
Your adventure begins as you arrive in Hawaii, where transport will be arranged to collect you from the Kauai island’s Lihue Airport. It’s well connected to the US and Europe, making your journey smooth and hassle-free.
To make the most of your trip, we recommend arriving in the morning or afternoon, giving you time to settle in and it’s a great opportunity to meet your fellow adventurers. If you’re arriving a day early, we can suggest excellent accommodation options to ensure a relaxed start to your journey.
For the duration of the trip, you’ll be based in Kapaa, right on the beach. This means you won’t have to carry all your belongings from place to place, and after each day of hiking, you’ll return to the comfort of a warm shower and a cosy bed. Get ready for an unforgettable week exploring one of US’ most spectacular mountain landscapes.

Click for Route Map : 📏 10 km ⏱️ 4–5 h ⬆️ ~500 m 💪 ●●●○○ — Moderate
Beginning from a quiet trailhead high above Waimea Canyon, the Awa‘awapuhi Trail winds through lush native forest filled with birdsong and filtered sunlight. The first stretch is cool and shaded, descending gradually along a well-maintained path lined with ferns and wild ginger. As you near the end, the trees open to reveal a breathtaking panorama of the Na Pali Coast — vast cliffs dropping straight into the turquoise Pacific, ridges layered in deep green and gold light.
The return is a steady uphill climb, but the forest shade and gentle grades make it manageable. Along the way, the shifting light through the canopy gives the trail an almost meditative rhythm. Most hikers take a long break at the viewpoint to soak in the silence and the sheer scale of the landscape. It’s one of Kauai’s signature hikes — dramatic, peaceful, and a perfect balance of effort and reward.

Click for Route Map : 📏 20 km ⏱️ 6–7 h ⬆️ ~650 m 💪 ●●●●○ — Challenging
The extended Jurassic Park Gate Trail offers a full-day adventure through some of Kauai’s most cinematic and remote landscapes. Beginning along the familiar red-dirt road through dense tropical forest, the route continues well beyond the original gate site, following a rugged path deeper into the valley and up toward the surrounding ridgelines.
As the trail climbs, the scenery unfolds in layers — steep green cliffs, waterfalls glinting in the distance, and wide vistas that feel straight out of a movie. The path alternates between open meadows and shaded forest, often muddy and uneven but rewarding at every turn. You’ll pass through areas where the sounds of birds and rushing streams replace all signs of civilization, offering a rare sense of isolation.
The return follows the same route, with long downhill sections and expansive views back toward the ocean. This longer version transforms a short photo stop into a true Kauai backcountry experience — remote, wild, and deeply atmospheric. Bring plenty of water, sturdy shoes, and expect to finish tired but exhilarated.

Click for Route Map : 📏 13 km ⏱️ 5–6 h ⬆️ ~650 m 💪 ●●●●○ — Moderate-Challenging
One of Kauai’s most iconic hikes, the Hanakapi‘ai Falls Trail combines coastal drama with lush jungle and a towering waterfall finale. Starting at Ke‘e Beach, the route follows the first section of the Kalalau Trail along the rugged Na Pali Coast, where cliffs rise sharply above turquoise waves and seabirds circle high overhead. After about two miles, you reach Hanakapi‘ai Beach — a wild, beautiful spot perfect for a short rest, though swimming is unsafe due to strong currents.
From there, the trail turns inland and begins a steady climb through dense bamboo forest and river crossings toward the falls. The path can be muddy and slippery, but the reward is unforgettable — Hanakapi‘ai Falls plunging nearly 90 meters down a sheer cliff into a cool, clear pool. Mist fills the air, and the sound of the water echoes through the valley.
The return retraces your steps along the same route, with sweeping views back toward the ocean. This trail captures the essence of Kauai’s wild side — lush, demanding, and breathtaking from start to finish.

A free day on Kauai without hiking opens up endless ways to slow down and explore the island’s more relaxed side. Start the morning with a drive along the south shore to Poipu Beach, where you can snorkel with sea turtles or simply enjoy the calm water and golden sand. Nearby, the Spouting Horn blowhole offers a dramatic display as waves surge through a lava tube and spray high into the air. For a more cultural start, visit the Kauai Coffee Estate for a tasting and a self-guided stroll among the trees — the views over the plantation and ocean are beautiful, and the samples are generous.
In the afternoon, take a scenic drive up Waimea Canyon Road for lookouts that require no hiking yet deliver incredible views across the “Grand Canyon of the Pacific.” On the return, stop in the small town of Hanapepe, known for its local art galleries, slow pace, and weekly Friday night art walk if you happen to be there. Alternatively, head north to Hanalei Bay for a relaxed lunch and a few hours on the beach. Rent a paddleboard, take a surf lesson, or just watch the changing light on the mountains. As evening falls, find a quiet spot on the west coast for sunset — Salt Pond Beach Park and Polihale State Park are both unforgettable places to end the day, with wide horizons, soft light, and the deep calm that makes Kauai so special.

