Portugal·September - April
Trail Pursuit Portugal
Alentejo | Wellness & Adventure in the Heart of Portugal
VIEW DATES
Portugal·September - April
Alentejo | Wellness & Adventure in the Heart of Portugal
VIEW DATES
Duration: 5 nights (Sat-Thurs) Group Size: Up to 14 Accommodation: Boutique Countryside Guesthouse (exclusive for us) Dates: 27 Sept - 2 Oct 2025 & 11 - 16 April 2026 Meet Point: Lisbon Airport Difficulty: Beginner friendly, for guests in good physical shape who love adventure! Discover a new kind of adventure in southern Portugal, where wellness meets the wild. Over 6 unforgettable days in the Alentejo region, you'll hike, trail run, and wild swim through sun-soaked countryside, flow through energising yoga sessions, and sail across serene Alqueva Lake. By day, explore peaceful trails and vineyard-lined landscapes. By night, paddle under the stars and take a moonlit dip you'll never forget. Stay in a charming guesthouse in the historic village of Terena, unwind by the pool, and savour local wines on a guided tasting tour. Join a like-minded group of 15 for a unique blend of movement, connection, and calm — an adventure designed to reset and recharge.
Get ready for beautiful guided trail runs through the rolling hills of Monsaraz. (10-12km)
Discover the beauty of Alqueva Lake — Europe’s largest man-made lake — framed by untouched nature and endless skies. One day, sail its tranquil waters aboard a traditional Dutch boat. Another, glide beneath the stars on a peaceful night-time kayak adventure.
Experience the wonder of the night sky with the renowned Dark Sky Alqueva team. Learn about constellations, planets, and galaxies in one of the world’s first Starlight Tourism Destinations.
Head out on a scenic 14km hike through Alentejo’s expansive landscapes, soaking up the golden light and peaceful solitude.
Visit a local vineyard to learn, taste, and toast to an unforgettable adventure!
A relaxing stay at Herdade D. Pedro, a peaceful, boutique countryside guesthouse exclusively reserved for our group. Nestled among olive groves and wildflowers in rural Alentejo, this charming stay offers rustic comfort, open skies, a pool to unwind by, and space to truly slow down.
Alentejo, with its rich history and natural beauty, is known for vast plains, ancient cork forests, and charming villages. Steeped in tradition, it offers a peaceful escape, where olive groves and vineyards stretch across the serene landscape.
On day 3, spend the afternoon sailing on a traditional Dutch boat or exploring the calm waters of Alqueva Lake with SUP or a refreshing swim.
Unwind with soothing yoga sessions, designed to relax and rejuvenate your body and mind.
Rooted in the wild beauty of Alentejo, Rebecca is a yoga teacher with a deep connection to nature. Certified through The Sacred Fig, she blends mindful movement, strength, and playfulness — bringing calm, joy, and presence to the wellness adventure.
Passionate adventurer, runner, and outdoors entrepreneur, Ed is the founder of Trail Pursuit and will help deliver the experience to ensure you have an incredible trip.
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DAY 1
Welcome to Portugal!
You'll be collected from Lisbon Airport & transferred to our guesthouse in Alentejo. After settling in and meeting your team, you’ll head out on a beautiful stargazing experience on the Alqueva Lake.
Meals Included: Chef dinner
Accommodation: Boutique Country Guesthouse
DAY 2
After a delicious breakfast, get ready for an incredible day on the trails runninng through Monsaraz.
Start your day with an invigorating 12K guided trail run through the scenic Monsaraz countryside, where sweeping views and fresh air set the tone for adventure. Afterwards, we’ll head into the historic hilltop town of Monsaraz for a well-deserved lunch, soaking in its medieval charm and panoramic vistas.
The day winds down with a grounding yoga session to restore and relax both body and mind.
Meals Included: Breakfast & dinner
Accommodation: Boutique Country Guesthouse
DAY 3
We’ll begin the day with an energising active yoga flow to awaken the body and set a positive tone.
Then, we’ll hop aboard a charming vintage Dutch sailboat for a peaceful cruise across Alqueva Lake. Enjoy a picnic of local cheese, fruit, cured ham, and wine as we sail. We'll stop at Golden Island for some sunshine, a walk, or a refreshing swim. On the way back, you can even jump into the lake from the boat! It's a relaxing and memorable experience that feels like a small adventure at sea.
