6:30 AM: Depart Paia early with a full tank of gas and snacks
7:30 AM: Twin Falls short hike and swim
9:30 AM: Wailua Valley lookout and Keanae Peninsula stop
Afternoon:
12:00 PM: Lunch from a Hana-side fruit stand or food truck
1:00 PM: Pipiwai Trail hike to Waimoku Falls (Kipahulu)
Waiʻānapanapa requires an advance entry and parking reservation for non-residents, with timed entry and an exit deadline; book a slot that fits the drive and visit.
Evening:
5:00 PM: Begin the return drive before dark
7:30 PM: Dinner in Paia or Kahului
Day 2: Haleakala Sunrise & Upcountry
Early Morning:
3:30 AM: Depart for Haleakala summit (reservation required)
5:45 AM: Sunrise at the crater rim, bundled in warm layers
Late Morning/Afternoon:
8:00 AM: Breakfast in Kula
9:30 AM: Kula Botanical Garden and lavender farm
11:30 AM: Ulupalakua Ranch and MauiWine tasting
Evening:
3:00 PM: Return to the coast, rest at your hotel
6:30 PM: Sunset dinner in Wailea or Kihei
Day 3: West Maui Beach Day
Morning:
8:00 AM: Breakfast in Kaanapali
9:00 AM: Snorkeling at Black Rock, Kaanapali Beach
11:00 AM: Whalers Village Museum and shopping
Afternoon:
1:00 PM: Lunch oceanfront in Kaanapali
2:30 PM: Relax at Napili Bay
4:30 PM: Lahaina Jodo Mission visit
Evening:
6:00 PM: Luau experience (check current venue) or sunset dinner cruise
Day 4: Ocean Day - Molokini & Whales
Morning:
6:00 AM: Board Molokini snorkel/whale watch boat from Maalaea Harbor
7:00 AM - 11:00 AM: Snorkeling Molokini Crater and coastal stop
Afternoon:
12:00 PM: Lunch in Kihei
1:30 PM: Maui Ocean Center aquarium
3:30 PM: Relax at Wailea Beach
Evening:
6:30 PM: Dinner along the Wailea coastal path
Day 5: Wailuku, Iao Valley & Central Maui
Morning:
9:00 AM: Bailey House Museum, Wailuku
10:30 AM: Kaahumanu Church
11:00 AM: Iao Valley State Monument and Iao Needle hike
Afternoon:
12:30 PM: Kepaniwai Heritage Gardens picnic
1:30 PM: Maui Nui Botanical Gardens
3:00 PM: Maui Swap Meet (Saturdays) or local shopping in Wailuku