Curator’s statement
A milestone celebration like a 40th birthday is the perfect excuse to mix high-energy city glamour with slow-living countryside luxury. Spending half our time at a design-forward boutique hotel in the heart of Florence and the other half at a private villa in the Tuscan hills gave our group the absolute best of both worlds. It’s that perfect setup where private chef-led dinners, exclusive artisan shopping, and sun-drenched vineyard lunches come together to turn a big birthday into an unforgettable core memory.
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Things to do in Florence & Tuscany
The entrance to I Massai, the ultimate destination for handcrafted, milestone jewelry pieces that capture the soul of Florentine craftsmanship. Photo Credit: Jordyn Tilley, Saturday Makers
Rooftop Aperitivo at Cosimo
To kick off the celebration, head to the highest private rooftop in Florence. Suspended between the sky and the city, sipping a crafted cocktail with a 360-degree view of the Duomo and the Arno River sets the exact right high-end tone for a milestone weekend.
Keepsake Shopping at Scuola del Cuoio (The Leather School)
Tucked behind the Santa Croce Basilica, this historic institution is the ultimate spot for a meaningful birthday keepsake. Watching the master artisans stamp and craft the gold-leaf detailing on genuine Florentine leather turns shopping into a cultural experience.
Custom Jewelry Hunting at I Massai
For a truly unique milestone gift, skip the generic boutiques and head to this local artisan workshop. Their hand-hammered gold and unique stone settings capture the soulful, Renaissance craftsmanship of Florence in a wearable piece of art.
Private Pizza-Making Class at Casetta Firenze
Gathering around the villa’s traditional wood-fired oven for a private cooking class was a total highlight. With the music playing and the wine flowing, it’s a hands-on, high-energy activity that perfectly balances the formality of a milestone trip.
A Serene Morning at the Friday Market in Siena
Timing our excursion to Siena for the Friday market allowed us to experience Tuscany like a local. It’s vibrant, colorful, and the perfect place to hunt for local linens, vintage ceramics, and regional specialties before retreating back to the peace of the villa.
Places to eat & drink in Florence & Tuscany
A quintessential Tuscan spread at La Volpe e l'Uva featuring incredible local cheeses, artisanal crostini, and exceptional wines from independent regional producers. Photo Credit: Jordyn Tilley, Saturday Makers
Winemaker’s Lunch at Antinori nel Chianti Classico
A short, scenic drive into the hills brings you to this striking architectural masterpiece. Booking a winemaker’s lunch at their rooftop restaurant, Rinuccio 1180, is an absolute must. The contemporary Tuscan plates are designed specifically to pair with their iconic, estate-grown Chianti Classico.
Artisan Scoops at Gelateria La Carraia
A daily gelato ritual is mandatory, and this spot just across the Carraia Bridge is my personal, undisputed favorite. Grab a cone of their exceptionally creamy pistachio or dark chocolate and enjoy it while walking along the river at sunset.
Contemporary Michelin Dining at Luca’s
Located right inside Hotel La Gemma, this freshly minted Michelin-starred gem brings incredible Art Deco style and modern execution to traditional Florentine flavors. The seasonal tasting menu is an absolute showstopper.
Grab a Panino from a Local Sandwich Walk-Up Window
For a fun, high-energy lunch that feels quintessential to Florence, skip the sit-down restaurants and head to one of the city’s famous street-side sandwich windows. Grabbing a warm schiacciata bread sandwich stuffed with fresh truffles, prosciutto, and stracciatella cheese to eat on a historic stone step is the ultimate way to fuel a heavy day of shopping. My absolute go-to for this authentic experience is I Fratellini.
Chic Sips at La Volpe e l’Uva
For an intimate, local wine bar vibe to break up the celebration, this hidden Oltrarno hotspot is unmatched. Tucked quietly away from the main tourist paths, it is the absolute perfect place to grab an outdoor table, sip an incredible glass of wine from an independent local producer, and share a board of artisanal cheeses and crostini before heading out for the evening.
Need to know
When planning a multi-generational or group milestone celebration in Tuscany, logistics are the ultimate differentiator. I highly recommend spending your first 24 to 48 hours in the walkable center of Florence to enjoy the rooftops and shopping, before transferring to a private villa estate via private driver.
Advisor Pro-Tip: The Serviced Villa Edge
When renting a Tuscan villa, the magic lies in the customization. As your advisor, I coordinate with the property prior to arrival to arrange on-site massages by the pool, dietary specifications for the chef, and private transportation for your vineyard excursions. This ensures that the host of the birthday gets to feel like a guest on their own trip.
Travel Advisor
Saturday Makers
Jordyn Tilley
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