Taste of Tuscany: Wine, Cuisine & Countryside
Cortona Countryside Villa for 7 Nights, Daily Breakfast, Cooking Class & Dinner, Wine Tour for Up to 4
This Experience for 4 Includes:
- 7-night stay in a private villa in Tuscany (Cortona, Italy)
- Daily chef-prepared breakfast and daily maid service
- Private cooking class & dinner in your villa
- Tours & tastings at 2 distinguished wineries
- Winspire booking & concierge service
Golden sunlight drapes across rolling hills, casting a warm glow over ancient stone farmhouses and fields lined with cypress trees that stand like timeless sentinels. Vineyards unfurl in every direction, their rows of vines painting the countryside in a patchwork of emerald and gold. The air is laced with the fragrance of rosemary and lavender carried on a gentle breeze, mingling with the aroma of freshly baked bread from a nearby village.
You awaken to the hiss of espresso and the buttery scent of warm pastries, lovingly prepared by your private chef. From your terrace, the landscape stretches endlessly — olive groves shimmering silver in the light, church bells echoing faintly in the distance. This is not a dream, but the daily rhythm of Tuscany — where time slows, senses awaken, and every moment feels touched by magic.
Your Tuscan Villa Retreat
Perched in the Cortona countryside, your charming two-bedroom, two-bath villa welcomes you with warmth and authenticity. Surrounded by olive groves and overlooking the serene valley of Val’ di Chiana, it is the perfect balance of seclusion and accessibility—just minutes from Cortona’s bustling piazzas.
The villa features:
- An outdoor terrace perfect for al fresco dining with panoramic valley views
- A private swimming pool and sun-dappled gardens for afternoons of leisure
- Modern comforts like air conditioning, Wi-Fi, and satellite TV, all wrapped within the villa’s authentic Tuscan architecture
Each morning, awaken to a chef-prepared breakfast that celebrates Tuscany’s simple yet exquisite flavors. Each evening, let the countryside quiet lull you into pure bliss.
Culinary Adventure
Nothing captures the soul of Tuscany more than its food — and here, you’ll do more than taste it, you’ll live it. Step into your villa’s kitchen, where the warmth of terracotta walls and the scent of fresh herbs set the stage for a hands-on cooking class with a private chef. Together, you’ll roll silky ribbons of handmade pasta, drizzle golden olive oil pressed from nearby groves, and simmer sauces that sing with flavors only Tuscany can produce.
As laughter fills the kitchen and conversation flows, the experience becomes more than a class — it’s a celebration of connection, tradition, and the art of slowing down. When the work is done, gather around the table for a feast you’ve created side by side. Each course tells a story: of family recipes passed down for generations, of simple ingredients elevated by time and care, of Tuscany’s enduring love affair with food.
This is not just dinner. It’s a memory woven from flavor, fellowship, and the unmistakable magic of dining “under the Tuscan sun.”
A Journey Through Tuscany’s Vineyards
Tuscany’s wine is more than a drink — it’s poetry in a glass, a story of soil and sun told sip by sip. Your journey begins at a renowned estate nestled between Cortona and Montepulciano, where rolling vineyards stretch to the horizon. Stroll through rows of Sangiovese vines, heavy with promise, before descending into cool stone cellars where oak barrels quietly work their magic. A guided tasting invites you to savor each note — cherry, leather, spice — perfectly paired with a leisurely Tuscan lunch that lingers into the afternoon.
The adventure continues at a boutique countryside winery, where rustic charm and authenticity infuse every detail. Here, the winemakers welcome you like family, sharing the traditions and secrets of their craft. Raise a glass of bold Chianti, swirl a smooth Brunello, and let the flavors transport you to a place where time slows and every pour is a celebration of life’s simple luxuries. Between the vineyard views, the aromas of earth and oak, and the warmth of Tuscan hospitality, you’ll discover why wine here is not just made — it’s lived.
NOTE: Cortona is approximately a 1.5-hour drive from Florence and a 2.5-hour drive from Rome. Nearby cities: Perugia 45 km; Siena 70 km; Florence 100 km; Rome 205 km; Pisa 200 km.
Villa stays typically run Thursday–Thursday or Saturday–Saturday, subject to availability.
