Shall We Wine Classes & Events

Explore lively classes and one-of-a-kind experiences featuring passionate storytellers, industry leaders, and rising stars of the wine & spirits worlds. SWW Classes & Events range from intimate mini-parties and exclusive tastings to regional deep-dives, food & wine pairing masterclasses, and so much more.

Classes & Events are open to the public (unless noted otherwise).

Check out our Upcoming Classes & Events

Reclaim Wellness – Silent Walk and Meditation

The Shall We Wine Silent Walk and Meditation is an intentional practice of self-care, reflection, and connection with nature and community. Come experience the power of silence, reflection and shared insights . – Reading of the Day: Our event begins [...]

Reclaim Rest – Deep Rest & Tea Tasting

Haji Healing Salon 4448 S. Cottage Grove, Chicago, IL, United States

Give yourself a moment to reclaim rest. Join Shall We Wine EXP for a blissful afternoon dedicated to unwinding, resetting, and embracing a state of deep relaxation. Deep Rest Session: Led by the gentle and melodic guidance of Aya Inti, [...]

Reclaim Wellness – Silent Walk and Meditation

The Shall We Wine Silent Walk and Meditation is an intentional practice of self-care, reflection, and connection with nature and community. Come experience the power of silence, reflection and shared insights . – Reading of the Day: Our event begins [...]

Reclaim Adventure – Curated Travel to Sonoma, CA

Step Into the Story—Your Sonoma Wine Adventure Awaits Join Shall We Wine EXP for a transformative journey to the heart of California wine country—Sonoma. This is more than a getaway—it’s an insider’s adventure that mirrors Regine Rousseau’s own globe-trotting wine [...]

Reclaim Wellness – Silent Walk and Meditation

The Shall We Wine Silent Walk and Meditation is an intentional practice of self-care, reflection, and connection with nature and community. Come experience the power of silence, reflection and shared insights . – Reading of the Day: Our event begins [...]

Reclaim Wellness – Silent Walk and Meditation

The Shall We Wine Silent Walk and Meditation is an intentional practice of self-care, reflection, and connection with nature and community. Come experience the power of silence, reflection and shared insights . – Reading of the Day: Our event begins [...]

Reclaim Community – Curated Travel to Paso Robles, CA

Reclaim Your Joy. Reclaim Your Peace. Reclaim Community. Join Shall We Wine EXP for an unforgettable curated experience in Paso Robles, California—a wine country gem where adventure, connection, and self-care meet. Over four unforgettable days, you’ll sip, savor, and soak [...]

Raise a Glass: Champagne Day Celebration (Members only)

TBA

POP. FIZZ. CLINK. Reclaim Fun by raising a glass with Shall We Wine EXP as we honor the world’s most iconic bubbly—Champagne! In celebration of Champagne Day, we invite you to indulge in an effervescent evening filled with luxury, laughter, [...]

Cheers to the Year – Shall We Wine EXP Member Holiday Celebration

TBA

Celebrate the season and toast to an unforgettable year with Shall We Wine EXP at our exclusive Member Holiday Celebration! This festive gathering is our way of saying thank you to our incredible community and closing out 2025 in style. [...]