Sailing Vacations with Freedom & Comfort

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Sailing holidays with Tubber

Imagine waking up to the sound of gentle waves, setting sail toward a secluded bay, and watching the sunset from the deck of your private yacht. A sailing holiday is the perfect way to explore stunning coastlines, discover hidden gems, and experience the ultimate sense of freedom on the open water. Whether you're island-hopping in Greece, exploring the Dalmatian coast in Croatia, or cruising through the Caribbean, every day brings a new adventure. With options for every experience level—from bareboat charters for seasoned sailors to skippered or cabin charters for those who prefer to sit back and relax—there’s a perfect sailing holiday for everyone. Whether you're traveling with family, friends, or solo, get ready for sun-soaked days, turquoise waters, and unforgettable memories at sea.

Why choose a sailing holiday?

A sailing holiday isn’t just a trip—it’s an adventure. Here’s why you’ll love it:

Ultimate freedom – Explore islands and hidden coves at your own pace. No fixed schedules, just endless possibilities.
Uncrowded & exclusive – Escape the tourist crowds and wake up in a different paradise every day.
Adventure & relaxation combined – Snorkel in crystal-clear waters, hike coastal trails, or simply sunbathe on deck.
Tailored to you – Whether you want full control at the helm or a professional skipper, there’s a sailing holiday to match your style.

From the Mediterranean to the Caribbean, sailing unlocks a world of breathtaking destinations.

Types of sailing holidays

Not sure which sailing holiday suits you best? Here’s a quick guide to help you choose:

Bareboat charter – Total independence

If you have sailing experience, a bareboat charter gives you complete freedom. Choose your own route, set your own pace, and enjoy a private yacht adventure with your crew.

Skippered charter – Relax & enjoy

No sailing licence? No problem! A professional skipper takes care of navigation, so you can sit back and soak up the experience. Perfect for beginners or those who just want to unwind.

Flotilla sailing – Social & fun

Join a group of yachts led by a professional guide. Enjoy the independence of sailing your own yacht while having the support of an experienced lead crew. Great for families, friends, and solo travellers looking to meet new people.

Cabin charter – No experience needed

Book a cabin on a shared yacht with a professional crew. Meet like-minded travelers, enjoy an all-inclusive sailing experience, and let the crew take care of everything. A great choice for solo travelers or couples.

Digital Flotilla – Freedom with online support

Prefer to sail independently but still want some guidance? A digital flotilla provides remote support, navigational tips, and local insights—ideal for those who like flexibility with a safety net.

The right yacht for your adventure

Choosing the right yacht depends on your travel style and group size. Here’s a quick breakdown:

Sailing yachts – Classic and wind-powered, ideal for a traditional sailing experience.
Catamarans – More space, stability, and comfort—perfect for families and groups.
Motor yachts – Speed and luxury combined, allowing you to cover more distance.
Gulets – Traditional wooden yachts with crewed service, great for a relaxed, all-inclusive experience.

No matter your choice, all our yachts are fully equipped, verified, and ready for adventure.

Hassle-free booking with Tubber

Booking a sailing holiday should be as smooth as the sea breeze. Here’s why Tubber makes it easy:

Verified yachts

Only high-quality, fully checked yachts.

Best price guarantee

Get the best rates with no hidden costs.

Personal support

From planning to sailing, we’re with you every step of the way.

Can I see a booking as confirmed, even when I have not heard anything from the owner?

To book a trip can be exciting and especially when you require an immediate response. We recommend waiting for the owner’s response even though it’s a last minute booking request.

Do I need a sailing license to rent a yacht?

In general, yes, but it depends on where you want to sail. Either a valid license is required, or a temporary one that we can facilitate and verified by the owner may be sufficient.

How do I search for yachts on Tubber?

Choose a destination, fill in any date, select the type of yacht, and search for the best yacht!

Can I rent a bareboat?

Most yachts are offered bareboat, unless indicated otherwise, e.g. crewed. All yachts are owned by local fleet companies. We can additionally facilitate flotillas, skippers, or other types of sailing holidays.

At which time do I check in and check out?

Standard check-in time is around 17:00 (mostly Saturday). Check-out is the afternoon before disembarkation, so standard check-out is Friday at 17:00, and disembarkation is Saturday at 9:00.

Can I rent a yacht with a skipper?

Yes, of course! If you don’t have a skipper license or don’t feel like skippering, you can book a skippered yacht!

Can I book water sports equipment along with my yacht rental?

Most yachts have snorkelling equipment included or as an optional extra, and also a stand-up paddleboard. Some may have other equipment as well. But SUPs are the most common extra to add for pleasure after sailing.

Can I rent a yacht for just one day?

Typically, all charters are based on weekly charters, but low-seasons can be variable.

How far in advance should I book my yacht rental?

This varies because prices are always changing. Early booking discounts only apply for so long. In general, the best yachts go first, so the sooner you are about to book the better your choices are.

Can I book a yacht on behalf of a friend/family member?

Yes, you can have several bookings in your name initially. We can change the booking to someone else at any given time. At check-in, the responsible person needs to be present however for the papers, as one person can't sail on several yachts at the same time.

Sailing Vacations