Visiting Oahu for four days is just enough time to get swept up in the island’s laid-back magic, catch some of the prettiest sunsets, and discover a mix of adventure, history, and unforgettable food. I spent my days chasing views, jumping into warm ocean waves, and squeezing in as much local flavor as possible. If you’re dreaming about island time but don’t know where to start, here’s exactly how I’d plan a 4 day Oahu itinerary—with personal tips to make your trip smoother, tastier, and even a little bit more memorable.
Day 1: Waikiki Wonders & South Shore Highlights
Morning:
My first stop was Waikiki Beach, and honestly, it lived up to the hype. Early mornings here are calm, the water feels extra warm, and the view of Diamond Head in the distance is iconic. I rented a paddleboard for an hour and just drifted, soaking up the sun.
- Waikiki Beach – Get here early for quieter sands and great swimming.
- Kuhio Beach Hula Mound – If your trip lines up, check out the free hula shows some evenings.
Midday:
After a quick acai bowl at Island Vintage Coffee (my favorite in Waikiki), I headed to Diamond Head State Monument. The hike is about 1.6 miles round trip. It’s a steady climb, but the 360-degree views from the top are worth every step.
- Diamond Head Hike – Reserve a time online in advance, especially in peak season.
Afternoon:
Lunch was at Rainbow Drive-In (the loco moco is comfort food perfection), then I drove east along the coast, stopping at:
- Halona Blowhole Lookout – The natural geyser is cool, but I loved the little cove (Eternity Beach) tucked just below.
- Hanauma Bay Nature Preserve – If you love snorkeling, this is the spot! The coral reefs are beautiful and there’s plenty of colorful fish. Tip: Reservations required and it’s closed on Mondays & Tuesdays.
Evening:
Back in Waikiki, I ended the day with poke from Ono Seafood (super fresh) and a sunset walk along the beach. If you’re up for it, try a Mai Tai at Duke’s or House Without a Key—both have live music and sunset views.
Day 2: North Shore Road Trip & Local Eats
Morning:
I hit the road early, coffee in hand, heading up the windward coast toward the North Shore. The drive itself is part of the adventure—lush mountains, roadside fruit stands, and ocean views the whole way.
First stop: Laniakea Beach (“Turtle Beach”). If you’re lucky, you’ll spot green sea turtles sunbathing right on the sand.
Midday:
Next, I wandered through historic Haleiwa Town. This little surf town is full of charm—art galleries, food trucks, and boutiques. Don’t skip Matsumoto Shave Ice (the line moves fast and it’s worth it).
Lunch:
You’ll find some of the best shrimp plates on the island at food trucks along Kamehameha Highway. I tried Giovanni’s and loved every garlicky bite. For a lighter option, The Beet Box Café in Haleiwa has great vegetarian fare.
Afternoon:
The afternoon was for beach hopping:
- Waimea Bay (great for swimming in summer, big waves in winter)
- Sunset Beach (laid-back, perfect for watching surfers)
- Banzai Pipeline (famous for winter surf competitions)
Evening:
I ended my North Shore adventure with sunset at Shark’s Cove—bring reef shoes for tide-pooling—or back at Sunset Beach. If you want to linger, Haleiwa Joe’s has a laid-back dinner vibe with ocean views.
Day 3: History, Culture & Hidden Beaches
Morning:
My third day started with a dose of history at Pearl Harbor. Reserve your tickets for the USS Arizona Memorial ahead of time. It’s a moving, important experience—plan at least two hours here.
Midday:
Afterward, I explored the Bishop Museum to dive deeper into Hawaiian culture. If you’d rather stay outdoors, try the Iolani Palace tour for a peek into Hawaii’s royal past.
Lunch:
For lunch, I wandered through Honolulu’s Chinatown. The energy here is electric—dim sum at The Pig & The Lady or noodles at Little Village Noodle House are always a win.
Afternoon:
I was craving a quieter beach, so I drove to Kailua Beach Park and Lanikai Beach on the windward side. The turquoise water and soft sand felt worlds away from Waikiki, and parking is easier if you come in the afternoon.
Evening:
Dinner was in Kailua—Buzz’s Original Steakhouse is a classic spot, or try Uahi Island Grill for something casual. On the way back to Waikiki, I stopped at Pali Lookout for panoramic views over the island (windy, but breathtaking!).
Day 4: Sunrise Hikes, Coastal Drives & Last Bites
Early Morning:
My last day began before dawn with a sunrise hike up Lanikai Pillbox Trail. The climb is short but steep, and the reward is unforgettable—the sun rises right over the ocean, painting the Mokulua Islands in golden light.
Morning:
After hiking, I refueled with pastries and coffee at Cinnamons in Kailua (the guava chiffon pancakes are legendary). If you’re feeling adventurous, rent a kayak to the Mokulua Islands for a few hours of paddling and snorkeling.
Midday:
The last few hours were all about soaking in as much Oahu beauty as possible. I cruised the scenic Kalanianaole Highway, stopping at Makapu’u Point for lighthouse views and, if it’s winter, a chance to spot humpback whales.
Afternoon:
For a final treat, I grabbed malasadas (Portuguese doughnuts) from Leonard’s Bakery on my way to the airport. The perfect sweet ending to an unforgettable trip.
Where to Stay in Oahu
- Waikiki: The classic choice for first-timers—close to beaches, shops, and nightlife. I liked The Surfjack for its retro pool and friendly vibe.
- North Shore: Ideal if you want quiet, surf, and a small-town feel. Look for vacation rentals or Turtle Bay Resort.
- Kailua/Lanikai: Perfect for laid-back beach days and a more local experience. Great for families or anyone seeking calm.
Essential Oahu Travel Tips
- Rental Car: Highly recommended for this itinerary, especially for North Shore and Windward Coast adventures.
- Reservations: Book ahead for popular activities (Hanauma Bay, Pearl Harbor, Diamond Head).
- Weather: Pack light layers—rain showers are common, but they’re usually brief.
- Respect: Remember you’re a guest. Please be mindful of local customs, wildlife, and beach safety.
FAQs
What’s the best time of year to visit Oahu?
I love late spring or early fall—fewer crowds, good weather, and calmer surf on the North Shore.
Is 4 days enough for Oahu?
You’ll get a great taste of the island! If you want more beach time or slow mornings, you might wish for a fifth day.
Should I stay in one place or split my time?
I found it easiest to base myself in Waikiki, but if you love surfing or quiet nights, spend a night or two on the North Shore.
Can I get around Oahu without a car?
It’s possible, especially if you stay in Waikiki, but a car makes exploring the island so much easier.
Ready to plan your Oahu adventure?
If you have any questions or want more personal recommendations, explore my other Oahu travel guides or send me a message—I’d love to help you map out your perfect trip!