Or you can try stand-up paddle boarding for a bit of fun and movement. We’ll end the day with a gentle evening yoga session to unwind and restore under the Alentejo sky.
Meals Included: Breakfast & Dinner
Accommodation: Boutique Country Guesthouse
DAY 4
We’ll start the day with a scenic 14K guided hike from the accommodation to the historic village of Monsaraz, taking in the peaceful countryside and sweeping views along the way. As night falls, the adventure continues on the water. Our evening kayak experience on Alqueva Lake, part of the renowned Dark Sky Alqueva activities, begins at sunset, when the sky shifts through a stunning palette of colours.
As we paddle, your guide will share stories about the lake’s rich natural and cultural history. We’ll stop on a small island to enjoy local snacks and, for those who wish, a magical night swim. On the return journey, we’ll glide silently under a sky blanketed with stars, where the lake and heavens seem to merge into one unforgettable scene.
Meals Included: Breakfast & Dinner
Accommodation: Boutique Country Guesthouse
DAY 5
We’ll start the day with a guided (10-12K) trail run through the scenic countryside near Terena, exploring the stunning landscape of what locals call the Sacred Valley of Lucefécit. With its rolling hills, woodlands, and winding stream (if flowing), this culturally rich and spiritual area offers the perfect backdrop for a mindful and invigorating looped run starting and ending at our accommodation. Afterwards, cool down with a refreshing dip in the pool.
In the afternoon, we’ll head to the renowned Esporão estate for a relaxed and elegant wine tasting experience. Set among olive groves and vineyards, this historic estate showcases the Alentejo region’s diversity of soils and sustainable winemaking practices. We’ll tour the vineyards and learn about their organic methods before enjoying a guided tasting of two white and two red wines, either in the atmospheric cellar or out on the terrace with views of the surrounding plains.
Meals Included: Breakfast & Dinner
Accommodation: Boutique Country Guesthouse
DAY 6
After a restorative and adventure-filled week in the heart of Alentejo, it’s time to say goodbye. We’ll share one final morning together, perhaps a quiet coffee, a last dip in the pool, or simply a moment to soak in the stillness of the surroundings, before guests begin their journeys home. We leave with full hearts, new friendships, and memories rooted in nature, movement, and connection. Until next time!
Transfers back to Lisbon Airport.
Qualified Guides
Private transport in Portugal
x5 nights boutique countryside guesthouse (exclusive for us)
x2 guided trail runs (10-12km)
x1 guided hike (14km)
x1 Dutch sail boat experience
x2 vinyasa flow yoga sessions
Stargazing session with Dark Sky Alqueva Team
Local vineyard & wine tasting tour
x1 guided night kayak under the stars
Meals: 5 breakfasts, 5 dinners, all dietary types catered for
Wild swim spots and use of guesthouse pool
Pickup and drop off from Lisbon Airport
All route planning and logistics taken care of
An incredible adventure exploring Portugal's rural landscapes!
Flights to & from Lisbon Airport, Portugal
Lunches
Travel Insurance
Alcoholic drinks
Participants are required to be healthy & in good physical shape, managing a mix of activities across 6 days. Your adventure is completely customisable & you can participate in as many or as few activities as you wish!
A comprehensive kit checklist will be sent to all guests ahead of travel, this includes: - A good quality waterproof jacket - A fleece jacket or similar - Lightweight tees & shorts - Something warm for the evenings - Trail running shoes & run kit - Swimsuit - Trainers, hike boots & flip flops - Day rucksack - Cash - Personal toiletries & sun cream - Sunglasses - Quick dry towel / beach towel - A personal water bottle – you will be able to refill this - Dry bag (keeping personal items dry near water - i.e phone/camera)
You are required to take out cover, which most activity insurance companies will provide, this needs to include emergency evacuation and medial care. Sports Cover Direct offer a comprehensive range of sports travel insurance.
The itinerary and duration of the activities are subject to change due to group abilities and preferences, weather conditions and forecasts, water levels, special events of interest, etc. Trail Pursuit guides will do their utmost to ensure the best possible experience for their guests without compromising safety at any time. This may mean changing the original itinerary to avoid discomfort or risk which could be caused by exceptional situations, and Trail Pursuit reserves the right to alter the itinerary accordingly.
