Wine Down in California’s Wine Country
Private Tasting at Lambert Bridge, Rooftop Dinner at The Matheson, and 3‐Night Stay for 2
This Experience for 2 Includes:
- Private wine tasting at Lambert Bridge Winery
- Rooftop dining experience at The Matheson Healdsburg, featuring a 5-course tasting menu
- 3-night weekday stay (Sunday–Wednesday) at Hotel Trio in a studio king suite in the heart of Healdsburg
- Winspire booking & concierge service
The Heart of Sonoma Wine Country is home to Healdsburg: Where vineyard-lined hills meet tree-shaded plazas, Healdsburg captures the spirit of California wine country with equal parts sophistication and small-town warmth. Here, world-class wineries, farm-to-table restaurants, and artisan boutiques surround a charming central square. It’s a place to slow down, sip something extraordinary, and savor the simple pleasures of good company, great wine, and golden sunsets.
A Tasting at Lambert Bridge
Tucked among redwood-shaded hills, Lambert Bridge Winery is a hidden gem known for small-lot, handcrafted Bordeaux-style wines. This family-owned estate is built on a philosophy of sustainability and craftsmanship — where every bottle reflects the heart of Sonoma’s terroir.
Your private seated tasting takes place in their stunning Redwood Barrel Room, surrounded by rows of aging oak barrels and the gentle scent of wine-soaked wood. Led by an expert Wine Educator, you’ll explore both red and white wines, perfectly paired with light bites that highlight the flavors of the region. It’s an intimate and memorable experience that celebrates the artistry behind every pour.
Rooftop Experience at The Matheson
As evening falls, the energy of Healdsburg comes alive at The Matheson, one of California’s most celebrated dining destinations. At Roof 106, sip handcrafted cocktails as the sun dips behind the hills, then indulge in a 5-course tasting menu that showcases the “Best of the Best” – a culinary journey inspired by local farms and seasonal ingredients.
Your experience includes a cocktail each and a bottle of The Setting Sauvignon Blanc for the table. Chef and owner Dustin Valette, whose culinary roots run deep in Healdsburg, honors his grandfather’s legacy – a beloved baker once known for his sourdough and hospitality – by crafting dishes that blend tradition with innovation. From the rooftop’s sweeping views to the thoughtful flavors on every plate, this dinner is an expression of the Wine Country’s soul: authentic, vibrant, and unforgettable.
Modern Comfort Meets Wine Country Charm
Your retreat is the stylish Hotel Trio Healdsburg, a contemporary boutique property that feels like a warm welcome home. Settle into a spacious studio king suite with a sofa bed and kitchenette and enjoy daily breakfast for two.
Spend leisurely mornings by the pool, borrow a bicycle for a ride through vineyards, or gather around the fire pits with a glass of local Pinot Noir. The hotel’s location – just a mile from historic Healdsburg Plaza – makes it easy to explore tasting rooms, boutiques, and galleries, with complimentary shuttle service for effortless evenings out.
Note: Healdsburg is approximately 1.5 hours north of San Francisco and Oakland.
Why This Experience Captivates Donors and Closes Bids
- Wine Country Dream: Healdsburg is one of California’s most sought-after destinations — luxurious, approachable, and endlessly scenic.
- Balanced Indulgence: A mix of relaxation and refined adventure — from private tastings and chef-driven dining to boutique accommodations with modern comfort.
- Broad Appeal: Perfect for couples, friends, or anyone who loves food, wine, and laid-back sophistication.
- High Perceived Value: Multi-night stay, exclusive winery access, and a Michelin-level rooftop dinner — all wrapped in one effortless package.
- Turnkey Ease: Every detail managed by Winspire’s concierge service — donors simply book, show up, and savor every moment.
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 Tasting at Lambert Bridge, Rooftop Dinner at The Matheson, and 3‐Night Stay for 2
This Experience for 2 Includes:
- Private wine tasting at Lambert Bridge Winery
- Rooftop dining experience at The Matheson Healdsburg, featuring a 5-course tasting menu
- 3-night weekend stay (Thursday-Sunday) at Hotel Trio in a studio king suite in the heart of Healdsburg
- Winspire booking & concierge service
The Heart of Sonoma Wine Country is home to Healdsburg: Where vineyard-lined hills meet tree-shaded plazas, Healdsburg captures the spirit of California wine country with equal parts sophistication and small-town warmth. Here, world-class wineries, farm-to-table restaurants, and artisan boutiques surround a charming central square. It’s a place to slow down, sip something extraordinary, and savor the simple pleasures of good company, great wine, and golden sunsets.
A Tasting at Lambert Bridge
Tucked among redwood-shaded hills, Lambert Bridge Winery is a hidden gem known for small-lot, handcrafted Bordeaux-style wines. This family-owned estate is built on a philosophy of sustainability and craftsmanship — where every bottle reflects the heart of Sonoma’s terroir.
Your private seated tasting takes place in their stunning Redwood Barrel Room, surrounded by rows of aging oak barrels and the gentle scent of wine-soaked wood. Led by an expert Wine Educator, you’ll explore both red and white wines, perfectly paired with light bites that highlight the flavors of the region. It’s an intimate and memorable experience that celebrates the artistry behind every pour.
Rooftop Experience at The Matheson
As evening falls, the energy of Healdsburg comes alive at The Matheson, one of California’s most celebrated dining destinations. At Roof 106, sip handcrafted cocktails as the sun dips behind the hills, then indulge in a 5-course tasting menu that showcases the “Best of the Best” – a culinary journey inspired by local farms and seasonal ingredients.
Your experience includes a cocktail each and a bottle of The Setting Sauvignon Blanc for the table. Chef and owner Dustin Valette, whose culinary roots run deep in Healdsburg, honors his grandfather’s legacy – a beloved baker once known for his sourdough and hospitality – by crafting dishes that blend tradition with innovation. From the rooftop’s sweeping views to the thoughtful flavors on every plate, this dinner is an expression of the Wine Country’s soul: authentic, vibrant, and unforgettable.
Modern Comfort Meets Wine Country Charm
Your retreat is the stylish Hotel Trio Healdsburg, a contemporary boutique property that feels like a warm welcome home. Settle into a spacious studio king suite with a sofa bed and kitchenette and enjoy daily breakfast for two.
Spend leisurely mornings by the pool, borrow a bicycle for a ride through vineyards, or gather around the fire pits with a glass of local Pinot Noir. The hotel’s location – just a mile from historic Healdsburg Plaza – makes it easy to explore tasting rooms, boutiques, and galleries, with complimentary shuttle service for effortless evenings out.
Note: Healdsburg is approximately 1.5 hours north of San Francisco and Oakland.
Why This Experience Captivates Donors and Closes Bids
- Wine Country Dream: Healdsburg is one of California’s most sought-after destinations — luxurious, approachable, and endlessly scenic.
- Balanced Indulgence: A mix of relaxation and refined adventure — from private tastings and chef-driven dining to boutique accommodations with modern comfort.
- Broad Appeal: Perfect for couples, friends, or anyone who loves food, wine, and laid-back sophistication.
- High Perceived Value: Multi-night stay, exclusive winery access, and a Michelin-level rooftop dinner — all wrapped in one effortless package.
- Turnkey Ease: Every detail managed by Winspire’s concierge service — donors simply book, show up, and savor every moment.
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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