Experience the very best of the Aloha State on this unforgettable two-island adventure through Oahu and Maui. Begin your journey in vibrant Waikiki, where golden beaches, rich history, and Hawaiian hospitality set the tone for your stay. Then it's off to beautiful Maui, where the island’s natural splendor unfolds. With cultural experiences, breathtaking landscapes, free time to enjoy resort amenities, and thoughtful touches throughout, this tour offers the perfect blend of exploration and leisure. From captivating traditions to stunning vistas, this is Hawaii at its most welcoming and memorable.

Depart Portland (or your home base - we are happy to help with airfare from your home city) this morning and arrive in tropical paradise by mid-afternoon. Once we’ve landed, we’ll transfer to our oceanfront accommodations at the Outrigger Waikiki Beach Resort, ideally located along bustling Kalakaua Avenue.

Oceanfront accommodations at the Outrigger Waikiki Beach Resort, ideally located along bustling Kalakaua Avenue.

After settling in, we’ll enjoy a relaxing dinner just a short walk from the hotel as we begin our Hawaiian adventure.

After breakfast, take the morning to unwind, explore Waikiki Beach, or browse nearby shops.

In the afternoon, depart for the famed Polynesian Cultural Center. Along the scenic coastal route, stop for photos at Chinaman’s Hat. Upon arrival, enjoy time to explore six immersive island villages before a buffet dinner and the award-winning “HA: Breath of Life” evening show.

Enjoy a buffet dinner at the Polynesian Cultural Center before the evening show.

Return to the hotel after this unforgettable cultural evening.

Today we take a powerful and inspiring journey through history with Passport to Pearl Harbor admission, offering access to multiple sites within the Pearl Harbor Historic Sites.

We’ll begin with a visit to the USS Arizona Memorial.

Explore the exhibits at the Pearl Harbor Aviation Museum, where you can get an up-close look at historic aircraft and wartime relics.

Lunch will be on your own at the museum’s Hangar Café, a casual spot located right inside one of the original WWII hangars.

In the afternoon, we’ll enjoy a scenic drive through Punchbowl Crater.

Visit the regal ʻIolani Palace.

Stop for photos at the King Kamehameha Statue.

Return to Waikiki by late afternoon with the evening free to relax and explore.

After breakfast, we’ll board a short interisland flight to Maui.

Upon arrival, we’ll enjoy lunch at Café O’Lei before checking in to our oceanfront resort on Ka’anapali Beach.

Check in to our oceanfront resort on Ka’anapali Beach.

This afternoon, you may choose to join an optional Mo‘olelo storytelling session at the hotel.

This evening, we’ll enjoy dinner together at The Cliff Dive restaurant nearby.

Today we set out on one of Hawaii’s most iconic journeys—the legendary Road to Hana. Accompanied by a knowledgeable local guide, we’ll travel this breathtaking route through lush rainforests, past cascading waterfalls, dramatic seascapes, and hidden beaches. Along the way, we’ll stop at scenic overlooks and points of interest while learning about the island’s culture, legends, and natural wonders.

In Hana, enjoy lunch on your own at local food trucks offering authentic island fare.

We’ll begin our return journey in the early afternoon, arriving back at the resort with time to relax and refresh before enjoying dinner near the hotel.

Enjoy a peaceful morning at your own pace—stroll along Ka’anapali Beach, relax by the pool, or explore the shops and cafes nearby.

In the afternoon, journey to the summit of Haleakalā National Park, home to one of the most extraordinary volcanic landscapes on earth. Witness sunset from the summit as the crater glows with surreal colors and the clouds below turn brilliant shades of gold and pink—a truly unforgettable sight.

After sunset, enjoy a warm and cozy dinner at the charming Kula Lodge, nestled on the slopes of the mountain, before returning to the hotel for the night.

Today is yours to enjoy! Lounge poolside, walk the beach, or take advantage of the resort’s many amenities.

In the evening, we’ll gather for a traditional Hawaiian Luau at the Sheraton, complete with Polynesian music, dancing, and a delicious island feast—an ideal way to wrap up our time in paradise.

Our final morning begins with breakfast and a special Kukuli Lei Ceremony as we say aloha to the islands.

We’ll depart for the airport late morning and begin our journey home, arriving in Portland in the evening. Thank you for joining us on this unforgettable Hawaiian adventure!