We have 3 options for you to choose: Payment Options: 1) Payment Plan - £150 deposit & then spread the balance over 4 monthly instalments 2a) Pay a 25% deposit & the balance by 1st Aug 2025. (SEPT 2025 TRIP) 2b) Pay a 25% deposit & the balance by 1st Mar 2026. (APR 2026 TRIP) 3) Pay in full Book with confidence: - 14 day cooling off period - If Trail Pursuit have to cancel or postpone the trip due to any reason, you can either be credited to a future trip or receive a full refund.
Really the best trip I’ve had in a while! Highly recommend Trail Pursuit to anyone who wants a fully organised, fun adventure with like minded people and full of activities. I spent 5 days in Slovenia staying beside beautiful Lake Bohinj with an amazing bunch of people and we managed to fit in hiking, swimming, kayaking, canyoning, trail running, zip-lining and cycling. A wonderful mix of being outdoors in stunning surroundings, having fun and challenging/pushing yourself. I also felt the trip was well planned and all activities had adequate guides and equipment to feel safe Highly recommend, thank you :)
Tamsin
Recently just completed the Slovenia trip with Trail Pursuit and it was an absolute blast. Ed, our guide and facilitator was extremely knowledgeable and thorough in making sure we were prepared and ready for each day. The pace of the trip was blended perfectly with downtime and activities where I never felt rushed or worn down. If I could give 10 stars I would. For me, it wasn't so much about the activities, it was the community and friendships I made over the week that have followed me back to London. It's a great networking opportunity to meet like minded people. I definitely would be back again.
Luke
I recently went on the Trail Pursuit Norway trip. It was truly an outstanding holiday - well organised and fun with the best guides. The views were spectacular, food was amazing and I loved the range of different accommodations (from tree tents to a fancy eco lodge with hot tubs!). All activities (trail running, hiking and kayaking) were well planned and paced. Special thanks to Ed and David for making this trip one in a million.
Katie
Top week of surfing, trail running and yoga in Morocco with amazing people, food and accommodation! I’m still buzzing from the whole trip and can’t wait to go surfing again next year!
Philly
Joined the Trail Pursuit events in the Lake District, Brecon Brecon, and most recently Norway. Great events, fantastic experiences, and met some awesome people there. Fully recommend to anyone who loves adventure!
Gavin
Absolutely loved my time on the TP Croatia trip. SO special to be able to explore wilder parts of Croatia and get right into nature. Whilst I loved each day and all the different activities, I feel that the people I met and connected with on the trip is what made it so incredibly special. 12/10 would recommend.
Lauren
I’ve just got back from the Morocco trip and what can I say… such an amazing trip with the most incredible people. Ed made everything so smooth with all activities thoroughly planned and prepped for. The accommodation was perfect, so relaxed (a real nice retreat after a long day of surfing, hiking, or running). I can’t recommend TP enough! Jump in!
Dan
Back in June 2022 I had the privilege of being part of the first 'team' to live the Norway experience. Having found the courage to travel by myself, I found it utterly fantastic from start to finish. Yes, it had its moments of challenge but this helped to make it such an amazing experience. Such a stunning location and well thought out loop above/within the majestic fjord. One of the best experiences I've ever had! As for the 'team' they were all such amazing people and it was a pleasure to share the experience with them, thank you!
Caroline
This was an incredible trip! I loved every minute! Amazing views and landscapes, challenging, beautiful hikes and the kayaking was awesome! We stayed in an amazing variety of accommodation and the food was plentiful and delicious! Can’t recommend enough! Thank you guys! I’ll be booking again! X
Laura
Completely surpassed my expectations, was an utterly magical week in Morocco - made some beautiful memories and friendships. It was my first time travelling solo, so needless to say I was a little nervous but I couldn’t have felt more supported and been surrounded by a friendlier and kinder group of people. The Trail Pursuit team were incredible from start to finish, answering my many questions pre-booking to planning one of the funnest weeks away. If you’re toying with going away with them - go for it! You won’t regret it!
Camille
I had the best time on a Trail Pursuit Adventure to Norway. It was a perfectly organised trip with an amazing range of activities. Ed was very friendly and inclusive of everyone. Would highly recommend TP to adventure seekers!
Emily
Nestled near the village of Terena, Herdade D. Pedro offers a tranquil retreat in the heart of Alentejo, exclusive for our group. Relax in the pool surrounded by nature, you'll come away feeling recharged!
Your own peaceful space to unwind.
The kind of evenings you'll wish could last forever.
All dietary types catered for. Please specify at checkout.
