California Uncorked: Culinary & Wine Favorites
Private Tastings, Michelin‐Recognized Dining, and 3‐Night Stay in Wine Country for 2
Your Experience for 2 Includes:
- Private seated tasting of The Setting Wines, at the Montage Healdsburg
- Elevated private tasting experience at Aperture Cellars Estate, highlighting the most limited of offerings
- Premier Experience at The Matheson — 5-course tasting menu with curated wine pairings
- 3-night weekday stay (Sunday – Thursday) at Hotel Trio with daily breakfast in the heart of Healdsburg
- Winspire booking & concierge service
Where Wine Country Dreams Come to Life: Tucked in the heart of Sonoma County, Healdsburg captures everything that makes California wine country so irresistible — rustic charm, refined flavor, and rolling hills draped in vineyards. Here, mornings begin with golden light filtering through redwoods, afternoons are filled with cellar tastings and farm-fresh meals, and evenings unfold over candlelit tables and world-class wines. This is where passion meets palate — a celebration of craftsmanship, creativity, and connection.
The Setting Wines at Montage Healdsburg: A Tasting Crafted by a Master
Step into the serene elegance of Montage Healdsburg, where your private The Setting Wines tasting awaits — an experience crafted to showcase some of the most celebrated wines in California today.
Your host guides you through a selection of five limited productions, highlight acclaimed single vineyard designated wines from Napa – The Setting Wines — a label made famous by Jesse Katz, Wine Enthusiast’s Winemaker of the Year and the visionary behind some of the most sought-after small-production wines in the country.
Each glass reveals his signature style: precision, purity, and power wrapped in velvet texture. Rich Cabernet Sauvignons, expressive Bordeaux blends, and beautifully lifted whites unfold one layer at a time. A chef-curated locally sourced cheese and charcuterie board enhances every sip, featuring artisan cheeses, cured meats, local honey, and seasonal accompaniments.
Set against vineyard views and the refined backdrop of the Montage, this tasting is both luxurious and deeply personal — a chance to savor wines crafted by one of the most acclaimed winemakers of our time.
Aperture Cellars: A Private Tasting
Step inside Aperture Cellars and you’ll immediately understand why this estate has become one of California’s most talked-about destinations. Here enjoy a private tasting which unfolds in a pristine, light-filled room with floor-to-ceiling windows overlooking the estate vineyards — a space designed to make every moment feel elevated and intimate. You’ll begin with a glass of French grower Champagne, the perfect prelude to the journey ahead.
From there, your host guides you through a curated flight of six limited-production wines, each one showcasing a different expression of cool-climate Bordeaux varietals sourced from premier vineyard sites across Sonoma County. Every pour is accompanied by thoughtful, seasonal food pairings crafted to highlight the depth, texture, and personality of each wine. This is more than a tasting; it’s an immersion into craft, creativity, and the captivating beauty of Sonoma wine country.
The Matheson: A Culinary Love Letter to Wine Country
Dinner at The Matheson, led by acclaimed chef Dustin Valette, is an intimate journey through the heart of Sonoma’s culinary landscape. Your evening begins with a playful sense of discovery at the restaurant’s iconic 88-bottle Wine Wall, where each guest receives a tasting card to explore, swirl, and sip at their own pace — creating a flight as personal as it is delicious.
From there, settle into the warm glow of the dining room for a five-course tasting menu that captures Sonoma’s soul. Every plate is crafted from the region’s seasonal bounty, transformed with the finesse and artistry that define Valette’s cuisine. Each course is thoughtfully paired with wines from The Setting, Aperture, and Valette, elevating flavors and weaving a story of the vineyards and people behind them.
Your evening concludes with a sweet, spirited flourish: a handcrafted cocktail, cordial, or port served tableside — the final chapter in a meal that feels less like dinner and more like a sensory love letter to wine country.
Hotel Trio: Wine Country Comfort & Style
Your home base is Hotel Trio Healdsburg, a modern boutique retreat just minutes from the historic plaza. Your studio king suite features a kitchenette, sofa bed, and thoughtful touches designed for relaxation. Each morning, enjoy breakfast for two before setting out to explore the nearby vineyards, trails, and farm stands. In the evenings, return for bocce ball by the fire pits or a dip in the pool under the stars. With bikes available, shuttle access to town, and the welcoming warmth that defines California hospitality, Hotel Trio is the perfect place to unwind between indulgent adventures.
Note: Healdsburg is approximately 1.5 hours north of San Francisco and Oakland.
Why This Experience Captivates Donors and Closes Bids
- Bucket-list destination: Healdsburg is Sonoma’s hidden gem — a wine country retreat that feels both refined and relaxed.
- Multi-sensory appeal: Private tastings, Michelin-star dining, and artfully paired wines create a symphony of flavor and experience.
- High perceived value: Boutique winery access, elevated culinary experiences, and luxury accommodations combine for an indulgent getaway that feels truly VIP.
- Broad donor appeal: Perfect for couples, foodies, and wine enthusiasts seeking a balance of sophistication and comfort.
- Effortless planning: With Winspire’s concierge service handling every detail, donors can simply sip, savor, and enjoy the magic of Sonoma wine country.
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 US holidays and major local events. Additional dates may apply.
