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
  • Sold out

1.020€

per Person

Not taxable according to § 3b para. 1

Extra 5% off
Sold out
This trip is fully booked. Ask us about the waitlist.

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Your cabin
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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
Excellent4.9140 reviews
4.9
Excellent140 reviews
Excellent4.9139 reviews
4.9
Excellent139 reviews
Excellent5.01 reviews
5.0
Excellent1 reviews
Posted on Google Google
Aurelia W
September 15, 2025
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+2
Sicily tour was the best decision ever. Had a blast. As a solo traveller I met many lovely people aboard. Nice balance between sailing time and activities. Nice spots for sleepovers. And the team really knows what they‘re doing, incredibly skilled skippers and chefs. A little helping e.g. for cooking is required. Also, the team works as volunteers and they take tips so there will be some extra costs. Hoping to book a trip again next year <3
Posted on Google Google
Sarah S
April 26, 2026
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+0
Sailermoon and Songoku in Sa Calobra Bay, Torrente de Pareis, near Sóller/Mallorca. ⛵️🌅 It was my first sailing trip and I'm absolutely thrilled. Great crew, delicious food, unique spots. I discovered Mallorca in a whole new way. Highly recommended. Thank you so much for this amazing experience! 💙🧡💚

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Friederike F
January 25, 2022
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simply awesome, whether alone or with friends. A unique experience ✨

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Tim0
April 21, 2024
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+0
I was on the tour around Mallorca and it was an amazing week! I can only recommend it to everyone! :D

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Posted on Google Google
Simão V
June 24, 2024
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Cool vibes, cool people and cool views! We had an amazing week with Pirates of Paradise with lots of sailing. The crew is very experienced, always with safety as a priority and very friendly. We also met some incredible people there to share the boat with. You’ll basically going to be part of the crew, help with cooking, doing the dishes and also help with sailing, if you want. That’s what makes the trip so authentic
Posted on Google Google
Lobke T
August 24, 2026
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Pirates of paradise is a fantastic organisation to go for a nice, relaxing and fun sailing trip! We went to such beautiful places, I met the sweetest people and enjoyed the trip from the first to the last moment.
Posted on Google Google
Anika S
May 24, 2026
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+0
Honestly, this trip changed something in me. Pirates of Paradies made it easy from the start, their website tells you everything you need to know upfront. The seamails were such a sweet touch that made me feel part of something special. The team is genuinely warm and attentive. Managing 18 people with different wishes and moods, and actually pulling it off, is no small thing. Even when the wind didn’t cooperate, they found the most stunning spots I never would have discovered on my own. But what I’m taking home more than anything: the courage to step outside my comfort zone, and a bunch of wonderful people I wouldn’t have met otherwise. A thousand thanks for that.
Posted on Google Google
Farina K
January 25, 2022
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Do you want adventure? You get adventures! What do you want "sea"? If you want salt on your skin, wind in your hair and a boat under your back, Pirates is the right place for you. I particularly liked the hammock as a place to sleep: one eye clink at sunrise and the next clink you'd jump into the sea. Hoist the sails and send off the mail. See you again on deck.

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Bianca
August 24, 2026
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Highly recommend to anyone. Great vibes ans great people. Will come back again!
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.

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Posted on Google Google
Benno P
August 6, 2021
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Volcano Route Italy I came alone, didn't know anyone in the group beforehand and it still felt like a vacation with good friends. Everyone on the boat, whether guests or crew, was super nice and uncomplicated. When we sailed off into the sunset on the first evening with good music and good wine, we knew immediately that it would be an unforgettable week and why so many people rave about Pirates holidays. Mille grazie and gladly again!

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Vivien L
August 5, 2020
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I went to Italy this year (Vulcano Route) and it was the best and most beautiful vacation of my life! ⛵️ I've never been sailing before and I didn't know anyone from vacation before. But the impressions on Instagram made me definitely want to be part of this journey. And it was really worth it! ☺️ After the week it felt like we had known everyone for a lot longer, even though they were all strangers a few days ago. 🥰 From a volcano hike at sunrise to swimming in the water at night and watching the starry sky, everything was there. 😊 So I can really recommend anyone who wants to go on a trip like this to have this experience with Pirates of Paradise! And feel free to do the trip alone 😊 Thanks to Yenzi and the whole Pirates of Paradise team for making these trips and incredible experiences possible 🧡

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Jade V
October 7, 2025
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+3
Would highly recommend this unique, unforgettable experience. The crew was amazing, the food on board was plentiful and delicious, and the friendships made are irreplaceable.
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
Philipp F
December 11, 2019
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It's a completely different holiday experience when you're at sea most of the time. You get a completely different view of the country and the landscape. I booked into Pirates of Paradise with 5 of my best friends and we had an amazing time together. The Pirates boys are all in a good mood and have a very family atmosphere. The skippers are great and make everyone have fun. (Thanks to Marius & Johanna <3) It definitely wasn't the last time I booked myself there!

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Julius W
January 4, 2018
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The two years (2014 & 2015) that I went on a sailing vacation with Pirates of Paradise were the most exciting, fun and literally paradisiacal vacations I have had so far. The freedom and adventure you feel when cruising the Mediterranean was indescribable. You have to experience it yourself! I would go on vacation with Pirates of Paradise again in a heartbeat, only time constraints prevented me from doing so the last few times.

(Translated by Google, see original)
Posted on Google Google
Christopher L
March 22, 2019
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Yenzi knows great spots to anchor away from tourist spots and involves the crew in route/activity planning. Super equipped yacht, delicious food thanks to Marlen and the other nice sailors.

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Madline H
April 14, 2024
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+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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Timo W
May 31, 2026
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+1
The absolute best sailing crew I have ever seen! The team is incredibly friendly and experienced in sailing and the boats are better equipped then any other boat I have seen – fresh filtered water, dishwashers, starlink WIFI and so on. I had such a nice week sailing with them around Sardinia and will for sure come back! And not to forget: the food on board is delicious! THANK YOU CREW <3
Posted on Google Google
Charly
September 17, 2018
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Thanks to Pirates of Paradise for this incredibly great week and a vacation that I would consider to be one of the most beautiful I have had the pleasure of experiencing so far. From days where you simply spend the whole day in the sea and on deck in the sun, to unforgettable nights on board or on land with a crew that grows from a bunch of strangers to a small family within 7 days, it was all there ! I already miss the morning swim in the turquoise blue water, the breakfast and dinner together on board, the overnight stays in the most beautiful bays under the most amazing starry sky I have ever seen and all the conversations late into the night with a good glass of wine. With Pirates of Paradise you don't just book any summer vacation, you book memories that last :)

(Translated by Google, see original)
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!

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