Tuscany with Friends: Villa Life, Florence Days & a Celebration in the Hills
Leg 6 of our Italy trip shifted into something softer and more meaningful, less sightseeing intensity and more connection. This was the chapter of friends, slow mornings, long dinners, and a beautiful celebration set in the Tuscan hills.
Day 13: Arrival in the Tuscan Hills & Villa Life Begins
We were picked up at the Rignano sull’Arno–Reggello train station and immediately eased into countryside living as we wound our way through olive groves, vineyards, and rolling green hills.
Before heading to the villa, we stopped at Coop Firenze Rignano sull’Arno to stock up on groceries. The plan was simple: settle in, cook together, and enjoy being in one place for a few days.
From there, we arrived at Poggio Tre Lune, a private Tuscan villa perched above the Arno Valley. The property felt like a hidden retreat carved into the hills, stone buildings wrapped in terracotta tones, shuttered windows, and panoramic views that stretched endlessly across the landscape.
What made it special wasn’t just the setting, but the feeling of it, quiet mornings, golden light spilling across olive trees, and an infinity-style pool that seemed to melt into the valley below.
After unpacking, the day quickly turned into what this leg was all about, pool time, conversation, and easing into vacation mode. As evening arrived, we shared a relaxed dinner together at the villa, followed by late-night laughter and the arrival of a final friend we stayed up to welcome.
It already felt like home.
Steps: 7,000
Day 14: A Full Day in Florence
We started the morning slowly with cappuccinos and croissants at the villa café before heading back to the train station and taking the short ride into Florence.
The city greeted us with its mix of history, energy, and unmistakable beauty.
We spent the day exploring some of Florence’s most iconic landmarks:
The breathtaking Cathedral of Santa Maria del Fiore (Florence Cathedral), where the marble façade and Brunelleschi’s red dome dominate the skyline and stop you in your tracks no matter how many photos you’ve seen.
We wandered across the Ponte Vecchio, with its rows of jewelry shops built directly into the historic bridge over the Arno River.
In the heart of the city, Palazzo Vecchio rose over Piazza della Signoria like a fortress of Renaissance power and politics.
Nearby, we paused at the Fountain of Neptune (Florence), known locally as “Il Biancone,” surrounded by mythological figures and tucked into one of the city’s most famous squares.
We also visited the First Glass Wine Window, one of Florence’s revived Renaissance wine windows, a tiny opening in the wall where wine is served directly to the street, a charming reminder of how deeply history lives in this city.
Lunch was unforgettable: we headed to the rooftop of the Grand Hotel Baglioni, where we looked out over Florence’s terracotta rooftops, domes, and winding streets while enjoying a long, relaxed meal.
We ended the city portion of the day with gelato near Santa Maria Novella before heading back to the train.
Back at the villa, everything slowed again. Pool time, rest, and a reset after a full day of walking.
That evening, Dave cooked an incredible dinner, carbonara from scratch, paired with a fresh caprese appetizer. We gathered around the table, then ended the night laughing, talking, and playing cards long after dinner was finished.
Steps: 10,600
Day 15: Celebration Day
We eased into the morning again with cappuccinos and croissants at the villa café, followed by a slow, relaxed start to the day.
Leftovers from the night before became an easy lunch of carbonara and sandwiches, and by midday everyone migrated back to the pool under an 87° Tuscan sun. It was the kind of afternoon where time disappears, sunlight, water, sunscreen, and long conversations in between swims.
The villa felt like its own world.
As evening approached, the tone shifted. It was time to celebrate our friends’ marriage.
Everyone got dressed up and gathered for a beautiful evening that began with drinks and appetizers and flowed into a catered dinner starting at 6pm. The setting was everything you’d hope for in Tuscany, a long table, warm light, laughter carrying into the hills, and that golden-hour glow fading into night.
Dinner turned into storytelling, and eventually music. The night ended with singing, laughter, and a group of friends fully present in one of those rare, perfect travel moments you don’t forget.
A celebration in every sense of the word.
Steps: 4,000
