Hawaii is a natural marvel and is filled with endless opportunities for outdoor recreation, including a vast selection of hiking trails and tours. Hundreds of trails across the island chain offer hiking, mountain biking, and climbing opportunities. While I’ve covered guides on a huge chunk of them, I know some travelers prefer to be guided by expert guides from local tour companies. 

 

These hiking tours expand all across the Aloha State in the most popular islands like Maui, Oahu, Kauai and Big Island. Many of these are local companies that have been operating for years now and which I’ve had my fair share of experiences with.  

 

Ensure you read through the section below outlining the basics of what you need to wear for your hiking tour and what I recommend for any hike. 

What To Wear For Hiking

First things first, check the weather before heading out and plan accordingly. Rain showers occur unexpectedly in Hawaii so it’s always good to be prepared. Where you plan to hike and the conditions around the trail can help determine what you need wear and what you can safely leave behind. 

 

The most important part of your gear is your footwear, which can make or break your hiking experience. You should opt for a hiking boot or shoe that you can comfortably wear for hours, preferably a pair that has already been broken in. The terrain across Hawaii can vary greatly and you’ll be best served by footwear that is at the very least water resistant, has firm traction on wet surfaces, and padded insoles for all-day walkability. 

 

After you’ve got your footwear sorted, the rest will depend on the tour and hike itself. Generally speaking, you’ll want loose, light layers that you can shed as needed. You should be able to get by almost year-round with shorts, a pair of fully cushioned socks, and a light top. If you see rain in the forecast, bring along a raincoat layer and if you would like a little extra space, bring along a small backpack. Some hikes, like the Kalalau Trail, will also require extra hiking equipment like hiking poles. 

 

Read through the guidelines of the tour you plan on taking, and often you’ll find a handy list of gear that might be useful for your specific trip. When in doubt, never be afraid to ask the tour operator what you need. 

1. Wailua River and Secret Falls Kayak and Hiking Tour

The island of Kauai is famous for secluded natural spots and this tour puts you face to face with one of them. It all starts with a kayak trip up the Wailua River, exploring the winding waterways surrounded by lush green forests.

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Along the way, your expert guide will discuss the wildlife and Hawaiian legends surrounding the location. This brings the trip to life and allows you to learn about the sacred nature of the place. After an exploration of the Wailua River Valley, you’ll park the kayaks and make a short trek to Secret Falls, also known as Uluwehi Falls. Visitors get the chance to walk through the waterfall and cool off with a refreshing and one-of-a-kind natural shower.

 

If you’re new to kayaking, instruction is provided, as well as all equipment necessary for the tour. The trip takes approximately 5 hours start to finish. 

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2. Maui Small Group Waterfall and Rainforest Hiking Adventure

Enjoy the benefits of a small group tour with this excursion through the lush beauty of East Maui. You’ll meet up at Kahului Park & Ride with the rest of the group of no more than 9 guests before being shuttled off to the trailhead down the iconic Hana Highway.

 

The hiking tour allows you to see and learn all about Maui’s ecosystems, traverse basalt rocks, and bask in the refreshing spray of several waterfalls. This will take up most of your day as it lasts 5 hours total. 

 

This tour includes transportation to and from the meetup spot, a seasoned local guide to describe everything in great detail, and a nutritious lunch. Wear comfortable shoes and swimwear since you’ll get the chance to enjoy waterfalls and freshwater pools.

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3. Diamond Head Crater Tour

Diamond Head Crater is near the top of things to see and do while in Hawaii, and this tour can take you directly to the iconic 760-foot summit trail.

 

After reaching the top of the crater, hikers can enjoy an unparalleled panoramic view of Oahu. With clear skies, it’s easy to spot the beauty of Honolulu to the west, and the many beaches that line the coast to the east. It’s a moderate hike but you can take your time and explore at your leisure.

 

The entrance fees and roundtrip transportation from Waikiki accommodations are included, as well as bottled water. This is a self-guided tour, and it’s a great deal for what you get. It’d be a great couple or small family outing, but you can enjoy it solo. 

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4. Napali Cliff Top & Waimea Canyon Hike

Kauai Hiking Tours offers a wide selection of hikes on the Garden Isle including this spectacular full-day adventure to the top of Napali Cliff. During the trek, you’ll climb to a peak that sits thousands of feet above the sea. There will be a breathtaking panorama of the lush green bounty that gives Kauai its name.