Why This Experience Captivates Donors and Closes Bids
- Timeless Appeal Meets Broad Donor Excitement: Tuscany embodies the ultimate travel dream—rolling hills, Renaissance towns, world-class wine, and authentic Italian cuisine. This package appeals across generations and donor profiles.
- Bucket-List Destination: A private villa stay in the Cortona countryside is the quintessential Italian experience—on par with Paris or the Amalfi Coast. It’s a true once-in-a-lifetime trip that donors instantly recognize as extraordinary.
- Exclusive Access: Daily chef-prepared breakfasts, a private cooking class and dinner, plus tours and tastings at boutique wineries deliver an immersive experience that can’t be booked off the shelf.
- Emotional Storytelling: From gathering around the villa’s table to sipping Brunello in a vineyard, this experience provides intimate, unforgettable moments bidders will relive and share for years.
- Turnkey Ease: With Winspire’s full-service booking and concierge team handling every detail, this package is seamless for your winning bidders and completely risk-free for your nonprofit.
Package Redemption
Winspire Travel packages and experiences must be booked within one year of the purchase date. The actual travel date must occur within two years of the purchase date.
Booking & Concierge Services
Winspire provides a team of seasoned travel professionals to help you redeem your experience. We will book all travel-related details and reservations for every part of your experience. Included within our services, Winspire can assist with extra hotel nights, airfare, and additional guests as a full-service travel agency.
Additional Information
Reservations are subject to availability, blackout dates, and major holidays. Reservations must be booked 60 days in advance of travel. Purchases through charity fundraisers are non-refundable.
Blackout Dates
The week of major holidays and major local events. Additional dates may apply. This package is available from Saturday to Saturday or Thursday to Thursday.
Cortona Countryside Villa for 7 Nights, Daily Breakfast, Cooking Class & Dinner, Wine Tour and Private Driver for Up to 4
This Experience for 4 Includes:
- 7-night stay in a private villa in Tuscany (Cortona, Italy)
- Daily chef-prepared breakfast and daily maid service
- Private cooking class & dinner in your villa
- Tours & tastings at 2 distinguished wineries
- Private driver for 8 hours a day during your stay
- Winspire booking & concierge service
Golden sunlight drapes across rolling hills, casting a warm glow over ancient stone farmhouses and fields lined with cypress trees that stand like timeless sentinels. Vineyards unfurl in every direction, their rows of vines painting the countryside in a patchwork of emerald and gold. The air is laced with the fragrance of rosemary and lavender carried on a gentle breeze, mingling with the aroma of freshly baked bread from a nearby village.
You awaken to the hiss of espresso and the buttery scent of warm pastries, lovingly prepared by your private chef. From your terrace, the landscape stretches endlessly — olive groves shimmering silver in the light, church bells echoing faintly in the distance. This is not a dream, but the daily rhythm of Tuscany — where time slows, senses awaken, and every moment feels touched by magic.
Your Tuscan Villa Retreat
Perched in the Cortona countryside, your charming two-bedroom, two-bath villa welcomes you with warmth and authenticity. Surrounded by olive groves and overlooking the serene valley of Val’ di Chiana, it is the perfect balance of seclusion and accessibility—just minutes from Cortona’s bustling piazzas.
The villa features:
- An outdoor terrace perfect for al fresco dining with panoramic valley views
- A private swimming pool and sun-dappled gardens for afternoons of leisure
- Modern comforts like air conditioning, Wi-Fi, and satellite TV, all wrapped within the villa’s authentic Tuscan architecture
Each morning, awaken to a chef-prepared breakfast that celebrates Tuscany’s simple yet exquisite flavors. Each evening, let the countryside quiet lull you into pure bliss.
Culinary Adventure
Nothing captures the soul of Tuscany more than its food — and here, you’ll do more than taste it, you’ll live it. Step into your villa’s kitchen, where the warmth of terracotta walls and the scent of fresh herbs set the stage for a hands-on cooking class with a private chef. Together, you’ll roll silky ribbons of handmade pasta, drizzle golden olive oil pressed from nearby groves, and simmer sauces that sing with flavors only Tuscany can produce.
