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Your Next Adventure Awaits
Solo Travel, Shared Experiences
Our trips are designed for solo adventurers, creating the perfect environment to meet like-minded people and build lasting friendships.
Unforgettable Destinations
We take you to some of the most awe-inspiring hiking destinations. Each trip is carefully curated to offer the perfect balance of adventure and discovery.
Stress-Free & Fully Organised
We handle all the logistics, from accommodations to trail routes and group activities. All you need to do is pack your bag, show up, and immerse yourself in the experience.
Comfort & Connection
Stay in comfortable, communal accommodations designed to encourage group bonding and relaxation after a day of adventure.
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Get started with handpicked top rated trips.
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30+ Incredible Destinations
Don’t just take our word for it
EXCELLENT Based on 68 reviews Posted on Alice DykesTrustindex verifies that the original source of the review is Google. I had a great time in Madeira with Trailmates! I felt like our guide was really accommodating and did his best to support everyone. He was great at keeping our spirits up with humour too when the weather wasn’t playing ball. I loved the hiking and got some great photos. The final day when we climbed Boca da Corrida was amazing! Thanks so much for a fab trip!Posted on Daniel MarshTrustindex verifies that the original source of the review is Google. I went on the March 2026 trip to Madeira with Trailmates and loved every second of it, the organisation was amazing, and Paulo the guide and Miquel the driver were so friendly and great at what they do. Our group had an amazing bond with each other, it was my first ever solo trip and the whole experience made me learn so much about myself, I’d highly recommend Trailmates to anyone!Posted on Emilia NicolaeTrustindex verifies that the original source of the review is Google. Hiking Madeira with trailmatesadventures was an unforgetable experience. The island is an outdoors heaven for nature enthusiasts and hiking lovers, having had the chance to enjoy Madeira with trailmatesadventurs meant brain was switched off not having to do with any organising bits, everything was thoughtfully planned, from airport pickup with Niki welcoming us with a bright smile and ready to answer all our questions and help out. Also, they made sure we did have some comfort to ease into the hikes with the morning stop for great coffee and fuel for the day. Paulo was our guide and was leading the group with a lot of good energy and made sure everyone had their adventure wishes fullfilled at their own pace. Accomodation was in the heart of the old town, what else could one ask for?! As a bonus, the fellow hikers I've met were such an amazing bunch of people, hiking alongside the group was awesome. 100% recommend trailmatesadventures!Posted on Karolina LitwinTrustindex verifies that the original source of the review is Google. I joined the trailmates in Madeira March 2026 and I loved it. The guide Paulo is very dedicated and passionate about his job, Miquel the driver was also very friendly. Any requests I had were delivered right away. Niki is so helpful with organising any extra stuff outside of hikes. I met some lovely people and learned a lot about myself during the trip. Madeira is a paradise. Can’t wait for another trip with trailmates. I feel refreshed and well rested!Posted on Magatha MarquettiTrustindex verifies that the original source of the review is Google. I had an amazing trip to Madeira with Trailmates! Everything was very well organised and the hikes were absolutely beautiful. The group atmosphere was friendly and fun, which made the whole experience even better. I would definitely travel with Trailmates again and highly recommend them!Posted on Alessandra MazzolaTrustindex verifies that the original source of the review is Google. I did the hiking trip in Madeira. It was such a great experience , I did enjoy the challenge of the hike rewarded by spectacular view. We had a very nice and expert guide. The local representative was really kind. Perfect organisation. I do recommend this trip !Posted on William von ArendTrustindex verifies that the original source of the review is Google. I joined their trip in Oman and had a great time. The group was fun, the trip was well organised and great value, they had planned some beautiful routes, I would definitely recommend this tour.Posted on Iveta KrškováTrustindex verifies that the original source of the review is Google. I joined Georgia trip in September 2025 and it was super nice experience :) Hiking with the group was fun as we matched on sense of humor perfectly, food was delicious, local people welcoming and mountain sceneries just breathtaking! Hope to join soon again in another destination! :)Posted on Silvy ConstantinTrustindex verifies that the original source of the review is Google. I enjoyed the hiking trip to Oman even more than I expected! Good planning, good accommodation, amazing landscapes, very cool hikes and canyoning! Make sure to dress modestly, the locals will appreciate it.Posted on LaraTrustindex verifies that the original source of the review is Google. My trip to Oman (Feb 2026) was a great mixture of challenging hiking and rewarding scenery. It was really awesome to experience a new country this way and with a lovely group of people. Big thanks to Trailmates Adventures and to Rawnaq Travel Oman for the organization and activities!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
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Book Your Trip Online
Choose your dream hiking adventure and secure your spot in just a few clicks. No stress, no hassle—just pure excitement as you prepare for the journey ahead!
