A Hawaii itinerary review is where you send me the trip you’ve already planned and I tell you what works, what doesn’t, and what I’d change. It costs $50.
This post is a real Hawaii itinerary review example, so you can see exactly what you’d get back: the plan a client sent me, what I flagged, and what I told her to change.
I’ve kept her anonymous and left out her travel dates. Everything else is from the actual review.
The trip she sent me
A family of three with a 9-year-old daughter, heading back to Hawaii for their second trip. Two weeks over New Year’s: seven nights on Kauaʻi and six on Maui.
On Kauaʻi they planned three nights in a North Shore vacation rental and four at a south shore resort. On Maui, a resort in Wailea.
She told me their last trip felt rushed because they planned it last minute. This time they wanted to be prepared, with early mornings, relaxed afternoons, and more resort time on Maui.
The itinerary was 15 pages, with every day timed out and a reservation tracker at the end. It had all the signs of a plan built with an AI tool, and it looked finished.
The itinerary before my review
| Day | Plan |
|---|---|
| 1 | Land on Kauaʻi late afternoon, drive to the Princeville rental |
| 2 | Hanalei Bay, Tunnels Beach, Maniniholo Dry Cave, Limahuli Garden, sunset drinks at 1 Hotel Hanalei Bay |
| 3 | New Year’s Eve: slow morning, Hanalei shops, dinner at The Dolphin |
| 4 | New Year’s Day: Kīlauea Lighthouse at 10am, Anaina Hou, groceries, move to the south shore resort |
| 5 | Helicopter tour, resort pool |
| 6 | Mountain tubing, dinner at Merriman’s |
| 7 | Waimea Canyon lookouts starting at 7am, then a dinner sail with a 1:45pm check-in |
| 8 | Fly to Maui, check into the Wailea resort |
| 9 | Whale watch, pool |
| 10 | Snorkeling, pool, dinner out |
| 11 | Resort morning, Mama’s Fish House |
| 12 | Maui Tropical Plantation, Upcountry stops, Haleakalā sunset |
| 13 | Flexible last day |
| 14 | Fly home |
On paper it’s a great trip, and it includes a couple of my favorite restaurants.
Before and after: what the plan said and what I told her
| What the plan said | What I told her |
|---|---|
| Three nights in a North Shore vacation rental | Winter is Kauaʻi’s wetter season. Pick a North Shore resort with pools and easier cancellation instead. |
| “Reserve” The Dolphin for New Year’s Eve | The Dolphin doesn’t take reservations. It’s first come, first served, so plan for a wait. |
| Kīlauea Lighthouse at 10am on New Year’s Day | The refuge closes for the holiday. Check before you count on it. |
| Waimea Canyon lookouts on a weekday morning | The road had recurring weekday closures for construction. Check closer to the trip. |
| Whale watch, company and time still to pick | Yes, do it. Go with a smaller boat. |
| Maui is “intentionally lighter” | Both islands are packed start to finish. Leave a few days completely open. |
What I flagged and why
The weather wasn’t in the plan
This was the big one. The North Shore gets a lot of rain, especially in winter, and it’s entirely possible to get three straight days of it.
It happened to us. We visited Kauaʻi over winter break one year, I’d only planned one day for the North Shore, and it was completely rained out.
We still got lunch at a restaurant, but so did everyone else up there, so it was quite a wait. We never made it to Limahuli Garden or Hanalei Bay, and even walking around the Hanalei shops wasn’t great. The whole day felt like a bust.
Limahuli Garden and Hanalei Bay were both on her Day 2.
A vacation rental doesn’t give you much of a fallback when that happens. She’d also told me they’d been burned by a rental on a previous trip and were nervous about booking this one.
I suggested looking at the Westin Princeville Ocean Resort Villas or The Cliffs at Princeville. Same North Shore location, but with real pools, easier cancellation policies, and more to do if a day gets rained out.
She hadn’t booked yet, so this was the right time to catch it.
The holiday details were wrong
The plan had a checkbox to reserve The Dolphin in Hanalei for New Year’s Eve. The Dolphin doesn’t take reservations. It’s first come, first served, so on New Year’s Eve you’re looking at a wait.
It also had Kīlauea Lighthouse on New Year’s Day, complete with a note about when to book the timed entry. The refuge closes for the holiday.
Neither one ruins a trip, but both are a scramble you don’t want in the middle of a holiday week.
The canyon morning had no room for a road closure
Her Waimea Canyon morning was timed tightly to make a 1:45pm check-in for the dinner sail. The road had recurring weekday construction closures at the time, so I told her to check its status closer to the trip.
It didn’t match what she’d asked for
She wanted this trip to feel slower, with more resort time. The plan said Maui was “intentionally lighter,” but both islands were scheduled from start to finish.
