⚠ Lūʻau scheduling conflict — resolve this. This plan lists a lūʻau on Oʻahu (~Sun Aug 23) marked "book ASAP." But the Old Lahaina Lūʻau on Maui is already booked and paid (conf 9018404) for Tue Aug 18, 6:15 PM — which is also the Road to Hana day. Either keep the paid Maui lūʻau on the 18th (and drop the Oʻahu one), or call Old Lahaina (808-667-1998) to move/cancel. Don't double-book.
Trip at a glance
| Date | Island | Main plan |
|---|---|---|
| Sun 8/16 | Maui | Arrival + groceries |
| Mon 8/17 | Maui | 2 PM timeshare presentation + easy day |
| Tue 8/18 | Maui | Road to Hana + Rainbow Eucalyptus (+ paid lūʻau 6:15 PM) |
| Wed 8/19 | Maui | Haleakalā sunrise + crater hike + KOAST |
| Thu 8/20 | Maui | Flexible day + laundry |
| Fri 8/21 | Oʻahu | Honolulu arrival + Liliha Bakery + Friday fireworks |
| Sat 8/22 | Oʻahu | USS Arizona + optional stops + Waikiki + ZIGU |
| Sun 8/23 | Oʻahu | Wayfinder → Hyatt + flexible / lūʻau |
| Mon 8/24 | Oʻahu | Waikiki Beach + soba + ʻIolani Palace |
| Tue 8/25 | Oʻahu | Manoa Falls + tonkatsu + resort hopping + Pig & The Lady |
| Wed 8/26 | Oʻahu | Departure |
Plus a floating North Shore day to slot in wherever it fits.
The days
Day 1Sun, Aug 16 · Maui — Arrival + Groceries
- Arrive in Maui, get settled. Grab a meal and a couple of cocktails.
- Check into the hotel (Westin Kāʻanapali, check-in 4 PM) and unload luggage.
🛒 Grocery run
Send 1–2 people to Foodland or Safeway while everyone else settles in. Get local/Hawaiian coffee, cereal, breakfast foods, eggs, rice, chicken, sandwich/lunch supplies, fruit, snacks, water & drinks. Definitely get Foodland poke by the pound.- Evening: unpack groceries, relax, pool/beach if desired, easy dinner, early night.
Day 2Mon, Aug 17 · Maui — Timeshare + Easy Day
- 2:00 PM — You + Dustin attend the timeshare owners presentation. ~1 hour; politely decline additional points and collect the promotional gift.
- Everyone else relaxes — pool/beach or explore. Keep the rest of the day flexible.
Day 3Tue, Aug 18 · Maui — Road to Hana
- Leave relatively early; make the drive itself the experience. Take frequent short stops rather than long hikes.
🌈 Rainbow Eucalyptus stop
Short optional mini-hike/walk (~20 min) to see the multicolored bark. Continue along the coast depending on how everyone's doing. Keep Cody's comfort in mind — the road is long and winding, so stops are optional.Already booked: Old Lahaina Lūʻau, 6:15 PM (conf 9018404, 4 adults, paid). This lands on the same day as Road to Hana — plan the drive to be back in time, or move the lūʻau. See the conflict note at the top.
- Evening: return to hotel, easy dinner, relax.
Day 4Wed, Aug 19 · Maui — Haleakalā Sunrise
- ~3:00 AM — Leave the hotel; drive to Haleakalā summit for sunrise.
🧥 Pack for cold weather
Sweatshirt/fleece, pants, windbreaker, long sleeve, warm socks, hiking shoes, hat/beanie, water & snacks. Confirm the Recreation.gov sunrise reservation and park entrance requirements.🥾 Crater hike
~2-mile out-and-back toward the crater edge (do NOT hike down into the crater). Primarily a you + Dustin + whoever-wants-to activity.- Lunch after coming down the mountain. Afternoon intentionally unscheduled — pool, nap, beach, shower, relax.
- Evening: dinner reservation at KOAST / Coast.
Day 5Thu, Aug 20 · Maui — Flex Day + Laundry
- Open day: beach, pool, shopping, a short hike, anything missed, or spontaneous exploring.
🧺 Laundry
Do one substantial load toward the end of the Maui stay so everyone has fresh clothes for Oʻahu. Finish packing and separate Oʻahu clothes.Day 6Fri, Aug 21 · Oʻahu — Honolulu Arrival
- Fly Maui → Honolulu around midday (Hawaiian, ~1:28 PM). Do not rent cars at the airport. Take an UberXL to the hotel.
- Check into The Wayfinder Waikiki and settle in.
🍽️ Dinner
Casual dinner at Liliha Bakery — walk if practical or a short Uber. Then Friday-night fireworks. Keep the rest of the evening easy.Day 7Sat, Aug 22 · Oʻahu — Pearl Harbor + Flexible Honolulu
- ~7:00–7:30 AM — Uber to nearby Avis. Pick up two intermediate SUVs (likely CX-5/CX-50 or similar). Load everyone + Cody's travel car seat.
