Sip & Paint Instructors
--The Painted Trail--
Join The Painted Trail as a featured instructor and bring your art to life! Our sip & paint events take place on a coastal horse ranch, surrounded by ocean views and good vibes. You’ll choose the painting, we’ll fill the room, and our team will handle the logistics—so you can focus on the fun.
Responsibilities
- Lead group painting events in a fun, beginner-friendly way
- Choose your own artwork (must align with our rustic, coastal, and equestrian themes)
- Provide step-by-step painting instruction to guests
- Bring high energy and a welcoming vibe
- Collaborate with support staff for a smooth event experience
Must Have
- Confident in acrylic painting techniques
- Comfortable teaching groups of all experience levels
- Great communication and positive energy
- Experience with group classes or public speaking is a plus
- Love for nature, horses, or coastal environments is a bonus
We Provide
- We book the event—no need to bring your own audience
- All painting materials and setup
- vent crew to handle logistics, cleanup, check-in, and refreshments
- Marketing and promotions—we handle guest bookings and promotion
- Per-event pay
- Flexible scheduling—you accept the dates that work for you
What's great in the job?
- The Painted Trail offers a one-of-a-kind opportunity for artists to lead engaging sip & paint sessions at one of the most scenic locations in the Bay Area—Ocean View Stables. With ocean views, horse pastures, and vibrant sunsets, you’ll guide groups through a fun and laid-back painting experience that feels more like a party than a class. If you’re creative, social, and love sharing your passion for art, this is your perfect gig.
- We take care of the logistics: you focus on the art and the fun. You’ll get to choose your painting each session (as long as it fits our nature/equestrian theme), and we’ll fill the room with excited guests ready to paint. Whether you’re a working artist, art teacher, or someone who shines in front of a crowd—this contract role is flexible, rewarding, and designed to support your creative lifestyle.
The experience
What We Offer
We handle everything so you can focus on creating an unforgettable experience. From setting up the easels to filling the seats, our team ensures you're supported every step of the way.
Creative Freedom
You choose your painting for each event (within our brand theme)
Support Staff
We provide setup, cleanup, and event coordination so you don’t have to.
All Materials Provided
Paints, brushes, canvases, aprons—just show up and lead
Per-Event Pay + Tips
- Competitive contract rates with gratuities often from happy guests