Click for Route Map : 📏 18 km ⏱️ 6–7 h ⬆️ ~750 m 💪 ●●●●○ — Challenging
The long version of the Waimea Canyon Trail showcases the full scale and beauty of Kauai’s “Grand Canyon of the Pacific.” Beginning near the Kukui Trailhead, the route descends through forested slopes alive with birdsong before opening to sweeping views of red and green canyon walls carved deep by the Waimea River. As you follow the rim and interior paths, the landscape shifts constantly — rugged cliffs, narrow ridgelines, and pockets of lush vegetation glowing in the sun.
Midway through, the trail dips toward the canyon floor, where the temperature rises and the air feels still and wild. Crossing streams and open sections, you’re surrounded by towering walls streaked with color — ochre, rust, and emerald — a reminder of how ancient and alive this landscape is. The return climb is demanding but deeply rewarding, each bend revealing another glimpse of the vast canyon and the ocean beyond. This full-day route captures the essence of Kauai’s backcountry: raw, remote, and unforgettable.

Click for Route Map : 📏 11 km ⏱️ 4–5 h ⬆️ ~300 m 💪 ●●●○○ — Moderate
The Alaka‘i Swamp Trail offers a completely different side of Kauai — high, misty, and otherworldly. Starting from the Pu‘u O Kila Lookout at the end of the road in Koke‘e State Park, the trail crosses boardwalks and muddy forest paths through one of the wettest places on Earth. Instead of beaches or ridgelines, you’ll find cloud forest filled with native ferns, moss-covered trees, and the songs of rare Hawaiian birds echoing through the mist.
On clear days, the payoff is extraordinary: a sweeping view of the Wainiha and Hanalei valleys from Kilohana Lookout, with the ocean shimmering far below. More often, though, the landscape reveals itself in glimpses — clouds drifting through the trees, sudden patches of sunlight, and the quiet sense of being far above the rest of the island. The trail can be slippery and slow-going, but it’s well worth it for those who love Kauai’s wild and mysterious side. Bring sturdy shoes, layers, and be ready for weather that can change in minutes.

