Portugal, Gibraltar, Morocco & Spain

21.03.

 – 28.03.2026

Monkey Mountain Route

  • Sold out

Monkey Mountain Route

Our youngest and probably most funkiest route, and we’re taking you along for the ride. Set sail from the stunning Algarve, where golden atlantic cliffs meet turquoise waters, and hidden bays invite you to anchor and explore. Swim, snorkel, or simply relax on deck as the sun kisses the horizon.

We continue south to Gibraltar, where dramatic rock formations rise from the sea and the vibrant town offers a mix of British culture, history, monkeys, and breathtaking views. From there, the journey leads across the Strait of Gibraltar to Ceuta, a Spanish enclave in North Africa, Morocco. Experience a fascinating blend of European and African vibes, explore local markets, and wander charming streets framed by stunning coastal scenery.

This route is for adventurers who love hidden gems, turquoise waters, and discovering the unexpected. Every day is a new experience: from secret beaches to lively coastal towns.

Come aboard and be among the first to explore this unique Mediterranean adventure!

21.03.
 – 28.03.2026
//

1.020

Highlights

  • The Atlantic
    Where European charm meets Atlantic soul.
  • Oriental
    This trip bringst you from Spain to North Africa. Join us to Morocco.
  • British culture
    Parts of this journey are in british Gibraltar. Feel reel UK vibes in the middle of Spain.
Sea State

Every Trip has some swell, but it is always bearable. The scale indicates whether the trip is rather calm or you have to expect a bit more swell.

Nature

The nature on our trips is always stunning, but some trips offer more focus on nature than others.

Adventure

Incredible experiences never come amiss with us. Some trips are more relaxed, while others provide a lot of action, e.g. in nature.

Sailing Time

The scale shows whether these Trips include more or less time for just sailing at sea.

Sea State
Nature
Adventure
Sailing Time

What you need to know

Start
Finish

* The exact meeting point and location of the boats will be communicated on Saturday.

Included
Excluded
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1.020

per Person

Not taxable according to § 3b para. 1

Extra 5% off
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4.9
Top Rated Trips
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Sailing Boat

Your cozy home on the water

Philosophy

This is what Pirates stands for
Individual travel

Those who know us know that we focus on quality instead of quantity. For us, it's the person behind every booking that counts! With us, small group sizes instead of mass tourism are the order of the day.

Group feeling

As a small organizer, this is our hobbyhorse. Pizza nights, road trips, night hikes, funny stories. Be prepared for teamwork on board and shared experiences that you won't soon forget!

Safer space

It is important to us that every guest feels comfortable on board, regardless of their origin or sexual orientation. Therefore, for us it is quite clear: There is no place for racism, sexism, homophobia or discrimination of any kind! Solo female travelers can also count on a guaranteed female cabin pairing, so you always feel at ease on board.

Sustainability

We care about nature! We design our trips to be as environmentally friendly as possible. Our focus is on protecting the sea - we let ourselves drift with the wind, rely on environmentally friendly soaps and avoid unnecessary waste. Our merch is fair trade - even our web host is green!

Plant-based

Vegan lifestyle and a memorable vacation? With us, nothing stands in the way. We cook vegan food on our yachts. During our joint restaurant visits ashore, you’ll have the chance to enjoy local dishes. So if you eat milk products, eggs or meat, you won’t miss out on land either.

Creativity and freedom

We are hungry for adventure and want to experience something. Freedom and creativity have been driving Pirates of Paradise since day 1. With us you can live your life to the fullest!

Reviews

What our guests say
All reviews
Google
Google
Trustindex
Trustindex
Excellent4.9136 reviews
4.9
Excellent136 reviews
Excellent4.9135 reviews
4.9
Excellent135 reviews
Excellent5.01 reviews
5.0
Excellent1 reviews
Posted on Google Google
Roberto E
June 25, 2025
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I joined the sail&learn trip and was the best decision ever. Best crew, fantastic people and authentic sailing experience. The passion and know how of the skipper made this trip super interesting. We had the chance to learn the basics of sailing and actually supporting the crew with hands on. We got spoiled with good healthy food, pizza night, wild hiking an and movie night (choice of the movie is debatable <3). I will go back for sure for another adventure.
Posted on Google Google
Amy A
August 9, 2026
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Best trip I've had! I spent a week on the boat travelling around Sicily. The trip was well thought out, with the option to opt in or out of any hikes and activities. The crew on board were super welcoming and made me feel very comfortable and extremely well taken care of throughout the trip. The boat was also well equipped with anything you could ever need, and the food was amazing! It was a beautiful experience full of amazing views, great connections and a perfect balance of relaxation and activity. Honestly I can’t recommend them enough. Will definitely be booking another trip with pirates of paradise 🫶🏼
Posted on Google Google
Niklas G
July 5, 2025
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I had a very nice and relaxing week with the Pirates. Yenzi does a great job as skipper and, despite the sailing and organizational stress, always has an open ear and time for conversation. Along with Yenzi, other Pirates crew members were on board who made sure that cooking, washing up, and cleaning up went smoothly. I've never experienced anything like that before. Simply outstanding! The pre-planned meals were always delicious and imaginative and even catered to me, a non-vegan. The boat has several upgrades and offers so many amenities that charter boats can't offer! Because the crew lives on the boat permanently, it's much more homely and lovingly furnished. I find little mementos of past trips everywhere in the boat, which quickly makes you feel at home. Overall, Pirates of Paradise simply puts more attention to detail, and in this respect, Yenzi and his crew are way ahead of larger providers. Definitely a reason for me to come back.

