Launch your first group trip challenge
🗓️ August 10-14, 2026
In just 5 days, you'll create an action plan to launch your first profitable group trip – no big following required.
🎁 Bonus: Get an Implementation Workbook (including a Group Trip Profitability Calculator) and access to the giveaway!
Meet Your Hosts
Jessie Festa
Jessie Festa is a travel blogger and educator who helps creators turn their passions into profitable, sustainable businesses. As the founder of Jessie on a Journey, she has spent years mastering creative monetization strategies—including building her own successful NYC photo tour brand—and is passionate about giving others the exact roadmaps they need to scale.
Brittany Verlenich
Brittany Verlenich is a group trip host, travel agent, and content creator who sold out her very first group trip with a small audience. Since then, she’s been leading incredible tours around the world—from Ireland to Croatia to Puerto Rico—and now helps fellow creators bring their communities together offline for unforgettable travel experiences.
How it works...
Grab your free seat
Shortly after signing up, you'll receive a welcome email with full challenge instructions, an implementation workbook, and giveaway details.
Mark your calendar
Each day, you'll receive a powerful video lesson with actionable next steps — so you actually leave the challenge with a strategy in place!
Enter the giveaway
Send in your completed workbook by August 16 @ 11:59pm ET to be entered to win prizes that can help you grow as a creator and profitably launch your tour business!
🎁 Giveaway Prizes Include:
- Access to the Group Trip Accelerator ($697 value), Brittany's course & group coaching program for people hosting their first group trip.
- 1 year of Brittany's FAM Finder Newsletter ($108 value), which shares heavily discounted and fully-comped trips for tour operators, travel agents, and creators.
- 1 month of Travel Blog Prosperity ($49 value), Jessie's membership for creators looking to grow their traffic, email list, and income — plus get a bonus list of 130 paying creator opportunities ($69.93 value).
*Note: To win, you must not currently be enrolled in or subscribed to the specific prize program.
You'll learn how to:
- Build a standout group trip brand that people want to book with
- Pinpoint a profitable tour structure from TrovaTrip to DIY hosting — and weave in extra affiliate income
- Properly price your tour (free calculator included)
- Choose the perfect destination to host your first trip
- Get potential customers excited and generate leads before you officially launch
- And more!
Ready to launch your first group trip?
