Escape to a world filled with cascading waterfalls, lush rainforests, and towering oceanside cliffs. A world where white sand and brilliant blue waters stretch as far as the eye can see. With our exclusive recommendations, your O’ahu vacation will feel custom-tailored to you. Experience delicious restaurants, explore natural wonders, and adventure beneath the surface of the deep with our O’ahu itinerary for a 5-day vacation.
Our team has carefully crafted an exceptional 5-day experience perfect for couples or families. From hikes to historic landmarks, this itinerary will help you experience the magic of our island.
In addition to our O’ahu 5-day itinerary, you can get more details and suggestions for your trip when you download our complimentary Vacation Guide!
Your 5-Day O’ahu Itinerary
Before you begin planning your dream 5-day itinerary in O’ahu, it’s important to think about how you’ll be getting around the island. When you arrive at the airport, there will be plenty of options for transportation that will fit your itinerary needs.
Check out our vacation guide for more help preparing for a stress-free getaway. Or figure out when is the best time to visit O’ahu by reading our blog post!
Day 1: Friday
Once you’ve enjoyed a delicious breakfast in your luxury Private Homes Hawaii vacation rental, it’s time to begin the day’s adventure! Head to Diamond Head State Monument for an incredible hike with one of the most rewarding views on O’ahu. Note – reservations are required for non-Hawai’i residents and can be acquired via the Hawai’i State Parks Department.
Diamond Head encompasses more than 475 acres and overlooks the eastern edge of Waikiki’s coastline. The hike to the summit is .8 miles, with a steady gain of 560 feet as you ascend. When you reach the summit, take a moment to enjoy sweeping views of downtown Honolulu and the expansive shoreline as it stretches from Koko Head to Wai’anae.
After your hike, you’re sure to have worked up an appetite. Head to family-owned South Shore Grill for the best fish tacos on the island. Or, if you skipped breakfast, you can make up for it with brunch at Bogart’s Café where fresh acai bowls, savory crab cakes, and fluffy pancakes await.
If you’re craving a sweet treat, the Diamond Head Grill bakery offers decadent cakes and pastries that are guaranteed to satisfy.
Round out your afternoon with a stroll through Waikiki as you visit local shops and search for your perfect souvenir. Finish the day with Friday night fireworks at South Shore’s Hilton Hawaiian Village Waikiki Beach Resort.
Day 2: Saturday
After breakfast and a warm cup of coffee on your expansive lanai, it’s time to pack a lunch and hit the road. For day two of your 5-day itinerary in O’ahu, we’re taking you off the beaten path to a landmark most are content to simply observe from the shore: The Mokes.
Hawaiian Watersports guided tour to The Mokulua Islands ensures you get the most out of your journey. Keep a look out for sea turtles and tropical fish as you paddle through the crystal-clear water. Explore tide pools on the island and snorkel off the shore of these protected nesting areas.
Enjoy your lunch on the shore as you watch for endangered shearwaters that nest on the smaller of the two islands.
After you return from The Mokulua Islands, spend the rest of the afternoon swimming in the shallow waters of Lanikai Beach as you soak in the sunshine and scenery. After you shower off the salt and sand, head to Buzz’s Steakhouse for delicious surf and turf dinner. Their lobster tail and fresh fish are second to none and are the perfect way to cap a day spent on the water.
Day 3 – Sunday
Snorkeling at Hanauma Bay is one of the ultimate activities for any O’ahu vacation, and that’s exactly what day three has in store. Make sure you have a reservation for this coveted location. To protect the delicate ecosystem, there is a cap of 1,400 people per day, and there are only 300 parking spots. Be sure to bring reef-safe sunscreen for this activity.
On your way to Hanauma Bay, grab breakfast at Island Brew Coffeehouse, where you can indulge in the richness of 100% Hawaiian coffee and espresso. After snorkeling, head to the Halona Blow Hole for incredible photo ops of the water splashing through the lava rocks. Finally, end the day with sunset views at the China Walls.
Day 4 – Monday
After three days of exciting outdoor adventures, we’re going to slow it down with a chance to smell the flowers at Little Plumeria Farms, where you’ll find the largest collection of rare hybrid plumerias in the world. Book a farm tour or a private tour to enhance your visit.
For lunch, enjoy a taste of classic O’ahu at Farm to Barn Café where fresh produce and island flavors combine for the perfect meal. Their Haleiwa location is located near Haleiwa Town’s colorful shops where you can explore architecture from the early 1900s. With myriad Hawaiian-made goods, it’s a haven of bespoke items waiting to be discovered.
End the day with a refreshing snow cone from Matsumoto Shave Ice as you watch the sun go down over sunset beach.
Day 5 – Tuesday
For the final day of your O’ahu 5-day itinerary, we’re visiting historical Pearl Harbor. This hallowed land receives more than 2 million visitors per year and is a true piece of American history. Reserve a time and take the 75-minute tour of the USS Arizona Memorial. Afterward, visit the USS Oklahoma Memorial, the USS Bowfin and Pacific Fleet Submarine Museum, and the Pearl Harbor Aviation Museum.
It’s easy to spend the entire day at Pearl Harbor, and you’ll want to make sure you don’t miss anything. So, take your time, and let this be the focus for your afternoon.
The perfect treat for your final night on O’ahu should be one of the island’s many luaus. Enjoy fantastical fire shows, traditional Hawaiian fare, hula performances, and more.
Book Your Hawaiian Vacation Directly with Private Homes Hawaii
Get rid of the jet lag and enjoy ultimate relaxation and comfort in a beautiful, luxury vacation rental on O’ahu. No matter how you choose to spend your time on the island, you can always look forward to being able to unwind, soak in a hot tub or private pool, and rest before another day of tropical adventures.
Our vacation rentals boast comfort, quality, and stunning tropical views. Each vacation home is conveniently located near the best attractions like Lanikai Beach, Kailua Beach, downtown Honolulu, Pearl Harbor, and more!
Our Niuiki property provides a soothing environment to rest your head between big adventures. Located halfway between Kahala and Hawai’i Kai, this location is ideal for those who wish to see all O’ahu has to offer. Check our availability and reserve this exquisite O’ahu vacation rental today!