Private Tastings, Michelin‐Recognized Dining, and 3‐Night Stay in Wine Country for 2
Your Experience for 2 Includes:
- Private seated tasting of The Setting Wines, at the Montage Healdsburg
- Elevated private tasting experience at Aperture Cellars Estate, highlighting the most limited of offerings.
- Premier Experience at The Matheson — 5-course tasting menu with curated wine pairings
- 3-night weekend stay (Friday & Saturday) at Hotel Trio with daily breakfast in the heart of Healdsburg
- Winspire booking & concierge service
Where Wine Country Dreams Come to Life: Tucked in the heart of Sonoma County, Healdsburg captures everything that makes California wine country so irresistible — rustic charm, refined flavor, and rolling hills draped in vineyards. Here, mornings begin with golden light filtering through redwoods, afternoons are filled with cellar tastings and farm-fresh meals, and evenings unfold over candlelit tables and world-class wines. This is where passion meets palate — a celebration of craftsmanship, creativity, and connection.
The Setting Wines at Montage Healdsburg: A Tasting Crafted by a Master
Step into the serene elegance of Montage Healdsburg, where your private The Setting Wines tasting awaits — an experience crafted to showcase some of the most celebrated wines in California today.
Your host guides you through a selection of five limited productions, highlight acclaimed single vineyard designated wines from Napa – The Setting Wines — a label made famous by Jesse Katz, Wine Enthusiast’s Winemaker of the Year and the visionary behind some of the most sought-after small-production wines in the country.
Each glass reveals his signature style: precision, purity, and power wrapped in velvet texture. Rich Cabernet Sauvignons, expressive Bordeaux blends, and beautifully lifted whites unfold one layer at a time. A chef-curated locally sourced cheese and charcuterie board enhances every sip, featuring artisan cheeses, cured meats, local honey, and seasonal accompaniments.
Set against vineyard views and the refined backdrop of the Montage, this tasting is both luxurious and deeply personal — a chance to savor wines crafted by one of the most acclaimed winemakers of our time.
Aperture Cellars: A Private Tasting
Step inside Aperture Cellars and you’ll immediately understand why this estate has become one of California’s most talked-about destinations. Here enjoy a private tasting which unfolds in a pristine, light-filled room with floor-to-ceiling windows overlooking the estate vineyards — a space designed to make every moment feel elevated and intimate. You’ll begin with a glass of French grower Champagne, the perfect prelude to the journey ahead.
From there, your host guides you through a curated flight of six limited-production wines, each one showcasing a different expression of cool-climate Bordeaux varietals sourced from premier vineyard sites across Sonoma County. Every pour is accompanied by thoughtful, seasonal food pairings crafted to highlight the depth, texture, and personality of each wine. This is more than a tasting; it’s an immersion into craft, creativity, and the captivating beauty of Sonoma wine country.
The Matheson: A Culinary Love Letter to Wine Country
Dinner at The Matheson, led by acclaimed chef Dustin Valette, is an intimate journey through the heart of Sonoma’s culinary landscape. Your evening begins with a playful sense of discovery at the restaurant’s iconic 88-bottle Wine Wall, where each guest receives a tasting card to explore, swirl, and sip at their own pace — creating a flight as personal as it is delicious.
From there, settle into the warm glow of the dining room for a five-course tasting menu that captures Sonoma’s soul. Every plate is crafted from the region’s seasonal bounty, transformed with the finesse and artistry that define Valette’s cuisine. Each course is thoughtfully paired with wines from The Setting, Aperture, and Valette, elevating flavors and weaving a story of the vineyards and people behind them.
Your evening concludes with a sweet, spirited flourish: a handcrafted cocktail, cordial, or port served tableside — the final chapter in a meal that feels less like dinner and more like a sensory love letter to wine country.
Hotel Trio: Wine Country Comfort & Style
Your home base is Hotel Trio Healdsburg, a modern boutique retreat just minutes from the historic plaza. Your studio king suite features a kitchenette, sofa bed, and thoughtful touches designed for relaxation. Each morning, enjoy breakfast for two before setting out to explore the nearby vineyards, trails, and farm stands. In the evenings, return for bocce ball by the fire pits or a dip in the pool under the stars. With bikes available, shuttle access to town, and the welcoming warmth that defines California hospitality, Hotel Trio is the perfect place to unwind between indulgent adventures.
Note: Healdsburg is approximately 1.5 hours north of San Francisco and Oakland.
Why This Experience Captivates Donors and Closes Bids
- Bucket-list destination: Healdsburg is Sonoma’s hidden gem — a wine country retreat that feels both refined and relaxed.
- Multi-sensory appeal: Private tastings, Michelin-star dining, and artfully paired wines create a symphony of flavor and experience.
- High perceived value: Boutique winery access, elevated culinary experiences, and luxury accommodations combine for an indulgent getaway that feels truly VIP.
- Broad donor appeal: Perfect for couples, foodies, and wine enthusiasts seeking a balance of sophistication and comfort.
- Effortless planning: With Winspire’s concierge service handling every detail, donors can simply sip, savor, and enjoy the magic of Sonoma wine country.
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 US holidays and major local events. Additional dates may apply.
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