After an incredible week exploring the wild beauty of Kauai, it’s time to pack your bags and begin your journey onwards. Transport will be arranged to take you to the airport.
If you’re extending your stay, there are plenty of incredible places to explore beyond the mountains. We’d be happy to share recommendations to help you make the most of your time.
As you leave Hawaii behind, you’ll take with you memories of emerald cliffs, turquoise waters, and unforgettable adventures in one of US’ most breathtaking landscapes. Until next time!
Please note: The itinerary may be changed due to weather or trail closures. Your safety is always our upmost priority. Your local guide will always keep you updated on what’s coming the next day and if there are any changes.
EXCELLENT Based on 52 reviews Posted on Sarah GTrustindex verifies that the original source of the review is Google. I joined the Oman hiking trip and it was a great experience! The program was well structured, with an amazing international group with a good age mix. The accommodation felt very authentic and each day offered different landscapes and nature, so every hike felt unique. It was my first trip with Trailmates and I can highly recommend!Posted on R. Th.Trustindex verifies that the original source of the review is Google. I just finished the Oman hiking trip with Trailmates Adventures, and it was spectacular. I was looking for a mix of genuine adventure and a great community, and Trailmates delivered on both. The group was incredibly welcoming. It felt less like a formal tour and more like a trip with a group of friends. We didn't just see the mountains, we experienced Omani hospitality and authentic local food. Everything was well-organized. It was an adventure with an amazing group of people!Posted on Ruben VlekTrustindex verifies that the original source of the review is Google. Just returned from a great week in Oman! It was one of the few really authentic trips which I made, and the first with Trailmatesadventures. I liked the mixed group (32-62 yrs) of inspiring people. The whole trip was well organized, but with enough room for flexibility (e.g. alternative hikes, activities). I’ve never joined any group trips before, but this was very relaxed just having to book the trip and flight (and seeing various highlights without having to do the research).Posted on Oksana BolkinaTrustindex verifies that the original source of the review is Google. I had a really enjoyable trip to Madeira, despite the unusual weather and unexpected flight cancellations. The hikes were great (our guide Paulo just amazing), and the orga on the island was very good. I didn’t have to worry about anything, which is exactly what I wanted for this trip.Posted on Peder OlesenTrustindex verifies that the original source of the review is Google. I very much enjoyed the hikes in beautiful Madeira. The company was excellent, and our guide André was extremely knowledgeable and helpful throughout the week. If I had to point to anything that could be improved it'd be at the arrival at the apartments; it wasn't clear where luggage could be safely stored until check-in, so we needed to improvise a bit at that point. Also, the lock in the apartment door wasn't in the best condition. However, these very minor issues don't really subtract from what was overall a superb experience!Posted on samantha lambertTrustindex verifies that the original source of the review is Google. My trip to Madeira was absolutely fantastic. I felt very safe with Andre as our guide, he was attentive and thoughtful, even adjusting some of the hikes to accommodate the group when the steep downhill sections proved challenging. The accommodation was great, especially the location, which was perfect for afternoon swims in the sea and easy access to restaurants in the evenings. I’d definitely consider booking again for a future adventure.Posted on Gillian OTrustindex verifies that the original source of the review is Google. Had a fantastic time in Madeira, a really nice mix of hikes to see different parts of the island and the organisation was brilliant, loved it!Posted on Cesar izquierdoTrustindex verifies that the original source of the review is Google. Incredible experience in Madeira. Very well organized trip, professional guides, nice combination of hikes with different difficulty levels and varied landscapes. If you want and adventurous holiday with no worries about organizing it, try it!Posted on Karen AlgeoTrustindex verifies that the original source of the review is Google. Did the Moffat, Scotland trip lead by Gary and Tom. Had such a good time, gorgeous views and we got crazy lucky with the weather in September. The duo were super receptive and flexible to the group’s ability and morale, and were quick to think on their feet to adjust the itinerary to work better for us all. A lovely group of female hikers too. Would definitely book in again with them ❤️Posted on Maja De BritoTrustindex verifies that the original source of the review is Google. I joined the Scotland hiking trip. A top notch, 5-star experience from planning stage to saying goodbye with the group and the guides. Garry was immensly helpful with bits and pieces of information that made organising my traveling to Scotland and arriving to the meeting place a smooth and pleasant experience. Communication throught Whatsapp was effortless and always with a very quick reponse. I felt everything was taken care of, with a ready and helpful response for every inquiry or need. The hikes themselves were wonderful, both guides were very flexible and adapted to our level of fitness, but also our interests. Very grateful that we had the opportunity to see some off the beaten track routes. I have several food intolerances and this was never a limitation on this trip. There were always options, be it through the possibility of preparing my own food as well as having many choices eating out. I've been recommending their hikes to my friends and will definitely join for other destinations.Verified by TrustindexTrustindex verified badge is the Universal Symbol of Trust. Only the greatest companies can get the verified badge who has a review score above 4.5, based on customer reviews over the past 12 months. Read more
Please note: Airfares and meals are not included in the trip price unless mentioned above. This gives you the flexibility to choose your preferred flights and enjoy local dining experiences at your own pace.
You’ll be staying at Kauai Shores Hotel. It’s a family run hotel, right next to the beach. You will be staying in a twin room with private bathroom. Private rooms are available on request for a supplemetal cost. There is the option to buy a hearty breakfast below the hotel. There is also Wi-Fi, a beach, garden, cafe, hair dryers and laundry.
Join fellow adventurers on an unforgettable journey through the stunning landscapes of Kauai. Spaces are limited, so secure your spot today and get ready for an epic mountain adventure in Hawaii.
Trip status
Trip status
Secure your place with a deposit of 30%. Final payment is due 30 days before departure. When booking a trip starting within 30 days, deposit payments are not accepted.
If your circumstances change and you can no longer make it, you can transfer your deposit to another trip up until 30 days before departure.
Prices are per person, based on two people sharing a twin room. For a private room, please add this at the checkout page.
Secure your place with a deposit of 30%. Final payment is due 30 days before departure. You can also pay in full immediately if you wish.
If your circumstances change and you can no longer make it, you can transfer your deposit to another trip up until 10 days before departure.
Prices are per person, based on two people sharing a room. Any supplemental costs will be shown on the next screen.