For the 50+ Traveler

Hawaii, the land of tropical views and warm scented breezes, is known worldwide as a haven for beach lovers. You could easily while away your days there just basking in the sun.

But while you’re in this genuine paradise on earth, why not delve a little deeper? Luckily, Hawaii has a range of hiking options that allow you to do just that. And many of the trails come with a healthy dose of the sandy beaches, sea breezes, and tropical vistas that you came to Hawaii to experience.

During my visits to Oahu and Maui, I took in a number of spectacular hikes, and I have a few favorites. For others, I consulted the state’s Go Hawaii tourism recommendations to compile a list of the best.

So, here -- from easy to strenuous, and from popular routes teeming with people to little-known byways -- are 11 of the most stunning trails of the Hawaiian Islands.

Views from the top of the Diamond Head Summit Trail.

1. Diamond Head Summit Trail, Diamond Head State Monument


This is my pick for the best hike in Hawaii. Check out TravelAwaits’ picks for the best hikes in all 50 states here. Anyone who has visited Honolulu’s lively Waikiki Beach has surely seen it -- the long mountainous cone that stretches along the southern tip of Oahu. Diamond Head State Monument is Hawaii’s most recognizable landmark, and its Diamond Head Summit Trail is among the most popular hikes on the islands.

Don’t expect solitude on the Diamond Head Summit Trail. Regardless of the time or season, you’re likely to be joined by throngs of hikers who all have a common goal in mind: getting to the summit to take in the startlingly beautiful view.

Although it’s fun to scramble up the trail’s steep switchbacks and through its 225-foot-long lighted tunnel, the real payoff is at the top. There, you get the postcard view of Honolulu’s gleaming skyline juxtaposed against the turquoise-blue waters and white sand of Waikiki Beach’s perfect crescent.

Be sure to get a photo of yourself at the top, with the view as a backdrop. It will be frame-worthy!

The Diamond Head Summit Trail involves a steep climb with more than 500 feet of elevation gain, including two long sets of stairs. The hike is rated as moderate, and it takes about 2 hours to complete.

Pro Tip: Be sure to time your hike so that you’re finished by 6 p.m. The last entrance is allowed at 4:30 p.m., and the gates are locked at 6 p.m. All visitors must be out of the park by then. For more tips, see this piece.

The Makapuu Point Lighthouse Trail in Hawaii.

2. Makapuu Point Lighthouse Trail, Kaiwi State Scenic Shoreline


Not only does the Makapuu Point Lighthouse Trail offer unparalleled ocean vistas from Oahu’s easternmost tip, but it also features stellar views of the point’s historic lighthouse (although the lighthouse itself is off limits).

Built in 1909, the pretty red-roofed lighthouse sits atop a 600-foot sea cliff that overlooks Makapuu Beach, one of Oahu’s best bodysurfing beaches.

The trail is 2 miles round trip and features a 500-foot elevation gain. It is rated as moderate and takes about an hour to complete.

Pro Tip: Bring binoculars if you’re hiking in the winter and spring, because the trail is known as an excellent place to spot migrating humpback whales from November through May.

The Kaena Point Trail in Hawaii.

3. Kaena Point Trail


Coastal sand dunes, a serene beach, and possible sightings of whales and monk seals -- they’re all right there on the Kaena Point Trail along Oahu’s westernmost point.

The trail leads to the Kaena Point Natural Area Reserve, a remote and scenic area that harbors some of the last vestiges of Oahu’s coastal sand dune habitat. It is home to native plants and seabirds and is also a great spot to see whales during the winter months.

The 3.5-mile trail, which follows an old railroad bed and former dirt road, has virtually no overall elevation gain and is rated as moderate. It takes 1 to 3 hours to complete.

Pro Tip: Although fairly flat, the hike can be hot and exposed to the sun, so remember to take plenty of water.

The Koko Crater Trail in Hawaii.

4. Koko Crater Trail


For a unique but intense hike, head to Honolulu’s Koko Crater Trail, where you will face more than 1,000 steep stairs, part of an abandoned railroad that ran along Koko Crater’s west side to the summit.

There’s plenty of payoff for your effort. The hike is known for its wildflowers and its stunning views. At the summit, you’ll be treated to a panorama of Diamond Head and the surrounding beaches.

Be prepared to work for it, though. The 1.8-mile out-and-back trail climbs nearly 1,000 feet in elevation gain and is rated as difficult. Depending on your pace, it will take you 1 to 2 hours to complete it.

Pro Tip: This trail is popular with fit runners, so expect to share it with plenty of others, regardless of when you go. To avoid the heat of the day, plan to get on the trail as early as you can.

The Sliding Sands Trail in Haleakala National Park.

5. Sliding Sands Trail, Haleakala National Park


Rather than Hawaii’s signature vivid greens and blues, expect rich earth tones on Haleakala National Park’s Sliding Sands Trail.

The 11-mile hike highlights the best of Maui’s massive Haleakala volcano, including the stark crater floor, the multicolored Pele’s Paint Pot, and the “bottomless pit” of Kawilinau.

