The first time I stepped onto Oahu, I was hit with that sweet mix of salty breeze and plumeria-scented air. From the buzzing energy of Waikiki to the peaceful beaches of the North Shore, Oahu felt like multiple worlds stitched into one. Over five days, I tried to soak in as much as possible: sunrise hikes, shave ice breaks, and plenty of swims in turquoise water.
If you’re planning a trip to Oahu and want a mix of adventure, culture, and downtime, here’s how I structured my 5-day itinerary based on my personal favorites. For even more ideas, check out my Ultimate Oahu Travel Guide and Best Things to Do in Oahu.
Quick Overview: 5 Days in Oahu
- Day 1: Waikiki + Diamond Head + Waikiki Beach Sunset
- Day 2: East Oahu Road Trip (Makapu‘u, Lanikai, Byodo-In Temple)
- Day 3: North Shore Adventure (Snorkeling + Haleiwa Town)
- Day 4: Pearl Harbor + Cultural Sites + Luau Night
- Day 5: Hike + Ko Olina Lagoons + Departure
Before You Go: Oahu Travel Tips
When to Visit
Oahu is great year-round, but April to June and September to mid-December offer pleasant weather with fewer crowds.
Getting Around
You can explore parts of Oahu with tours or TheBus, but I recommend renting a car for full flexibility, especially if you’re heading to the North Shore or East Coast.
Where to Stay
- Waikiki (Honolulu) – Best for first-timers, nightlife, and central access to most sights $$
- North Shore – Peaceful, remote, and surfy vibes $$
- Ko Olina – Resort-style comfort and lagoon beaches $$$
If it’s your first visit, Waikiki is a convenient base for the full 5 days. You can also read my 2-Day Honolulu Itinerary and Things to Do in Honolulu for more urban ideas.
Day 1: Arriving in Waikiki + Diamond Head Crater Hike
After landing at Daniel K. Inouye International Airport (HNL), I picked up my rental car and headed straight for Waikiki. The drive into Honolulu offered quick views of the city skyline and shimmering blue water and as soon as I checked into my hotel near Kuhio Avenue, I dropped my bags and walked barefoot to the beach. Nothing says “Welcome to Oahu” like a dip in warm water and a mai tai with a view of Diamond Head.
Morning
- Check into your hotel: I recommend staying close to Kuhio Avenue for walkability to restaurants, shops, and the beach.
- Brunch at Heavenly Island Lifestyle or Goofy Cafe: Both use local ingredients and offer a laid-back island vibe. Their acai bowls and fresh papaya plates are perfect after a red-eye flight.
- Optional: If you’re arriving early, walk down to Waikiki Beach and stretch your legs. It’s an ideal place to reset after the flight.
Midday
- Diamond Head Crater Hike: This popular trail is just a 10-minute drive from Waikiki. The 1.6-mile roundtrip hike offers stunning views of the coastline. Go early to beat the heat and crowds, and bring water, a hat, and reef-safe sunscreen.
- Lunch at Rainbow Drive-In: A local institution famous for its plate lunches. Try the loco moco or BBQ pork. Casual, nostalgic, and satisfying.
Afternoon
- Cool down at Kuhio Beach or grab a shaded bench under a banyan tree near the Moana Surfrider Hotel.
- Optional: Walk through the International Market Place if you need last-minute beachwear or sunscreen.
Evening
- Stroll along Kalakaua Avenue: This vibrant strip is full of energy, live music, and tiki torch-lit palm trees. I loved people-watching and grabbing snacks from ABC Stores.
- Catch a Waikiki beach sunset: Head to Queen’s Surf Beach or just outside the Duke Kahanamoku statue for an unforgettable first evening.
- Dinner at Marukame Udon or Tommy Bahama Rooftop Bar: Marukame is fast, affordable, and popular perfect if you’re hungry after the hike. For something upscale with sunset views, Tommy Bahama’s offers rooftop dining and tropical cocktails.
Related post: Best Beaches in Honolulu
Day 2: Windward Coast + Lanikai Beach
This day was all about coastal drives and scenic stops on Oahu’s lush east side. Compared to the busier city vibes of Waikiki, this part of the island feels slower, greener, and more tropical. Think dramatic cliffs, postcard beaches, and peaceful gardens.
Morning
- Makapu‘u Lookout & Lighthouse Trail: Start early to beat the sun and crowds. This paved 2-mile roundtrip hike rewards you with sweeping views of the coastline and, in winter, possible humpback whale sightings. Bring a camera the contrast of blue ocean and black lava cliffs is incredible.
