Hawaii, Four Islands · Aug–Sep 2022

01 / Maui

Maui — five days upcountry.

Aug 26 → 31 · Volcano summit · Road to Hana · West-side snorkel

Stay

God's Peace of Maui

Upcountry Makawao — central, between west beaches and east Hana.

~$160/night

Day 01

Aug 26

Friday

Arrival in Maui.

Fly EWR → OGG. Pick up rental car, drive upcountry to Makawao. Settle in at God's Peace, scout the lay of the land. If energy permits, sunset at Kapalua Cliff House overlook.

Day 02

Aug 27

Saturday

Haleakalā sunrise, west beaches, luau.

Pre-dawn drive up Haleakalā for sunrise — book the reservation two months in advance via REC.GOV (window: 7am HST, 48 hours out is too late)
Bike ride down from summit (optional, if booked separately)
Whaler's Beach at Kaanapali — snorkel, blackrock
Kapalua Bay and Napili Bay — both excellent snorkel
Drums of the Pacific Luau, 5pm — ~$200/person

Mama's Fish House dinner reservation, 2:45pm — book months ahead.

Day 03

Aug 28

Sunday

Road to Hana, sunrise to sunset.

Start before sunrise — the road is what matters, not the destination
Twin Falls (mile marker 2), Eucalyptus rainbow trees, Garden of Eden
Ke'anae Lookout — Aunty Sandy's banana bread (M–S, 2pm)
Wai'ānapanapa Black Sand Beach — reservation required, 3–6 PM slot
Pipiwai Trail — bamboo forest + Waimoku Falls (4 mi round trip)
Seven Sacred Pools / Oheo Gulch
Wailua Falls (mile marker 45), Hanawi Falls, Makapipi Falls
Iao Valley on the way back if time permits

Eat: Paia Fish Market (blackened mahi mahi), Coconut Glen vegan ice cream, Nahiku Marketplace coffee, Braddha Hut's BBQ (M–F until 2:30pm).

Day 04

Aug 29

Monday

West Maui — snorkel and sunset sail.

Snorkel Blackrock at Kaanapali (rent gear from Aston)
Sunset catamaran cruise from Lahaina
Optional: whale watching (seasonal), Iao Valley, Paia Fish Market lunch
Dinner at Kimo's, Lahaina — 5:15pm

Day 05

Aug 30

Tuesday

West Ridge Trail and Honolua Bay.

Waihe'e Ridge Trail — start at 8am, ~2 hours, 4.4 mi / 2,600 ft elevation gain
Olivine Tide Pools (Nakalele Blowhole, 10 min from viewpoint)
Honolua Bay — snorkel access trail (~15 min walk in)
Sunset at Kaanapali Beach — Japengo for dinner

Maui — top spots by region.

Kapalua Bay (NW)

Snorkel · turtle territory · calm

Tier 1

Napili Bay (NW)

Snorkel · sunset point

Tier 1

Kapalua Coastal Trail

2.5 mi · all bays

Tier 1

Honokeana Cove

Turtle snorkel · Napili

Tier 1

Ho'okipa Beach (N)

Turtle snorkel · windsurfers

Tier 1

Olowalu Beach (W)

Turtle snorkel · calm

Tier 1

Honolua Bay

Best snorkel on the island

Tier 1

Kahakuloa Head (N)

Dramatic coastal headland

Tier 1

Lahaina town (W)

Banyan tree · Front Street

Tier 1

Iao Valley (C)

Lush state park

Tier 1

Mākena Beach (W)

Big & Little Beach · use caution

Tier 2

Molokini Crater

Boat-only snorkel

Tier 2

Maui — eat where.

Mama's Fish House

East · book months ahead · 2:45pm

Paia Fish Market

Blackened mahi mahi · Hana day fuel

Cuatro

Wailea/Kihei · 5:30pm · Aug 28

Kimo's

Lahaina · 5:15pm · Aug 29

Aunty Sandy's Banana Bread

Ke'anae Lookout · M–S, 2pm

Coconut Glen

Hana road · vegan ice cream

Hāna Farms Roadside Stand

Pizza oven · Fri/Sat until 8pm

Leoda's Bakery

West Maui · pies and pastries

02 / Big Island

Big Island — two days, the volcano.

Aug 31 → Sep 2 · Volcanoes National Park · Kona side · Hapuna

Stay

Alii Kane Cottages with Loft

Volcano village — sleeps near Volcanoes NP gate, easy night-volcano access.

~$130/night

Day 06

Aug 31

Wednesday

Maui → Big Island, night volcano.

Drop rental, drive to OGG airport
OGG → ITO flight, 4:45 – 5:20 PM (Hilo side)
Pick up Big Island rental, drive to Volcano
Night volcano viewing — verify Thurston Lava Tube is erupting on arrival day

Day 07

Sep 1

Thursday

Volcanoes National Park, full day.

