oahu vacation Archives - Midway Vacations

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Vacationing in a lush, tropical island paradise this year means plenty of beach time, but don’t miss the opportunity to explore. Take a much-needed break to a place full of sand, sun, fun, and plenty of rest and relaxation. You’ll want to lace up your hiking shoes and find some hiking trails on Oahu beyond the beach where you can explore even more of Oahu’s natural beauty.

Diamond Head (Leahi) Trail

Possibly the most iconic volcano in the region, the trail to the summit of Diamond Head near Waikiki was forged as part of the U.S. Army Coastal Artillery defense system in 1908. The one-way 0.8-mile (one way) trail boasts a 560-foot elevation change from the crater floor. The out-and-back hike takes approximately two hours for a safe and leisurely round-trip. Be prepared for uneven ground and steep terrain, but the payout of 360-degree views of Waikiki, Honolulu, and the surrounding area are worth the effort. Reservations are required to visit, and parking is available to book in two-hour slots.

Koko Crater Railway Trail

The railway “stairs” hike is a short drive from the Diamond Head and Waikiki area. The tough, extremely inclined 2.8-mile out-and-back climb results in reaching the summit of the Koko Head Crater. The military constructed the railway to transport supplies to soldiers during World War II, and the site has seen many other functions until it was given to the City of Honolulu and became Koko Head Regional Park. You’ll experience a 990-foot elevation change that brings you 1208 feet above sea level. Count the railroad ties as you go and find there are 1,048 before another 30-foot climb to the lookout area.

Makapu’u Point & Lighthouse Trail

For breathtaking views of Oahu’s southeastern shoreline, including tall sea cliffs looking out to the blue ocean beyond, this trail is for you. The trail is situated off of Kalanianaole Highway on the southeastern tip of the island about 12 miles east of Honolulu. Makapu’u is a remnant of a volcanic ridge that rises over 600 feet from sea level. The lookout boasts panoramic views off Manana Island and Black Rock Island, as well as views of neighboring Molokai and Lanai.

Kuli’ou’ou Ridge Trail

The 4.4-mile round-trip trail is a short drive from Waikiki, with the trailhead located at the end of Kalaau Place. The moderately-challenging trail features stairs that make for an easier climb in some areas. Keep your eyes peeled for a variety of plants and trees on your way through the diverse landscape. The trail ends at a final plateau boasting breathtaking views of East Oahu. Schedule about four hours for the hike.

Ka’iwa Ridge Trail (Lanikai Pillbox Hike)

The trail is a great way to test your skills with an intermediate level of difficulty. There’s a steep grade throughout the climb, which starts just above Lanikai Beach. The 90-minute round trip offers scenery and breathtaking views, whether or not you opt to extend your trip another hour along the ridge. The payoff at trail’s end is stunning views on the island’s windward side, including the Mokulua Islands, Kailua Beach, and Lanikai Beach.

Manoa Falls Trail

Great for hikers of all skill levels, the trail is more of a “walking” trail than a “hiking” trail. The 1.6-mile round trip has a slight uphill grade that kids and beginners will negotiate fairly easily. The trailhead is located a quick 15-minute drive from Honolulu, where you’ll be transported to the lush, tropical views of Manoa Valley – a truly different world.

Ehukai Pillbox Hike

Get a great view of the crashing waves of Oahu’s North Shore, as well as the Seven Mile Miracle. The 1.5-mile out-and-back trail is a good 90-minute hike. Reserved for expert hikers, there are severe inclines at various places throughout the trail. Those weak of knees, heart, or any other physical challenges are encouraged not to take this trail. Those who can will be rewarded with views of the Banzai Pipeline and Sunset Beach.

Aiea Loop Trail

It’s another trail on the list for beginner hikers. The less than five-mile hike is shaded with flat pathways along the looped trail. Take in the beauty of native trees, lemon eucalyptus grove, Norfolk pine, native koa, and ʻōhiʻa trees. Located on the west side of the Hālawa Valley, you’ll have great views of places like Pearl Harbor, Diamond Head, and the Ko’olau Mountains from the ridge.

Hiking on Oahu

Rest and relax after a hike of one of Oahu’s best hiking trails in a vacation rental by Midway Vacations. From a cozy studio for a solo or sweetheart escape full of hiking exploration, to a two-bedroom for you and even more of your loved ones, we have a cozy vacation rental that’s just right for your tropical island trail hike. Arrive and feel the stresses and worries of home melt away and be replaced by the spirit of Aloha. Prepare trail snacks or any other meal of the day in a fully equipped kitchen, relax in an open living space, or retreat to a private bedroom.

Contact us today to start planning your Oahu hiking adventure!

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