Oahu Itinerary: 5 Days, Hikes First
Oahu packs a rain forest, a 1,200 foot ridge line, the best big wave coast in the world and a city into 600 square miles. Five days works as one day on the south east coast, one on the windward side, one on the North Shore, one in Honolulu with Pearl Harbor, and one for the leeward side or a second go at whatever you liked most. Book Diamond Head and Hanauma Bay entry ahead, hike before 9am, and rent a car, because the bus is slow and the trailheads are not on it.
Day 1: the south east coast
- Diamond Head at 6am. Under a mile and a half round trip up an old military track to a crater rim with the whole of Waikiki below. Out of state visitors need an entry and parking reservation booked in advance.
- Hanauma Bay. The best easy snorkelling on the island, in a flooded volcanic crater. Entry is reservation only, numbers are capped, and it closes some days each week for the reef.
- Koko Head Stairs, if your legs are up for it: 1,000 railroad ties straight up an old tramway, brutal and short, with the best view on this coast at the top.
- Makapuu Point lighthouse trail, paved and two miles, with whales offshore from December to April.
- Halona Blowhole and Sandy Beach as you drive round. Do not swim at Sandy Beach unless you genuinely know shore break.
Day 2: the windward side
- Lanikai Pillbox, the Kaiwa Ridge Trail, at sunrise. Under two miles, steep and dusty, and the view over the Mokulua islands is the photograph everyone comes for.
- Lanikai and Kailua beaches afterwards, and a kayak out to the Mokuluas if the wind is down.
- Kualoa Ranch, for the valley the films were shot in, or skip it and drive on.
- Byodo In Temple at the foot of the Koolau range, which is a good hour when the ridge is in cloud.
- Manoa Falls or Lyon Arboretum in the afternoon if you want rain forest: 1.6 muddy miles to a 150 foot fall, on the Honolulu side of the range.
Day 3: the North Shore
- Waimea Valley for a botanical garden walk to a waterfall you can swim in.
- Sharks Cove for snorkelling in summer, when the water is flat. In winter it is unsafe.
- Waimea Bay, Banzai Pipeline and Sunset Beach to watch the surf. From November to February the swell reaches 20 or 30 feet and the professionals arrive. In summer the same beaches are calm.
- Haleiwa town for shave ice and food trucks, and Kahuku for the shrimp trucks further round.
- Ehukai Pillbox for a short hike above Pipeline with a view of the whole coast.
Day 4: Honolulu and Pearl Harbor
The Arizona Memorial programme is free and timed, and tickets are released in advance online plus a small number the day before. Book it, because the walk up tickets go early. The Bowfin submarine, the Missouri and the aviation museum are separate paid sites on the same base and any two of them fill a morning.
Afternoon in Honolulu: Iolani Palace, the only royal palace on American soil, the Bishop Museum for Hawaiian history, or the Tantalus and Round Top drive for the view down over the city. Waikiki at the end of the day for a swim and a first surf lesson, which is genuinely what this beach is best at.
Day 5: the leeward side or a repeat
- Kaena Point, a five mile round trip on an old coastal road to the western tip, with albatross nesting from November to July and monk seals on the rocks. No shade at all, so go early.
- Ka Iwi coast or a second snorkel if the wind has changed.
- The Kuliouou Ridge Trail, five miles and 1,800 feet to a Koolau summit, and the best full ridge hike on the island that is legal and maintained.
- A catamaran or whale watch out of Waikiki, which is worth it between December and April.
Two things to leave alone: the Haiku Stairs, which are illegal to climb and have been closed and dismantled, and any unmaintained ridge scramble you read about on social media. Oahu's search and rescue teams spend most of their time on visitors who went up one.
Practical notes
- Reservations: Diamond Head and Hanauma Bay both require advance booking for non residents, and Pearl Harbor's memorial tickets are timed.
- Rent a car, and expect to pay for parking in Waikiki. The bus reaches the towns and not the trailheads.
- Where to stay: Waikiki for convenience and food, Kailua for the windward beaches, the North Shore if surf is the point. Driving Waikiki to the North Shore takes an hour and 15 minutes without traffic.
- Ocean safety: the surf that makes this island famous kills visitors every year. Swim at lifeguarded beaches, ask the lifeguard, and treat winter North Shore water as off limits.
- Reef safe sunscreen is the law in Hawaii, and chemical sunscreens are banned.
When to go
- April, May, September and October: the best value and the fewest people, with warm water and settled weather.
- November to February: big surf on the North Shore, whales from December, more rain on the windward side, and higher prices around the holidays.
- June to August: calmest water for snorkelling, hottest hiking, and the busiest beaches.
Have us plan the five days
Tell us your dates and how much hiking you want and we will build the days around the reservations and the wind. Planning is free, and we earn only if you book through us.
Oahu Itinerary: 5 Days, Hikes First FAQs
Yes. Five days covers the south east coast, the windward side, the North Shore, Honolulu with Pearl Harbor and one spare day. Adding a second island in the same week costs you most of a day in airports.
Kuliouou Ridge Trail for a full day, at five miles and 1,800 feet to a Koolau summit. Lanikai Pillbox for the best view per mile, and Diamond Head for the easiest walk with a real payoff. The Haiku Stairs are illegal and have been dismantled.
Yes, for out of state visitors, who must book entry and parking in advance. Hanauma Bay also requires a reservation with capped daily numbers, and it closes some days each week to rest the reef.
April, May, September and October for the best balance of price, weather and crowds. November to February brings big North Shore surf and whales, and June to August has the calmest water for snorkelling.
For hiking, yes. The bus system reaches the towns but not the trailheads, and the North Shore is an hour and 15 minutes from Waikiki. Budget for Waikiki parking, which is charged nightly.
Waikiki for food, nightlife and easy access to Diamond Head and Pearl Harbor. Kailua for quieter windward beaches and the Lanikai trail. The North Shore if surf is the main reason you came.