Volcanic crater national park — full day exploration
Eastern lava areas in afternoon
Drive west across to Kona side for night two

Day 08

Sep 2

Friday

Kona snorkel, west beaches, fly to Kauai.

Two Steps at Honaunau Bay — go left for easy snorkel
Pu'uhonua o Honaunau National Historical Park
Punalu'u Black Sand Beach — south side, en route
Hapuna Beach — white sand, swim
Manini'owali Beach (Kua Bay) — white sand, near airport
'Akaka Falls — easy boardwalk, dramatic drop
Flight KOA → HNL → LIH, 4:35 – 6:35 PM

Mauna Kea stargazing — book separately, requires a clear afternoon.

Big Island — top snorkel.

Hapuna Beach

White sand · kid-friendly swim

Richardson Beach Park

Easy · Hilo side

Kahalu'u Beach

Reef · easy entry

Honaunau Bay (Two Steps)

Morning · go left · easier

Captain Cook Monument

Kayak in · advanced

Kīkaua Point Park

Easy · west side

03 / Kauai

Kauai — four days on the garden island.

Sep 2 → 6 · Na Pali coast · Waimea Canyon · Hanalei · Poipu

Stay

Kauai Palms Hotel

Lihue — central, walking distance to airport, used as a base for both north and south day trips.

~$90/night

Day 09

Sep 3

Saturday

Na Pali coast — Holo Holo charter.

Na Pali coast Holo Holo Charters — full day boat tour
Snorkel stops along the coast, sea caves, dolphins likely
Recovery afternoon, swim at Lydgate Beach Park

Day 10

Sep 4

Sunday

North shore — Hanalei and Hā'ena.

Hā'ena State Park & Ke'e Beach — snorkel + Hanakāpī'ai Beach trail (4mi RT, reservation required)
Limahuli Garden and Preserve
Hā'ena Beach Park and Dry Cave — smoothie trailer
Hanalei Bay / pier — sunset, food trucks, bridge crossing
Anini Beach — snorkel, restrooms in county park
Kīlauea Lighthouse, Kīlauea Fish Market (M/W/F dinner only)

Day 11

Sep 5

Monday

South shore — Poipu and Koloa.

Shipwreck Beach + Mahaulepu Heritage Trail (rough water, scenic)
Poipu Beach — food, picnic, snorkel cove
Spouting Horn Park
Hanapepe town
Koloa town — old sugar mill, food trucks, shave ice

Day 12

Sep 6

Tuesday

Waimea Canyon and Kalalau lookouts.

Waimea Canyon State Park — drive the rim
Kekaha LO, Niihau LO, Pu'u Hinahina LO, Waipo'o Falls LO
Kalalau Lookout, Pu'u O Kila Lookout — cliff trail (0.8 mi, muddy)
Wailua Falls on the return
Fly LIH → HNL, 5:30 – 6:10 PM

Kauai — top spots by region.

Makana Charters (Na Pali)

Morning tour · 7:45am check-in

Tier 1

Hā'ena State Park · Ke'e Beach

Best snorkel + hike · reservation

Tier 1

Anini Beach

Snorkel · campground RR · high tide

Tier 1

Hanalei Bay & pier

Sunset · waterfall views · town

Tier 1

Poipu Beach

Snorkel + beach · south shore base

Tier 1

Tree Tunnel

500 trees · drive-through

Tier 1

Koloa town

Sugar mill · shave ice · art shops

Tier 1

Waimea Canyon

"Grand Canyon of the Pacific"

Tier 1

Wailua Falls

Roadside · twin falls

Tier 1

Beach House / Lawai

Snorkel left · 3–15 ft · RR

Tier 1

Kīlauea Lighthouse

Views · reservation

Tier 2

Shipwreck Beach

Hyatt · rough · Mahaulepu trail

Tier 2

04 / Oahu

Oahu — five days, Honolulu base.

Sep 6 → 11 · Pearl Harbor · Diamond Head · North Shore · Ko Olina

Stay

Marriott Ko Olina Beach Club

West side resort base — manicured lagoons, easy day trips to Honolulu and the North Shore.

Resort points

Day 13

Sep 7

Wednesday

Diamond Head + Waikiki.

Diamond Head Monument hike — 6–8am window, reservation via HAWAII.GOV
Waikiki beach, Honolulu lunch
USS Arizona Memorial — 3pm slot, REC.GOV booking 1 day before
Sunset back at Ko Olina

Day 14

Sep 8

Thursday

North Shore — Shark's Cove and food trucks.