That may just be how her family likes to travel. But if slower is really the goal, I’d leave a few more days completely open, especially on Kauaʻi, so a rained-out plan has somewhere to land.
Her questions
Hikes came up first. I pointed her to short, scenic walks near the Waimea Canyon lookouts and told her to skip Hanakāpīʻai this trip. The stream crossings get dangerous with flash flooding in winter, and the trail gets muddy and slippery when it rains.
My aunt hiked the Kalalau Trail one January years ago. She’s an avid hiker, and she said it was washed out and super scary. I don’t want anyone to have to come rescue me, and it’s not worth the risk with a 9-year-old along.
She also wondered if a Maui whale watch was worth it when they already had a Na Pali Coast catamaran booked. It is. You’re on a totally different coastline, and it’s one of the best things you can do on Maui. Since they don’t love big guided tours, I recommended a smaller boat.
For a photographer, I sent her to Flytographer (you save $20 with my link) and told her to book early because the good time slots go fast over the holidays.
What’s changed on Kauaʻi since this review
I reviewed this plan in early August. About a month later, Hurricane Lowell hit Kauaʻi.
As of early October, Kōkeʻe Road is closed, so you can’t drive up to the Waimea Canyon lookouts. The highway past Princeville toward Hāʻena is restricted, and Kīlauea Lighthouse is closed for repairs.
So her canyon morning, her Hāʻena day, and the lighthouse stop are all question marks again, for a much bigger reason than the ones I flagged. A review is a snapshot of the day I read your plan, which is why so many of my notes end with “check again closer to your trip.”
The most common problems I see in Hawaii itineraries
Another client sent me an itinerary from a travel agent that was clearly AI-generated. It had attractions on the wrong islands, a hotel switch every two days, and no driving times factored in. It was literally impossible to do.
I regrouped her must-dos by geography and by how much energy each one takes, and it became a balanced trip with adventure, attractions, and down time.
That’s not a knock on travel agents. Any itinerary benefits from a second look by someone who knows the islands. A few other problems I see a lot:
- Drive times left out. One group I reviewed had a volcano day that was really 10 to 12 hours once you counted the driving.
- Outdated booking info. An Aulani plan listed character breakfast as bookable 60 days out when the window was 30. Disney changes it a lot.
- The same thing twice. That Aulani plan also had two luaus in one week.
- Too many big days in a row with no down time for the kids.
How a Hawaii itinerary review works
Send me your itinerary as a Google Doc or PDF with up to 5 questions. It doesn’t matter if you built it yourself, got it from a travel agent, or asked ChatGPT.
I return it within 2 business days. You’ll hear what works, what doesn’t, and what I’d change.
I’m not a travel agent and I don’t book anything. You book it all yourself. My recommendations sometimes include affiliate links, so I may earn a small commission if you book through them, at no extra cost to you.
I’m a professional tourist with more than 40 Hawaii trips behind me, and I’m a Hawaii Tourism Authority Certified Hawaii Destination Expert.
If you don’t have an itinerary yet, start with my Hawaii trip planning page, my Kauaʻi travel guide for families, or my podcast, Hawaii Travel Made Easy. And if you’d rather talk it through, I work one-on-one as a Hawaii travel consultant for families.
Hawaii itinerary review FAQ
Can someone check my Hawaii itinerary?
Yes. That’s what my Hawaii itinerary review is. You send your plan, and a Hawaii travel expert who has made 40+ trips reads it day by day.
What does a Hawaii itinerary review include?
A full read of your itinerary, answers to up to 5 questions, and my notes on what works, what doesn’t, and what I’d change. You get it back within 2 business days.
Is it worth paying someone to review my Hawaii itinerary?
A Hawaii trip costs thousands. $50 to find out your New Year’s Eve dinner can’t be reserved, or that your rental has no rainy-day backup, is cheap.
That said, if your main goal is to sit by the pool or the beach and you only have one or two excursions, you probably don’t need a review.
Can you review an itinerary from ChatGPT or a travel agent?
Yes. The plan in this post looked great on paper and still missed a holiday closure, a restaurant’s no-reservations policy, and the rainy season.
Do you book my trip for me?
No. I’m not a travel agent, so you book everything yourself.
Send me your itinerary
If you’ve got a plan and you’re not sure it holds up, send it over for a Hawaii itinerary review. It’s much easier to fix now than once you’ve landed.
 | About the author: Marcie Cheung is a Hawaii travel consultant for families who has visited Hawaii more than 40 times. She is the founder of Hawaii Travel with Kids and host of the Hawaii Travel Made Easy podcast. She offers one-on-one Hawaii trip planning consultations and itinerary reviews for families, couples, and honeymooners. |