From festive parties and winter wonderlands to themed celebrations that capture the essence of each holiday, we specialize in crafting memorable and joyful holiday paint and sip events that bring families, friends, and colleagues together.
From anniversaries and baby showers to retirement parties, we bring your vision to life. Host a cozy snowman painting session, explore creative Halloween painting ideas, or elevate your gathering with a holiday wine tasting and paintnite experience at one of our venue partners.
We bring everything: All supplies • smocks • easels • guided artist + assistant • setup & cleanup • 60–120 min • Office or Venue • Toronto & Vancouver.
Why Book With Us: Short 5 years of praise • High return guest rate • Customer-first experience • Pro artists & assistants • Seamless winery coordination • Customizable themes & surfaces
Celebrate the Christmas season in style by gathering for a delightful paint-and-sip event. Unwind and explore your creative side in a festive atmosphere, painting while enjoying delightful sips.
Whether you’re asking someone to marry you or enjoy a low-key but immersive date night with a loved one, our luxury paint night experiences are for you!
Elevate Mother’s Day with delightful and exclusive You and I Paint™ events, offering a unique and creative way to express love and appreciation for the special women in your life. You need to check out our “sold out” yearly Mother’s Day public wine and paint events!
Indulge in a tailor-made holiday event with You and I Paint™, where your festive vision becomes a reality through custom-designed celebrations. Experience the holidays your way with our customized holiday paint and sip events, ensuring every detail and moment reflects your unique style and preferences.
Class length: ~2 to 2.5 hours (includes a 15-minute grace window for late arrivals).
Note: For our public events, we serve non-alcoholic beverages too, not all alcoholic and can
accommodate dietary restrictions when food is involved.
Please fill out the form provided with comprehensive details of your event. Include specific information regarding the purpose, particulars, and your envisioned outcome!
After our team receives your inquiry, allow up to 24 hours to receive an email or call back with all the details. Check your inbox and junk mail just in case!
Once we’ve gathered and exchanged all the details, the rest is on us! We take pride in our complete key turn service and put the main focus on you!
Yes! From Halloween and Christmas to Mother’s Day and Valentine’s Day, our custom holiday paint and sip events match your vibe and theme.
Everything! We provide paints, canvases, aprons, step-by-step instruction, and all the festive flair. Just bring the holiday cheer!
Tons! Our Mother’s Day painting ideas include florals, heartfelt quotes, and wine-themed art. Our Mother’s Day events are a local favorite and often sell out!
Yes! Celebrate with a romantic paint and cocktails night or intimate Table for Two session, perfect for anniversaries, Valentine’s, or just because. Paint love, Plan your date night now.
Our holiday paint and sip events blend luxury vibes with joyful creativity. With tailored themes, top instructors, and fun extras like cocktail pairings or holiday playlists, it’s more than an event; it’s an experience.
Absolutely! Gift cards or prepaid sessions make amazing experiences for friends, partners, or coworkers—way better than socks or scented candles.
Give the gift of creativity – Get a paint night gift card.
Not at all —Our classes are fully guided and beginner-friendly.
About 2, sometimes 2.5 hours, including a 15-minute grace window for late arrivals.
All paint supplies, canvas/surface, smocks, easels, setup, a pro artist + assistant, music, and full cleanup. A venue perk is included when noted in the event description.
We provide smocks, but we recommend clothing that’s comfortable for creative fun.
At winery-hosted events, a complimentary wine or wine tasting may be included; however, a non-alcoholic alternative is always available for any guest at no extra charge.
Yes. Most partner venues allow minors when accompanied by a parent/guardian. They can request a non-alcoholic alternative (e.g., charcuterie or another element) in place of a wine tasting. To arrange this, email events@youandipaint.com.
If an event has outdoor elements, the venue’s weather plan applies (covered space or reschedule or a full refund). We’ll notify registered guests by email with any updates.
If your party is larger than 8 guests, you may be qualified for a 15% discount – please contact events@youandipaint.com to inquire.
We offer full refunds up to 3 days before the event. After that window, no refunds or
credits are available, as venue costs are paid in advance.
“The most relaxing two hours of my week—left with a painting I actually love.”
“Perfect balance of guidance and creative freedom.”
