10 Day Hawai'i Itinerary: A Journey Through Paradise

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Advisor - Sarah Keim
Curated By

Sarah Keim

  • Active Travel

  • Adventure Travel

  • Beaches

  • Hawai'i

  • Oahu

  • Maui

  • Kaua'i

  • Island

  • Foodie

  • High-end

Palm trees on the beach view in Hawaii
Curator’s statement

Embark on a remarkable 10-day Hawai'i itinerary through the captivating islands of Oahu, Maui and Kauai, indulging in luxurious accommodations, savoring exquisite dining experiences and immersing yourself in the natural wonders of Hawai'i. Based on my past trips to Hawai'i, I built this 10-day itinerary to include prestigious hotels and highlights of the exceptional fine dining restaurants for a truly unforgettable Hawaiian getaway. Immerse yourself in luxury, tantalize your taste buds with exceptional dining and discover the natural beauty of Hawai'i's islands.

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Day 1-3: Oahu Oasis

A beautiful beach with people in Oahu, Hawaii.

Arrive in Honolulu on Oahu and settle into the luxurious Halekulani Hotel in Waikiki. Delight in a culinary experience at the renowned La Mer, Hawaii’s only AAA Five Diamond and Forbes 5 Star restaurant. Roy’s Waikiki is also a classic not to be missed!

In Honolulu, immerse yourself in the rich history and culture of Hawai'i by visiting the iconic Pearl Harbor and exploring the fascinating exhibits at the Bishop Museum. Soak in the multicultural side of Honolulu by taking a stroll through the vibrant neighborhood of Chinatown. Unwind on the sun-soaked shores of Waikiki Beach and witness the mesmerizing sunset views from Diamond Head.

Day 4-6: Maui Majesty

An aerial view over Maui, Napili Bay.

Fly to Maui and check into the exclusive Grand Wailea, A Waldorf Astoria Resort. Indulge in fine dining at Morimoto Maui, known for its exquisite Japanese fusion cuisine. For a more casual option, check out Monkey Pod (their happy hour is legendary!) Dedicate a day to taking a private tour to explore the enchanting Road to Hana. It’s also worth getting up early to witness the sunrise from atop Haleakala (again, a private tour is recommended.) Be sure to take time each day to walk along Wailea Beach.

Day 7-10: Kauai Paradise

Rocky hills during the day time.

Head to the idyllic island of Kauai and experience the grandeur of the Grand Hyatt Kauai Resort & Spa. Savor a memorable dining experience at Tidepools, offering delectable Pacific Rim cuisine amidst a romantic ambiance. Outdoor activities reign supreme on Kauai. Embrace the island's natural beauty by embarking on thrilling adventures like hiking the dramatic Na Pali Coast, kayaking along the Wailua River to reach the enchanting Secret Falls, and exploring the picturesque landscapes of Waimea Canyon. This is your best opportunity for a scenic helicopter tour. Take time to unwind on the breathtaking beaches of Kauai, especially nearby Poipu Beach.

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Advisor - Sarah Keim

Travel Advisor

Sarah Keim

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Looking for more travel inspiration? Check out my guide, Experience Award-Winning Female Chefs of Europe.

This guide is part of our ongoing series on travel to Hawaii.