You told us Hawaii
We handled
everything else.
No research. No tabs. No second-guessing. You share your vision and we build the trip — every detail, every experience, every logistic — around you. Hawaii is one destination we know deeply. Yours will be built the same way.
This is what a Hawaii
couples 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 couple behind this Hawaii trip, the answer was freedom with intention — space to explore without anything left to figure out when they landed.
We sourced the condo because we know the exact floor that delivers the view. We chose the sunset cruise because we’ve been on it. We scheduled the spa mid-week because we know the rhythm of a week in Oahu. None of it was guesswork — it was built from experience.
When we build yours, it starts the same way. You tell us the destination, the people, and what this trip needs to feel like. We take it from there — and you show up to something that was designed specifically for you.
Built
Experiences we curated
for this Hawaii couple.
These are real experiences from a real trip we built. Not a menu to pick from — a window into how we think. Your trip will be built with the same care, around what you actually want.
7 Nights
Example
Waikiki Banyan — Private Condo
We chose this over every hotel on the same street because we know the specific floor that delivers the view. A private lanai, full kitchen, and ocean sightlines that make coffee feel like a ceremony.
We source accommodation like this for every trip we build — the right property for the right people, not the easiest booking.
One Evening
Example
Star of Honolulu — Sunset Cruise
We put this in because we’ve been on it and we know what it does to an evening. Dinner, live Polynesian performance, and a Pacific sunset from the deck. The moment most couples describe as the highlight of the week.
We know which night of the week to schedule this for the best light. Details like that don’t happen by accident.
Mid-Week Reset
Example
Waikiki Wind Spa — Couples Massage
We scheduled this mid-week intentionally. It’s the reset that makes the second half of the trip as good as the first — and it’s the kind of timing decision that only comes from building dozens of trips, not reading a website.
For your trip, we’ll find the right experience at the right moment — whether that’s a spa, a sunset hike, or something else entirely.
Full Week
Example
Rental Car + Diamond Head — Total Freedom
Most packages skip this. We include it because freedom of movement changes the entire character of a trip. We also included Diamond Head entrance fees because we know the 5am timing that gets you the view before the crowds arrive.
We think about logistics that most planners ignore. Your version will have the same level of thought built in.
What this Hawaii trip included
This is the full picture of what we built for this couple — shared not as a fixed package, but as a real example of how we think when we’re building a trip. Yours will be built from the same logic, shaped entirely around you.
- 🏨7 Nights — Waikiki Banyan Tower 2Ocean view 1BR condo — chosen for the specific floor, the view angle, and the private lanai. Not just a condo that was available.
- 🌅Star of Honolulu Sunset CruiseDinner, live Polynesian show, and Pacific sunset for two. Chosen because we’ve done it and know exactly what it delivers.
- 💆Couples Massage — Waikiki Wind Spa60-minute side-by-side treatment, scheduled mid-week for maximum trip impact.
- 🚗Premium Rental Car — Full 7 DaysFull island freedom — the piece most pre-built packages skip entirely.
- ⛰️Diamond Head Entrance + Timing GuideEntrance fees covered, plus the exact timing to beat the crowds.
- 📞Concierge Support ThroughoutDerrek and Kayla reachable the whole trip for anything that comes up.
- ✏️Your trip will be built differentlyThese are the elements we chose for this couple. Yours will be built around your destination, your people, and what you want this trip to feel like.
- 🎯Nothing templatedWe don’t drop you into a package. We start from your vision and build outward — accommodation, experiences, logistics, timing.
- 🐢Only what we’ve personally verifiedEvery experience we recommend we know firsthand. We don’t add things to make a package look complete.
- 💬One conversation starts it allBook your Planning Session and we’ll 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 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 dream to departure,
we carry it all.
Four steps. Zero research on your end. No logistics to manage. You show up to something built entirely around you.
Tell Us Your Vision
Book your Planning Session and spend 60 minutes with Derrek and Kayla. You tell us the destination, the people, the vibe, and what you want this trip to do for you. Nothing is too specific.
We Do All the Research
We research before we build — operators, accommodation, timing, logistics, what to avoid and what’s worth every dollar. All of it drawn from destinations we know firsthand.
We Build Your Custom Plan
You receive a complete itinerary built around your vision — not a template adjusted to fit. Every choice has a reason. Every detail is handled. Nothing is left for you to figure out.
You Just Show Up
Arrive to a trip that was designed for you. Derrek and Kayla stay reachable the whole time — for questions, recommendations, or anything unexpected. You focus on the experience.
One conversation.
We do the rest.
You’ve seen what we built for this Hawaii couple. Tell us where you want to go — and we’ll build your version with the same depth of thought, shaped entirely around you.
🗺️ 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 itinerary, accommodation plan, experience recommendations, and full cost breakdown — applied to your trip in full.
Start Building Your 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 · Insider tips · Direct access to Derrek & Kayla
🔒 $200 applied in full to your trip · Cancel 90+ days for full refund
What couples say
The rental car was the thing that surprised me most. I thought it was a nice extra — it was actually what made the whole trip. We drove to the North Shore on a Wednesday with nothing planned and it was the best day. Nobody tells you to do that on a tour.
We almost didn’t do the sunset cruise because it felt touristy. Derrek basically told us we were wrong — and he was right. The Polynesian show, watching the sun go down over the Pacific, dancing on the deck — we talk about that night constantly.
The condo is not what I expected when I heard “Waikiki.” It’s quiet, it has a real kitchen, the lanai view is genuinely stunning. I would never have found this on my own — and that’s exactly why we used Traveling Turtle.
Free to Join · Always Active
See the trips we’ve built
before you book anything.
Tropical Beach Travelers is our free Facebook community — the best first step before starting your planning session. Real trip reports, destination intel, and direct access to Derrek and Kayla before you commit to a dollar.
Tropical Beach
Travelers
Free community · Where real travelers share what actually matters
Join the Group →facebook.com/groups/
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Custom-built. Expert-curated. Yours.
Ready to stop thinking about it?
Book your Dream Vacation Planning Session for $200 — applied in full to your trip cost. You tell us where you want 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 you to the places you’ve been dreaming about — without the research, the missteps, and the frustration of figuring it out alone. Every destination we work with, we know from personal experience. Every operator we recommend, we’ve vetted ourselves.
With 24 years of combined travel background experience and a genuine belief that intentional adventure builds real connection, every trip we build is designed to create the kind of memory that changes something — not just a nice vacation, but a shift in how you connect with the people you’re traveling with.