As laughter fills the kitchen and conversation flows, the experience becomes more than a class — it’s a celebration of connection, tradition, and the art of slowing down. When the work is done, gather around the table for a feast you’ve created side by side. Each course tells a story: of family recipes passed down for generations, of simple ingredients elevated by time and care, of Tuscany’s enduring love affair with food.
This is not just dinner. It’s a memory woven from flavor, fellowship, and the unmistakable magic of dining “under the Tuscan sun.”
A Journey Through Tuscany’s Vineyards
Tuscany’s wine is more than a drink — it’s poetry in a glass, a story of soil and sun told sip by sip. Your journey begins at a renowned estate nestled between Cortona and Montepulciano, where rolling vineyards stretch to the horizon. Stroll through rows of Sangiovese vines, heavy with promise, before descending into cool stone cellars where oak barrels quietly work their magic. A guided tasting invites you to savor each note — cherry, leather, spice — perfectly paired with a leisurely Tuscan lunch that lingers into the afternoon.
The adventure continues at a boutique countryside winery, where rustic charm and authenticity infuse every detail. Here, the winemakers welcome you like family, sharing the traditions and secrets of their craft. Raise a glass of bold Chianti, swirl a smooth Brunello, and let the flavors transport you to a place where time slows and every pour is a celebration of life’s simple luxuries. Between the vineyard views, the aromas of earth and oak, and the warmth of Tuscan hospitality, you’ll discover why wine here is not just made — it’s lived.
Private Driver — Explore Beyond
With your dedicated private driver at your service for 8 hours each day, the treasures of Tuscany open wide. Stroll the winding streets of Assisi, gaze at Brunelleschi’s dome in Florence, or indulge in pecorino tasting in Pienza. Explore the wine roads of Montalcino, the medieval towers of San Gimignano, or the sweeping piazzas of Siena — all within easy reach of your villa.
This is Tuscany without limits — where every journey is effortless and every destination unforgettable.
NOTE:
Maximum 4 guests, with a driving distance of 100 km (approximately 60 miles) from your villa. Airport transfers not included.
Cortona is approximately a 1.5-hour drive from Florence and a 2.5-hour drive from Rome. Nearby cities: Perugia 45 km; Siena 70 km; Florence 100 km; Rome 205 km; Pisa 200 km.
Villa stays typically run Thursday–Thursday or Saturday–Saturday, subject to availability.
Why This Experience Captivates Donors and Closes Bids
- Timeless Appeal Meets Broad Donor Excitement: Tuscany embodies the ultimate travel dream—rolling hills, Renaissance towns, world-class wine, and authentic Italian cuisine. This package appeals across generations and donor profiles.
- Bucket-List Destination: A private villa stay in the Cortona countryside is the quintessential Italian experience—on par with Paris or the Amalfi Coast. It’s a true once-in-a-lifetime trip that donors instantly recognize as extraordinary.
- Exclusive Access: Daily chef-prepared breakfasts, a private cooking class and dinner, plus tours and tastings at boutique wineries deliver an immersive experience that can’t be booked off the shelf.
- Emotional Storytelling: From gathering around the villa’s table to sipping Brunello in a vineyard, this experience provides intimate, unforgettable moments bidders will relive and share for years.
- Effortless Exploration: A private driver transforms the trip into a stress-free, customizable adventure — unlocking Florence, Siena, and hilltop villages at bidders’ fingertips, elevating both the exclusivity and value of the experience.
- Turnkey Ease: With Winspire’s full-service booking and concierge team handling every detail, this package is seamless for your winning bidders and completely risk-free for your nonprofit.
Package Redemption
Winspire Travel packages and experiences must be booked within one year of the purchase date. The actual travel date must occur within two years of the purchase date.
Booking & Concierge Services
Winspire provides a team of seasoned travel professionals to help you redeem your experience. We will book all travel-related details and reservations for every part of your experience. Included within our services, Winspire can assist with extra hotel nights, airfare, and additional guests as a full-service travel agency.
Additional Information
Reservations are subject to availability, blackout dates, and major holidays. Reservations must be booked 60 days in advance of travel. Purchases through charity fundraisers are non-refundable.
Blackout Dates
The week of major holidays and major local events. Additional dates may apply. Villa stays typically run Thursday–Thursday or Saturday–Saturday, subject to availability.
