
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 44 reviews 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.Posted on AlinTrustindex verifies that the original source of the review is Google. Amazing experience in Madeira, recommend itPosted on Arpana TikekarTrustindex verifies that the original source of the review is Google. Outstanding Hiking Tour in Montenegro – Highly Recommended! I had an incredible experience with this hiking tour company in Montenegro, which I found through Instagram. The itinerary was clear and well-planned, with no last-minute changes—everything ran smoothly. Our guide, Vera, was fantastic. She not only supported us throughout the hike but also helped with local touring advice and even assisted in booking activities with local guides. Her knowledge and kindness made a big difference. The tour was conducted in a sustainable and budget-friendly way, without compromising on quality. We also received great tips on local cuisine, places to explore, and shopping. I’m already planning my next hike with them. If you’re a hiking enthusiast looking for a trusted guide, this is the company to go with!Posted on Charlotte RobertsTrustindex verifies that the original source of the review is Google. It was honestly fantastic and the little additions like the meal with the driver and the local film at cinema Dede really added to the experience. Plus I was so lucky to have such a great group to share the experience with. I'd definitely look at another tour with Trailmates.Posted on Bty btyTrustindex verifies that the original source of the review is Google. I had such a great time in Montenegro. The hikes, the scenery, and of course the amazing company of our local tour guide. I felt very well looked after; everything was perfectly organized, and I truly appreciated the warm and friendly atmosphere that was created by our guides and group. 🥰🫶🏻 I’ll happily recommend Trailmates and I am already planning the next trip.Posted on Lian DelpeutTrustindex verifies that the original source of the review is Google. Ik heb echt een fantastische week gehad met Trailmates in Montenegro! Alles was goed geregeld en de organisatie was ook goed bereikbaar voor vragen. De transfers en accommodatie waren prettig. De hikes waren fantastisch en onze gids Vera was echt een topper! Normaal reis ik alleen dus ik vond het best even spannend om een week lang met anderen te zijn, maar we waren met z'n allen echt een fijne groep en ik vond het heel fijn om zoveel gelijkgestemden om me heen te hebben. Ik ben al aan het kijken naar een volgende trip met Trailmates dus dat zegt denk ik wel voldoende ;)Posted on Lynette CoxTrustindex verifies that the original source of the review is Google. I wanted to review this trip as my first experience of group travelling, it had been an incredible experience from start to finish, it was so well organised at every step with support provided when required. It was so nice to be in a group of like minded people making new connections even sharing accommodation which I was sceptical about in the beginning, but was totally comfortable from the start. Our guide Vera was incredible sharing so much information on the area always with a huge smile and encouragement when needed. As well as going the extra mile to help people organise out other activities outside of hiking such as spa treatments and water activities. The hikes themselves were incredible with stunning diverse scenery. Watching wildlife such as mountain goats was a personal highlight. The hikes were challenging with some small technical sections which made it more enjoyable. I would highly recommend this experience. Thank youPosted on Kylie SyTrustindex verifies that the original source of the review is Google. I’ve recently joined the Durmitor National Park hiking trip in Montenegro. As someone who enjoys exploring nature, but doesn’t know many people who are interested in doing so, I’m glad I found Trailmates Adventures, because I’m not comfortable hiking on my own on challenging routes. What I liked/went well: - I did not have to coordinate airport transfer on my own. I just had to arrive - The accommodation is close to the national park, supermarket, restaurants - Not having to bring my luggage around during the hikes - Option to have a private room for an additional cost. I also liked having a kitchen, especially the fridge, although I understand that it wasn’t initially the plan according to the description on the website - Our guide, Vera is a local and she shared with us some history and background of the places along the way. She also paced the hikes well and supported us on challenging points - Option to go rafting in the Tara River during the break - Meeting inspiring people from different backgrounds - Garry (Trailmates Adventures) is very responsive and helpful in the chats - Amazing views, mountain goats, dogs, swimming in the lake! What I underestimated and might help people who are similar to me: - For context, I mostly do strength training and short bursts of high intensity, and not a lot of endurance activities. My stamina definitely got challenged, but I managed to push myself to the summits in the end. I particularly found it difficult to hike down steeper, exposed declines due to fear and inexperience. I also did not know that there would be some light scrambling involved, but the former was more of the issue for me than the latter. Nevertheless, I was in a supportive and safe environment! - If you find that you’re too tired, you can always bail on going to the summit. I was just too stubborn to do that :D Overall, it was an eye opening experience for me, and I really enjoyed it! I’m looking forward to the next trip!Posted on Katie KissTrustindex verifies that the original source of the review is Google. Hi Garry, Oh, I can not describe in words what a wonderful week I had in Montenegro! Thank you for the great organisation from the first moment till the last! The group has been so lovely, we had great fun every day, and Vera was truly amazing! She is a gem with her kind nature. She guided us through our highs and lows and assisted with activities for the day off! We all loved her! Our accommodation was great, and the lady communicated well and assisted with fresh towels, etc, whenever we needed. Thanks again for the experience, and I am looking forward to coming for another trip!Posted on HaweaberryTrustindex verifies that the original source of the review is Google. I joined Trailmates Adventures for their hiking trip to Madeira and had an amazing experience. The hike selection was great, the organization smooth, and everything felt well thought through. What really made it special, though, were the people – such a fun and supportive group that turned the trip into something unforgettable.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.
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.
Trip status
Trip status
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.