Sail, Explore & Discover Amazing Places
Join Ben and Elena on their next adventures!
Sailing with Ben & Elena at JoinMyTrip
I'm the skipper, Ben . With a friend, I sailed around the world for almost 5 years. We experienced a lot on our trips, we got to know great people and created a lot of music (we are musicians and studied sound engineers). We filmed the whole thing and in 2019, our travel documentary "Blown Away" was shown in many German cinemas.

Benjamin Schaschek
And I am Elena. One day I onboarded a boat, after that I never left the sea. Now I live with Ben on our beautiful catamaran in the most beautiful place in the world in the South of Portugal. "Life is too short for someday" - I just love being able to live a crazy, free and different life and to be able to walk a path that fulfills me. I have been working in social media for 3 years and I capture our slightly different life in photos and videos. Curious? Then stop by here.

Elena Dostal
Discover their Sailing Adventures
SAIL, SURF & FLY auf Fuerteventura
Join our our special sailing and paragluiding trip along the coast of Fuerteventura. We'll swim, snorkel and drop anchor in the most beautiful bays and sleep outside on deck under the stars 🙂 If you are lucky, you might even watch dolphins or whales. Our Guitar and the ukulele are definitely on board!

When? 06.02. - 13.02.20
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SAIL & SURF auf Gran Canaria
Come with us on our adventure sailing trip, sail along the coast of Gran Canaria and find the most beautiful beaches and the perfect spots for surfing. We anchor on uninhabited islands, surf in secluded bays and sleep outside on deck under the starry sky!

When? 06.03. - 13.03.20
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SAIL, HIKE & YOGA auf Teneriffa
Join our our special sailing, hiking and Yoga trip along the coast of Fuerteventura. We'll swim, snorkel and drop anchor in the most beautiful bays and sleep outside on deck under the stars 🙂 If you are lucky, you might even watch dolphins or whales. Our Guitar and the ukulele are definitely on board!

When? 03.04. - 10.04.20
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SAIL, SURF & SKYDIVE an der Algarve
You are an adrenaline junkie? Then you are in the right place! Action is preprogrammed on this trip! We will discover the beautiful bays and beaches of the Algarve with our catamaran. We will catch perfect waves with our surfboards and go skydiving! In the evening we will watch the documentary "Blown Away" in our outdoor boat cinema, look at the starts in the sky and make music. Are you joining?

When? 17.05. - 24.05.20
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SAIL & YOGA on the Algarve, Portugal
On the Algarve you can expect breathtaking beaches, high cliffs, caves, beautiful bays, picturesque fishing villages and a wonderful climate. Surround yourself with a crew of like-minded yoga fans for a real yoga outdoor experience! On board is Iris! She has been self-employed for over 10 years and offers various yoga classes and trips.

When? 12.06. - 19.06.20
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How does it work
Find & Select
Choose your dream sailing trip from Ben's adventures or browse other trips in the community. Every trip is unique. For planning the trip, the TripLeader receives a small fee as an expense allowance.
Chat & Request
Send Ben or the TripLeader a request. Introduce yourself briefly and ask away all of your questions. As soon as your TripLeader has confirmed you, you will be on your dream trip.
Travel & Get to know Each Other
Enjoy your trip and share the cost, your experiences and memories with new friends. Don't forget to share your experiences with us on social media. Other travelers find it super exciting to see your adventure too!
I wanted to learn to sail, so I simply booked a trip with Ben. He was really relaxed and actually let me do everything myself. In the end I could steer the boat almost by myself! What an incredible experience! And to share all these moments together - sun, time on the boat, music ... Just wow :-)
The Croatia sailing trip with Captain Ben was an absolute highlight! Swimming, stand up paddling, diving, jumping from the mast, exploring cute harbor towns, chilling in the hammock, sleeping under the starry sky and making music together. Thank you Ben and the crew for the bombastic atmosphere on board, it couldn't have been nicer...preferably right away again!
What a journey! I have never been sailing or paragliding before. So this was a real adventure :-) And even if the crew was sometimes a bit chaotic, our captain always stayed calm, always kept his positive energy and was always there for everyone. The week went by super fast but it was a lot of fun!
Ben & Elena's Former TripMates
What is included in the price?
The price of the trip as quoted by the TripLeader includes transportation and accommodation on site - not the return flight to and from the start and end point of the trip, nor the activities on site. The cost of this may be included in the description of the trip. Otherwise just ask your TripLeader directly - they'll be happy to help!
Can I ask questions before I book?
Yes of course! When you have found yourself a suitable trip, you can send the TripLeader a request. Here you can ask your questions directly, the TripLeader will answer them before he confirms your request.
Can I book only a part of the trip?
It depends on your TripLeader. Just message him and ask directly. Some trips are more suitable for this than others.
How does the payment take place?
Quite simply, paying for the trip happens via our platform. You can pay with credit card, e.g., Visa or MasterCard. At the beginning, you pay 20% of the price of the trip and the remaining 80% before the departure date, which is determined by the TripLeader).
What happens after a TripLeader has confirmed me as TripMate?
As soon as your TripLeader has confirmed you, he will contact you. If it takes a little longer, don't be surprised - TripLeaders are only human. If he has not contacted you within 3 days, just write us on Facebook, WhatsApp or send an email to
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