Cortona Countryside Villa for 7 Nights, Daily Breakfast, Cooking Class & Dinner, Wine Tour for Up to 8
This Experience for 8 Includes:
- 7-night stay in a private villa in Tuscany (Cortona, Italy)
- Daily chef-prepared breakfast and daily maid service
- Private cooking class & dinner in your villa
- Tours & tastings at 2 distinguished wineries
- Winspire booking & concierge service
Golden sunlight drapes across rolling hills, casting a warm glow over ancient stone farmhouses and fields lined with cypress trees that stand like timeless sentinels. Vineyards unfurl in every direction, their rows of vines painting the countryside in a patchwork of emerald and gold. The air is laced with the fragrance of rosemary and lavender carried on a gentle breeze, mingling with the aroma of freshly baked bread from a nearby village.
You awaken to the hiss of espresso and the buttery scent of warm pastries, lovingly prepared by your private chef. From your terrace, the landscape stretches endlessly — olive groves shimmering silver in the light, church bells echoing faintly in the distance. This is not a dream, but the daily rhythm of Tuscany — where time slows, senses awaken, and every moment feels touched by magic.
Your Tuscan Villa Retreat
Perched in the Cortona countryside, your charming four-bedroom, three-bath villa welcomes you with warmth and authenticity. Surrounded by olive groves and overlooking the serene valley of Val’ di Chiana, it is the perfect balance of seclusion and accessibility—just minutes from Cortona’s bustling piazzas.
The villa features:
- An outdoor terrace perfect for al fresco dining with panoramic valley views
- A private swimming pool and sun-dappled gardens for afternoons of leisure
- Modern comforts like air conditioning, Wi-Fi, and satellite TV, all wrapped within the villa’s authentic Tuscan architecture
Each morning, awaken to a chef-prepared breakfast that celebrates Tuscany’s simple yet exquisite flavors. Each evening, let the countryside quiet lull you into pure bliss.
Culinary Adventure
Nothing captures the soul of Tuscany more than its food — and here, you’ll do more than taste it, you’ll live it. Step into your villa’s kitchen, where the warmth of terracotta walls and the scent of fresh herbs set the stage for a hands-on cooking class with a private chef. Together, you’ll roll silky ribbons of handmade pasta, drizzle golden olive oil pressed from nearby groves, and simmer sauces that sing with flavors only Tuscany can produce.
As laughter fills the kitchen and conversation flows, the experience becomes more than a class — it’s a celebration of connection, tradition, and the art of slowing down. When the work is done, gather around the table for a feast you’ve created side by side. Each course tells a story: of family recipes passed down for generations, of simple ingredients elevated by time and care, of Tuscany’s enduring love affair with food.
This is not just dinner. It’s a memory woven from flavor, fellowship, and the unmistakable magic of dining “under the Tuscan sun.”
A Journey Through Tuscany’s Vineyards
Tuscany’s wine is more than a drink — it’s poetry in a glass, a story of soil and sun told sip by sip. Your journey begins at a renowned estate nestled between Cortona and Montepulciano, where rolling vineyards stretch to the horizon. Stroll through rows of Sangiovese vines, heavy with promise, before descending into cool stone cellars where oak barrels quietly work their magic. A guided tasting invites you to savor each note — cherry, leather, spice — perfectly paired with a leisurely Tuscan lunch that lingers into the afternoon.
The adventure continues at a boutique countryside winery, where rustic charm and authenticity infuse every detail. Here, the winemakers welcome you like family, sharing the traditions and secrets of their craft. Raise a glass of bold Chianti, swirl a smooth Brunello, and let the flavors transport you to a place where time slows and every pour is a celebration of life’s simple luxuries. Between the vineyard views, the aromas of earth and oak, and the warmth of Tuscan hospitality, you’ll discover why wine here is not just made — it’s lived.
NOTE: Cortona is approximately a 1.5-hour drive from Florence and a 2.5-hour drive from Rome. Nearby cities: Perugia 45 km; Siena 70 km; Florence 100 km; Rome 205 km; Pisa 200 km.
Villa stays typically run Thursday–Thursday or Saturday–Saturday, subject to availability.