Trail Pursuit: Portugal is based in the Alentejo region — a peaceful corner of southern Portugal known for its rolling golden plains, ancient cork forests, and whitewashed villages. With a slower pace of life and vast, open landscapes, it’s a place to breathe deep, reset, and reconnect with nature.
Just 2 hours from Lisbon Airport, which is easily reached from most major European cities, it’s the ideal escape for those seeking wellness, adventure, and the raw beauty of Portugal’s countryside and coast.
Participants are required to be healthy & in good physical shape, managing a mix of activities across 5 days. Your adventure is completely customisable & you can participate in as many or as few activities as you wish!
If you have any concerns about your fitness level, please don’t hesitate to contact us so we can discuss your options and help you choose the right adventure holiday for you. hello@trailpursuit.com or call +44 7748 722282
We cater to all dietary preferences, so please share your requirements when booking. Our meals are prepared with fresh, high-quality ingredients and served in generous portions. The menu offers a variety of options, including chicken breast, seasonal vegetables, and both egg and meat-based dishes. You are welcome to arrive a day early & make your way back to the airport pickup if that is preferable.
Portuguese food is hearty, flavourful, and deeply rooted in tradition. It celebrates simple, high quality ingredients, think fresh seafood, olive oil, garlic, herbs, and seasonal vegetables. Dishes often reflect the country’s rural and coastal heritage, from grilled sardines and octopus rice to slow-cooked stews and creamy custard tarts. Meals are unhurried and generous, often shared around the table with local wine and plenty of warm conversation.
We provide all of the necessary equipment for the activities on our adventure holidays. This includes things like kayaks, helmets, harnesses, and other safety gear, as well as any specialised equipment that may be required for a particular activity.
Yes, the Trail Pursuit hosts and outdoor guides are very experienced with good English so you will have no problems in communication on the trip.
Nestled near the village of Terena, Herdade D. Pedro is a peaceful retreat in the heart of Alentejo. Surrounded by rolling hills and cork forests, the property offers rustic-style apartments with modern comforts including air conditioning, fireplaces, and fully equipped kitchens. Guests can relax by the pool and soak in the quiet beauty of the countryside. You will come away feeling recharged!
Twin rooms are available (same sex).
Yes spacious Twin Rooms with en-suites are available.
Same sex, similar age. If you are travelling with a friend and would like to be in the same room please let us know.
There will be a mix of guides hikes, trail running, kayaking, yoga & swimming. Included:
- x2 guided trail runs (10-12km)
- x1 guided hike (14km)
- x1 nigh-time kayak
- x2 yoga classes
- x1 Dutch sail boat experience
- Stargazing session with Dark Sky Alqueva Team
- Local vineyard and wine tasting tour
Yes, available payment options include:
1) Payment Plan - £150 deposit & then spread the balance over 4 monthly instalments (most popular)
2a) Pay a 25% deposit & the balance by 1st Aug 2025. (SEPT 2025 TRIP)
2b) Pay a 25% deposit & the balance by 1st Mar 2026. (APRIL 2026 TRIP)
3) Pay in full
Our meet point is Lisbon Airport & your hosts will meet you. Please let us know your flight details once you have booked & we will then coordinate pickups. You will be transferred to our Country Gueshouse in Alentejo, Portugal.
You are welcome to arrive a day early & make your way back to the airport pickup if that is preferable.
Lisbon Airport is served by direct flights from the UK and other major European airports, with flight times between 2-3 hours.
UK: Easyjet, TAP Air Portugal, Ryanair
Skyscanner is a great tool to see available flights. If you would like help coordinating, please do reach out hello@trailpursuit.com or call +44 7748 722282
Once you book your flight please let us know your arrival & departure times+day.
Yes, a Whatsapp Group will be made where we can confirm kit lists, logistics & answer any questions you may have. Team effort!
Absolutely, you are welcome to arrive earlier & stay longer after the trip if you wish. Please confirm your plan with us so we can coordinate transfers.
No, we welcome guests from all over the world!
Each group will have a maximum of 14 guests plus guides. We welcome guests of all ages who are in good physical health & up for adventure.
- A good quality waterproof jacket
- A fleece jacket or similar
- Lightweight tees & shorts
- Something warm for the evenings
- Trail running shoes & run kit
- Swimsuit
- Trainers, hike boots & flip flops
- Day rucksack
- Cash
- Personal toiletries & sun cream
- Sunglasses
- Quick dry towel / beach towel
- A personal water bottle – you will be able to refill this
- Dry bag (keeping personal items dry near water - i.e phone/camera)