Skipper
Skipper at sailwithus – Become Part of the Family:
You love sailing, maybe you even have a job already. But something’s missing? Join the sailwithus team as a skipper! At sailwithus, you’ll sail with a young and dynamic crew. You’ll embark on amazing sailing trips with one or more yachts in warm Mediterranean or overseas regions. Full-time or part-time – the choice is yours! Even if you’re an inexperienced sailor, you’re welcome with us. Contact us, and we’ll help you on your journey to becoming a skipper for sailwithus.
Join Our Team as a Sailing Holiday Pro!

Take the Helm
As a skipper for us, you’ll be the captain of modern yachts in beautiful, warm destinations. Together with your young crew, you’ll decide each day where to head next. If you’re not yet familiar with the various sailing areas, we’ve got you covered with a Skipper Guide that will make you as knowledgeable as a local. As a skipper, your main responsibility is to safely guide the crew through the sailing area. You’ll assign tasks and keep an eye on everything happening onboard.
Your crew will be around your age, ensuring you feel completely at ease. We strive for a balanced gender ratio on all our trips. Your crews are between 20 and 40 years old and fully aware that they’re participating in an interactive sailing holiday where everyone contributes.
We Handle the Organization
With us, you can fully focus on skippering. Our office team takes care of all the formalities, so you can lead your crew to their dream vacation.
Additionally, you can connect with a network of over 300 skippers, allowing you to continuously expand your sailing experience. On every trip, we also link our skippers with others in the same area. This way, you can plan evening meetups for a sundowner at a beach bar or organize flotilla sailing adventures.
Our office team is always there to support you in case of any complications. At sailwithus, you’ll never feel alone in any situation.


Our Training Trip
Do you want to become a skipper with sailwithus or refresh your skills as an experienced skipper?
Sign up for our skipper training in one of our stunning sailing areas and get to know the sailwithus skipper team. This is the perfect introduction to your own life as a skipper. Learn from the pros and gather tips to ensure your crew enjoys the best possible experience on your trips.
We offer you a week of skippering, sun, and fun! Afterward, you’ll be fully prepared to safely lead your crew on their dream sailing vacation. We’re happy to assist you with planning and travel arrangements. Upon request, you can also receive a special discount from us.
Skipper job totally your thing! What’s next?
Feel free to send us a brief skipper résumé, listing your certifications and previous skipper experience. It’s even better if you include the yacht sizes you’ve sailed on.
Once we receive your application, we’ll check if your qualifications align with our requirements. We’ll quickly reach out to arrange a casual introductory chat to get to know you personally. If you show us your passion for sailing, we’ll schedule a longer conversation with you to work out a plan for your involvement. From there, it’s full steam ahead—whether you join a skipper training trip, sail independently, or participate in a flotilla!
If you have any questions about the skipper job, feel free to email us at info@sailwithus.de.

Skipper Job – Look Forward to It!
A fantastic team spirit, a young and agile crew, and well-equipped charter yachts from renowned providers—this is the triple advantage sailwithus offers you. While we don’t focus on hardcore regatta sailing, you’ll work with highly motivated sailing beginners on our yachts. Your most important task? Creating unforgettable holiday memories. Let them feel the freedom of the sea, explore diverse cultures ashore, party in nightclubs, and enjoy delicious food and drinks.
Your Responsibilities:
Your Qualifications
Your Benefits as a Skipper with sailwithus:
★★★★★
"Ich segle seit Mitte 2020 als Skipper für Sailwithus und jeder einzelne Törn bereitet mir wahnsinnig viel Freude. Die Abstimmung mit dem Office-Team ist absolut unkompliziert und ihnen liegt die Zufriedenheit jedes einzelnen Kunden und Skippers sehr am Herzen. Sailwithus chartert fast ausschließlich neue Boote, welche selten älter als 2-3 Jahre sind. Die Boote haben meist eine Größe zwischen 45-51 Fuß und bieten damit ausreichend Platz und Komfort für alle."