SAILING HOLIDAYS

The Earth is two-thirds water, yet we spend most of our lives on land. So cast off, take the plunge and discover the life-changing freedom of a sailing holiday. VentureSail offers 400+  sailing adventures to amazing destinations around the world on unusual boats run by passionate crews. Get hands-on and learn the ropes, or relax on deck and enjoy the journey wherever it takes you. There’s a huge choice across the fleet, from luxury yachts and catamarans with private ensuite cabins to traditional sailing on a classic boat or tall ship. So much of the world is waiting to be explored; discover it under sail.

PRIVATE CHARTER

If privacy, freedom and bucket list locations are high on your holiday checklist, a private boat charter is the perfect opportunity to make great memories with your loved ones.

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EXPERIENCES

Our experiences range from ski and sail expeditions in the Arctic to historic taster weekends in the UK, and even yoga retreats in the Mediterranean. Which adventure will you choose?

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Latest from our Adventure Journal

Be inspired to discover the world under sail! Read our latest journals below.

The Best of the 2026 Maritime Festivals

The Best of the 2026 Maritime Festivals

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Our Top Five Family Friendly Sailing Holidays for 2026

Our Top Five Family Friendly Sailing Holidays for 2026

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Luxury Sailing in the British Virgin Islands

Luxury Sailing in the British Virgin Islands

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Why Your Next UK Holiday Should Be a Sustainable Sailing Adventure

Why Your Next UK Holiday Should Be a Sustainable Sailing Adventure

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VIEW OUR ADVENTURE:

Why Travel With Us

Trusted Experience

Trusted Experience

We partner with independent boat owners and passionate operators to build long-standing relationships. Each boat is carefully selected for its sailing quality, comfort, and crew to deliver memorable holidays on the water.

Our Unique Fleet

Our Unique Fleet

We partner with independent boat owners and passionate operators to build long-standing relationships. Each boat is carefully selected for its sailing quality, comfort, and crew to deliver memorable holidays on the water.

Low Impact Travel

Low Impact Travel

Travelling with the power of the wind is naturally a more sustainable form of holiday. We support marine conservation and reforestation efforts worldwide, planting a tree for every booking made. All our skippers and guests respect responsible travel guidelines to ensure our impact on the environment is minimal.

Book with Confidence

Book with Confidence

Your booking is protected through a secure, transparent process and covered under the Package Travel Regulations, where applicable. Choose to pay in Pounds or Euros, whichever suits you best.

Trusted Experience

Trusted Experience

We partner with independent boat owners and passionate operators to build long-standing relationships. Each boat is carefully selected for its sailing quality, comfort, and crew to deliver memorable holidays on the water.

Our Unique Fleet

Our Unique Fleet

We partner with independent boat owners and passionate operators to build long-standing relationships. Each boat is carefully selected for its sailing quality, comfort, and crew to deliver memorable holidays on the water.

Low Impact Travel

Low Impact Travel

Travelling with the power of the wind is naturally a more sustainable form of holiday. We support marine conservation and reforestation efforts worldwide, planting a tree for every booking made. All our skippers and guests respect responsible travel guidelines to ensure our impact on the environment is minimal.

Book with Confidence

Book with Confidence

Your booking is protected through a secure, transparent process and covered under the Package Travel Regulations, where applicable. Choose to pay in Pounds or Euros, whichever suits you best.

Sailing Holidays

Our sailing holidays take guests far beyond the ordinary and we have a vast array of life-changing adventures to choose from.

Experience the magic of ski and sail trips in Norway, encounter incredible wildlife from puffins to whales, orangutans to whale sharks and even Komodo Dragons. Explore the raw beauty of Arctic sailing, unwind and destress with a yoga retreats at sea, or simply choose to soak up warm, tropical sunshine and gentle breezes.

From the fragile wilds of Svalbard to the tropical rainforests of Indonesia; untamed islands of the Scottish Hebrides to Caribbean cruises; the sun-soaked Mediterranean to the rugged Cornish coast. We have hundreds of unforgettable sailing holidays waiting to be discovered.

And just as diverse as the destinations are the boats themselves. Choose from private ensuite cabins on luxury yachts to shared berths on historic tall ships or comfortable cabins on expedition vessels. Each boat delivers its own style of experience, whether it’s hands-on sailing, relaxed voyaging, or immersive experiences.

Whether you dream of ski and sail adventures, wildlife-rich voyages, peaceful yoga retreats, or simply chasing the sun, our fleet and far-flung routes open the door to a world which is best discovered under sail.

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