Labor Day Weekend: 10+ fun things to do on Oahu in September

With so many cultural activities taking place on and around Labor Day in Oahu, you might as well familiarize yourself with a deep dive at the Polynesian Cultural Center before you do anything else, right? This cultural institution is as good an intro to Polynesian history, culture and customs as you're likely to find. Set aside at least a half day to explore its six (count 'em) distinct village areas, each representing a different Polynesian island nation. So you might be sampling Tahitian coconut bread one minute, experiencing a New Zealand haka the next, then bringing it all back to Hawaii with a fun hula lesson. 

Pro-tip: Entry to the Polynesian Cultural Center is included with a Go City Oahu pass, which can save you $$$ when visiting multiple attractions on and around the island. It also includes entry to your choice of some of Oahu's biggest traditional luau experiences – at the Aloha Tower and Sea Life Park – allowing you to go maximum cultural immersion mode ahead of the various major events taking place on and around Labor Day

The Makani Catamaran is an Oahu icon, a super-luxury vessel that allows you to indulge your inner celebrity as you don supersize sunglasses and set sail along the coastline, glass of bubbly in hand. Hit the nets to catch some rays, soundtracked by the soothing splash of the waves, snap selfies against the Waikiki skyline, or keep your eyes firmly on the water, where you might just spot the occasional playful spinner dolphin, flying fish or curious sea turtle cruising on by.

A daytime catamaran cruise is included with the Go City attraction pass and – for a mere $20 more – you can upgrade your adventure to a sunset sailing. Drinks are included with your upgrade and the chance to watch the sky turn pink and orange over Diamond Head from this angle is one not to be missed.

You’re traveling to Oahu to make the best of those last summer days, so why not immerse yourself (quite literally) in the tropical waters of Hawaii? The sheltered waters of Hanauma Bay Nature Preserve are the gold standard on Oaho – think calm, clear waters full of marine critters, a soft sandy bottom and plenty of family-friendly facilities. The reef and its wildlife here are protected and visitor numbers are limited, so be sure to go online to book a spot well ahead of your planned visit.

Our guide to Oahu's best snorkeling beaches has more info on Hanuma Bay, plus several more of the island's top snorkeling spots. You can also take the stress out of planning by booking yourself on a guided excursion, like this one to Turtle Canyon just off Waikiki, where, as well as the obvious, you'll also spot rainbows of reef fish and maybe even the occasional dolphin or two.

It's amazing how much extra ground you can cover with a bike. Rent yours to make Honolulu your oyster then choose your adventure: a whiz along the coastline to Diamond Head? Quick tour of hip Honolulu 'hoods like Kaimuki and Kaka'ako? Or grab a poke picnic and cycle inland to the lush jungle landscapes of the Manoa Falls Trail?

And if that all sounds a little too much like hard work, well, you could always rent a moped instead, which has the twin benefits of a) saving your legs and b) opening up attractions a little further afield – Sandy Beach for the win.

Traveling with a bigger crew? This beer bike tour of Kaka'ako, which pauses for refreshment at legendary Oahu brewpubs like Honolulu Beerworks and the Waikiki Brewing Company, might be more your speed. Cheers!

Oahu's wild, mountainous, jungle-draped landscapes are manna for hikers of all stripes, meaning there's something for everyone – from novice ramblers to climbers with thighs like thoroughbred racehorses. We tend to err on the side of 'novice rambler'. If you're in the same camp as us, you'll find a couple of suitable walks that have shuttle transfers bundled with the Go City Oahu pass, neither of which compromise on views in any way.

First up, Diamond Head is an Oahu must-do thanks to easy access from Waikiki, a relatively moderate hike to the summit, and the glittering reward of Honolulu skyline and Pacific views. Or follow the trail up to the iconic Makapu'u Lighthouse, with a stop at Halona Blowhole en route.

Meanwhile, those who prefer something a little more glute-troubling should make for Koko Crater Railway Trail with its 1,048-step staircase, or the near-vertical triple peaks of Mount Olomana.

Bag yourself a unique souvenir at the monthly First Friday Art Walk in Honolulu's Chinatown. There's often a Labor Day theme at the September event but, in any case,  you'll discover a trail crammed with local artists and vendors displaying their wares – in hip galleries, hidden warehouses, and even on the streets themselves. Take a wander, get to know the artists and artisans and, who knows, you might come away with a new favorite painting, ceramic pot or necklace.

There's a bit of a festival feel to the whole thing, with many local businesses getting in on the fun, too, and often offering free food and drink samples to passersby. 

Hawaii's annual Aloha Festivals take place throughout the month of September, kicking off with the Royal Court Investiture and Opening Ceremony, usually on or around Labor Day weekend. This stately ceremonial event honors Hawaii's ruling chiefs, so expect eye-popping traditional regalia and cultural performances including – yes – a heavy dose of hula.

The festivities continue with the Waikiki Hoolaulea, which turns Kalakaua Avenue into one big block party, complete with street food, craft stalls and live music and dance. A floral parade winds up the month-long party in late September, painting Kalakua Avenue with bloom-festooned floats, colorful marching bands and elegant pa'u riders (Hawaiian horsewomen) as it weaves its way to Kapiʻolani Park.

This celebration of Okinawan culture is one of Hawaii's largest ethnic festivals,. Honoring Okinawan immigration to Hawaii since 1900, it's held at the Hawaii Convention Center and includes everything you'd expect from such an event: live music, cultural performances and some frankly amazing Okinawan culinary specialities. Slurp your way through a satisfying bowl of Okinawa soba, then get stuck into deep-fried-then-dipped-in-sugar andagi. Fear not, you can work it all off at the evening bon dance – a lively traditional Japanese folk dance intended to honor ancestral spirits.

There's plenty for the kids here, too. We're talking hula dancing, taiko drumming, storytelling and games galore. It's a great way to better understand this part of Hawaii's immigration story, and discover how it has contributed to island traditions and cuisine.

Not for the faint of heart (or weak of limb), this event brings swimmers from all over the world to challenge the rough waters of Waikiki's coastline along a 2.4 mile course. You'll need to be a strong, seasoned swimmer and to register well in advance to join the other thousand-or-so swimmers along the open-water route from the shadow of Diamond Head all the way to the other side of Waikiki Beach. You may even encounter the odd honu (native green sea turtle) along the way.

Alternatively, take the far more sensible approach of grabbing a coffee and croissant and heading for one of the spectator points for around 8AM. It's definitely easiest to nab a spot on Waikiki Beach, but you could also try Kapahulu Pier or the finish line at Duke Kahanamoku Beach.