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Oahu & Maui Explorer

A perfect balance of Oahu's vibrant culture and Maui's breathtaking natural landscapes, featuring world-class beaches and iconic hikes.

7days
19stops
198km
DAY01

Waikiki Beach → Diamond Head State Monument

4 km · 15m driving · Overnight in Diamond Head State Monument
  1. 14:00
    Waikiki Beach· start
  2. 4 km · 15m
  3. 16:00
    Diamond Head State Monument· overnight
Accommodation
Waikiki Beachfront
Food
  • Duke's Waikiki · Classic beachfront dining known for Hula Pie and fresh fish.
  • Marukame Udon · Hand-made noodles that are a local favorite for a quick, delicious meal.
Costs
Lodging
$350
Food
$80
Diamond Head Entry
$5
DAY02

Hanauma Bay → Lanikai Beach

23 km · 45m driving · Overnight in Lanikai Beach
  1. 08:00
    Hanauma Bay· start
  2. 3 km · 10m
  3. 11:00
    Halona Blowhole
  4. 20 km · 35m
  5. 13:30
    Lanikai Beach· overnight
Accommodation
Waikiki Beachfront
Food
  • Kona Coffee Purveyors · Incredible pastries and high-end Hawaiian coffee.
  • Over Easy · Modern brunch spot in Kailua with local ingredients.
Costs
Hanauma Bay Entry
$25
Food
$70
Gas
$15
DAY03

Laniakea Beach → Haleiwa Town

13 km · 25m driving · Overnight in Haleiwa Town
  1. 10:00
    Laniakea Beach· start
  2. 5 km · 10m
  3. 12:30
    Waimea Valley
  4. 8 km · 15m
  5. 15:30
    Haleiwa Town· overnight
Accommodation
North Shore / Turtle Bay
Food
  • Giovanni's Shrimp Truck · The original North Shore garlic shrimp. Messy and delicious.
  • Matsumoto Shave Ice · A North Shore institution since 1951.
Costs
Waimea Entry
$25
Food
$60
Lodging
$450
DAY04

Kahului Airport → Paia Town

35 km · 55m driving · Overnight in Paia Town
  1. 11:00
    Kahului Airport· start
  2. 15 km · 25m
  3. 14:00
    Iao Valley State Monument
  4. 20 km · 30m
  5. 16:30
    Paia Town· overnight
Accommodation
Paia or Kihei
Food
  • Paia Fish Market · Fresh catches served in a casual, communal setting.
  • Mama's Fish House · The most famous restaurant on Maui. Book months in advance.
Costs
Flight
$95
Car Rental
$80
Food
$90
DAY05

Twin Falls → Hana Town

55 km · 2h driving · Overnight in Hana Town
  1. 08:30
    Twin Falls· start
  2. 50 km · 1h 45m
  3. 12:30
    Wai'anapanapa
  4. 5 km · 15m
  5. 15:00
    Hana Town· overnight
Accommodation
Hana
Food
  • Hana Farms · Incredible banana bread and wood-fired pizzas.
  • Thai Food by Pranee · Authentic Thai food in the middle of the jungle.
Costs
Wai'anapanapa Entry
$15
Food
$60
Gas
$40
DAY06

Haleakala → Makawao Town

35 km · 1h 5m driving · Overnight in Makawao Town
  1. 10:00
    Haleakala· start
  2. 10 km · 20m
  3. 13:00
    Hosmer Grove
  4. 25 km · 45m
  5. 16:00
    Makawao Town· overnight
Accommodation
Wailea
Food
  • Komoda Store & Bakery · Famous for cream puffs and stick donuts since 1916.
  • Kula Lodge · Dining with a panoramic view of the island.
Costs
Park Entry
$30
Food
$80
Lodging
$550
DAY07

Makena Beach (Big Beach) → Kahului Airport

33 km · 50m driving
  1. 09:30
    Makena Beach (Big Beach)· start
  2. 8 km · 15m
  3. 14:00
    Wailea Beach Path
  4. 25 km · 35m
  5. 17:00
    Kahului Airport
Food
  • Monkeypod Kitchen · Famous for Mai Tais with lilikoi foam and local fish.
  • Coconut's Fish Cafe · Award-winning fish tacos in a casual setting.
Costs
Food
$70
Gas
$20
Souvenirs
$50
Booking timeline
Book these before you go
  1. Day 4Flight · Kahului Airport
Heads Up
  • Book rental cars and popular restaurants months in advance
  • National Park reservations are mandatory for sunrise/certain entries
  • Respect local wildlife and 'Kapu' (forbidden) signs
  • Day 3: hotel change (Waikiki Beachfront → North Shore / Turtle Bay) — allow 1-2h check-out + transfer
  • Day 4: hotel change (North Shore / Turtle Bay → Paia or Kihei) — allow 1-2h check-out + transfer
  • Day 5: hotel change (Paia or Kihei → Hana) — allow 1-2h check-out + transfer
  • Day 6: hotel change (Hana → Wailea) — allow 1-2h check-out + transfer
  • 🛫 Route includes 1 flight + 0 rail segments. Map shows them as dashed lines (connection only, not real road).