
AI-Generated Itinerary
Your complete day-by-day guide to Maui — handpicked attractions, dining recommendations, and local tips for an unforgettable 10-day trip.
Day 1
Morning
8:00 AM - 11:00 AM
Fly into Kahului Airport (OGG) and pick up your rental car
Collect your car and stock up on water, snacks and reef-safe sunscreen at a Kahului grocery store.
Late Morning
11:00 AM - 1:00 PM
Check in to a Kihei or Wailea base
Drive about 30 minutes south and settle in. The south shore is sunny, central and close to Molokini departures.
Afternoon
1:00 PM - 5:00 PM
First swim at Kamaole Beach Park
Shake off the flight at one of Kihei's three Kamaole beach parks, with lifeguards, restrooms and gentle water.
Evening
5:00 PM - 9:00 PM
Sunset and a poke bowl dinner
Watch the sun set over Kahoolawe and Lanai, then grab poke or a plate lunch from a local seafood counter.
Day 2
Morning
8:00 AM - 11:00 AM
Morning snorkel cruise to Molokini Crater
Depart from Maalaea or Kihei on an early boat to the crater's clear inner basin, often with a stop at Turtle Town.
Late Morning
11:00 AM - 1:00 PM
Turtle Town and the return cruise
Swim with green sea turtles along the lava reef, then cruise back with views of Haleakala.
Afternoon
1:00 PM - 5:00 PM
Stroll the Wailea Beach Path
Walk the paved 1.5-mile coastal path linking Wailea's beaches and lava points, with a swim at Wailea Beach.
Evening
5:00 PM - 9:00 PM
Sunset at Makena (Big Beach)
Head to wide, golden Makena Beach in Makena State Park for sunset. Heed the strong shore break warnings.
Day 3
Morning
3:00 AM - 7:00 AM
Sunrise at the summit of Haleakala
With your Recreation.gov sunrise reservation, leave around 3:00 AM and watch dawn break over the crater. Bring warm layers.
Late Morning
7:00 AM - 10:00 AM
Crater views and the Sliding Sands Trail
Walk a short way down the Keoneheehee (Sliding Sands) Trail and look for silversword plants at the overlooks.
Afternoon
10:00 AM - 3:00 PM
Lunch and browsing in Kula and Makawao
Descend to upcountry Kula for farm views and lunch, then wander Makawao's paniolo (cowboy) town shops and galleries.
Evening
3:00 PM - 8:00 PM
Early night before the Road to Hana
Rest after the early start, pack snacks and water, and fuel up for tomorrow's long drive.
Day 4
Morning
7:00 AM - 11:00 AM
Early start from Paia on the Hana Highway
Leave Paia by 7:00 AM and stop at the Twin Falls area, Ke'anae Peninsula and roadside banana bread stands.
Late Morning
11:00 AM - 1:00 PM
Waiʻānapanapa State Park black sand beach
Use your reserved time slot to see the black sand beach, sea arch and lava caves along the coastal trail.
Afternoon
1:00 PM - 4:00 PM
Pipiwai Trail in Haleakala's Kipahulu district
Continue past Hana to hike the 4-mile round-trip Pipiwai Trail through a bamboo forest to 400-foot Waimoku Falls.
Evening
4:00 PM - 8:00 PM
Drive back before dark
Return the way you came, aiming to clear the winding stretch by dusk, and grab dinner in Paia.
Day 5
Morning
8:00 AM - 11:00 AM
Iao Valley State Monument and the Iao Needle
With your reserved entry, walk the short loop to the Iao Needle lookout while clouds are still high.
Late Morning
11:00 AM - 1:00 PM
Drive to Kaanapali
Take the coastal Honoapiilani Highway to West Maui, about 45 minutes. Be respectful passing Lahaina, which is still rebuilding after the 2023 fire.