Why This Experience Captivates Donors and Closes Bids
- Timeless Appeal Meets Broad Donor Excitement: Tuscany embodies the ultimate travel dream—rolling hills, Renaissance towns, world-class wine, and authentic Italian cuisine. This package appeals across generations and donor profiles.
- Bucket-List Destination: A private villa stay in the Cortona countryside is the quintessential Italian experience—on par with Paris or the Amalfi Coast. It’s a true once-in-a-lifetime trip that donors instantly recognize as extraordinary.
- Exclusive Access: Daily chef-prepared breakfasts, a private cooking class and dinner, plus tours and tastings at boutique wineries deliver an immersive experience that can’t be booked off the shelf.
- Emotional Storytelling: From gathering around the villa’s table to sipping Brunello in a vineyard, this experience provides intimate, unforgettable moments bidders will relive and share for years.
- Turnkey Ease: With Winspire’s full-service booking and concierge team handling every detail, this package is seamless for your winning bidders and completely risk-free for your nonprofit.
Package Redemption
Winspire Travel packages and experiences must be booked within one year of the purchase date. The actual travel date must occur within two years of the purchase date.
Booking & Concierge Services
Winspire provides a team of seasoned travel professionals to help you redeem your experience. We will book all travel-related details and reservations for every part of your experience. Included within our services, Winspire can assist with extra hotel nights, airfare, and additional guests as a full-service travel agency.
Additional Information
Reservations are subject to availability, blackout dates, and major holidays. Reservations must be booked 60 days in advance of travel. Purchases through charity fundraisers are non-refundable.
Blackout Dates
The week of major holidays and major local events. Additional dates may apply. Villa stays typically run Thursday–Thursday or Saturday–Saturday, subject to availability.
Cortona Countryside Villa for 7 Nights, Daily Breakfast, Cooking Class & Dinner, Wine Tour and Private Driver for Up to 8
This Experience for 8 Includes:
- 7-night stay in a private villa in Tuscany (Cortona, Italy)
- Daily chef-prepared breakfast and daily maid service
- Private cooking class & dinner in your villa
- Tours & tastings at 2 distinguished wineries
- Private driver for 8 hours a day during your stay
- Winspire booking & concierge service
Golden sunlight drapes across rolling hills, casting a warm glow over ancient stone farmhouses and fields lined with cypress trees that stand like timeless sentinels. Vineyards unfurl in every direction, their rows of vines painting the countryside in a patchwork of emerald and gold. The air is laced with the fragrance of rosemary and lavender carried on a gentle breeze, mingling with the aroma of freshly baked bread from a nearby village.
You awaken to the hiss of espresso and the buttery scent of warm pastries, lovingly prepared by your private chef. From your terrace, the landscape stretches endlessly — olive groves shimmering silver in the light, church bells echoing faintly in the distance. This is not a dream, but the daily rhythm of Tuscany — where time slows, senses awaken, and every moment feels touched by magic.
Your Tuscan Villa Retreat
Perched in the Cortona countryside, your charming four-bedroom, three-bath villa welcomes you with warmth and authenticity. Surrounded by olive groves and overlooking the serene valley of Val’ di Chiana, it is the perfect balance of seclusion and accessibility—just minutes from Cortona’s bustling piazzas.
The villa features:
- An outdoor terrace perfect for al fresco dining with panoramic valley views
- A private swimming pool and sun-dappled gardens for afternoons of leisure
- Modern comforts like air conditioning, Wi-Fi, and satellite TV, all wrapped within the villa’s authentic Tuscan architecture
Each morning, awaken to a chef-prepared breakfast that celebrates Tuscany’s simple yet exquisite flavors. Each evening, let the countryside quiet lull you into pure bliss.
Culinary Adventure
Nothing captures the soul of Tuscany more than its food — and here, you’ll do more than taste it, you’ll live it. Step into your villa’s kitchen, where the warmth of terracotta walls and the scent of fresh herbs set the stage for a hands-on cooking class with a private chef. Together, you’ll roll silky ribbons of handmade pasta, drizzle golden olive oil pressed from nearby groves, and simmer sauces that sing with flavors only Tuscany can produce.
