You said let’s take the kids to Hawaii.
We build the trip
your kids describe forever.
No research. No logistics. No second-guessing. You share what your family wants this trip to feel like — we handle every detail, every experience, every moving piece. Hawaii is one destination we know deeply. Yours will be built the same way.
This is what a family
Hawaii trip looks like
when we build it.
Every trip we build starts with one question: what do you actually want this experience to feel like? For the family behind this Hawaii trip, the answer was adventure with real breathing room — moments the kids would carry for years, without anyone burning out managing logistics.
We sourced the 2-bedroom home because we know what a family of four actually needs at the end of a full day. We chose the waterfall tour because we know how it lands with kids. We included the rental car because we know Oahu — and we know that freedom of movement changes the entire character of a family trip. None of it was guesswork.
When we build yours, it starts the same way. You tell us the destination, your family, and what this trip needs to feel like. We take it from there — and you show up to something designed specifically for you.
Built
Six moments from a
family trip we built.
Not a list of activities. The actual scenes from a real trip — the ones that became stories. This is the kind of thing we design for. Your family’s version gets built the same way.
Day One Morning
No alarm clocks. No school stress. Just the sound of the Pacific and kids realizing — in real time — that they’re actually in Hawaii. They run to the window. The energy in the room is different from any vacation morning you’ve had before.
“Mom! Dad! We’re in HAWAII!”
The Sea Turtle Moment
Somewhere between a quiet beach and a snorkeling afternoon, one of the kids surfaced with their eyes wide open. They’d just come face to face with a Hawaiian green sea turtle. It swam right toward them. Nothing you could have bought them comes close to that look.
“It was RIGHT THERE!”
The Waterfall
Waimea Valley on the Circle Island Tour. The kids standing at the base of a 45-foot waterfall, then swimming in the pool beneath it. They were shrieking. The parents were taking the photo they’d frame. And nobody planned a single detail — the tour guide handled all of it.
“Can we do this every day?”
The Luau
Fire dancers spinning flames after sunset. Kids learning to hula. An authentic Hawaiian feast and the drums beating as the sky turned orange over the ocean. The picky eater tried the kalua pork. The youngest didn’t stop talking about the fire for three days.
“The fire guy was actually on FIRE.”
Diamond Head at Sunrise
Nobody was happy about the early wake-up. At the summit, the youngest turned to their parent and said the thing that got repeated for months: “Dad, I climbed a volcano.” The family photo with all of Oahu spread out behind them. The teenager actually smiled.
“I climbed a VOLCANO!”
The North Shore Drive
Tuesday morning, nothing scheduled, everyone in the rental car heading north. A shrimp truck on the side of the road. Pro surfers on waves bigger than a house. The teenager took off their headphones and looked out the window. That’s the one the parents still mention first.
“This is actually so cool.”
Experiences we curated
for this Hawaii family.
These are real experiences from a real trip we built. Not a menu — a window into how we think when we’re putting a family trip together. Yours gets built with the same depth of thought, around what your family actually wants.
One Evening
Example
Paradise Cove Luau
We included this because we know what it does to a family evening — fire dancers, hula lessons, lei making, and a feast at sunset. The authentic Hawaiian experience that kids describe at school on Monday. We’ve seen it be the most-talked-about night of every trip we’ve built it into.
For your trip, we’ll choose the right signature evening experience for your family’s energy and kids’ ages.
Full Day
Example
Circle Island Tour + Waimea Waterfall
We chose this because it’s genuinely one of the best full-day experiences on Oahu for families — and because having a guide handle the driving and narrative means the parents get to be present instead of navigating. The 45-foot waterfall swimming hole is the moment kids talk about most.
We always include at least one full-day guided experience so there’s a day where you do absolutely nothing logistical.
Entrance Included
Example
Diamond Head Sunrise Hike
We included this specifically because of what it produces: the “I climbed a volcano” story. A 1.6-mile round trip achievable for most kids, 360° views at the top, and the rental car making the early morning access simple. The payoff is a family moment that gets repeated for years.
We always build in one meaningful physical challenge — the kind kids feel genuinely proud of completing.
Full Week
Example
Rental Car — Full Week Freedom
We include this on every family Hawaii build because we know what it changes. With kids, having your own vehicle is the difference between a great trip and a logistically exhausting one. Drive when you want. Stop when they spot something interesting. The North Shore Tuesday morning was unplanned — that’s what the car made possible.
Logistics like this are what most planners skip. We think through every piece that affects how the trip actually feels day-to-day.
Where we put
this family.
Accommodation is one of the highest-leverage decisions in any family trip. We chose a 2-bedroom home with a pool because we know what a family of four needs at the end of a full day in Hawaii — and it isn’t two hotel rooms stacked in a corridor. When we build your trip, we source with the same logic.
Example
Spacious 2-Bedroom Vacation Home
Real bedrooms — kids in their room, parents in theirs. A full kitchen that saves significantly on meals. A living space where everyone actually decompress together at the end of the day. We chose this over every hotel on the same street because we know what a family needs to genuinely rest.
For your family, we’ll source the right space for your group size, your kids’ ages, and what this trip needs to feel like.
Example
The Private Pool
After Diamond Head or a full day on the North Shore, the pool is where the afternoon recovery happens. Kids stay occupied. Parents actually get to exhale. It’s a detail that sounds minor until you’ve done a 7-night family trip without it — then you understand exactly why we include it.
We think about recovery built into the trip structure — not just the activities. Your accommodation will be chosen with this in mind.
