Signature Series: Italy - Allure of Renaissance Tuscany

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2 travelers

$17,240.00

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Your Advisor

Kathryn Moutray

Traveling JetSetter | Mediterranean Travel

FL SOT: ST15578

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kathryn@travelingjetsetter.com

314-833-0425

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Overview


Small Group, Guided (14 max) | 8 Days

Savour Tuscany’s elegance through its wines, Renaissance cities, and enduring traditions 

The essence of Tuscany unfolds in the Renaissance splendour of Florence and the timeless elegance of Siena, where art, architecture, and history shape every view. From the cobbled streets to soaring domes, these cities tell stories of creativity and culture that echo through the hills. Led by your handpicked Signature Guide, and based in a privately owned medieval village, you’ll journey through a land defined by beauty and craft, where flavours and traditions reflect centuries of refinement. This is the story of Tuscany: revealed in every piazza, every masterpiece, every glass raised in celebration.

Venture to the very heart of each destination on our Signature Collection, where every journey is shaped by our unrivalled local connections and insider expertise. Step beyond the ordinary with private invitations, rare encounters, and experiences few will ever share. So when someone says, “I’ve been there,” you’ll simply smile, knowing you’ve experienced it differently.

Signature Day: Experience our distinctive Signature Day, choosing between included activities such as e-biking through olive groves, a Chianti vineyard visit, a private jewellery heritage tour, or a hands-on Tuscan cooking class

Signature Stay: Stay at Castello di Gargonza, a fortified medieval village restored into a characterful countryside retreat

Signature Guide: Let your hand-picked Signature guide lead you to the region’s soul — sharing their home, heritage, and heart

Travel Protection will be quoted

Airfare can be bundled

Trip Details


Arrival and departure transfers information

Arrival airport: Florence Airport (FLR). Your adventure begins with a welcome reception at 4.15pm on Day 1 at our first accommodation. Departure airport: Florence Airport (FLR). Your adventure concludes after breakfast on the final day. Compliment...

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Day 1 · Castello di Gargonza


Arrival and transfer from Florence to Castello di Gargonza

After a transfer from Florence, arrive at our Signature Stay, Castello di Gargonza, a privately owned medieval village nestled in the Tuscan countryside and perched on a quiet hill overlooking the Val di Chiana.

Village introduction and tower visit

Village introduction and tower visit Before the welcome reception, join your Signature Guide for an introduction to the village, tracing stone pathways and ascending the 14th-century tower that once sheltered the great Italian poet, Dante.

Welcome reception and dinner at 2 Stone Room

Welcome reception and dinner at 2 Stone Room As dusk softens the courtyard, gather at 2 Stone Room in the garden for an aperitif, followed by an intimate dinner to begin your Tuscan journey.

Stay at Castello di Gargonza (nights 1–7)

Check in to Castello di Gargonza, a fortified medieval village restored into a characterful countryside retreat set within 500 hectares of Tuscan woodland. Restored towers and medieval alleys reflect centuries of history, while suites pair heritag...

Day 2 · Arezzo


Private olive oil tasting at Buccia Nera estate

Begin the day at Buccia Nera, a family estate framed by vineyards and olive groves in the hills of Arezzo. You are welcomed for a privately guided tasting and introduced to their extra virgin olive oils as part of your Signature Experience.

Lunch at Osteria Cuprena

Continue into the countryside for lunch at Osteria Cuprena, enjoying a seasonal menu of produce from their garden.

Stroll through Arezzo

Stroll through Arezzo Later, take a short stroll through Arezzo, moving from modern boulevards into medieval lanes and pausing at the Pieve, Piazza Grande, and the lawns of Il Prato.

Dinner at Osteria dei Mercanti

As evening settles, gather at Osteria dei Mercanti, where traditional Tuscan hospitality and produce combine for an enchanting meal.

Day 3 · Florence


Signature Experience: Florence Cathedral roof terraces

Enjoy privileged access to the roof terraces of Florence Cathedral, guided by an expert who brings the city’s history into focus. From this rarely visited vantage point, the city unfolds in layers – red-tiled rooftops, narrow streets, and the soft...

Lunch at B-Roof with city views

Lunch at B-Roof with city views After your cathedral visit, enjoy lunch at B-Roof, where the city stretches out below the terrace as you dine.

