This coastal enclave is located on Oahu's southeastern side. At its northern (Kailua-side) end is Alala (lit "awakening") Point. Wailea (lit. "the waters of Lea") Point sits a mile and a half away on Lanikai's southern (Waimanalo) side. Alala and Wailea were also Hawaiian fish gods who guarded the offshore waters in the area. To the west, separating Lanikai from Keolu Hills and Kaelepulu Pond (aka Enchanted Lakes) is a ridge called Ka'iwa (lit. "the frigate bird").
Hawaiian legend says that Ka'iwa was a royal female who resided in Ka'ohao. She caught the eye of a konohiki (overseer) named Ahiki, who sought Ka'iwa's love but was prevented from seeing her by a warrior named Kana. Smitten and frustrated, Ahiki became the southernmost of the three peaks in triple-pointed Mount Olomana. Ahiki, not surprisingly, is the peak furthest away from Ka'iwa.
A scenic trail system exists atop Ka'iwa Ridge. The most readily accessible trailhead is just past the entrance of the Mid-Pacific Country Club on Kaelepulu Drive (off of Mokulua Drive in Lanikai). Seventy yards beyond the MPCC entrance is a gated community called Blue Stone. On the left of Kaelepulu, just before the turnaround circle fronting the Blue Stone gate, a private driveway ascends the hillside. At the point where the driveway veers left, an obvious trail that initially follows a fence leads to the top of the ridge.
The initial section of the trail is fairly steep and over slippery, eroded red dirt. If wet, this path can be a bit tricky to negotiate. It's just slightly better when dry. Fortunately, stands of koa haole along the trail help to assist one's ascent and descent.
After a few minutes of puffing and huffing, you'll leave the dry, hot haole koa forest behind and emerge onto a windswept ridge overlooking Lanikai, the Mokulua (Twin) Islands [18k jpg image], and the ocean. The Lanikai community park sits directly below you.
Continue climbing the open, broad ridgetop, loose gravel and eroded lava rock underfoot. The beauty of this section is that you can pause at any moment to catch your breath and ogle the wonderful scenery. Bristling in the wind propelled over the summit, long-stemmed brown grass, similar to the kind used in hula skirts, grows thickly down the ridge's ocean-facing side.
As you continue your ascent, you'll arrive at a rocky outcropping that you can either scale (if you're into rock climbing) or skirt around via a trail to the right (if you're feeling conservative). Thereafter, the climb is a short one to first one then another concrete bunker. Most people hike to the second bunker, rest there, take in the wonderful panoramic view, and return the way they came. Depending on your pace and conditioning, the hiking time to the second bunker (elevation 565 feet) will take in the neighborhood of 20 to 30 minutes.
Do take some time to climb atop the upper bunker to enjoy the 360 degree view--Mokapu Point and Kailua Bay to the north; massive Pu'u Lanihuli and twin-crowned Pu'u Konahuanui in the Koolau Range to the west; Mount Olomana and the peak named after the banned lover, Ahiki, to the southwest; Bellows Beach and the community of Waimanalo to the south; and the shimmering ocean and twin islands to the east.
If you want more exercise or want to explore further, you can follow the trail southwest (inland) for a half mile to the actual peak of Ka'iwa (elevation 603 feet) that overlooks Keolu Hills and Enchanted Lakes. The trailside environment becomes increasingly drier and warmer as you move away from the ocean's cooling breezes. Koa haole, kiawe, and low-lying prickly ground cover dominate there.
An indistinct junction is located near Pu'u Ka'iwa. At that point one can proceed right and descend a ridge down to the Keolu Hills side of the Blue Stone community. The trail, crowded by koa haole for the most part, also continues left (basically due east toward the ocean) from the junction, and after dropping into a saddle, ascends to Pu'u o Lanikai before ending at Wailea Point. Plan on a two-hour roundtrip from the trailhead to Wailea Point and back.
If you're out on the windward side, give the Ka'iwa Ridge trail a go. For an hour or two of effort, you'll be treated to a wonderful experience and can end your visit with a dip in the world-famous waters you were perched high above just minutes before.