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Hi, I’m Kaia.

Kaia Hollerback, SYB marketing manager

SYB marketing manager

KaiaHollerback.

Jacksonville@kaiahollerback
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Kaia has led 3 SYB trips in 2 countries. Next up: Bali, leaving in 14 days.

See Kaia’s trips

Travelwith Kaia.

Bali Activated, SYB’s trip to Bali, IndonesiaNov 22026Bali ActivatedBali, Indonesia. Nov 2 to 8See the tripIsland Takeover, SYB’s trip to CroatiaJun 202027Island TakeoverCroatia. Jun 20 to 26See the trip

Booking because of Kaia? Type Kaia Hollerback in the “Who sent you?” box at checkout.

Trip reviewswith Kaia.

SYB trip photo, Nicaragua

Kaia’s Nicaragua trip, Jan 2026

“Huge shoutout to Kaia, our group leader.”

“She led with fun and adventure without ever feeling bossy or “in charge.” It was more like, damn… she’s got everything handled.”

Joey V. on Google

Kaia’s Croatia trip, Jul 2026

“An unforgettable trip filled with nonstop fun, incredible people, and Kaia, Eli, and Lizzie were amazing leaders who made the whole experience feel effortless.”

Jeff K. on Google

Kaia’s Nicaragua trip, Jan 2026

“Major shout out to Kaia’s leadership: she made everything feel seamless and her positivity was contagious. And shout out to Brycen for taking some amazing photos while always making the group laugh!”

Adam J. on Google

Kaia’s Nicaragua trip, Jan 2026

“Kaia and Brycen were great at organizing the activities and capturing every moment of the great memories that we made. This was my first SYB and I was a little hesitant to book at first since I am in my late 40s.”

Fabian S. on Google

Kaia’s Nicaragua trip, Jan 2026

“This came down to not only the people that booked the trip with me, but our leaders, Bradford and Kaia. … But nope, this was Kaia’s first trip after finishing SYB’s Leadership Academy.”

Travis H. on Google

Kaia’s Nicaragua trip, Jan 2026

“To top it off, Jenny, Kaia, and Brycen were a well-balanced group of leaders who kept the workouts hard and kept the group on track.”

Paul B. on Google

Kaia’s Nicaragua trip, Jan 2026

“Kaia and Brycen were outstanding…taking charge with ease and pivoting w grace. So many amazing people ..silliness …and unexpected enlightenment. Well done SYB…thank you so much for an incredible trip to Nicaragua!”

Suzanne C. on Google

Kaia’s Nicaragua trip, Jan 2026

“Kaia and Bradford are one of those rare combinations that make you glad you’re alive. They were our SYB guides. They are endlessly fun, deeply loving, and completely attuned to energy — not just noticing it, but guiding it.”

Miles D. on Google

SYB has a 4.9 on Google from 300+ reviews. Read more

MeetKaia.

Kaia is the strategist and storyteller behind SYB’s social, shaping the voice, look and rhythm of the brand on every platform. With 8+ years in social media and content, a degree in marketing and a career as a professional photographer, she runs the daily social and writes the emails that actually get opened. Her camera roll is basically a passport stamped with sunsets, surfboards, and strangers turned forever friends.

How did you find SYB?
Through a camera. I came to shoot, and I stayed for the people.
Favorite SYB moment?
Croatia 2026. Island days, sunset swims, and a crew that turned into family by day three.
Something people wouldn’t guess about you?
Before SYB, I worked as a professional photographer.
What are your specialties?
  • Instagram
  • Storytelling
  • Photography
  • Surf trips
  • Strangers to friends

Trips Kaia has led

3 trips in 2 countries so far.

  • Nicaragua
  • Croatia
  1. 2026
  2. Island TakeoverCroatiaJul
  3. Surf Yoga BeerNicaraguaJan
  4. Surf CampNicaraguaJan

Come solo.Leave with a crew.

SYB has run active and social group trips out of NYC since 2014. Most people come solo. By the last night, nobody feels like it.

Travel with KaiaJoin the Jacksonville chat
See every SYB trip