Florence Renaissance walk and restoration lab visit

Step into the streets that shaped the Renaissance, from cathedrals and civic palaces to workshops that nurtured generations of artists. A private visit to a restoration lab reveals the meticulous work involved in conserving historic tapestries, te...

Aperitivo-style dinner at La Ménagère

Aperitivo-style dinner at La Ménagère End the evening at La Ménagère, where a shared aperitivo-style dinner unfolds in a library-like setting of botanical-themed books.

Day 4 · Castello di Gargonza


Signature Day option: E-bike countryside ride and lunch

On your Signature Day, you may choose to cycle quiet country lanes by e-bike, pausing in an olive grove for bruschetta, honey, and cheeses before returning for a lunch of local produce.

Signature Day option: Chianti winery visit and tasting

Alternatively, sip your way through Chianti, visiting a renowned winery for a tasting that uncovers the region’s rich winemaking heritage.

Signature Day option: Cortona jewellery heritage visit

Another option is to step inside a 14th-century palace in Cortona, joining the DelBrenna family for a private introduction to their jewellery heritage.

Signature Day option: Tuscan cooking class in Gargonza

Signature Day option: Tuscan cooking class in Gargonza You may also choose to stay within Gargonza for a hands-on cooking class, mastering fresh pasta with the castle’s chef before sitting down to lunch.

Dinner at leisure at Castello di Gargonza

In the evening, dinner is at leisure at Castello di Gargonza, allowing you to relax and dine at your own pace in the tranquil surroundings.

Day 5 · Volterra


Truffle hunt and home-cooked truffle lunch

Meet a renowned truffle-hunting family whose knowledge spans generations. Walk into the woods with their skilled dog, learning how to recognise quality truffles and the traditions surrounding them, before settling into a home-cooked truffle-based ...

Guided exploration of Volterra and alabaster demonstration

Guided exploration of Volterra and alabaster demonstration Continue to Volterra for a guided afternoon steeped in ancient craftsmanship. Perched high on a ridge, this Etruscan city reveals layers of history in its Roman theatre, fortified walls, a...

Dinner back at Castello di Gargonza

Return to the hotel for a relaxed dinner of regional cuisine, reflecting the flavours of Tuscany.

Day 6 · Pienza


Farm tour and lunch at Podere Il Casale

Travel to the family-run farm of Podere Il Casale, where a guided walk reveals farm life from stable to dairy. Discover the craft behind their celebrated pecorino cheeses and estate wines, followed by a seasonal lunch. This farm and dairy tour for...

Afternoon stroll through Pienza

In the afternoon, stroll through Pienza, the ‘ideal city’ envisioned by Pope Pius II and designed around harmony and proportion. Discover its elegant piazzas, warm stone façades, and stunning vistas over the Val d’Orcia – Tuscany at its most beaut...

Montepulciano walk, cantina dinner and wine tasting

Continue to Montepulciano for a relaxed walk through its historic centre and end the day in a cantina, where a light dinner is paired with a curated tasting of local wines.

Day 7 · Siena


Expert-led walking tour of Siena

Overview An expert-led walk brings Siena to life, revealing its character in layers, from the curve of Piazza del Campo to the cathedral’s intricate marble. Learn about the city’s rich history and heritage as you explore.

Private lunch in medieval Torre di Roccabruna

For lunch, enjoy a private invitation to dine in the medieval Torre di Roccabruna, once one of Siena’s tallest towers. Your four-course meal is served high above Siena with privileged views across the city and surrounding hills.

Farewell dinner at Castello di Gargonza

Farewell dinner at Castello di Gargonza Return to Gargonza for your farewell dinner set within a medieval wine cellar and its charming garden terrace. A seasonal three-course menu, thoughtfully prepared by Chef Davide Canella, highlights local and...

Day 8 · Florence


Leisurely final morning at Castello di Gargonza

Leisurely final morning at Castello di Gargonza After breakfast, take a final moment to breathe in the quiet of Gargonza, appreciating its courtyards, its stillness, and its gentle sense of place. Those with later flights may wish to linger over o...

Return transfer to Florence

Later, return to Florence for your onward journey or flights home. This chapter may close, but Tuscany’s spirit is one that stays with you long after departure. You may also choose to speak to your Signature Collection travel expert about extendin...