- Halona Blowhole & Eternity Beach: Just a short drive north, this scenic stop lets you watch waves shoot through a lava tube while Eternity Beach (to the right of the lookout) is a hidden cove popular with locals. Be careful if you decide to climb down surf can be rough.
Midday
- Hanauma Bay Nature Preserve (closed Tuesdays): This protected bay is ideal for snorkeling with sea turtles and colorful fish. Reservations are required, so book in advance. If you’ve already done it, skip to…
- Lanikai Beach: My favorite beach in Oahu clear turquoise water, soft white sand, and the iconic twin Mokulua Islands offshore. Parking can be tricky, so go early or park in Kailua and walk over.
- Lunch in Kailua: I recommend Over Easy for savory dishes or Cinnamon’s for macadamia nut pancakes. This town is laid-back and has cute boutiques, too.
Afternoon
- Byodo-In Temple: Nestled in the Valley of the Temples, this replica of a Japanese Buddhist temple is incredibly serene. Ring the peace bell, feed the koi, and just breathe for a moment.
- Ho‘omaluhia Botanical Garden (optional but worth it): Known for its dramatic backdrop and Instagram-worthy entrance road, this free garden has hiking paths, picnic spots, and lush tropical scenery. It’s a peaceful place to slow down.
Evening
- Dinner in Kailua or return to Waikiki: If you stay on the east side, check out Buzz’s Original Steakhouse near Kailua Beach Park for casual island fare.
- Shave Ice at Island Snow: President Obama’s favorite! Try the li hing mui flavor or mix it up with a scoop of ice cream on the bottom.
If you’re up for the drive, catching the twilight view over Pali Highway on your way back to Honolulu is a great way to close out the day.
Day 3: North Shore Day Trip
North Shore was a highlight of my trip. The surf, the shrimp trucks, the laid-back pace, and the friendly, artsy vibe of Haleiwa Town I loved every bit. It’s the perfect escape from the bustle of Waikiki and a chance to experience a different, more rugged side of Oahu.
Morning
- Drive up via H-2 and stop at Green World Coffee Farm: Start your day with a local-style coffee tasting. This charming spot near Wahiawa is a great place to grab caffeine for the road and maybe pick up a few edible souvenirs.
- Quick detour to Dole Plantation: While a bit touristy, it’s still worth a short visit for the pineapple soft serve (Dole Whip), a stroll through the gardens, or a ride on the Pineapple Express train.
- Arrive at Waimea Bay or Shark’s Cove: Waimea Bay is great for swimming in the summer and wave-watching in the winter. Shark’s Cove, just north, is a snorkeler’s dream with lava rock tide pools and clear water full of marine life. Bring reef-safe sunscreen and water shoes!
Midday
- Lunch at Giovanni’s Shrimp Truck: You’ll likely smell it before you see it. The garlic shrimp plate is legendary, but if the line is long, try other nearby food trucks like Fumi’s or Big Wave.
- Stroll through Haleiwa Town: This artsy surf town is filled with boutiques, galleries, and colorful murals. I enjoyed browsing the handmade soaps at North Shore Soap Factory and picking up a few postcards.
- Cool off with Matsumoto Shave Ice: Yes, it’s touristy but the rainbow shave ice with condensed milk drizzle is worth the hype. Try it with ice cream on the bottom.
Afternoon
- Watch surfers at Banzai Pipeline: Especially in winter, the waves here are massive and awe-inspiring. Even if you’re not a surfer, it’s amazing to watch the pros ride these giants.
- Swim or relax at Sunset Beach: If the surf is too high to swim, just chill on the soft sand. It’s one of the best spots to unwind with a good book.
- Optional hike to Ehukai Pillbox: This short uphill trail offers sweeping views of the coastline. Go late in the afternoon for a magical golden-hour view.
Evening
- Dinner back in Waikiki or extend your North Shore adventure and dine at Haleiwa Joe’s (the one in Haleiwa, not Kaneohe). Try the prime rib or the fresh catch with a mai tai.
If you’re staying nearby or want to explore more, consider adding a stop at Laniakea Beach to spot sea turtles, or head toward Waianae for even quieter beaches.
Related post: Best Beaches in Oahu
Day 4: Culture, History & Luau
Time to dive into Oahu’s deep cultural roots. This day balances powerful WWII history, Hawaiian royalty, traditional art, and one of the island’s most beloved traditions a luau under the stars.
