This is the year to do it. Make it memorable. Surround your special loved one (or yourself) with wine, food, and good company. We got your back on this one! We have long-standing relationships with some great wine bars and restaurants in Chicago. We’ll do all the work, make all the arrangements, and work with you to plan the schedule.

Our friendly wine tour guides will take you and your group to some of the hottest spots in the Chicago area to experience our unique wine and food scene! No worrying about reservations, who’s driving or “did I pick the right spot?” – we’ve got your back on this one.

Our tours give you an opportunity to celebrate with your family and friends, enjoy the moment as you create memories, and not have to worry about all of the details. You can leave that up to us!

We’re ready to help give you the birthday party you deserve!

What’s Included on Every Tour:

• 6 curated wine tastings from celebrated global regions and local vineyards
• Charcuterie & appetizers
• Chef-prepared entrees
• Dessert for those “guilty pleasures” because the night should end on a sweet note
• Luxury Mercedes Sprinter transportation throughout the entire tour
• Free pickup & drop-off within the city (additional charge may be applied for locations outside the area)
• Dedicated expert tour guide for the full experience
• Gratuity for servers included at every location, so no awkward math at the end
• Bottled water throughout the tour
• A bottle of wine served in the Sprinter between stops
• Approximately 4 hours of immersive experience

Enhance Your Experience

Take your private tour from unforgettable to once-in-a-lifetime. Add any of these upgrades when booking:

Celebration Upgrade – Custom signage (Happy Birthday, Bride to Be, etc.), reserved premium seating where possible, champagne toast on arrival

Premium Wine Upgrade – Reserve wine experience — upgraded wines at two stops with higher-end and reserve selections

Signature Dining Experience – Chef-selected premium entree, reserve wine upgrade, and possible upgraded venue experience when available

Captured Experience – Professional photographer for key moments throughout the tour, edited photo gallery delivered post-tour

VIP All-Access Experience – Includes Reserve Wine Upgrade + Signature Dining Experience + Celebration Experience + priority flow & seating — the ultimate evening

Just add at checkout!