The Best Oahu Itinerary for a 5-Day Vacation
For such a small island, Oahu boasts endless adventure. Experience the meaning of “Aloha” while basking in the sun’s rays and surrounded by crystal blue Pacific waters. Planning the perfect trip to your dream destination can be overwhelming. We’ve designed the perfect 5-day Oahu itinerary that allows you to enjoy the best the island has to offer. Between volcanic exploration and deep-sea snorkeling, enjoy sweeping views. Life is too short not to follow your dreams. It’s time to take that leap!
Our 5-day Oahu itinerary serves as a great starting place when planning your trip. For more details and suggestions, download our complimentary vacation guide!
Your Go-To 5-Day Oahu Itinerary
Day 1: Hike Diamond Head Trail and Explore Honolulu
With so many things to do in Oahu, be sure to fuel up with a hearty breakfast. Hikers from around the globe gather on the island to experience Diamond Head, one of the most beautiful natural wonders the planet has to offer. Sweeping, panoramic views span the blue horizon and the colorful city below.
Stop through Honolulu for a light and refreshing lunch at Uncle Clay’s House of Pure Aloha. While in the city, check a few things off your list. Visit the Pearl Harbor and WWII Monument or visit the National Memorial Cemetery of the Pacific. Before heading back to your Private Homes of Hawaii vacation rental, have dinner in the city and try a tasty poke bowl.
Day 2: Kayak, Snorkel, and Catch the Sunset
Make kayaking and snorkeling your next big Oahu excursions. Take a tour that requires paddling through the waves in a kayak. The Hanauma Bay Nature Preserve welcomes you to explore coral reefs and diverse marine wildlife. Expect to see sea turtles, colorful fish, and a vibrant underwater ecosystem. After a few hours of snorkeling, grab a quick bite at a nearby cafe.
Spend a few hours lounging on the beach and then head west towards to Kaena Point. The sunsets from the most western point of the island inspire and make for an amazing photo op. You’ll remember this moment for the rest of your life. Vibrant reds and pinks paint the sky above lava shorelines and tidepools. After the sun sets and the moon rises, indulge in a little Honolulu nightlife. Make reservations ahead of time at a Japanese restaurant like Nanzan Giro Giro or an Asian-Hawaiian fusion establishment like Alan Wong’s Restaurant for a taste of Hawaii’s fine-dining scene.
Day 3: Chase Waterfalls and Indulge in Authentic Cuisines
No Hawaii vacation is complete without discovering the best waterfall hikes on Oahu. Hike through lush Hawaiian jungles and encounter towering trees and rushing waterfalls. For large groups and families, consider hiking the Maunawili Falls trail or check out the popular Manoa Falls. If you’re up to the challenge of a more strenuous hike, the Lulumahu Falls appeal to your adventurous side. Explore bamboo forests and come face-to-face with a 50-ft waterfall.
After exerting so much energy in the hot sun, take the time to unwind a little. Dine in luxury, sip fine wine, and soak in gorgeous ocean views. Choose between some of the best restaurants on Oahu. From Vietnamese noodles dishes and vegan pho to Japanese-Peruvian cuisine and authentic Hawaiian food, the dining options leave nothing to be desired.
Day 4: Relax, Meditate, and Soak Up the Sun
Your body needs some tender love and care as you near the end of your vacation. Start your day with a relaxing massage or facial at a highly-acclaimed spa. Once you’re feeling renewed, embark on a journey to the Byodo-In Temple in the Sacred Valley of the Temples. Admire the beauty and surround yourself with a sense of calm in this meditative setting.
Absorb the healing qualities of the salty ocean and humid air. Allow yourself plenty of time to kick back on one of Oahu’s best beaches. You don’t want to miss the opportunity to visit the most popular beach in the world. Waikiki once served as a playground for Hawaiian royalty and, thanks to Duke Kahanamoku, became the birthplace of modern surfing. Listen to the sound of the tide roaring in, feel the sun’s warmth on your skin, take a surfing lesson, and savor each moment you have left on the island.
Day 5: Celebrate Hawaiian Culture
Dive into Hawaiian culture by attending an Oahu annual event. Enjoy an exciting hula show, explore local artwork, or take part in some of the major food festivals. You can also visit the Honolulu Art Museum or the Polynesian Cultural Center to learn even more about Hawaii.
Wrap up your vacation by spending your last evening in nature. Check out Sunset Beach, Haleiwa Beach Park or Waimea Bay and appreciate the natural beauty of the island. By this point, you may already have a return trip in mind.
Make One of Our Vacation Homes Your Hawaii Home
Our 5-day Oahu itinerary leaves room for flexibility and adaptation depending on your lifestyle preferences. However you choose to spend your time on the island, be sure to spend your nights in a high-quality home. Our vacation rentals boast comfort, quality, and stunning tropical views.
Our Niuiki property provides a soothing environment to rest your head between big adventures. Located halfway between Kahala and Hawaii Kai, this location is ideal for those who wish to see all Oahu has to offer.