Couple’s Wine Tour – CHI
Tour Description
You don’t need another night out. You need a night worth remembering.
Between work, responsibilities, and everything else life throws at you, finding time to slow down and enjoy each other can be harder than it should be. And when you finally decide to plan a date, there’s still the question: Where are we going? What are we doing? Where should we eat?
Leave the planning to Raise A Glass.
We’ll take you on a curated journey through Chicago’s hidden gems, hand-selected wine destinations, great food, and unexpected experiences. You won’t know exactly where you’re going or what you’ll be tasting until you arrive. That’s part of what makes the experience special.
Just bring each other. We’ll handle the route, reservations, transportation, wine, food, and all the details in between.
You discover new places. You try new wines. You slow down, reconnect, laugh, and enjoy being together.
Because the best date isn’t always about where you go. It’s about who you’re with and the memories you make along the way.
Perfect for date nights, anniversaries, birthdays, romantic getaways, or couples looking for a unique Chicago wine and dining experience without having to plan every detail.
✨ Want the complete experience? Add the 3-Stop Signature Experience at checkout.
What’s Included on Every Tour
- Curated wine tastings at every stop
- Food pairings or full dinner, depending on the tour selected
- Luxury Mercedes Sprinter transportation
- Complimentary Pickup & drop-off within our service area
- Dedicated tour host
- Bottle of wine in the Sprinter
- Bottled water
- Gratuity at each stop
Enhance Your Experience
Take your private tour from unforgettable to once-in-a-lifetime. Add any of these upgrades when booking:
Champagne Toast – Start your experience with a celebratory champagne toast. Because some nights deserve a proper beginning.
Premium Wine Upgrade – Reserve wine experience — upgraded wines at two stops with higher-end and reserve selections.
Signature Dining Experience – Upgrade to our 3-stop Signature Dining Experience featuring appetizers and light bites, sharable small plates, and a decadent dessert experience all paired with wine throughout your tour.
Captured Experience – Professional photographer for key moments throughout the tour, edited photo gallery delivered post-tour.
VIP All-Access Experience – Take your Raise A Glass experience to the next level with our most elevated tour experience. Enjoy everything included in our 3-stop Signature Dining Experience, plus premium wine selections, a celebratory champagne toast, elevated dining, and exclusive VIP touches designed to make your day truly unforgettable.
Includes:
- 3-Stop Signature Dining Experience
- Premium Wine Upgrade
- Champagne Toast
- Elevated Dining Experience
- Exclusive VIP touches throughout your tour
Available for the entire group.
Just add at checkout!
Our Private Couple’s Party Wine Tour starts at $499.99 per person with a minimum of 2 guests. Our packages are completely customizable to fit almost any group. A 50% deposit will hold any tour time for you and your group!
Note: If you have more than 2 guests please check out our Small Group Wine Tours or our other Private Wine Tour experiences that are designed for larger groups.
Have a question?
Call or text us at or info@RaiseAGlassTours.com