The out-and-back hike descends 2,800 feet to the crater floor. It is rated as difficult and can take a full day to complete.

Pro Tip: The entire Sliding Sands Trail is recommended only for very fit adventurers, but hikers can get a good taste of the trail by doing the moderately difficult first 2.5 miles and turning back at the Ka Luu o ka Oo cinder cone.

The Pipiwai Trail in Haleakala National Park.

6. Pipiwai Trail, Haleakala National Park


For another side of Haleakala, head to the lush Kipahulu section of the national park in southeastern Maui and try the Pipiwai Trail. The iconic trail winds through a freshwater stream to the stunning payoff of the 400-foot-high Waimoku Falls.

The 4-mile round trip traverses a mostly well-maintained trail but also includes some challenging, steep terrain, so wear your hiking boots! The hike features an 800-foot elevation gain and is rated as moderate. Expect to spend 2 to 3 hours on the hike.

Pro Tip: Access to the Pipiwai Trail is via the Road to Hana, a winding 64-mile route that can take hours to navigate. Plan for a very early start if you intend to drive the route and hike the Pipiwai Trail on a day trip. Or stay the night before in the town of Hana, located 12 miles from the trailhead.

The Wailea Oceanfront Boardwalk Trail in Hawaii.

7. Wailea Oceanfront Boardwalk Trail


More a walk than a hike, the Wailea Oceanfront Boardwalk Trail rates low on the difficulty scale but high on the payoffs.

Along the 1.8-mile oceanfront route, you will be treated to endless ocean views, scenes of sea turtles frolicking in the lovely coves, and some of the most luxurious resorts around. The paved path has a few gentle ups and downs, but for the most part, it’s an easy, leisurely walk.

Pro Tip: Wailea Beach is a premier spot for taking in the sunset, and an evening stroll along the Boardwalk Trail will yield many spots for watching the sky turn to rich pinks and oranges as the sun dips below the horizon.

The Maunakea Trail in Hawaii.

8. Maunakea Trail

Big Island

Known as the big hike on Hawaii’s Big Island, the Maunakea Trail climbs the highest mountain in Hawaii.

The trail to the summit is 6 miles (12 miles round trip), and it traverses a whopping 4,600 feet in elevation gain -- climbing from 9,200 feet to 13,800 feet.

The Maunakea Visitor Station website cautions, “The average round-trip hiking time for experienced hikers is approximately 8 hours. Please know that your trip may take longer!” Hikers must be back at the visitor station by sunset or risk being stranded on the trail in the dark.

Pro Tip: Obviously, only the fittest of the fit should attempt the Maunakea Trail. But completing the arduous hike is an accomplishment to remember.

Akaka Falls State Park in Hawaii.

9. Akaka Falls Loop, Akaka Falls State Park

Big Island

Located about 3.5 miles from the former sugar plantation town of Honomu is the Akaka Falls State Park, where hikers can take in a relatively short, easy hike featuring two picturesque waterfalls.

The 0.4-mile trail traverses lush rainforest terrain and passes by the 100-foot Kahuna Falls and the 442-foot Akaka Falls.

Pro Tip: For those who cannot walk long distances, the Akaka Falls Loop offers relatively easy access to scenic waterfalls, although it does include some stairs and is not handicap accessible.

The Kalalau Trail in Hawaii.

10. Kalalau Trail


Crossing above towering sea cliffs and lush valleys, Kauai’s Kalalau Trail offers the only land access to the tropical paradise of Kalalau Beach.

It’s not an easy trek, however. The 11-mile trail (22 miles round trip) passes through five valleys, and is “mostly never level,” according to the website for Kalalau. Still, it is an iconic hike that is known worldwide for its access to the beautiful Napali Coast.

Pro Tip: For an easier but still challenging taste of the Kalalau Trail, plan to do the first 2 miles (4 miles round trip), starting from the north shore and ending at the remote Hanakapiai Beach. Reservations are necessary.

The Ke Ala Hele Makalae trail in Hawaii.

11. Ke Ala Hele Makalae, Royal Coconut Coast


For a less intense but still spectacular trail on Kauai, head to the paved Ke Ala Hele Makalae on Kauai’s Royal Coconut Coast.

The trail covers 8 miles over two sections and is perfect for walking, jogging, and bike riding.

Both the stretch between Lydgate Beach Park and Wailua Beach and the section between Kapaa and Ahihi Point offer plenty of opportunities to stop to take in the views or catch a sunrise.

Depending on which route you choose and your mode of transportation, the hike could take anywhere from 1 to 3 hours.

Pro Tip: Because the paved trail is separate from the road, it is a great place for kids, as well as for strollers and wheelchairs.

Plenty of other beautiful hikes are out there waiting to be discovered, including those on the less-visited islands of Molokai and Lanai.

This article is presented by KEEN Footwear. With their abundance of sandy beaches and tide pools, Hawaii’s trails are the perfect places for the lightweight KEEN SOLR Sandal. In hot-weather hiking, I love the airy feeling of a supportive sandal like the SOLR. The grippy sandals also support your feet on rocky hikes. Shop KEEN’s SOLR and other hiking shoes here.