Shark's Cove / Pupukea Beach — snorkel before 10–11am for best visibility
Waimea Beach, Laniakea (turtle beach)
Kahuku — Giovanni's shrimp truck (or Roy's Beach Club)

Day 15

Sep 9

Friday

East side — Hanauma and Lanikai.

Hanauma Bay — 7am HST reservation, book 2 days out
Lanikai Beach — white sand, calm
Waimanalo Beach — long stretch of white sand

Day 16

Sep 10

Saturday

Waimea Valley waterfall hike.

Waimea Valley waterfall hike
Kuilima Cove (turtle bay) — N snorkel, right side of cove

Day 17

Sep 11

Sunday

Fly home.

Pack up, last beach walk, return rental, HNL → EWR.

Oahu — top snorkel.

Shark's Cove / Pupukea (N)

Beginner south side · before 10am

Tier 1

Hanauma Bay (S)

Reservation · west side better

Tier 1

Kuilima Cove (N)

Right side of cove · turtles

Tier 1

Wailea Beach (E)

Snorkel

Tier 1

Papa'iloa Beach (N)

Turtles · 5 parking

Tier 1

Ko Olina (W)

Resort lagoons · calm

Tier 1

Laniakea (WNW)

Turtles on beach

Tier 1

Queen's Beach (S)

Next to the wall

Tier 2

Waimea Beach (N)

Beginner snorkel · winter waves

Tier 2

Electric Beach (W)

Non-beginner · open water

Tier 2

05 / Reservations

Reservations to book ahead.

Hawaii has tightened access to its most popular sites since 2020. Several of these have hard caps and book up; the rest are easy walk-ups with confirmation. Book the top three the day windows open.

Site	Window	Time slot	Book at	Island
Haleakalā sunrise	48 hours out	7am HST	recreation.gov	Maui
Wai'ānapanapa Black Sand	30 days	3–6 PM	state park site	Maui
USS Arizona Memorial	1 day before	3pm HST	recreation.gov	Oahu
Diamond Head	30 days	6–8am	hawaii.gov	Oahu
Hanauma Bay	2 days out	7am HST	hanaumabay site	Oahu
Hā'ena State Park	30 days	any	state park site	Kauai

06 / Lessons

What I'd change.

Honest notes from the trip — what worked, what didn't, what I'd do differently.

Skip / Less time

Big Island deserves more than two days.

Hilo and Kona are effectively two trips. Two days felt rushed — pick a side or budget four full days minimum. Volcano on the east, snorkel on the west, and the drive between them eats half a day.

Add

Mauna Kea stargazing is non-negotiable.

If you have a clear afternoon on the Big Island, go. The summit closes at sunset, but the visitor center observation site stays open for stargazing — book a tour or DIY in a 4WD.

Lock in early

Mama's Fish House. Two months out, minimum.

The single hardest reservation on Maui. Book the moment the calendar opens; lunch slots are easier than dinner.

Pacing

Road to Hana is a full day, not a half.

Start before sunrise, expect to be back after dark. The lookouts and falls are the trip; rushing past them defeats the point. Don't try to combine Hana with anything else.

Snorkel

Honolua Bay (Maui) was the best of the trip.

Better than Molokini, better than Hanauma. The 15-minute walk in keeps casual tourists out, water is clear, fish are everywhere. Go early.

Stay

Upcountry Maui beats the resort strip.

God's Peace in Makawao was a great choice — central, quiet, real Maui. The Kaanapali resort run is fine for a luau day but I wouldn't sleep there.

Hawaii, four islands,seventeen days.

Maui — five days upcountry.

Arrival in Maui.

Haleakalā sunrise, west beaches, luau.

Road to Hana, sunrise to sunset.

West Maui — snorkel and sunset sail.

West Ridge Trail and Honolua Bay.

Maui — top spots by region.

Maui — eat where.

Big Island — two days, the volcano.

Maui → Big Island, night volcano.

Volcanoes National Park, full day.

Kona snorkel, west beaches, fly to Kauai.

Big Island — top snorkel.

Kauai — four days on the garden island.

Na Pali coast — Holo Holo charter.

North shore — Hanalei and Hā'ena.

South shore — Poipu and Koloa.

Waimea Canyon and Kalalau lookouts.

Kauai — top spots by region.

Oahu — five days, Honolulu base.

Diamond Head + Waikiki.

North Shore — Shark's Cove and food trucks.

East side — Hanauma and Lanikai.

Waimea Valley waterfall hike.

Fly home.

Oahu — top snorkel.

Reservations to book ahead.

What I'd change.

Big Island deserves more than two days.

Mauna Kea stargazing is non-negotiable.

Mama's Fish House. Two months out, minimum.

Road to Hana is a full day, not a half.

Honolua Bay (Maui) was the best of the trip.

Upcountry Maui beats the resort strip.

Hawaii, four islands,
seventeen days.