private “Inferno” tour through the Palazzo Vecchio, exploring hidden chambers, rafters above the Hall of the Five Hundred, and even the secret room where Medici spies once eavesdropped on political dealings. Day two was packed with masterpieces, starting with Michelangelo’s David at the Accademia, followed by close-up encounters with sculptures by Michelangelo and Donatello at the Bargello. We wandered the Boboli Gardens, stepped inside the Buontalenti Grotto (yes, the same one from Inferno), crossed the iconic Ponte Vecchio, and stood in awe at the Uffizi Gallery, face-to-face with Botticelli’s Birth of Venus – a moment that felt like stepping directly into the heart of the Renaissance. We capped it all with sunset views from Piazzale Michelangelo, gelato in hand from the Gelato Festival, including the best gelato we’ve ever tasted. Florence wasn’t just a city – it was an open-air museum, a thriller novel, and a full-on love letter to the Renaissance.
Our three-day adventure through Tuscany was the ultimate mix of wine, hill towns, and jaw-dropping views – with a few surprises (and cats) along the way. We kicked things off in Greve in Chianti, sipping wine in the tiny medieval village of Montefioralle, visiting the rumored birthplace of Mona Lisa at Villa di Vignamaggio, and touring the legendary Castello di Verrazzano before settling into Castellinuzza B&B, a dreamy vineyard stay with 22 cats and some of the warmest hospitality we’ve ever experienced. From there, we explored the fortified village of Monteriggioni, where we stepped back in time at the Templar Museum, trying medieval armor and weapons. We wandered the streets of Siena and savored pici pasta. We then made our way to Montalcino, tasting our way through Brunello at stunning estates like Castello Banfi and Poggio Antico. That night, we checked into Castello di Spedaletto, a 12th-century castle-turned-agriturismo complete with a working mill and peaceful countryside views. On our final day, we visited Pienza for pecorino and Renaissance charm, had a wine-with-a-view moment in Monticchiello, and explored Montepulciano’s underground wine cellars, where we met Adamo, the charismatic and passionate vintner at Contucci. Tuscany stole our hearts with every sip, view, and cobblestone step.
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.










