Raffle

You win... You pick!
Your choice of 4 amazing Winspire getaways!

Raffle tickets will be available to purchase by event attendees the evening of the event.
1 Ticket for $25 or 5 tickets for $100

It is also important to note that each trip comes with Winspire booking & concierge service. This talented team can also (in most cases) help customize your adventure by (for appropriate added fees) adding travel dates/participants.

Option 1: A Taste of California’s Wine Country

Your Choice of One Signature Culinary Experience & 2-Night Stay at the Valette Guest House for 2

This Experience for 2 Includes:

• 2-night stay at the Valette Guest House, a refined hideaway in the heart of Healdsburg

• Your choice of one of three unforgettable culinary experiences

• Winspire booking & concierge service — seamless planning from start to finish

Tucked among rolling vineyards and sun-drenched hills, Healdsburg is where Sonoma’s culinary soul comes alive. Mornings unfold slowly with coffee and quiet streets. Afternoons invite leisurely strolls past tasting rooms and boutiques. Evenings glow with the hum of conversation, clinking glasses, and the unmistakable warmth of wine country hospitality.

option 2: Glamping by the Great Lakes

Wine Tasting, Glamping Picnic, and 2 Nights of Outdoor Luxury for 2

This Experience for 2 Includes:

● Wine Tasting at Modales Winery

● Glamping Picnic for 2

● 2-night stay in a Deluxe Tent with ensuite bathroom and power

● Daily breakfast prepared fresh onsite

●Winspire booking & concierge service

Michigan’s Lakeside Gem: Nestled along the golden shores of Lake Michigan, South Haven is a sanctuary of natural beauty and small-town charm. Days here unfold at an easy pace - from strolling along sun-kissed beaches and exploring scenic trails to browsing local boutiques filled with artisanal finds. As evening falls, the town glows with lakefront sunsets and the aroma of farm-fresh cuisine from cozy eateries. Equal parts adventure and serenity, South Haven invites you to slow down, soak it in, and savor Michigan’s most enchanting coastal escape.

option 3: Under the Tuscan Sun: Wine, Cuisine, & Charm in Cortona, Italy

Italy Escape for 4 with Wine Tasting & Private Chef Dinner

 This Experience for 4 Includes:

●        Your choice of a 3-night weekend (Fri–Sun) or 4-night weekday (Mon–Thu) stay in Tuscany for 4 guests

●        Wine tasting in Cortona featuring 4 local wines from one of the world’s most celebrated regions

●        Private chef-prepared 3-course dinner served in your apartment

●        Winspire booking & concierge service — seamless support from planning to departure

 Imagine strolling cobblestone streets at golden hour, the rooftops of Cortona glowing in the late-day light as church bells echo across the valley. In every direction, vineyards and olive groves roll toward the horizon, while the scent of freshly baked bread and simmering sauces drifts from nearby trattorias. For four lucky guests, this is Tuscany not as a tourist sees it, but as a local feels it — intimate, authentic, and unforgettable.