⚓ 10:00 AM — USS Arizona Memorial
Pearl Harbor visitor center/museum, boat to the floating memorial, time there, boat back. Allow several hours rather than rushing.- Optional split-up — La Mariana Sailing Club: tiki fans stop for a drink + T-shirt; others head back to the hotel.
- Optional — Bailey's: take Cody to pick a Hawaiian shirt (vintage collection optional).
- Afternoon: pool, Waikiki Beach, relax, shower/change.
🍶 Dinner — ZIGU
Izakaya-style Japanese: soba, sushi, sashimi, poke, tempura, fish cake, grilled sweet-miso salmon. Evening open.Day 8Sun, Aug 23 · Oʻahu — Hotel Change + Flex Day
- Check out of The Wayfinder Waikiki → move to Hyatt Regency Waikiki (~5-min walk apart). Use Hyatt points/free room to save money.
- Keep the day flexible until lūʻau timing is confirmed.
🌊 Possible surf viewing
Diamond Head Road Vista Point — recommended for summer surfing; waves break below the cliffs, viewable from above.Lūʻau: this plan says "book/confirm ASAP and build the day around it" — but remember the Maui Old Lahaina lūʻau (Aug 18) is already paid. Decide which one before booking a second.
Day 9Mon, Aug 24 · Oʻahu — Waikiki Beach Day
- Sleep in, relaxed morning. Grab beach gear from the hotel if available. Walk ~10+ min to Waikiki Beach — swim, walk, sit, relax. Back to Hyatt, shower/change.
🍜 Lunch — Soba noodles
Confirm the reservation.👑 Afternoon — ʻIolani Palace
You + Dustin visit; others choose hotel, pool, Waikiki, or another activity.- Optional — Magic Island: easy walking, calm water, views and sunset; good low-effort option if there's energy.
Day 10Tue, Aug 25 · Oʻahu — Manoa Falls + Final Honolulu Day
- Early morning — Manoa Falls hike. Bring hiking shoes, water, small backpack; use the toddler carrier if needed.
🍤 Lunch — Tonkatsu
Confirm the reservation.🏨 Afternoon — Waikiki resort hopping
Visit the Royal Hawaiian and Moana Surfrider — walk around, explore, drinks.🍽️ Final dinner — The Pig & The Lady
Move/confirm the reservation here.Day 11Wed, Aug 26 · Oʻahu — Departure
- Fly home — Alaska #802, Honolulu → LAX 9:22 PM. SuperShuttle pickup at LAX 9:40 PM → San Gabriel.
FloatingNorth Shore Day — to place
- Flexible day depending on the lūʻau and final schedule. Drive the North Shore with the GuideAlong app so the drive becomes the tour.
- Crouching Lion — optional short hike: ~0.4 mi round trip, ~219 ft gain; skip if anyone (especially Cody) isn't feeling it.
- Continue north with scenic stops, beaches, food, Haleʻiwa, shrimp, local shops, short walks.
- Don't make this day about giant waves in August — Diamond Head Road Vista Point is the better planned summer surf-viewing stop.
Reference
🎒 Packing & logistics
- Hiking shoes — Haleakalā, Manoa Falls, Crouching Lion, short Maui hikes.
- Haleakalā layers — fleece, pants, windbreaker, long sleeve, warm socks, optional beanie.
- Small daypack, water bottle, sunscreen, snacks.
- Toddler carrier.
- Cody's travel car seat — for rental cars and Ubers.
- Laundry: one major load in Maui near the end; don't rely on laundry in Honolulu.
🍍 Food & agricultural rules
- Don't assume all food is banned — ag restrictions apply differently to specific foods, plants, produce.
- Before flying, avoid casually packing fresh fruit/produce unless you've verified that item is allowed.
- Packaged foods are generally easier; check individual items when unsure.
- Maui → Oʻahu: be careful with fresh produce, plants, other regulated ag products.
- Best strategy: use fresh Maui groceries in Maui, buy fresh again on Oʻahu.
Things to confirm / book ASAP
- ☐ Call Wayfinder — confirm the room has a usable refrigerator (808-922-4744)
- ☐ Book/confirm the lūʻau ⚠ Maui one already paid — Aug 18
- ☐ Confirm the soba lunch reservation
- ☐ Confirm the tonkatsu reservation
- ☐ Confirm ZIGU
- ☐ Confirm KOAST / Coast
- ☐ Confirm The Pig & The Lady
- ☐ Confirm USS Arizona reservation
- ☐ Confirm Haleakalā sunrise reservation (Recreation.gov)
- ☐ Confirm Haleakalā park entrance/pass requirements
- ☐ Confirm Avis rental cars + pickup details
- ☐ Confirm Friday fireworks timing
- ☐ Check Hawaii agricultural rules for any food brought into / between islands
Trip philosophy
Anchor activities + open blocks. The trip intentionally avoids filling every hour. The major reservations and hikes are protected, while the rental cars, two-car setup, and open afternoons let the group split up, explore, relax, or just enjoy Hawaii without rushing.