Afternoon
1:00 PM - 5:00 PM
Snorkel Black Rock on Kaanapali Beach
Check in to West Maui and snorkel around Black Rock with turtles and reef fish, then relax on the sand.
Evening
5:00 PM - 9:00 PM
Sunset at Napili Bay
Watch the sun sink behind Molokai from Napili's crescent cove, then dine at a West Maui restaurant.
Day 6
Morning
8:00 AM - 11:00 AM
Kapalua Coastal Trail
Walk the easy trail from Kapalua Bay past lava points and Oneloa Beach, with whale spouts offshore in winter.
Late Morning
11:00 AM - 1:00 PM
Honolua Bay snorkel or surf lookout
In calm summer months snorkel this marine conservation area; in winter watch big-wave surfers from the cliffs.
Afternoon
1:00 PM - 5:00 PM
Lazy afternoon at Napili Bay
Return to Napili for a nap on the sand and a turtle-spotting swim.
Evening
5:00 PM - 9:00 PM
Dinner and live music in Kaanapali
Stroll the Kaanapali Beachwalk and catch the Black Rock torch-lighting and cliff dive at sunset.
Day 7
Morning
8:00 AM - 11:00 AM
Whale-watching cruise (December-April)
Humpback whales gather in Maui's warm channels each winter; book a naturalist-led boat. Outside whale season, take a snorkel sail.
Late Morning
11:00 AM - 1:00 PM
Brunch and shave ice
Refuel with a local-style brunch and cool off with rainbow shave ice.
Afternoon
1:00 PM - 5:00 PM
Pool, spa or beach time
Keep the afternoon free for the pool or a massage. A slower day is part of the Maui experience.
Evening
5:00 PM - 9:00 PM
Sunset catamaran from Kaanapali Beach
Several boats board right off the sand for a sunset sail with Lanai and Molokai on the horizon.
Day 8
Morning
8:00 AM - 11:00 AM
Lavender farm and goat dairy in Kula
Visit a lavender farm with panoramic views and a family-run goat dairy farm for cheese tasting on Haleakala's slopes.
Late Morning
11:00 AM - 1:00 PM
Farm-to-table lunch upcountry
Enjoy a relaxed lunch made with island-grown produce at a cafe in Kula or Makawao.
Afternoon
1:00 PM - 5:00 PM
Paia town and Hookipa Beach Park
Browse Paia's surf shops, then watch windsurfers and basking turtles at Hookipa lookout.
Evening
5:00 PM - 9:00 PM
Fresh fish dinner on the North Shore
Have dinner of the day's catch near Paia before driving back to West Maui.
Day 9
Morning
8:00 AM - 11:00 AM
Drive up to Haleakala
No reservation is needed after sunrise hours. Your entrance receipt covers 3 days; otherwise pay at the gate.
Late Morning
11:00 AM - 1:00 PM
Hike the Keoneheehee (Sliding Sands) Trail
Descend among cinder cones; remember the climb back at 10,000 feet is twice as hard as going down.
Afternoon
1:00 PM - 5:00 PM
Leleiwi and Kalahaku overlooks
Stop at the overlooks on the drive down for sweeping crater and cloud views.
Evening
5:00 PM - 9:00 PM
Farewell dinner in West Maui
Celebrate your last night with a sunset dinner back near Kaanapali or Napili.
Day 10
Morning
8:00 AM - 11:00 AM
Morning swim at Napili Bay
Take a last snorkel with the turtles in the calm morning water.
Late Morning
11:00 AM - 1:00 PM
Pick up local souvenirs
Buy Maui coffee, macadamia nuts and locally made crafts from small West Maui businesses.
Afternoon
1:00 PM - 5:00 PM
Drive to Kahului Airport
Allow about 45 minutes plus time to return the car, and refuel before you arrive.
Evening
5:00 PM - 9:00 PM
Fly home from OGG
Arrive 2 hours before your flight; agricultural inspection applies to mainland-bound bags.
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