7 BEST O'AHU TOURS.
Surf, Sail & Slow Days
Discover the seven best Oʻahu tours, from surfing lessons and sunset sails to hidden island experiences.
Oʻahu is where Hawai‘i’s contrasts meet — Waikīkī’s city lights, North Shore surf breaks, calm reefs, and historic harbors. This guide brings together seven of the best Oʻahu tours: small-group surfing lessons, sunset sails, kayak trips, and hidden island experiences you won’t find on a crowded bus itinerary. We select each one for travelers who want the island’s most trusted operators, small-group or private experiences, and unique ways to see an authentic side of Oʻahu.
1. Surfing Lessons — Waikiki & North Shore
No list of Hawai‘i must-dos leaves out surfing — and Oʻahu’s breaks make it beginner-friendly whether you paddle out under Diamond Head or head north to the gentle spots tucked inside Turtle Bay. Waikīkī is the classic first lesson: warm water, rolling reef breaks, instructors who keep it fun and relaxed, and views of Diamond Head every time you pop up. See our Waikīkī surf lesson pick here.
The North Shore is surfing’s legendary proving ground — but not every break here is a giant wave. At Turtle Bay, you’ll find a protected cove with gentle rollers that make it easy to learn, even during winter swell season when other spots roar. Local instructors know exactly when the ocean’s at its friendliest and make sure you catch your first clean ride with confidence. See our top North Shore surf lessons here.
2. An Intimate Lu'au Experience
Big buffet luaus with bus crowds? Skip them. The original Hawaiian lūʻau was never a tourist show — it was simply a gathering: friends, family, food, hula, and stories passed across the mat. When the first hotels rose in Waikīkī in the 1950s, the luau evolved into a full performance — weaving in dances from across Polynesia: Tahitian drums, Samoan fire knife, Māori haka, all stitched together to give visitors a taste of island spectacle.
That’s still fun in its own way, but the best luaus today feel closer to the old spirit — smaller, more personal, and more Hawaiian at heart. This one keeps it simple: good local food, live hula under soft lights, slack key guitar, and stories that bring the dances into the present. You’ll leave with a full belly and a quiet sense you’ve been invited in, not just sold a ticket. See our top Oʻahu luau pick here.
3. Kayak & Snorkel
Kailua: Paddle to the Mokulua Islands
If you want clear water and an easy paddle, Oʻahu’s Windward side is the calm classic. Just 30–40 minutes from Waikīkī, the beach town of Kailua feels like another island entirely — quiet residential streets, soft white sand, and shallow turquoise water that calls you out. A guided kayak tour here drifts you offshore to the Mokulua Islands, two small islets just beyond Lanikai Beach. The paddle is gentle but rewarding: seabirds overhead, reef fish below, tide pools to explore if you land.
The Mokuluas (locals just say “The Mokes”) are a snapshot of what makes this coast special — protected waters, the chance to see a resting monk seal or green sea turtle, and views back to the Koʻolau mountains that fold the sky behind you. Bring a mask: the reefs around the landing cove are alive with color and safe for drifting slow. See our top Kailua kayak tours here.
North Shore: Outrigger Canoe & Snorkel
For a wilder spin on paddling, head north to the beaches near Haleʻiwa, where outrigger canoe tours swap the solo kayak for teamwork and tradition. You and your crew push off from calm coves, paddling channels that run just outside some of the world’s most famous surf breaks. Winter might bring big wave views in the distance, but your guide keeps you close to shore in safe water — perfect for beginners and families.
Most tours also include a stop for a quick snorkel over reef patches where sea turtles drift and reef fish flash in the shallows. In summer, the ocean settles into glassy blues that make the whole ride feel peaceful and open. It’s part surf heritage, part easy adventure, and one of the best ways to see the North Shore from the water. See our North Shore outrigger canoe picks here.
4. Oahu Helicopter Tour
Sometimes you need to see the whole island at once — reef to ridge, valley to hidden waterfall. A small-group helicopter tour lifts off near Honolulu Airport and sweeps you over Waikīkī, Diamond Head, the Koʻolau mountains, and Oʻahu’s secret corners you can’t reach on foot. Go doors-off if you want a thrill (and better photos). Flights often include Sacred Falls, Pearl Harbor, and patches of forest you’ll never spot from the highway — it’s one of the best ways to understand just how green, folded, and water-bound this island really is. See our Honolulu helicopter tour pick here.
5. Outrigger Canoe Surfing in Waikiki
Small-Group Outrigger Surfing
Before surfboards, there were canoes. Waikīkī’s gentle reef makes it the perfect place to try the ancient Hawaiian sport of outrigger canoe surfing — paddling hard, catching a wave, and riding it in together with salt spray and grins all around. Go small-group if you want to meet new people, share the stoke, and feel the push of a wave in classic Waikīkī style. See our small-group outrigger selection here.
Private Outrigger Charter
If you’re bringing friends or family, a private outrigger charter lets you paddle together with just your own crew — up to six people per canoe. It’s the same thrill but with more room to share stories, high-fives, and photos when you ride a gentle reef wave all the way back in. See our private outrigger option here.
6. Sailing & Snorkel Charter from Waikiki
Small Group Sailing Option
A good sailing day off Waikīkī feels like a pocket of calm in the middle of the city: soft trade winds, turtles drifting below the surface, Diamond Head steady on the horizon. Group catamarans run daily, letting you slip out past the breakwater, drop anchor at a reef, and slide in for an easy snorkel where colorful fish and coral fan out beneath you. Back on deck, there’s shade when you want it and sun when you don’t — plus that quiet glide back to the harbor with salt on your skin and the skyline just starting to light up. See our group sailing & snorkel option here.
Private Sailing Charter
If you’re traveling with friends or family, a private charter means you pick the pace — reef snorkel stops, a sunset anchor spot, maybe a swim session far from the crowds. These charters can be big enough for a wedding party or small enough for a birthday sail with just your closest crew.
For groups of 6 and under, this affordable $400 private charter on a nimble 31-foot racing trimaran makes for a great outing. Or, for more luxury and larger groups this 40-foot catamaran is a great option, starting from $1200.
7. Sunset Cruise from Waikiki
If there’s a ritual worth repeating on Oʻahu, it’s ending the day on the water — sails up, sun down, skyline in the distance. A sunset cruise off Waikīkī gives you front-row seats to that soft pink horizon. Bring a drink, leave your shoes at the dock, and watch the island light up behind you. See our top Waikīkī sunset cruise pick here.
For something smaller, our intimate catamaran option feels like your own floating lanai, with room for a handful of guests and an unhurried drift back to shore. See our intimate Waikīkī sunset sail here.