Maui, Mom & Me

01 Arrival Day Mon Sept 15

Morning

Depart homeGet to airport early — inter-island connections can be tight

Afternoon

Land OGG, pick up carBook car early — September is shoulder season but Maui rentals run short

Evening

Grocery stop at Safeway Lahaina Stock breakfast supplies, snacks, water, sunscreen food

Night

Check in, walk the beach, easy dinnerKaanapali Beach Hotel or Ka'anapali Beach Club — confirm reservation

02 Kapalua & the Coastal Trail Tue Sept 16

7–9 am

Kapalua BayBest snorkel in West Maui. Go early before the tour boats; park at the small lot off Kapalua Placeocean

9–11 am

Kapalua Coastal Trail2.3 mi bluff walk, Kapalua Bay to D.T. Fleming Beach. Easy, paved, gorgeous. Flip-flop friendly.land

11 am–1 pm

D.T. Fleming BeachBodysurfing beach — rougher water, no snorkel here, but beautiful for swimming if conditions allowocean

Afternoon

Pool + restSeptember sun is real. Hotel pool until 4 pm.rest

Evening

Dinner at Merriman's KapaluaBook ahead — farm-to-table, ocean views, solid fishfood

03 Snorkel Sail Wed Sept 17

7–8 am

Board at Lahaina HarborPacific Whale Foundation or Trilogy — both depart ~7:30. Book online 2+ weeks ahead.

8 am–12 pm

Molokini CraterHalf submerged volcano, 40-ft visibility. Whale sightings possible in September.ocean

12–1:30 pm

Turtle Town snorkel stopGreen sea turtles — almost certain encounter at this second stopocean

Afternoon

Lahaina town walkOld Lahaina Courthouse area; check what's rebuilt post-fire. Pay respects, shop lightly.land

Evening

Early dinner, early bedLong day on the water

04 Road to Hana Thu Sept 18

6 am

Early depart from KaanapaliLeave by 6 to beat tour buses. Download Gypsy Guide app or Road to Hana audio tour the night before.

8–9 am

Twin FallsFirst major stop, easy 20-min hike. Good warm-up.land

9:30–10:30 am

Waikamoi Ridge TrailShort bamboo forest loop. Cool and quiet.land

11 am

Garden of Eden lookout & Puohokamoa FallsPaid entry ($20/person) but worth it for the falls view without the crowd hikeland

12:30 pm

Lunch at Halfway to Hana standBanana bread. Non-negotiable.food

2–3 pm

Wai'anapanapa State ParkBlack sand beach. Reserve day-use entry in advance on the Hawaii DLNR site ($10/person).ocean

3:30–4 pm

Hana townQuick stretch — Hasegawa General Store, fudge at Hana Farms if still openfood

4 pm–dark

Drive backSame road, less traffic. Allow 2.5 hrs. Do not attempt Piilani Hwy at night — poorly marked.

05 Rest Day Fri Sept 19

Morning

Sleep in, coffee on the lanaiYou earned it after Hana.rest

Mid-morning

Kaanapali Beach walk north to south3 miles round-trip on the beach path. Whaler's Village at the midpoint for an açaí bowl.land

Afternoon

Book a massage or just the poolThe Westin Kaanapali has a good spa if you want a treatrest

Sunset

Sunset from Black RockPu'u Keka'a cliff dive happens at sunset — walk over to watch. Free, spectacular.

Evening

Dinner at Leilani's on the BeachSolid fish tacos, right on the sand, no-fuss atmospherefood

06 Haleakalā & Upcountry Sat Sept 20

3:30 am

Depart for Haleakalā SummitReserve sunrise entry permit on recreation.gov — required and sells out weeks ahead. Bring real layers: it'll be 35–45°F at 10,000 ft.

5:45 am

Sunrise at the summitAbove the clouds if you're lucky. One of the best things you can do on Maui.land

7:30–9 am

Short summit trail walkHalemau'u overlook or Pa Ka'oao — 30–45 min, still above cloud line. Wind, moonscape, silence.land

10–11 am

Upcountry: KulaDrive down through farm country. Stop at Kula Lodge for late breakfast/brunch — great eggs Benedict.food

11:30 am

Ali'i Kula Lavender FarmShort walk, lavender everything, views down to the coast. Good gift stop.land

Afternoon

Back to resort — nap mandatory4 am start catches up with yourest

Evening

Low-key dinner in KaanapaliMaui Brewing Co. in Kaanapali or Japengo at the Hyattfood

07 Honolua Bay & Last Full Day Sun Sept 21

7–9 am

Honolua BayBest kept snorkel spot on the island. Park along the road, walk the trail down. No facilities. Bring your own water.ocean

10–11 am

Nakalele Blowhole20-min hike to a dramatic coastal blowhole. Stay back from the edge — it's powerful.land

Noon

Lunch at Leoda's Kitchen & Pie ShopIn Olowalu on the way back — banana cream pie is the whole pointfood

Afternoon

Last swim, pack upReturn any gear rentals. Do one final Kaanapali Beach swim.ocean

Evening

Nice dinner outLast night — Mama's Fish House in Paia if you can get a reservation (book very early). Otherwise Star Noodle in Lahaina.food

08 Departure Mon Sept 22

Morning

Check out, coffee, airportOGG requires 90 min before departure. Return car with a full tank or get hit with the premium.

Flight

Head home with a tan and no regrets

Maui,
Mom & Me

Book before you go

Left on the table