Unforgettable Luxury Getaway on the Hawaiian Island of Oahu

The Hawaiian island of Oahu is a vacation paradise, with over 110 miles of coastline, warm sand beaches, delicious food, and the perfect mix of stunning tropical landscape and big city amenities.

It’s the third largest (and also the most populated) of Hawaii’s islands, and is divided into five regions, each with its own culture and vibe: the western Leeward Coast with rural towns and remote beaches; the serene Windward Coast, recognizable from the many TV shows and movies such as Jurassic Park and Lost that were filmed there; Central Oahu, a fertile valley region that’s home to the Pearl Harbor Memorial and the Dole Plantation; the bustling capital city of Honolulu along the southern shore; and the famous North Shore region, known as the big wave surfing capital of the world.

For this trip, you’ll have the opportunity to explore the history, culture, and natural beauty of the island from two locations. First, you’ll spend three nights in Honolulu’s Waikiki neighborhood, where you’ll be close to world-class, high-end  shops and restaurants as well as the golden sands of beautiful Waikiki Beach. Then you’ll spend two nights on the popular North Shore, with its own incredible beaches, laid-back surf towns, and rich island heritage rooted in tradition and the Hawaiian concept of Aloha ʻāina—love and care of the land.

In both Waikiki and North Shore, you’ll have deluxe accommodations at two of Oahu’s top luxury beach resorts, with spacious guest rooms, premium in-room and resort amenities, family-friendly services and activities, onsite dining, and warm Hawaiian hospitality, all steps away from the sand and surf.

You’ll also enjoy a buffet of planned excursions that we’ve arranged to make your vacation extra special and highlight the best of Oahu.

The first is a full-day private tour of Pearl Harbor, complete with transportation, an experienced guide, and admission to the memorial sites. Travel to Central Oahu and take a step back in time as you view films and exhibits at the visitor center, take a short boat ride on a Navy vessel to see the USS Arizona Memorial, and tour the USS Missouri on Ford Island, learning more about Pearl Harbor’s history and legacy.

The next day, you’ll head down to Waikiki Beach for a private surf lesson for two. With a friendly, experienced instructor and all gear provided, you’ll spend about two hours learning the basics on land and in the water, paddling out and riding gentle surf back to shore while soaking up the sun.

For your third adventure, you’ll immerse yourself in the unique and tasty cuisine of Oahu, with a private food tour curated by Emmy Award winner, Lanai Tabura. This three-hour outing will take you on a journey through some of Hawaii’s most popular and authentic dishes at some of Oahu’s best-loved restaurants and food trucks. Transportation, lunch, and other eats are included, and it’s an excellent way to discover and taste the real flavors of the islands with a fun and experienced guide.

On the North Shore, we’ve arranged for you to visit the Honu turtles on Laniakea Beach and take a one-hour tour with a volunteer docent. Learn more about these amazing sea turtles and their place in Hawaiian culture, see them up close on the beach, and find out what’s being done to protect them and their habitat. 

Finally, you’ll head over to the stunning Waimea Valley to end the day with a traditional luau. Your VIP package includes a flower lei, cultural activities, a cooking demonstration, special seating area, and a fantastic luau feast and Polynesian show. While at Waimea, you’ll also have admission to the lush onsite tropical botanical garden and the famed Waimea Falls, where you can jump into the water for a swim if you’d like. 

In between the incredible planned activities, you’ll have plenty of free time to enjoy Oahu on your own. Explore the shops, restaurants, and open-air Grand Lanai of Waikiki’s International Market Place. Rent a bike and ride along the shore. Visit Diamond Head State Monument. Hike the trails at Turtle Bay. Watch the surfers at the famed Banzai Pipeline. Swim with sharks. Or spend a leisurely afternoon in the small town of Haleiwa. 

When you need to rest and recharge, you can lounge by the hotel pool or on the beach, grab an island cocktail or Hawaiian shave ice, and watch the sky turn amazing shades of yellow and orange as the sun goes down at lovely Sunset Beach.

After your stay on Oahu, you can choose to fly home or combine this trip with one of our other Hawaiian island getaways for an extended—and truly unforgettable—vacation experience.