Arrive & Meet Your Crew
From the moment you land, we’ve got you covered! Enjoy a seamless airport pickup and meet your fellow adventurers—soon to be your new trail family!
Hike, Explore & Connect
Breathe in the fresh mountain air, take in breathtaking views, and share unforgettable moments with an incredible group of like-minded explorers!LIMITED SPOTS. LIFELONG MEMORIES.
Ask Us Anything
We can often accommodate early arrivals or extended stays. Additional nights are subject to availability and standard rates apply.
We organise you an airport pick-up to be taken to your accommodation to meet the group and guides.
We also organise you a drop-off at the end of your trip and these costs are included.
We provide towels and bedding. It’s essential to bring comfortable walking shoes. Prior to your trip, we’ll advise you on appropriate clothing based on the expected weather conditions. No technical equipment is needed.
Don’t worry, we’ve got you! You definitely won’t be alone as we hear this multiple times on every trip. Many of our guests overthink it and then have the best holiday of their lives and wish they’d done it sooner. You’ll meet lots of people in the same situation as you and get enjoy this wonderful experience with new friends from all walks of life.
Yes, private rooms are available upon request. Please note that there is an additional cost for single occupancy, which varies depending on the destination. You will be able to select this option at the checkout page. If you’re happy to share then a twin room is included in the price and you’ll have the chance to get to know one of your fellow travellers much better.
Our tours include accommodation, transfers, guided hikes, transportation to and from trailheads. Some locations also include a kitchen or complimentary breakfast. Please check individual destination pages for a full inlcusion list.
Although we have business insurance to cover you, personal travel insurance is mandatory in case of flight cancellations, medical emergencies or any other unforeseen circumstances.
Our groups are very international and we have guests from all over the world so we ask that you book your own flights. Details of the meeting point and time can be found on the individual destination pages or you can contact us first if you aren’t sure.
You can choose to make a 30% deposit and pay the remaining balance at least 30 days before the tour starts, or alternatively, pay the full amount in one go.
For cancellations, a full refund will be given provided you notify us at least 30 days before your trip. After this time, refunds are not available.
Our hikes are designed for individuals with a good general level of fitness. While the trails are mostly non-technical, expect several hours of walking each day. On our most challenging hikes we try to offer an alternative for those who feel like have an easier day.
If fitness is a concern, please contact us.
Our groups usually consist of individuals aged between 27 and 49 years old. If you are outside of this range but feel like you’re a great fit for one of the trips, you’re also very welcome!
The group sizes can vary, however we typically have groups of 8-15 people plus guide(s).
The groups are a great mix of nationalities and usually around 50:50 male/female ratio. If you’re interested to know who is joining a particular group, just ask!
All the trips you can see on our website are guaranteed to run so you can make your travel arrangements right after booking without worrying about cancellations.
That’s completely up to you! If you’d like to give something to the driver or guide at the end, then you’re more than welcome. The amount you give is also completely at your discretion and can be done privately if you wish.
Yes! We can create a private trip package for groups in any location for dates of your choice. For this kind of package it should be booked long in advance. Contact us for more information.
We work with local guides who know the towns, hikes and people better than anyone else. We are constantly assessing things on the ground and your safety is always our upmost priority.
Of course! Although our groups are made up of mostly solo travellers you are more than welcome to come with friends or family members.
A few weeks before every trip we set up a WhatsApp group chat for you to get to know your fellow Trailmates or ask any questions you may have. You can also use the group to share photos/videos during the trip and keep in touch afterwards.
We know that some companies allow you to see information of exactly who is signed up to each trip but we believe that there is no advantage in trying to match yourself to people you have never met. Personalities and characters are nothing to do with age, gender or nationality.
Of course! If you want a free day, want to visit something else, don’t feel or 100% or all of the above then there is no issue in skipping a hike. You can do as many of the hikes as you like, some days may also have an option to do a partial hike or explore a village while the others are hiking so please ask if you are ever thinking about this.
One month before your trip a WhatsApp group will be created for you to see who’s going to be joining you on the trails. It’s also a great place to share photos and make dinner arrangements during the trip.
We try to keep driving to a minimum each day so most hikes are less than an hour’s drive from your base, some we can even start the walk from the accommodation. Our general rule is no more than 1,5 hours driving unless a place is really special and worth the extra journey. If driving time is a concern for you just let us know and we can give you more details about a specific destination.