Morning
- Pearl Harbor & USS Arizona Memorial (book ahead): Begin your day with a visit to one of the most emotional sites in Hawaii. The memorial floats above the sunken USS Arizona and honors the lives lost in the 1941 attack. Entry is free, but timed reservations are required book in advance at recreation.gov. Plan to spend 1.5 to 2 hours here, and consider visiting the Pearl Harbor Aviation Museum or Battleship Missouri for extra depth.
- Iolani Palace & King Kamehameha Statue: Head back into downtown Honolulu to visit Iolani Palace the only royal palace in the U.S. It’s beautifully restored and offers insight into Hawaii’s monarchy and overthrow. Just across the street, snap a photo with the iconic gold-leaf statue of King Kamehameha I.
Midday
- Lunch at Highway Inn or Aloha Table: For an authentic Hawaiian plate lunch, Highway Inn is my go-to kalua pork, laulau, poi, and lomi salmon. If you’re near Waikiki, Aloha Table is a great alternative with Hawaiian-Japanese fusion dishes and island cocktails.
- Explore Bishop Museum or Honolulu Museum of Art: The Bishop Museum is perfect for cultural context, with interactive exhibits on Hawaiian history, Polynesian voyaging, and native traditions. Art lovers might prefer the Honolulu Museum of Art for its tranquil courtyards and diverse collections from Hawaiian painters to global masterpieces.
Evening
- Luau Night: Wrap up the day with an unforgettable luau. Paradise Cove in Ko Olina offers a picturesque oceanfront setting with cultural activities like lei-making and Hawaiian games before the feast begins. Or check out Chief’s Luau, which is high-energy and known for its storytelling, fire knife dancing, and audience participation.
- What to Expect: Most luaus include an all-you-can-eat buffet of traditional dishes like kalua pig, poke, and haupia (coconut pudding), plus unlimited mai tais or fruit punch. Dress comfortably and bring a light jacket it can get breezy after dark.
Related post: 1-Day Honolulu Itinerary
Day 5: Hike + Ko Olina Lagoons + Departure
On your last day, keep it light and relaxing before your flight. This is the perfect time to slow down, reflect on your trip, and enjoy one last swim or scenic drive across the island.
Morning
- Hike Manoa Falls: This lush, shaded trail is a gentle 1.6-mile roundtrip hike through rainforest. The waterfall itself is about 150 feet tall and especially pretty after recent rain. Go early to avoid crowds and muddy paths. If you love waterfalls checkout my guide on the best waterfalls in Oahu.
- Or Makiki Valley Trail: If you’ve already done Manoa Falls or want something less touristy, Makiki offers a quiet, forested loop with birdsong and bamboo groves. Great for travelers who love secluded nature walks.
- Leonard’s Bakery: Before heading west, swing by Leonard’s for their iconic Portuguese-style malasadas pillowy, fried dough rolled in sugar with optional fillings like haupia (coconut) or custard. Get a few for the road!
Midday
- Ko Olina Lagoons: These man-made coves are ideal for relaxing, especially if you’re traveling with kids or want gentle water. The lagoons are public, but parking can be limited, so arrive before noon. Bring a towel, floaties, and a snack if you’re not dining nearby.
- Lunch at Monkeypod Kitchen: One of my favorite places in Ko Olina. Their farm-to-table menu features fresh fish tacos, wood-fired pizzas, and craft cocktails. Try the lilikoi foam mai tai for a memorable farewell drink.
- Optional: Short detour to Waianae: If you’re not rushed, drive 20 minutes north along the Leeward Coast for fewer crowds, wild beaches, and dramatic mountain views. Pokai Bay is great for swimming, and the pillbox trail near Maili offers a quick workout with a view.
Evening
- Return drive to Honolulu Airport (HNL): Give yourself plenty of buffer time traffic can be unpredictable, especially around Kapolei and H-1 during the late afternoon.
- If you have extra time before your flight, you can stop at Ala Moana Center for last-minute shopping or a meal.
Pro tip: Keep your swimwear and toiletries handy in your carry-on so you can freshen up before boarding.
Packing Tips for Oahu
- Reef-safe sunscreen (required by law)
- Water shoes for lava rock areas
- Lightweight rain jacket
- Snorkel gear (or rent locally)
- Portable phone charger
Final Thoughts
Oahu surprised me. I expected beaches and luaus but didn’t anticipate how deeply I’d connect with the island’s rhythm. If you only have five days, this itinerary gives you a taste of everything: city life, surf towns, sacred history, and quiet moments under swaying palms.
Got more time? Check out my 3-Day, 4-Day, 6-Day, or 7-Day Oahu Itinerary too!
Happy travels,
Zee
