Tips From Ali Jackson: Framing Group Travel for Your Community

Insights from a Top TrovaTrip Host

If you’ve ever wondered how to successfully sell out a trip (or six) while staying authentic, relatable, and not losing your mind trying to be everywhere at once—meet Ali Jackson.

In a recent webinar, Ali—creator, coach, and seasoned TrovaTrip Host—shared exactly how she built a travel program her community couldn’t wait to book. Spoiler alert: it’s not about the fanciest itinerary or having a million followers. It’s about knowing your people and building real connections.

Here’s what we learned from her “Framing Group Travel for Your Community” session:

Know Your People & Their “Why”

Want to fill a trip? Start by understanding who you’re talking to—and why they’d want to travel with you.

Ali cracked the code when she narrowed in on her sweet spot: single, community-loving women who want meaningful travel experiences…but zero interest in planning them. That insight now guides everything from her marketing voice to the destinations she picks.

Her favorite tools? DMs, Instagram question boxes, and good old-fashioned Google Forms. These let her dig into what her community’s craving and what’s getting in the way.

Top pain points she uncovered:

• “All my friends are partnered or too busy to travel.”
• “I’m not into solo travel—it’s intimidating.”
• “I can plan a trip... I just don’t want to.”

The fix? Be the trusted go-to who takes care of the details—and makes travel feel like showing up to a party where everyone already wants to be friends.

Curate the Right Trip

Once you know who you’re planning for, build an experience they’ll love—and that you’ll love too.

Use Custom Surveys Strategically

Yes, the TrovaTrip survey is a solid start (and something we always recommend!). But Ali goes even deeper. She adds her own questions to get granular on things like blackout dates, trip style, and vibe preferences. That way, when she launches a trip, she already knows her audience is into it and available.

Pick Itineraries You’re Actually Excited About

If you wouldn’t want to go, don’t plan it. Ali skips the highly-strenuous, jam-packed trips in favor of breezy beach days, cultural eats, and time to relax. And that alignment shows—her Travelers love what she loves.

Build in Breathing Room

Reminder: a four-hour bus ride doesn’t count as downtime. Ali intentionally removes at least one activity from every itinerary to create more space for connection and recharge. She also schedules optional group dinners—so people always have a chance to bond if they want to, without the pressure.

Blackout Dates Are a Big Deal

Even if someone is obsessed with your trip, they can’t go if the timing doesn’t work. Ali learned this the hard way after a quiet Argentina launch. Now, blackout dates are a standard part of her pre-launch surveys.

Market with Intention (and Personality)

Know Where Your Bookings Come From

Ali tried promoting trips on TikTok and other platforms, but she dug into the data provided in her TrovaTrip portal, and saw that nearly all her sign-ups came from Instagram. The takeaway? Double down on what’s working and stop trying to be everywhere at once.

Repeat Yourself

Let us say this again—repeat yourself! (Ha…see what we did there? 😅). You may feel like you’ve said it a million times, but most of your audience hasn’t seen it yet. Ali keeps her trip promos in rotation—stories, posts, reels, and more—so she stays top of mind without sounding like a broken record.

Be Yourself, Not Someone Else

Don’t force the aesthetic reels or voiceovers if that’s not your thing. Ali leans into what her community loves: her face, her voice, and her honest takes. That connection is what sells.

Make It Easy to Say “I’m In”

Her best CTA? “Comment 🐘 and I’ll DM you the link.” It was scrappy and manual at first—she watched her comments like a hawk—but it worked so well, she now uses ManyChat to automate it. The magic is in how simple and low-pressure it feels.

Follow Up, But Keep It Chill

If someone expresses interest and doesn’t book, she follows up with a helpful nudge: “What more questions can I answer for you?” No guilt trips, no hard sells—just an open door.

Start Building Community Before Takeoff

The trip doesn’t start at the airport—it starts when they book. Ali invites Travelers to a dedicated Discord server and hosts a couple of Zoom calls before the trip. It gets people chatting, excited, and way more comfortable before they even meet in person. The result? Better group vibes and more repeat bookings.

The Big Picture

Ali’s success isn’t about chasing trends or growing the biggest following. It’s about listening to her audience, planning with care, and showing up as herself. That’s what makes her trips stand out—and keeps Travelers coming back for more.

Take what fits your style, experiment with what doesn’t, and remember: you don’t need to reinvent the wheel. Just make sure it rolls in the direction your community wants to go.

About Ali Jackson

Ali is an NYC-based dating coach here to help us love our lives, regardless of relationship status. She's fostered a community of kindred spirits who rock their lives to the fullest, whether flying solo or not. And now, she’s taking that show on the road bringing that community on amazing trips!

View Ali's Host Profile