What this family trip included
The full picture of what we built for this family — shared as a real example of how we think, not as a fixed package. When we build your trip, we start from your family and build outward from there.
- 🏠7 Nights — 2-Bedroom Vacation HomeFull kitchen, pool, parking, WiFi, beach equipment. Chosen because we know what a family of four actually needs at the end of a full day.
- 🎭Paradise Cove LuauFire dancing, hula, lei making, traditional feast at sunset. The night this family still talks about first when someone asks about the trip.
- 💦Circle Island Tour + Waimea WaterfallGuided full-day tour — the parents didn’t navigate or plan a single thing. The kids swam under a 45-foot waterfall.
- ⛰️Diamond Head Entrance + Timing GuideHike fees for the whole family covered, plus the exact morning timing that gets you the views before the crowds arrive.
- 🚗Premium Rental Car — Full 7 DaysThe piece that made the North Shore Tuesday morning possible. Full island freedom for the whole trip.
- 📞Concierge Support ThroughoutDerrek and Kayla reachable the entire trip for anything that came up — restaurant questions, changed plans, all of it.
- ✏️Your trip will be built differentlyThis is what we chose for this specific family. Yours will be built around your destination, your kids’ ages, your travel style, and what you want this trip to produce.
- 🎯Nothing templatedWe don’t drop you into a package. We start from your vision and build — accommodation, experiences, logistics, and daily structure designed for your family.
- 🐢Only what we’ve personally verifiedEvery experience we recommend, we know firsthand. We don’t add things to make a trip look complete on paper.
- 💬One conversation starts everythingBook your Planning Session and we spend 60 minutes understanding exactly what you want. Then we take it from there — completely.
💳 Your investment
Starts with a $200 Planning Session — applied in full to your trip cost. We’ll build your custom plan, walk through every detail, and give you a complete cost breakdown before you commit to anything.
Flexible payment options including interest-free installments available on your Planning Session call.
From “we want to go to Hawaii”
to the trip that changes things.
Four steps. Zero research on your end. Zero logistics to manage. You show up to something built entirely around your family.
Tell Us Your Vision
Book your Planning Session and spend 60 minutes with Derrek and Kayla. You tell us the destination, your kids’ ages, the vibe, and what you want this trip to do for your family. Nothing is too specific.
We Do All the Research
We research before we build — operators, accommodation, timing, what works with kids and what doesn’t, what to avoid and what’s worth every dollar. All drawn from destinations we know firsthand.
We Build Your Custom Plan
You receive a complete family itinerary built around your vision — not a template adjusted to fit. Every choice has a reason. Every detail is handled. Nothing left for you to figure out.
You Just Show Up
Arrive to a trip that was designed for your family. Derrek and Kayla stay reachable the whole time. You focus on being present for every moment — because someone else already handled the rest.
One conversation.
We handle everything.
You’ve seen what we built for this Hawaii family. Tell us where you want to go — and we’ll build your version with the same depth of thought, shaped entirely around your family.
🗺️ Dream Vacation Planning Session — $200
A private 60-minute call with Derrek and Kayla. We research your destination before we talk, then build your custom family itinerary, accommodation plan, experience recommendations, and full cost breakdown — applied to your trip in full.
Start Building Your Family Trip
Book your Dream Vacation Planning Session — $200, applied in full to your trip. We handle everything from here.
🗺️ Book My Planning Session — $200Real trip reports · Family travel intel · Direct access to Derrek & Kayla
🔒 $200 applied in full to your trip · Cancel 90+ days for full refund
What parents say
We almost skipped the luau because it felt like a tourist thing. Our kids are still talking about the fire dancers three years later. Derrek told us not to skip it — and he was right. That’s the kind of advice you only get from someone who’s actually thought about what works with families.
The 2-bedroom home was the thing that made the whole trip work. We’ve done Hawaii before with hotel rooms and it was logistically exhausting. Having a real kitchen, separate bedrooms, and a pool to decompress — completely different experience. Our daughter wrote about the waterfall in her school essay.
My son said “I climbed a volcano” for months. The rental car was a game changer — we drove to the North Shore on a random weekday because we could. No tour schedule, no waiting. That spontaneity with a 9-year-old and a 12-year-old is what made it feel like an actual adventure rather than a managed vacation.
Free to Join · Always Active
See the family trips we’ve built
before you book anything.
Tropical Beach Travelers is our free Facebook community — the best first step before your Planning Session. Real family trip reports from past clients, destination intel for traveling with kids, and direct access to Derrek and Kayla before you spend a dollar.
Tropical Beach
Travelers
Free community · Where real families share what actually matters
Join the Group →facebook.com/groups/
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Custom-built. Expert-curated. Yours.
Ready to stop planning and start going?
Book your Dream Vacation Planning Session for $200 — applied in full to your trip cost. You tell us where your family wants to go and what you want it to feel like. We research, plan, and build everything from there. You just show up.
We plan trips the way we’d
want ours planned.
Traveling Turtle LLC exists to get families to the places they’ve been dreaming about — without the research, the missteps, and the frustration of figuring it out on your own. Every destination we work with, we know from personal experience. Every operator we recommend, we’ve vetted ourselves.
With 12 years of curated family trips and a genuine belief that shared adventure builds real family connection, every trip we build is designed around the specific moments that matter — not just a packed itinerary. You’re not getting a template adjusted for your group. You’re getting two people who care about your trip working on your behalf.
