Coast, Cliffs & Back by Lunch
The best of O'ahu's southeast coast and windward side in one morning, with never more than three guests aboard. Pickup at your Waikīkī hotel at 7:45am, back by 12:00–12:30pm — scroll the stops, or tap any marker on the map to jump ahead.
Scroll the stops — or tap a marker to jump ahead
Diamond Head Lookout
Your morning begins at Le‘ahi — Diamond Head — the 300,000-year-old volcanic tuff cone that frames the Waikīkī skyline and once served as a key military lookout guarding the island. We pause at one of its scenic lookouts for sweeping views over the southeast shoreline and the open Pacific — a perfect first taste of what the morning holds.
Leonard’s Malasadas
A Hawai‘i must. Sink your teeth into hot, fresh-from-the-fryer Portuguese doughnuts — crispy on the outside, pillowy on the inside, and rolled in sugar while still warm. Brought to the islands by Portuguese plantation workers and perfected by Leonard’s Bakery since 1952, the malasada is a beloved piece of local food culture. Try the classic, or go for one filled with haupia (coconut cream) if you’re feeling adventurous (malasadas not included in tour price).
Halona Blowhole & Eternity Beach
Two natural wonders share one dramatic stretch of lava coastline. The Halona Blowhole — formed thousands of years ago by molten lava tubes reaching the sea — funnels incoming swells through a submerged lava shelf and launches geysers of seawater high into the air; the bigger the surf, the bigger the show. From the same lookout, gaze down on Halona Cove, better known as Eternity Beach, where the famous surf-side embrace in the 1953 classic “From Here to Eternity” was filmed. It’s one of O‘ahu’s most photogenic views — and most visitors drive right past it.
Makapu‘u Lookout
Perched above the easternmost point of O‘ahu, the Makapu‘u Lookout delivers breathtaking views of turquoise water, windward sea cliffs, and the offshore seabird sanctuaries of Mānana (Rabbit Island) and Kāohikāipu. In winter months, keep your eyes on the channel — humpback whales cruise these waters and often put on a show. On clear days you can see all the way up the windward coastline you’re about to explore.
Stop 05Local Gift Shop in Waimanalo
A favorite little stop in the heart of Waimanalo — country O‘ahu at its most charming. Browse locally made gifts, crafts, and island treats you won’t find in the Waikiki ABC Stores, and take home a souvenir with a real story behind it. Supporting small local businesses is part of how we tour — and this one is a gem.
En Route · Scenic DriveCruise the Windward Side
This is the O‘ahu that takes people’s breath away. As we cruise the windward coast, the fluted cliffs of the Ko‘olau range tower thousands of feet above the road — the eroded remains of a massive shield volcano, carved by a million years of wind, rain, and epic volcanic forces. Around every bend: dramatic pali, offshore islets rising from turquoise bays, sleepy fishing villages, and postcard ocean views the entire way. Cameras ready — this stretch is pure magic.
Macadamia Nut Farm at Kualoa
Up the windward coast in the shadow of the Kualoa cliffs, we pull in at a family-run macadamia nut farm. Sample fresh-roasted macadamias in flavors from honey-glazed to chocolate-dipped, sip island-grown coffee, and learn how Hawai‘i became the macadamia capital of the world — with some of the most dramatic mountain scenery on O‘ahu as the backdrop.
Stop 07Nu‘uanu Pali Lookout
Our last stop is one of the most dramatic — and most historic — views on the island. More than a thousand feet up in the Ko‘olau range, the Pali Lookout looks straight down the windward cliffs to Kāne‘ohe Bay and Kailua, the coast you’ve just driven. In 1795 this ridge was the site of the Battle of Nu‘uanu, where Kamehameha I won control of O‘ahu on his way to uniting the Hawaiian Islands. Hold onto your hat: the trade winds funnel through the pass, and it’s famously windy up here. From the lookout it’s a short drive over the mountains back to Waikīkī.
The Journey
Every day on the island is a little different — stop order and timing may shift with weather, traffic, and the day's flow. That flexibility is how we keep the magic in the journey.
Hawaiʻi GET added at checkout. Food and drinks not included.