(Translated by Google, see original)
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Giulia N
September 25, 2023
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We went to Greece and didn't know exactly what to expect or what it would be like. In the end we were just thrilled, we met great new people, we had adventures and relaxation, we swam in caves, jumped off cliffs, had great food and spent wonderful evenings on the sea. The whole crew has grown close to our hearts and we definitely weren't there for the last time.

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Posted on Google Google
Patricia R
May 7, 2026
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Great crew, good vibes, a beautiful boat, and really good food – what more could you want? Sailing with the Pirates is not only an adventure but also the perfect way to unwind and relax. An unforgettable experience with many special moments. I'm already looking forward to the next sailing trip!

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Posted on Google Google
Dustin D
August 4, 2025
Trustindex verifies that the original source of the review is Google.
10/10 experience. I now have an earring/stud.

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Posted on Google Google
Martin K
January 14, 2019
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+0
One of the best vacations I've taken. It was the perfect mix of tension in secluded bays, celebrations in awesome locations and nice get-togethers. The yacht was also modern and in good condition. Only recommended!

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Stavros A
January 26, 2022
Trustindex verifies that the original source of the review is Google.
A good friend saw a post on Instagram and gave me the idea. I hadn't done anything similar before so I didn't know how the week would go. On the first day I was very happy to have embarked on this little adventure. The people were friendly and open so it wasn't difficult to get on the same wavelength. The group quickly became a small family with whom I laughed and experienced a lot. There are many beautiful moments that I could list here, such as sleeping on deck under a clear starry sky, sitting around the campfire or celebrating with the whole group. In 2021 we were on the Athens route and we have already booked another route for 2022. Best regards Stavros

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Posted on Google Google
Isabel K
January 24, 2022
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I had an incredibly nice sailing trip with the Pirates. With lots of good food, spontaneous adventures and great people! After a week it felt like a family. I can recommend it 1000%.

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Posted on Google Google
Svenja M
August 29, 2024
Trustindex verifies that the original source of the review is Google.
For the cool kids. We were on a crossing as a couple. This is not an officially advertised trip, but it is just as commercial and set up with the same general conditions. Basically, everything is as described on the website: the crew is nice, the waters and destinations are amazing, and we cook fresh and delicious vegan food together every day. I think the idea and concept are great, but I see room for improvement in the implementation. Unfortunately, criticism was reacted to very sensitively and dismissed as very far-fetched. I therefore don't want to go into my own personal impression any further, I think it just wasn't a good fit on a human level. In my opinion, the following things are important to know before booking a trip with Pirates: The trips are designed for young people. This is also how it is described on the website and this is also reflected in everyday life, which is free and flexible, at times unstructured and chaotic. I myself am in my mid-30s and consider myself to be quite a free spirit, but at times I felt really old and worn out. The conditions on board are cramped. Some crew members do not have their own cabin and sleep in the common area or on deck. During our stay on board, a toilet was also broken, which smelled and looked very unpleasant. The heat below deck is sometimes unbearable, especially when cooking, and sleep is out of the question on warm nights. If mosquitoes have found their way on board or the crew, who were previously too tired to wash up, turn up the volume again and make a fuss right above your bunk... you will feel a few years older by the next morning at the latest. But still: you can cope with little sleep and privacy for a week, it's worth it. I would recommend everyone to see for themselves... just don't do too many Insta stories, otherwise you'll miss the real magic of this tour.

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Monique B
January 24, 2022
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Montenegro Tour: Simply an amazing trip that you won't soon forget in your life. Great people, relaxed sailing and a great organization. Want to book the next trip straight away ☺️😍

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Maximilian J
October 12, 2024
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Extraordinary trip, with a special crew and unbelievable places. This isn't an all inclusive trip, it's a unique travel experience for cool people, who are fine with small cabins and almost no privacy. Even as a introvert you can connect to new people and an awesome crew. Once in a life time experience, If you don't book a second time.
Posted on Google Google
Moritz W
January 7, 2018
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I've already been on three tours. It was always fun and I experienced a lot. What I like best is the combination of adventure trip and party. Between steep cliffs and beautiful, secluded bays there is often a party metropolis.

