Island Dreams Unveiled: A Look at Hawaii from Oahu to Kauai

The rhythmic dance of hula, the serenity of sunsets painting the Pacific, and the adventurous spirit of exploring beautiful beaches and volcanic gems make every moment a celebration of Hawaii's boundless allure.
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Aloha and welcome to the ultimate Hawaiian adventure! This carefully designed itinerary invites you to surrender to the enchanting embrace of the Aloha State’s most iconic destinations. From the vibrant energy of Oahu’s bustling streets and the allure of Waikiki Beach to the pristine shores of Maui, the ethereal beauty of Haleakala and Molokini Craters, and the untamed magnificence of Kauai’s Nāpali Coast, each island presents a unique chapter in Hawaii’s narrative of paradise.

Sway to the rhythm of the islands, where lush landscapes, vibrant traditions, and the spirit of aloha converge to create breathtaking memories.

Hawaii, Oahu Beach
Explore Oahu’s remarkable beaches.

Day 1:  Arrive on Oahu

Join us in Ko Olina and find your very own place of joy.

Check-in at Four Seasons Resort at Ko Olina

Four Seasons Resort at Ko Olina is a beachfront island resort that sits on Oahu’s wild and rugged western coast, where vast ocean views and lively pools and lagoons provide the setting for an unforgettable adventure.

Take the family for a ride on an outrigger canoe, splash around in the turquoise waters of our white-sand beach, play a round of golf as you weave through waterfalls at Ko Olina Golf Club, or spend the day reconnecting with your inner self at Naupaka Spa & Wellness Centre. Whatever the perfect vacation looks like to you, the luxury Oahu Resort on the beach has it.

Day 2:  Explore the North Shore

Grab a quick and light breakfast in or around the hotel. Hit the road and head to the other side of the island. Take your time and explore the laid-back North Shore. This could include Haleiwa (great little shops), one of the many beaches to watch surfers, see the turtles, or catch the sunset (Banzai Pipeline, “Turtle Beach” and Sunset Beach).   At lunch, take a break – shrimp truck and shaved ice! If time allows, check out the Polynesian Cultural Center – a favorite of many.

Return to your hotel and hit the beach or pool. End the night with dinner and live music or other entertainment.

Day 3:  Pearl Harbor

The morning and early afternoon will be spent at Pearl Harbor. Try to get there as early as possible – afternoons can get VERY crowded.  If you are taking an organized tour (ensure it includes the USS Arizona), follow the instructions on where to meet and enjoy!

If you are traveling there by car, leave ample time for the drive and traffic in order to secure tickets to the Arizona Battleship Memorial. You’ll likely be there until around lunch. Return to your hotel, grab some food, and spend some time on the beach or at the pool before heading out on a luau tonight.

Hawaii, Pearl Harbor
“Remember Pearl Harbor!” — The United States’ battle cry in 1941

Authentic Hawaiian Luau

Your Hawaiian Luau will begin with a tropical Mai Tai greeting and traditional Hawaiian music to set the festive mood of the evening. Casually stroll through the Hawaiian Village and learn the arts and crafts of the islands or test your skills at our Hawaiian Games.

Go for a canoe ride in the Cove (no swimming allowed!). Witness the time-honored techniques of underground oven cooking at the Imu Ceremony.

The evening will continue with a feast in the company of friends, old and new. Bring your appetite to fully enjoy Paradise Cove’s extensive menu which tastefully blends the best of traditional Hawaiian dishes, local favorites, and continental cuisine.

With the most spectacular Hawaiian sunset as a backdrop, award-winning performers will entertain and amaze you with an unforgettable display of songs and dances of Hawaii and Polynesian culture at the incomparable Paradise Cove Extravaganza.

Day 4:  Explore Waikiki Beach

After a morning by the pool or beach cove, spend the rest of the day exploring Waikiki Beach. Kalakaua Avenue is the main road that runs along the famous Waikiki Beach. Luxury shops such as Gucci, Louis Vuitton, and Hermes are lined down the street. Woven in between are authentic Hawaiian shops featuring unique items.  Grab dinner, drinks, and live music at one of the beach’s hotels to end the night!

Day 5:  Onward to Maui

You will have a grab-and-go breakfast before heading to the airport. Ensure you leave enough time to account for the drive, rental return, and check-in. Relax and enjoy your quick island-hopper flight to Maui (OGG).

Check into the hotel and spend the rest of the day getting settled and at the beach! If you’re feeling up for it, head to Lahaina in the evening – enjoy the local shops, galleries, bars, and restaurants, where you’ll grab dinner.

Check-in at The Ritz-Carlton Maui, Kapalua

Get ready for a true Hawaiian luxury resort experience at The Ritz-Carlton Maui, Kapalua. Cultural and environmental appreciation combined with world-class amenities and facilities delivers a true escape. From beachfront dining to Hawaiian spa treatments, luxury poolside cabanas, and cultural and recreational activities, this Kapalua, Maui resort is a memorable island oasis.

Nestled on 54 acres, The Ritz-Carlton Maui, Kapalua showcases 466 guestrooms, including 107 residential suites, dark wood floors, and Hawaiian-inspired artwork. The Spa beckons with treatment rooms framed by private garden showers, volcanic stone grottos, and a fitness center with ocean views.

