Under the Tuscan Sun:

An 8-Day Escape to Florence & the Countryside

 
Luxury hotel suite in Florence with elegant seating area and king bed framed by floral wallpaper

Day 1 - ciao firenze

Upon arrival in Florence, your private driver will escort you to your boutique hotel, perfectly situated in the heart of the historic center.

Once you have settled in, step out for a leisurely orientation walk past Florence’s most iconic treasures, from Piazza della Signoria and the historic Ponte Vecchio to the grand Piazza del Duomo.

Spend the remainder of the afternoon enjoying the city at your own pace. Browse hidden artisan boutiques, or relax over an espresso at an elegant outdoor café.

As day turns to dusk, toast the start of your journey with a rooftop aperitivo overlooking the Arno River before discovering Florence’s celebrated culinary scene.

Day 2 - Artistic Masterpieces of Florence

Begin your day with a privately guided tour of the renowned Uffizi Gallery, followed by an intimate view of Michelangelo’s iconic David at the Accademia Gallery. Afterward, stroll to the magnificent Florence Cathedral to marvel at Brunelleschi’s revolutionary dome.

Enjoy the afternoon at leisure to explore Florence at your own pace. Discover hidden artisan leather workshops and historic perfume ateliers, or simply wander through the city's charming medieval streets.

The octagonal Tribuna room inside the Uffizi Gallery in Florence with classical sculptures, oil paintings, and ornate marble floor
Outdoor dining table for two on a terrace overlooking rolling Tuscan vineyards and hills at sunset

Day 3 - A day in chianti

Leave Florence behind for an unforgettable day immersed in the rolling vineyards of Chianti.

Joined by your expert private guide, you'll visit exclusive boutique estates where generations of winemakers honor centuries-old traditions. Indulge in private tastings of world-class Tuscan vintages, followed by a leisurely, gourmet lunch overlooking the estate slopes.

Return to Florence in the late afternoon with time to explore a new neighborhood or unwind over an intimate final dinner.

Day 4 - South to Siena & San Gimignano

This morning, travel south through Tuscany’s breathtaking countryside toward Siena. Accompanied by your private driver and expert guide, you’ll journey along scenic backroads, pausing at idyllic viewpoints along the way.

Step into the medieval splendor of Siena to admire the iconic, shell-shaped Piazza del Campo and the magnificent Duomo. Afterward, continue to San Gimignano, famed for its striking skyline of medieval towers.

In the late afternoon, retreat to your luxury boutique hotel, nestled amidst the rolling Sienese countryside or hidden within Siena’s historic heart. Unwind with a quiet, elegant evening surrounded by sun-drenched vineyards and olive groves.

Panoramic view of the Siena Cathedral dome and bell tower rising above historic terracotta rooftops in Siena Italy
Golden sunlight illuminating rolling green hills and cypress trees in the Val d'Orcia countryside of Tuscany Italy

Day 5- Val d’Orcia: Tuscany’s Finest

Spend the day immersed in the postcard-worthy landscapes of the UNESCO-listed Val d’Orcia.

Discover the picturesque Renaissance town of Pienza before continuing to Montepulciano, a hilltop jewel renowned for its elegant architecture and celebrated Vino Nobile. Along the way, journey past Tuscany’s iconic cypress-lined roads, pausing at panoramic viewpoints to take in the rolling hills.

Savor a leisurely farm-to-table lunch at a rustic local estate before making your scenic way back through some of Italy’s most breathtaking countryside.

Day 6 - The Gentle Pace of the Tuscan Hills

Today is intentionally unhurried.

Unwind at your boutique countryside retreat, or choose from a selection of curated Tuscan experiences. Indulge in a restoring spa treatment, craft your own custom vintage during a private wine-blending workshop, or ride horseback through the vineyards. Alternatively, simply spend the afternoon lounging by the pool while soaking in Tuscany’s serene landscapes.

As evening falls, gather for a memorable dinner paired with exceptional regional wines to toast to an amazing journey.

Aerial view of a luxury infinity pool carved into stone cliffs overlooking rolling green hills at Borgo Pignano in Tuscany
Hot air balloons floating above rolling green vineyards and hills in Tuscany at sunrise

Day 8 - cheers to tuscany

After breakfast, your private driver will escort you to Florence Airport or Florence Santa Maria Novella railway station for your onward journey.

Leave Tuscany with unforgettable memories of Renaissance art, medieval villages, celebrated wines and the timeless beauty of the Italian countryside.

Day 7 - ultimate tuscan farewell

Spend your final full day experiencing Tuscany entirely your own way.

Drift silently above the vineyards during a sunrise hot-air balloon flight, ride through picturesque villages by e-bike, or enjoy a private picnic set among the rolling hills.

For an extraordinary finale, celebrate the end of your journey with an exclusive private dinner inside a historic Tuscan castle.