Oahu + Maui

8-Day All-Inclusive
From City Buzz to Island Bliss
This thoughtfully crafted two-island itinerary gives you the best of both worlds - the vibrant energy of Waikīkī paired with Maui's lush beaches and relaxed luxury. Start with Oʻahu's cultural landmarks, surfing beaches, and nightlife before trading city lights for Maui's scenic drives, farm-fresh cuisine, and unforgettable ocean adventures. Designed for first-time Hawaii travelers who want a seamless, insider-guided experience blending Mauka (mountain) and Makai (sea) life.


Prices from $999.00 per person (not including airfare)**


What's Included
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Roundtrip airfare from U.S. mainland (major gateways)
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7 nights accommodations (4-star standard)
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Inter-island flight from Oʻahu to Maui
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Airport transfers or rental car with GPS
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Daily breakfast and full-menu dinners
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Private and guided excursions (custom options available)
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Fresh flower lei greeting and tropical welcome drink
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Personalized Hawaii-based travel advisor support
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Curated day-by-day itinerary following Mauka to Makai flow
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Cancel-for-any-reason travel protection available
Day-by-Day Itinerary
Day 1: Aloha Arrival in Oʻahu
Step off the plane and into paradise with a traditional lei greeting and private transfer to your Waikīkī hotel. Ease into island life with sunset views and tropical flavors by the sea.
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Fresh flower lei greeting at Honolulu Airport
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Private transfer to ocean-view Waikīkī hotel
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Welcome cocktail reception
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Dinner at Tiki's Grill with live slack key guitar


Day 2: Circle Island Secrets & Cultural Insights
Discover the real Oʻahu with a full-day guided tour around the island's sacred sites, hidden beaches, and roadside treasures - with plenty of insider stories along the way.
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Private Circle Island guided tour
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Stops: Byodo-In Temple, Makapuʻu Lookout, North Shore beaches
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Tropical fruit stand tastings
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Sunset beachfront dinner at Duke's Waikīkī
Day 3: Mauka Jeep Adventure to North Shore
Explore Oʻahu's mountains and coastlines with your own Jeep, armed with a hand-picked map of local favorites and hidden adventures.
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Jeep rental with custom GPS routes
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Drive through coffee country and local farms
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Visit shrimp trucks and waterfall hikes
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Surf-watching at Waimea Bay
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Dinner at a hidden-gem Honolulu restaurant


Day 4: Leisure + Lūʻ au at Sunset
Relax and recharge. Whether you dive into Waikīkī's waves, explore Pearl Harbor, or simply lounge by the pool, today moves at your pace - capped off by a lively traditional lūʻau.
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Free day (surf lessons, museums, spa day optional)
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Optional tour: Pearl Harbor & USS Arizona Memorial
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Sunset lūʻau with buffet dinner, hula, and fire-knife performances
Day 5: Inter-Island Transfer to Maui
Switch gears from city buzz to island bliss. After a short flight, settle into your coastal resort in Maui's charming Lāhainā or Kāʻanapali.
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Morning flight to Maui (Oʻahu to Kahului)
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Rental car pickup at Maui Airport
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Scenic coastal drive to hotel
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Dinner at Star Noodle - Asian-fusion local favorite


Day 6: Snorkel & Sail to Lānaʻ i
Set sail across the ʻAuʻau Channel to snorkel Maui's protected marine sanctuaries and savor a toes-in-the-sand dinner on return.
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Catamaran snorkeling cruise to Lānaʻi reefs
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Snorkeling with tropical fish and green sea turtles
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Onboard light breakfast or lunch included
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Dinner at Māla Ocean Tavern (beachfront dining)
Day 7: A Hui Hou
(Until We Meet Again)
Choose your adventure:
Option 1: Road to Hana Adventure
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Guided deluxe tour or self-drive with GPS
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Stops at waterfalls, lava tubes, and black sand beaches
Option 2: Upcountry Maui Escape
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Visits to lavender farms, ranches, and botanical gardens
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Explore historic Makawao Town Evening:
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Dinner at your resort or Mama's Fish House for fine dining


Day 8: Departure
Savor a final quiet morning in paradise before your transfer back to the airport.
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Breakfast at your hotel (optional)
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Beach stroll, spa visit, or last-minute shopping
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Private transfer to Maui Airport for return flight home
Perfect for travelers seeking the ultimate Hawaiian duo. Explore vibrant Oʻahu and magical Maui with ease and luxury.

Important Notes and Customization Options
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Custom upgrades and personalizations available (luxury accommodations, private tours)
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"Bare Bones" Package = Airfare + Hotel + Transfers + Itinerary Planning included
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Final price depends on travel dates, departure city, and upgrades
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Use our Airfare Estimator Tool to get your personalized quote
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Optional Add-Ons
Airport
Lei Greeting
Guided Pearl
Harbor Tour
Snorkeling and Sailing
Adventure
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