As laughter fills the kitchen and conversation flows, the experience becomes more than a class — it’s a celebration of connection, tradition, and the art of slowing down. When the work is done, gather around the table for a feast you’ve created side by side. Each course tells a story: of family recipes passed down for generations, of simple ingredients elevated by time and care, of Tuscany’s enduring love affair with food.
This is not just dinner. It’s a memory woven from flavor, fellowship, and the unmistakable magic of dining “under the Tuscan sun.”
A Journey Through Tuscany’s Vineyards
Tuscany’s wine is more than a drink — it’s poetry in a glass, a story of soil and sun told sip by sip. Your journey begins at a renowned estate nestled between Cortona and Montepulciano, where rolling vineyards stretch to the horizon. Stroll through rows of Sangiovese vines, heavy with promise, before descending into cool stone cellars where oak barrels quietly work their magic. A guided tasting invites you to savor each note — cherry, leather, spice — perfectly paired with a leisurely Tuscan lunch that lingers into the afternoon.
The adventure continues at a boutique countryside winery, where rustic charm and authenticity infuse every detail. Here, the winemakers welcome you like family, sharing the traditions and secrets of their craft. Raise a glass of bold Chianti, swirl a smooth Brunello, and let the flavors transport you to a place where time slows and every pour is a celebration of life’s simple luxuries. Between the vineyard views, the aromas of earth and oak, and the warmth of Tuscan hospitality, you’ll discover why wine here is not just made — it’s lived.
Private Driver — Explore Beyond
With your dedicated private driver at your service for 8 hours each day, the treasures of Tuscany open wide. Stroll the winding streets of Assisi, gaze at Brunelleschi’s dome in Florence, or indulge in pecorino tasting in Pienza. Explore the wine roads of Montalcino, the medieval towers of San Gimignano, or the sweeping piazzas of Siena — all within easy reach of your villa.
This is Tuscany without limits — where every journey is effortless and every destination unforgettable.
NOTE:
Maximum 8 guests, with a driving distance of 100 km (approximately 60 miles) from your villa. Airport transfers not included.
Cortona is approximately a 1.5-hour drive from Florence and a 2.5-hour drive from Rome. Nearby cities: Perugia 45 km; Siena 70 km; Florence 100 km; Rome 205 km; Pisa 200 km.
Villa stays typically run Thursday–Thursday or Saturday–Saturday, subject to availability.
Why This Experience Captivates Donors and Closes Bids
- Timeless Appeal Meets Broad Donor Excitement: Tuscany embodies the ultimate travel dream—rolling hills, Renaissance towns, world-class wine, and authentic Italian cuisine. This package appeals across generations and donor profiles.
- Bucket-List Destination: A private villa stay in the Cortona countryside is the quintessential Italian experience—on par with Paris or the Amalfi Coast. It’s a true once-in-a-lifetime trip that donors instantly recognize as extraordinary.
- Exclusive Access: Daily chef-prepared breakfasts, a private cooking class and dinner, plus tours and tastings at boutique wineries deliver an immersive experience that can’t be booked off the shelf.
- Emotional Storytelling: From gathering around the villa’s table to sipping Brunello in a vineyard, this experience provides intimate, unforgettable moments bidders will relive and share for years.
- Effortless Exploration: A private driver transforms the trip into a stress-free, customizable adventure — unlocking Florence, Siena, and hilltop villages at bidders’ fingertips, elevating both the exclusivity and value of the experience.
- Turnkey Ease: With Winspire’s full-service booking and concierge team handling every detail, this package is seamless for your winning bidders and completely risk-free for your nonprofit.
Package Redemption
Winspire Travel packages and experiences must be booked within one year of the purchase date. The actual travel date must occur within two years of the purchase date.
Booking & Concierge Services
Winspire provides a team of seasoned travel professionals to help you redeem your experience. We will book all travel-related details and reservations for every part of your experience. Included within our services, Winspire can assist with extra hotel nights, airfare, and additional guests as a full-service travel agency.
Additional Information
Reservations are subject to availability, blackout dates, and major holidays. Reservations must be booked 60 days in advance of travel. Purchases through charity fundraisers are non-refundable.
Blackout Dates
The week of major holidays and major local events. Additional dates may apply. Villa stays typically run Thursday–Thursday or Saturday–Saturday, subject to availability.
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