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Sailing Holiday with Skipper: Join Trips Worldwide

Embark on a sailing trip with an experienced skipper in incredible destinations worldwide. Discover unique moments far away from crowded tourist spots. No prior experience required. 7 days starting at 890 EUR.

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Sail with sailwithus - your sailing adventure

Step on board and we set sail! Whether you are an experienced sailor or stepping onto a boat for the first time, you are always welcome at sailwithus. Our sailing trips combine adventure, community, and pure relaxation. You become an active part of the crew, experience life at sea firsthand, and take in breathtaking landscapes right from the water.

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What it means to sail along

What it means to sail along

"Sailing along" puts teamwork and shared moments front and center. Our experienced skippers are experts at finding pristine routes and hidden bays while bringing everyone together as a team. They show you the thrill of life at sea and welcome you to get involved. Whether you want to trim the sails, steer the boat, or help cook meals on deck, you are a valued member of the crew. At the same time, there is always time to soak up the sun and enjoy the pure ease of life on the water. Best of all, you choose your own pace. Relax completely or take the wheel, making every moment an unforgettable experience.

Who is sailing along suitable for?
Who is sailing along suitable for?

Who is sailing along suitable for?

Our sailing trips are for everyone who:

  • loves the sea and wants to discover the world from the water,
  • wants to meet new people and travel in a relaxed atmosphere,
  • is looking for an alternative to boring all inclusive vocations,
  • wants to experience an adventure as a solo traveller, couple or friends.

Sailing with us is uncomplicated: You don't need any previous experience, just a desire for the sea and discovery!

Segler beim schönem Sonnenuntergang
The highlights of your sailing adventure

The highlights of your sailing adventure

  • Unrivaled Nature: Wake up in a new bay every day, dive into pure waters, and experience the sea up close.

  • Flexibility: Guided by the wind, we keep our route open to discover the best spots along the coast.

  • Community: Sail, laugh, and relax together with people who quickly become friends for life.

  • Sustainability: Sailing offers a genuinely eco conscious way to travel while treading lightly on the planet

What awaits you on board
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What awaits you on board

A mix of comfort and adventure awaits you on board our modern yachts. You share a cabin, have access to all areas on board and enjoy a relaxed, informal atmosphere. Whether you want to sail along, relax and unwind or get active on exciting shore excursions – you decide!

Set Sail!
Set Sail!

Set Sail!

Dreaming of escaping the daily routine and seeing the world from a fresh perspective? Joining a sailing trip with sailwithus turns that dream into reality. Whether you are exploring picturesque bays in Croatia, hopping across the Greek islands, or sailing the exotic waters of the Caribbean, your journey starts here. Our most popular destinations include Croatia, Greece, and Italy. Looking for expert destination advice? Check out our Mediterranean sailing guide for local tips and insights.

Sailing holiday with skipper
Zwei Maenner in gelben Skipper-Shirts zeigen auf sich mit griechischer Flagge im Hintergrund – Skippertraining Griechenland sailwithus

Sailing holiday with skipper

The sailwithus concept delivers a complete package: a yacht with three to six cabins for five to twelve guests, an experienced skipper, and a flexible weekly itinerary. Every day, you can adapt the route together with your crew based on your preferences. Your skipper always has local insider tips to share to help tailor the journey. Depending on the destination, you will spend around three to six hours sailing each day before dropping anchor in a bay or mooring in a harbor.

What our customers say

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Frequently Asked Questions

Before Your Trip

Is sustainable travel possible?

Yes.

Some sailing destinations can be reached by train, ferry or long-distance bus.

Examples: Baltic Sea, Sardinia, France, Croatia.

Which insurance policies are useful?

Insurance is not mandatory, but recommended:

- Travel cancellation insurance

- International health insurance

- Accident insurance

- Liability insurance

How do I get from the airport to the marina?

All travel information is available by e-mail and here:

https://sailwithus.de/gut-zu-wissen/anreiseinformationen/

What is the best way to pack my travel bag or suitcase?

You can find packing tips here:

https://sailwithus.de/gut-zu-wissen/packliste/

When does the crew meet and can I come outside the recommended arrival time?

The crew usually meets between 2 and 4 p.m. in the marina or a nearby café.

From around 5 p.m., the skipper can board the yacht and carry out the handover. Meanwhile, the crew goes shopping.

Late arrival is possible in exceptional cases by arrangement.

Saturday is an organization day - sailing usually takes place on Sunday after the safety briefing.

Which piece of luggage is best?

A sports bag or hiking rucksack is best.

Please do not bring a hard-shell suitcase - there is no storage space for it and it is always in the way.

Recommendation: Packing list on the website.

YouTube:

- https://www.youtube.com/embed/5dPxMRSR9OM

- https://www.youtube.com/embed/JGboVfN5hVQ

What happens after I book my cruise?

After your booking, you will receive further information by email at regular intervals. This includes tips on packing, advice on meal planning, etc.

About a week before the start of the trip, we create a Whatsapp group where you can get to know each other as a crew and the skipper.

Approx. 5 days before the start of the cruise you will receive the final arrival information including a harbor plan and berth.

And then it's time to cast off!

Do I need a passport or identity card?

That depends on the area.

An identity card is sufficient in most districts.

A passport is required for overseas destinations (Thailand, Caribbean, Seychelles, etc.).

Recommendation: Check current information with the Federal Foreign Office.

Will I get to know my fellow sailors before departure?

Yes, a WhatsApp group will be created in the week before your trip. You can discuss travel and organization there.

Are there bed linen, pillows and towels on board?

Yes, you will be provided with bed linen and a towel.

But bring another towel yourself.

A beach towel is not necessary - you jump straight into the sea.

Frequently Asked Questions