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Ali Jackson's Tips for Being a Host Your Travelers Can’t Forget
Sold out trips and happy Travelers don’t happen by accident. Great Hosts know it’s not just about the destination—it’s about building community, earning trust, and creating adventures people never forget.
That’s exactly what we covered in our latest TrovaTrip webinar, The Art of Becoming a Super Host, led by Ali Jackson (@findingmrheight) one of our most seasoned travel Hosts.
Ali has 10 Confirmed trips under her belt (with 4 more already planned through 2026!) and has guided over 100 Travelers around the world. Even more impressive? 55% of her Travelers return for more, and 20% have joined her on 3+ trips—some are even on track to hit five by the end of 2026! With a 5-star rating across the board, Ali knows exactly what it takes to lead group trips that inspire loyalty and sell out fast.
Here are the biggest lessons she shared for anyone dreaming of becoming a successful Host:
1. Community Comes First
At the heart of every great trip is connection. Ali reminded us that being a trip Host isn’t just about choosing a destination—it’s about helping strangers become friends. On her trips, Travelers often leave with more than just memories; they walk away with a community they keep coming back to. Some even plan their own reunions after the trip ends!
Takeaway: Hosting is about so much more than logistics. It’s about creating spaces where genuine community can thrive.
2. Build Excitement Before Departure
Ali believes the magic of group travel starts long before the plane takes off. She sets the tone early by creating group chats, sparking introductions, and encouraging her Travelers to arrive a little early if they can. By the time the trip begins, people already feel like they’re traveling with friends—not strangers.
Takeaway: The more you can build excitement and comfort ahead of time, the smoother (and more fun!) the trip will be once you’re on the ground.
3. Team Up with Your Local Guide to Elevate the Experience
Some of the most memorable moments come from embracing local culture. Ali shared examples from her own trips—like taking Travelers to a mud bath in Colombia or exploring food markets in Mexico City—that gave her groups a deeper connection to the destination.
As a Host, you don’t have to know everything yourself—that’s where your local Guide comes in. By teaming up with your Guide, you can recommend incredible experiences beyond what’s already on the itinerary, giving Travelers ideas for how to spend their free time and make the trip their own.
Takeaway: Partnering with your local Guide to highlight authentic cultural touches helps transform a trip from a vacation into an experience Travelers will rave about.
4. Small Gestures, Big Impact
It doesn’t take grand gestures to make Travelers feel special. For Ali, it’s the little things—like checking in one-on-one or creating space for people to share their own stories—that help Travelers feel seen and valued.
She also loves surprising her groups with curated gift bags tailored to the destination. On her trip to Japan (a cash-heavy destination), she gifted everyone coin pouches. In Mexico, it was mini sunscreens—simple, thoughtful touches that show she’s paying attention to her Travelers’ needs.
Beyond on-trip moments, Ali also sets her groups up for success before departure by creating a custom landing page for each trip. It’s a one-stop hub with everything her Travelers need to know, helping them feel prepared and confident before they even pack their bags.
Takeaway: Whether it’s a small gift, a thoughtful check-in, or a clear resource, the simplest acts of care often leave the biggest impression.
5. Hosting Is a Journey for You, Too
Hosting isn’t just about giving Travelers an amazing experience—it changes you too. Ali shares how leading trips has helped her grow as a leader, a traveler, and a friend. Every adventure leaves her with something new, whether it’s a lesson or a lifelong connection.
Takeaway: Hosting isn’t just about guiding others. It’s about growing right alongside your Travelers.
Final Thoughts
Ali's story proves that learning how to host group trips is less about following a checklist and more about leading with heart. From sparking connections before departure to weaving in cultural experiences and offering thoughtful touches along the way, Ali shows us what it really means to be a Super Host.
If you’re ready to take the leap and become a travel Host yourself, TrovaTrip is here to help you create unforgettable adventures and build communities that last well beyond the trip. Learn more about hosting with TrovaTrip.
Read the blog on Ali's first webinar in this series, Framing Group Travel for Your Community.
About Ali Jackson
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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!