Jean-Michel Cousteau’s Ambassadors of the Environment offers all levels of activities from land to sea. Also featured are six dining experiences, an indoor/outdoor meeting space, and a lush organic garden. It is enveloped by picturesque Kapalua Resort’s two championship golf courses, dining, and a century-old pineapple plantation.

The Ritz-Carlton Maui, Kapalua
A world of luxurious relaxation is waiting for you at The Ritz-Carlton Maui, Kapalua.

Day 6:  Road to Hana with Haleakala

Today, you have options, and it’ll be an early day. So grab breakfast quickly! The Road to Hana must be explored early.

Your private guide will take you on an eight to twelve-hour adventure, incorporating stops at the many waterfalls and beaches. Your expert guide will take you around Maui’s eastern volcano to see breathtaking ocean and mountain views. Hana Highway features over 600 coastal turns and nearly 60 bridges, most are only one lane. As you come around the eastern side of the island you will be able to marvel at the amazing Haleakala Crater, Maui’s active Volcano.

Spend the evening in or around the hotel where you can grab dinner and drinks and relax from your adventurous day.

Day 7:  Leisure Day at the Resort

Today is your day to indulge in spa treatments and relax on the beautiful beach or pool. It is highly recommended to have a Hawaiian Lomi Lomi massage. Based on the Hawaiian concepts of working with the body, mind, and spirit, this therapeutic treatment is powerful, yet gentle, using light to moderate pressure. Massage techniques are adapted to your needs to help increase circulation, relieve muscular tension, and smooth away stress.  If desired, transform this into a couples massage.

Day 8:  Snorkeling at Molokini Crater

Climb aboard your private boat for a trip to Molokini Crater for some of Maui’s best snorkeling. There is a Certified Marine Naturalist aboard who facilitates a “Fish Class” if you are interested. Swim among colorful fish, and majestic sea turtles and possibly encounter a dolphin…or two.

Day 9:  Head to Kaui

It will be another grab-and-go breakfast before heading to the airport. Ensure you leave enough time to account for the drive and check-in. Relax and enjoy your quick island-hopper flight to Kauai (LIH).

Check into your hotel and spend the rest of the day getting settled and at the beach! If you’re feeling up for it, explore the local area.

Check-in at 1 Hotel Hanalei Bay

If you like modern decor and contemporary accommodations, 1 Hotel Hanalei Bay is the most spot-on place to stay in Kauai. Its design is completely unique compared to any other hotel on the island. Despite being ultra-luxurious, 1 Hotel Hanalei Bay also revolves around sustainability and carbon neutrality. A stay here promises world-class wellness, and guests have access to incredible fitness programming and cutting-edge spa treatments. The ultimate bonus? 1 Hotel is one of the only resorts on Kauai that doesn’t charge extra resort or parking fees!

There are two on-site restaurants at 1 Hotel Hanalei Bay focusing on farm-to-table cuisine. One of them is the seafood-focused Kauai Grill and the other is Makana Terrace, which serves classic Hawaiian fare. On the property, you’ll also find a serene spa, a picturesque golf course, direct beach access, a premier swimming pool with a swim-up bar, and even access to the hotel’s fully electric Audi e-tron.

Hawaii, Nāpali Coast Aerial View
The Nāpali Coast has an absolutely stunning view from the top.

Day 10:  Kauai Helicopter Tour

Kauai is a natural masterpiece. For over six million years, the powers of nature have been sculpting and reshaping Kauai, creating some of the most beautiful scenery in the world. Appropriately named the “Garden Isle,” the island of Kauai is draped in lush green valleys, towering sea cliffs, thick jungle vegetation, winding rivers, and gorgeous cascading waterfalls.

Without a road encircling the island, many of Kauai’s most stunning sights are inaccessible by land. Among these remote scenic attractions is the famous Nāpali Coast, spanning 17 miles along Kauai’s North Shore and boasting 3000 ft. sea cliffs and valleys. Then to the Southwest is the Waimea Canyon, coined the “Grand Canyon of the Pacific.” With so much to explore, a Kauai helicopter tour is truly the only way to experience all of Kauai’s most epic scenery.

Day 11:  Explore the Nāpali Coast by Power Catamaran

For a more intimate experience, you will explore the Nāpali Coast by a six-person power catamaran.  The tour guide passes their knowledge conversationally, and instead of being a face in the crowd, this tour feels more like hanging out on a boat with friends. Due to the smaller nature of the boat, it is able to fit into all of the various sea caves along Nāpali, with the added benefit of fewer passengers and more comfort.

Day 12:  Fly Home

If time allows, grab a leisurely sit-down breakfast in or around the hotel before heading to the airport. Remember to leave ample time to make it to the airport and check in.

As you venture back to your world, may the echoes of ukulele melodies, the scent of plumeria, and the warmth of Hawaiian smiles remind you of the paradise that became a part of you. Until the next time you return to these enchanted islands, may the spirit of Hawaii’s aloha accompany you on your journey.

Planning a trip? We can help!

Majestic Destinations Travel is a Connecticut-based boutique travel agency specializing in custom itineraries and personalized planning support. Get in touch to learn about how we can make your next vacation a stress-free success.

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