The Best of Oahu: The Island’s 5 Prettiest Lookouts

Photo of Kailua’s Lanikai Pillbox, a Breathtaking Oahu Lookout.Hawaii’s island of Oahu remains one of the most beautiful and biodiverse landscapes on the globe, with its semi-arid Wai’anae Mountains, pristine Waikiki beaches, and lush, moisture-swept easterly Ko’olau range. The island features seven jaw-dropping peaks that tower over 1,000 feet above the sea, including the 4,003-foot-tall Mount Ka’ala. Thus, Oahu boasts a bevy of breathtaking, undeniably picturesque lookouts, many of which are a short distance from award-winning Prince Waikiki. 2021 will no doubt be a year of fitness and wellbeing, which is why the Prince team recently curated a rejuvenating Wellness Retreat package.

5 Jaw-Dropping Lookouts in Oahu

This 20-part wellness challenge outlines Oahu’s various outdoor pursuits, including beach yoga, nocturnal paddleboarding, and Waikiki Beach surfing. However, a brief, albeit semi-strenuous jaunt to and from one of Oahu’s most spellbinding overlooks should also be on that list. Each of these lookouts provides awe-inspiring, panoramic views of the rolling terrain, as well as ample outdoor acreage for social distancing and aerobics.

1. Lanikai Pillbox

Kailua’s Lanikai Pillbox (as pictured above) may not reach 600 feet above sea level, but it remains the prettiest panoramic lookout in Oahu (and all of Hawaii, for that matter). The Pillbox boasts stunning views of Lanikai Beach’s Nā Mokulua islets, Kailua Bay, and Mōkapu Point. Be prepared for a subtly-steep, 550-foot climb to the summit.

Coastal View from the Makapu'u Point Lighthouse, a Stellar Oahu Lookout.2. Makapu’u Point Lighthouse

Travelers often exclaim that Waimanalo Beach is the prettiest stretch of sand on the island. A few ticks southeast of the beach and 600-plus feet above the ocean’s surface lies an oft-photographed lighthouse. Surprisingly, the lighthouse itself pales in comparison to the vibrant, eye-popping mountains north of the sandy beach. Interestingly enough, the Lanikai Pillbox rests on the other side of that cliffside mountain chain.

3. Mount Tantalus

Mount Tantalus towers above the heart of Honolulu, approximately 4.7 miles north of Prince Waikiki (as the crow flies). The short, 0.9-mile out-and-back trek bestows faraway views of Diamond Head State Monument, Honolulu’s skyscrapers, and the always enthralling Honolulu Watershed Forest Reserve, which houses countless waterfalls, exotic birdlife, and acres upon acres of untouched natural beauty.

Photo of Hanauma Bay, a Jaw-Dropping Oahu Lookout.4. Hanauma Bay

Between the aforementioned Makapu’u Point and Diamond Head lies a hidden, south-facing marvel known as Hanauma Bay, an ultra-popular aquatic activity hub. Sunbathers, snorkelers, aspiring surfers, and paddleboarders frequent this bowl-shaped cove. Locals revere this section of sand for its glorious sunsets, post-storm rainbows, and all of that crystal-clear turquoise water.

5. Diamond Head

Diamond Head narrowly thwarted Nu’uanu Pali to nab the final spot on this Oahu lookout index. The state monument itself is a volcanic tuff cone, formed by a long-ago Koʻolau Volcano eruption. Volcanic ash, dust, and rock helped create this remarkably symmetrical crater, leaving behind a visually-stunning, postcard-esque natural marvel. From the summit, hikers obtain unobstructed views of the vast Pacific, downtown Honolulu (and Prince Waikiki), and the crater’s interior, home to the visitor center.

Prince Waikiki: The Best Hotel in Oahu

Thanks to Prince’s eclectic mix of wellness packages, it’s never been more enticing to stay at this modernized, Ala Wai Harbor-front respite. Prospective guests are urged to read the Prince Promise, a meticulously-crafted pledge that includes a bevy of essential information, including employee training, cleaning guidelines, and food and beverage options. Several recently-created packages only enhance the already stellar experience, such as the Book Now, Stay Later offer and the Escape to Prince extended stay. Click the Book Now button to reserve a spot in Hawaiian paradise! Please be sure to review and follow all State of Hawaii pre-travel requirements and guidelines when visiting Hawaii.