(Translated by Google, see original)
Posted on Google Google
Mohammed A
October 6, 2025
Trustindex verifies that the original source of the review is Google.
Joining a trip with Pirates of Paradise will probably be the best decision you make this year. Great people, great food, great views, and a fantastic sailing experience.
Posted on Google Google
Zuki Z
July 13, 2026
Trustindex verifies that the original source of the review is Google.
Pirates of Paradise is by far the most welcoming and authentic sailing trip provider I have ever come across. Everyone is welcome, and nobody feels left out. They truly care about sustainability and zero waste, and everything is completely vegan and feminist. Especially as a woman, I felt very comfortable and safe on the boats. Our skipper Maurice was incredibly relaxed and taught us how to sail, which was such an exciting and rewarding experience. Meals on board are taken care of, and the volunteers, with the support of the guests, prepare delicious, balanced vegan meals. The boat is very well equipped and has a cozy atmosphere. I felt completely comfortable throughout the entire week. A huge thank you to the crew and to Yenzi for making this experience so special. The only very small downside was that sometimes it felt like nobody was entirely sure what the plan was, and things could get a little chaotic at times. Also, the advertised cozy pizza night, which was supposed to be included in the trip, ended up being a dinner at a rather unrelaxed restaurant, which was a little disappointing. Nevertheless, the week was absolutely worth it, and I am grateful that I got to be part of this crew. I will definitely sail with Pirates of Paradise again!
Posted on Google Google
Maren L
September 16, 2026
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+0
An amazing trip along the Montenegrin coast. The crew are brilliant and the food is excellent (vegan). You get to meet lots of lovely people and have loads of fun! Thank you, everyone! ❤️
Posted on Trustindex Trustindex
Christina T
September 27, 2025
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Sicily Trip I had a wonderful time with Pirates of Paradise in Sicily. The crew was such a great match, was very friendly and everyone took great care of us. It was a good mix of activities on land and relaxing time on the boat. Everything was organized in such a way that it was easy to just enjoy and go with the flow. The boat is very comfortable furnished, so you immediately feel at home and can quickly settle into the group and get to know new people. Sicily is definitely worth a visit. This was my first solo trip and I am very happy I did it with Pirates. I would definitely do it again!
Posted on Google Google
Jonas H
August 31, 2024
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Incredibly great trip with beautiful nature and a great route through Croatia. The boat is very spacious and offers a level of comfort that is not usually found on charter boats. The crew is very nice and knows their job. I would be happy to go back anytime!

(Translated by Google, see original)
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Alexandra S
August 8, 2023
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Was a wonderful week! Great landscape and great people, it was very familiar and I will come again!

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Denise J
May 27, 2026
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+4
We spent a week with Pirates on a sailing trip in Mallorca as part of an educational leave program. It was my first time on a sailboat, so I didn’t really know what to expect. :D The boat was very well equipped, with cozy cabins and plenty of spots to relax (and even plenty of space for individual and group work as part of our educational program). We got delicious food three times a day — including a pizza night with a high-end pizza oven while enjoying the sunset. There was 24/7 access to snacks, fruit, coffee and tea — basically no chance for tired or hangry brains onboard. Everything being fully vegan, they were also really thoughtful about my slightly picky eater preferences (haha), which I really appreciated. 🫶🏽 And we actually sailed. The crew really gave their all to make the experience unforgettable for everyone. They even sacrificed a full night of sleep to sail us from Cabrera to the north of Mallorca so we could wake up in crystal clear turquoise water and spend the next days learning and swimming in beautiful bays. Even when the sea and weather conditions got a bit rough at times, we always felt completely safe and well taken care of. One of my highlights was seeing a completely different side of Mallorca — pure nature, hidden bays and places you would probably never get to experience from land (we even saw dolphins). The whole crew was professional, welcoming and just created a nice atmosphere throughout the trip. There’s clearly a lot of effort, experience and heart behind the whole Pirates concept. It was a unique mix of adventure, learning new things and meeting new people which I’d recommend to anyone. Huge thanks to Yenzi, Mara and the whole crew 🤍⛵
Posted on Google Google
Madline H
April 14, 2024
Trustindex verifies that the original source of the review is Google.
+2
It was a wonderful experience on the sailing boat. The crew is incredibly friendly and you feel totally at home. I can only recommend it to everyone 🌞

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