Our Top 5 Skippered Sailing Holidays in the UK

Skippered sailing holidays in the UK

Whether you’re an experienced sailor or you’re new to the nautical world and are wanting to try a sailing experience, our incredible range of skippered sailing holidays in the UK offer an adventure to suit everyone.

Why Choose a Skippered Sailing Holiday in the UK?

The benefits of a skippered sailing holiday, where you can book a berth, cabin, or even the whole boat, are extensive. Firstly, you’re able to truly relax, knowing that a fully qualified crew and skipper are taking care of all safety measures and planning the best sailing routes, whatever the weather. This gives you plenty of opportunity to learn the ropes and get hands on with sailing the boat or sit back take in the view – the choice is yours! Secondly, all meals are included in the ticket price of our skippered sailing holidays in the UK which are prepared fresh each day by a dedicated chef on board. Time on the water can certainly boost your appetite so you can be sure of good quality local produce and freshly baked treats with a warming cuppa along the way. With all other distractions of a busy life out of the way, you can truly relax and enjoy all the benefits that come with spending time out on the water, immersing yourself in the natural world whilst discovering new destinations.

1. Skippered sailing holidays in the Hebrides
For many, the search for a skippered sailing holiday in the UK starts with the renowned Hebrides. This enchanting collection of Scottish islands are undoubtedly best explored by boat, with each isle different from the next. These world-class sailing waters are home to a fantastic array of wildlife; from whales to basking sharks, sea birds to seals, otters, deer and even the occasional orca pod! Our skippered sailing holidays in the Hebrides provide plenty of time to wildlife watch whilst soaking up the breathtaking scenery, anchoring in deep lochs and exploring the rich and varied landscape ashore.

Tempted? Then join Dutch ketch Steady to sail this ancient landscape in comfort, climb aboard beautiful yacht Stravaigin for some of the best wild swimming opportunities in the world, or travel with motor cruiser Fleur de Lys for wildlife watching and walking holidays in the Hebrides. If you’d like to learn more about the Hebrides, read our journals about sailing the Hebrides, the Small Isles, and the islands surrounding Mull.

2. Skippered Sailing Holidays to St Kilda
Steeped in mystery and wonder, the uninhabited isles of St Kilda are known as ‘the islands at the edge of the world’ and for good reason. Now recognised as a UNESCO World Heritage site for both natural beauty and cultural significance, St Kilda has earned its place on many a bucket list. Only accessible by boat, these alluring isles are one of our top picks for a unique skippered sailing holiday in the UK. Approaching the islands, one can’t help but appreciate the wild beauty and sheer remoteness, marvelling at how the residents fared until their evacuation in 1930. Stepping ashore, you will uncover the eerie remnants of civilisations combined with sweeping vistas across the iconic sea stacks and rugged natural landscape, populated with an abundance of native flora and fauna that can’t be found elsewhere.

Zuza St Kilda Scotland anchor

Sail here with tall ship Blue Clipper to immerse yourself in traditional sailing, or join expedition yacht Zuza for smooth and steady sailing to St Kilda. Make sure to check out our journal to learn more about sailing with Zuza, or read more about sailing to St Kilda.

3. Skippered sailing holidays in Devon
Fondly referred to as ‘the English Riviera’, pretty Devon offers some of our favourite skippered sailing holidays in the UK and with good transport links, they offer the perfect way to while away a long weekend. Whether you’re a beginner or experienced sailor, Devon is a great choice for getting out on the water offering a fabulous combination of sheltered waters and exhilarating coastal sailing. Enjoy time exploring traditional fishing towns, soak in the tranquillity along peaceful rivers sailing all the while taking in the magnificent views.

Devon is home to historic ship Pilgrim of Brixham, offering traditional coastal sailing adventures, or spend some time on board classic yawl Escape for short breaks – perfect for beginners and families! Read our journal to learn more about beginner sailing in Devon, or discover the best hidden bays of Devon.

4. Skippered Sailing Holidays in Cornwall
The home of VentureSail, our list of skippered sailing holidays in the UK would not be complete without mentioning the iconic Cornwall. Sail and explore an incredibly diverse and ever changing coastline, discover hidden coves and deep estuaries, marvel at the towering dramatic cliffs and visit quaint traditional harbours to enjoy a pasty or Cornish ice-cream. Rich in maritime history, sailing in Cornwall offers the chance to learn many local legends including tales of pirates, smugglers and even the odd mermaid or two!

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Experience life on a traditional Cornish lugger Grayhound , join historic tall ship Bessie Ellen to explore the coastline, or try some exhilarating sailing on pilot cutter Pellew – built by hand in Cornwall! If you’d like to learn more about sailing in Cornwall, why not read our seasonal guide to sailing in Cornwall, the history of Cornish pilot cutters, or discover life on a Cornish lugger.

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5. Skippered sailing holidays in the Isles of Scilly
If you’re looking for a skippered sailing holiday in the UK that feels just a touch more exotic, why not venture to the sub-tropical archipelago of the Isles of Scilly. The crossing from Cornwall is truly exhilarating, offering incredible sailing with majestic views of the west Cornish coast. Sailing around the Isles of Scilly offers a slower pace of life, sit back on deck and take in the incredible views, swim or snorkel in incredibly crystal clear waters whilst basking in the warmer than average temperatures. Often described as ‘a place like nowhere else in England’ you would be easily forgiven for thinking you’re on a sailing holiday in the Caribbean. The remote nature of this archipelago means a sailing holiday is the only way to discover it all, and we allow plenty of time to step ashore to roam the islands at will. From incredible walking trails, to archaeological sites, powder soft deserted beaches and tempting eateries, there is plenty to occupy every traveller. And after a heavenly day exploring, lie back to take in the star-filled skies – the Isles of Scilly are an official Dark Sky area proffering magnificent star-gazing opportunities. 

Set sail from Newlyn with classic gaff ketch Maybe, or venture to these incredible isles with traditional tall ship Irene. Learn more about sailing the Isles of Scilly by reading our island by island guide.

If a skippered sailing holiday in the UK sounds like it might be for you, or would like to find out more please don’t hesitate to get in touch! You can reach one of our friendly team on 01872 487288, or at info@venturesailholidays.com.