 

This is a hike meant for enthusiasts who are not afraid of a little mud, slippery terrain, and a steep overall climb. Keep this in mind when figuring out if you want to go on this journey, as it does require a moderate amount of physical fitness. If you’re up for the challenge, you will enjoy rewards for your effort along the entire hike, leading up to the grand finale at the top. Waimea Canyon to Waipo’o Falls is one of my favorite hikes and I’ve covered it extensively in the past.

 

 

 

5. North Shore & Waimea Waterfall Tour

If you’re looking for a tour that covers the North Shore of Oahu, book this full-day option that includes pickup and dropoff from Waikiki, full narration by a local expert, and admission to a botanical garden.

 

This is a true full-day exploration of all that the North Shore of Oahu has to offer. There are many stops along the way including Diamond Head State Monument, Halona Blowhole, Mokoli’i Island, and a stop at the famous Dole Plantation for a chance to enjoy some Dole Whip. These are some of the landmarks that anyone coming to Oahu should consider checking out. 

 

Throughout the course of the trip, you will pass by Hanauma Bay, Makapu’u Point, and the Banzai Pipeline, highlighting the many stunning natural features of the island.

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6. Hungaro Explorer Three Peaks Tour

Hungaro Explorer is a private company offering a thrilling 5 hour tour of the iconic Three Peaks of eastern Oahu. This stunning geological feature displays three jutting stone peaks in a row, and in this challenging hike, travelers summit all three in a day.

 

Over the course of a 4.5-mile trek, you will enjoy a good cardio climb, arrive at the exposed ridge line, and scramble your way up each peak. It’s part hike, part rock-climbing adventure, and all intense outdoor fun in the unrivaled Hawaiian outdoors.

 

It goes without saying but this is an adventure meant for those with an intermediate level of fitness and familiarity with rough terrain. There is work to be done and the payoff is worth it for those willing to put in the effort. I’ve mentioned Nando who runs Hungaro Explorer before in some of my other hiking guides, so I know he delivers excellent experiences.

 

 

 

7. Hawaii Forest & Trail Hidden Craters Hike

Hawaii Forest & Trail company hosts this spectacular adventure to the slopes of Kona’s volcano, Hualalai. You’ll get an exclusive view of the terrain that is only available thanks to Hawaii Forest & Trail’s relationships with private landowners in the area. It’s an insider’s scoop on some of the most impressive scenery just outside of Volcanoes National Park.

 

Guests trek 3-4 miles with a gain of nearly 1,000 feet of elevation, providing a stunning view of the west coast of the island as well as a better spot to view the front range of Mauna Loa to the east. 

 

Once you’re near the top of the volcano’s rim, you can climb through a once-active lava tube. It is a face-to-face encounter with the incredible forces that molded the entire Hawaiian island chain.

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8. Waikiki Tours Haleakala Hiking Tour

With Waikiki Tours, you can visit the Haleakala National Park, one of the crown jewels of the island of Maui. They offer an action-packed day of hiking, sightseeing, and a guided tour of the many features of Haleakala including the Rainbow Bridge, Hosmer Grove, and the crater of the volcano itself.

 

The price of admission includes transportation to and from, snacks, water, lunch, and outdoor gear upon request. If you need a warm jacket or a backpack and didn’t bring one along, they’ll provide one for your convenience.

 

Please note that this hike requires basic comfort with physical activity at high altitudes, as you’ll be hiking around 10,000 feet. If you’d like a less strenuous option, check out Waikiki Tours’ website for their full list of tours.

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9. Manoa Waterfall Hike

Get away for an afternoon during your stay on Oahu with this self-guided hike to the Manoa Waterfall. This is one of the easier and quicker hikes which makes it a great fit to fill out a few hours between other activities. 

 

In my experience, it is a bit touristy so expect to see traffic if you come during a busy time like in the afternoon. I’ve also covered in the past an alternative to Manoa Falls for those looking for something more isolated. 

 

All required fees, bottled water, bug spray, and a walking stick are included with your ticket purchase as well as a shuttle to where it starts. You’re free to take your time on this one and enjoy the untouched wilderness. Just be sure to wear comfortable footwear and bring along a layer for rain just in case.

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