Tuscany
Rolling Vineyards and Sipping Chianti in the Countryside
Tuscany was a dream - breathtaking scenery, endless vineyards, and unforgettable wine tastings. We spent our days hopping from winery to winery, soaking in the beauty of the rolling hills. Coming here before our elopement made it even more special - it was the perfect lead-up to our big day!
Wine Hopping, Pasta Making, and the Best Wedding Pre-Game
Tuscany had been on our bucket list, and when we got the chance to visit for a friend’s wedding, we were all in. It was the perfect mix of wedding celebrations and doing our own thing - basically, an excuse to drink endless wine, eat absurd amounts of pasta, and pretend we lived in a postcard. Spoiler: Tuscany did not disappoint.
Wedding Festivities: A Villa, A Pool Party, and a Whole Lot of Vino
The wedding kicked off with a pool party at the couple’s villa, which was basically the ideal way to get to know everyone. Picture this: drinks flowing, sun shining, and a bunch of wedding guests who had just met but were already acting like lifelong friends. It was a solid warm-up before the big day.
And the wedding itself? Stunning. Intimate. Full of love and laughter. Imagine saying "I do" with rolling vineyards as your backdrop, followed by a dinner that made us rethink every meal we've ever had. Then the party started, and let’s just say... Italians know how to keep a dance floor alive.
Staying in Pienza: Small Town, Big Charm
We stayed in Pienza, a tiny, ridiculously cute town that felt straight out of a movie. The first morning, Zak and I decided we needed to move our bodies after all the travel (and pre-wedding indulgence), so we found a local gym. Because nothing says romantic Italian getaway like hitting the treadmill next to a 70-year-old Italian man who clearly didn’t understand why we were there.
Another morning, I went for a run along the countryside, and wow - just me, winding roads, rolling vineyards, and a view that honestly made me forget I was exercising. Highly recommend if you ever want to trick yourself into enjoying cardio.
Pasta-Making 101: Featuring New Friends and a Farm-to-Table Feast
One of the best things we did was a pasta cooking class - because when in Italy, you have to learn how to make pasta from scratch. We met another couple from the U.S. and between trying to knead dough properly and not embarrass ourselves, we had a hilarious time. The best part? Almost everything we cooked with came straight from the farm in the backyard. Can confirm: food just tastes better when someone else grows it for you.
Wine Hopping & Living Our Best Life
One of our favorite days was spent doing absolutely nothing structured - just wandering through Pienza, popping into cute little shops, stopping for aperitivos, and, of course, hopping from one vineyard to the next. No plans, no rush, just pure “this is what vacation should feel like” energy. We galavanted (yes, that’s the right word) through the countryside, sipping wine and soaking in views that looked like they belonged on a postcard.
Final Thoughts on Tuscany
Tuscany was everything we hoped for and more - beautiful, laid-back, and full of carbs and wine. Between the wedding, the food, and the small-town charm, it was the perfect place to slow down and just enjoy life. We already can’t wait to come back… preferably with an extra suitcase just for wine.
Now that you've heard my Tuscany story, keep reading for my top tips and recommendations!
Travel Tips
Best Time to Visit
Spring (April–June): Ideal weather and blooming countryside!
Fall (September–October): Wine season and golden landscapes. Grape harvest season (vendemmia) means wineries are extra lively.
Summer (July–August): Hot, busy, but still beautiful. Best time for poolside villa stays and coastal visits!
Winter (November–March): Quiet and cozy, but limited options. Fewer tourists and lower prices, but some smaller towns and wineries close.
Rent a Car: Public transportation is limited outside major cities, and Tuscany’s best spots (those dreamy rolling hills and hidden vineyards) are best explored by car.
Location: Florence and Siena are beautiful, but staying in a smaller town like Pienza, Montepulciano, or San Gimignano gives you a more authentic, peaceful experience. Plus, nothing beats waking up to vineyard views.
Plan Wine Tastings in Advance: Many wineries require reservations, so book ahead to secure your spot - especially at smaller, family-run places.
Packing Essentials: Cobblestone streets and not high-heel friendly! Opt for comfortable sneakers or sandals
Be Ready for Siesta Time: Shops and restaurants in smaller towns close in the afternoon (usually from 1-4 PM), so plan accordingly. Use that time for a leisurely lunch, a long walk, or - if you’re truly embracing the Italian lifestyle - a nap.
Accommodations
Borgo Poggiardelli - Located near Pienza, this charming farmhouse stay offers breathtaking views, cozy rustic rooms, and a serene countryside vibe.
Highlights:
Stunning vineyard & olive grove surroundings
Spacious, cozy rooms with rustic charm
Relaxing outdoor pool & gardens
Close to Pienza & Montepulciano for easy exploring
Top Things to Do in Tuscany
Explore Florence - Visit the Duomo, Uffizi Gallery, and Ponte Vecchio in the birthplace of the Renaissance.
Wine Tasting in Chianti - Sip world-famous Chianti wines while touring vineyards.
Val d’Orcia - Drive through rolling hills, visit Pienza and Montepulciano, and see the famous cypress-lined roads.
Visit Siena - Walk through the historic city center, see the Piazza del Campo, and visit the Siena Cathedral.
Leaning Tower of Pisa – Take the classic tourist photo and explore Piazza dei Miracoli.
Take a Cooking Class - We booked ours at Ristorante La Pecora Bianca al Podere Spedalone
We made fresh pasta and classic Tuscan dishes in a rustic farmhouse setting with incredible hospitality, local ingredients, and a cozy countryside atmosphere!
Restaurants & Food Picks
Tuscany is known for its simple, high-quality ingredients and rustic, flavorful cuisine. The region’s food highlights include local olive oil, pecorino cheese, truffles, fresh handmade pasta, and world-class wines. A must-try dish is pici, a thick, hand-rolled pasta!
Ristorante La Pecora Bianca al Podere Spedalone (Pienza) - Traditional Tuscan dishes with fresh, local ingredients. Their cooking classes are a must! We devoured everything we made
Osteria Acquacheta (Montepulciano) - Famous for its Florentine steak.
La Bottega del 30 (Villa a Sesta) - A Michelin-starred spot.
Trattoria Mario (Florence) - A legendary family-run trattoria serving authentic Tuscan comfort food in a lively setting.
Osteria Le Logge (Siena) - Features local truffles, pici, and fresh handmade pasta.
Wineries
We stayed in Pienza, and these were the wineries we visited that were close to where we stayed!
Podere Il Casale (Pienza) - A biodynamic winery and farm offering organic wines, pecorino cheese tastings, and stunning views of the Val d’Orcia.
Palazzo Massaini (Pienza) - A beautiful estate with wine and olive oil tastings, plus breathtaking views of the Tuscan countryside.
Tenuta Valdipiatta (Montepulciano) – Known for its Vino Nobile di Montepulciano, this winery offers tours and barrel tastings.
