Hawaiian Paradise: Luxe 7-Day Oahu & Maui Escape
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$$$$ Treat Yourself

Hawaii

Hawaiian Paradise: Luxe 7-Day Oahu & Maui Escape

Indulge in a splurge-worthy week splitting time between vibrant Oahu and serene Maui, featuring iconic hikes, sunset cruises, fine seafood dining, and boutique luxury stays. This itinerary balances bucket-list adventures with romantic relaxation, perfect for a special vacation treating yourself to Hawaii's finest.

Where to Stay

Halekulani Hotel
Stay

Halekulani Hotel

Iconic oceanfront luxury in Waikiki with elegant rooms, multiple pools, and world-class spa.

$600/night
Hotel Wailea
Stay

Hotel Wailea

Adults-only boutique resort on 15 acres of tropical gardens with private plunge pools and panoramic views.

$800/night
Maui Coast Hotel
Stay

Maui Coast Hotel

Modern beachfront property in Kihei with spacious rooms, free bikes, and direct ocean access.

$400/night

Good to Know

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Know

Book Diamond Head Reservations Early

Reserve 30 days in advance for morning slots to beat crowds and heat.

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Rent a Car for Flexibility

Essential for Road to Hana and island exploration; opt for 4WD if possible.

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Pack Reef-Safe Sunscreen

Required by law; choose non-chemical formulas to protect marine life.

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Fly Between Islands Mid-Trip

Book Oahu to Maui flight Day 4 morning; allow 3-4 hours total travel.

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Tip Generously for Service

15-20% standard; higher for exceptional experiences like luaus.

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Respect 'Kapu' Signs

Obey no-entry zones at sacred or private sites like beaches.

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Hydrate and Use Bug Spray on Hikes

Bring plenty of water and DEET for trails like Hana.

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Check Whale Watching Season

Winter months (Dec-Apr) offer humpback sightings from shores or cruises.

Your Week Itinerary

Diamond Head State Monument
Domorning

Diamond Head State Monument

Steep hike to summit for panoramic Oahu coastline views; book reservations 30 days ahead.

2h
$10
Beachhouse at the Moana
Eatevening

Beachhouse at the Moana

Verandah dining under historic banyan tree; order the seafood tasting menu.

2h
$100-150 per person
Star of Honolulu Dinner Cruise
Eatevening

Star of Honolulu Dinner Cruise

Luau-style dinner with live music and hula on sunset sail.

3h
$100-140 per person
Bishop Museum
Doafternoon

Bishop Museum

Focus on Hawaiian Hall for island history, culture, and erupting volcano exhibit.

3h
$25
Moana Sailing Company Sunset Cocktail Sail
Doevening

Moana Sailing Company Sunset Cocktail Sail

Boozy sunset cruise with ocean views, cocktails, and lively vibe.

2h
$80
Helena's Hawaiian Food
Eatmorning

Helena's Hawaiian Food

Traditional Hawaiian plates; order kalua pig and poi.

1h
$60-80 per person
Mauka Warriors Luau
Doevening

Mauka Warriors Luau

Polynesian history-focused show with dinner.

4h
$146

21 activities across 7 days

Map

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