Go Sailing
From relaxed escapes to longer adventures, sail your way
Sailing adventures
Whether you’re new to sailing or ready to head further afield, Sailing Scallywag offers unforgettable UK sailing holidays shaped by the wind, tides and your ambitions.
From relaxed cruising in the Solent to longer adventures along the South Coast, across to France, or on to the Channel Islands, every trip blends hands-on sailing with memorable destinations. Whether you’re learning the ropes or building sea miles, our sailing experiences combine proper sailing, comfortable yachts and good company.
Which trip is right for you?
New or beginner sailors
Perfect if you’re new to sailing or want to build confidence. Expect relaxed Solent cruising, friendly guidance and plenty of time to learn, sail and enjoy life onboard, no experience required.
These UK sailing holidays are ideal if you’d like to experience the freedom of being at sea while building skills at your own pace.
Experienced sailors
Ready to push further afield? These sailing holidays UK adventures focus on passage making, navigation and longer distances, heading to Dorset, Devon, Cornwall. France or the Channel Islands.
If you’re looking to log miles, refine your decision-making and experience more challenging conditions, these trips deliver rewarding, real-world sailing.
Explore our sailing getaways
Explore a range of sailing getaways designed to suit different experience levels, timeframes and ambition, each one offering a unique way to enjoy life on the water.
Yacht Charters
Looking for flexibility? Our charters allow you to enjoy sailing holidays in the UK with the freedom to shape your own itinerary.
Corporate Yacht Charter
Our corporate sailing experiences combine teamwork, communication and adventure, ideal for client entertainment, team building or rewarding standout performance with a memorable UK sailing holiday.
Experience Days
Short on time? Our sailing experience days offer a taste of life at sea, perfect for complete beginners, gift experiences or anyone curious about trying sailing for the first time.
Weekend Getaway
Looking to escape for a sailing weekend? Step aboard and swap dry land for sea air, good company and proper sailing. Whether you’re keen to learn the ropes, sharpen your boat handling skills, or simply relax.
Channel Hops
Cross the Channel and experience true passage making. These trips focus on tidal planning, navigation and confidence, making them a rewarding step up for sailors looking to expand their horizons beyond UK waters.
Beginner Sailing Experiences
New to sailing? These supportive, hands-on UK sailing holidays are designed to introduce you to life onboard, from sail handling to simple navigation, all in a relaxed and encouraging environment.
Adventure Sailing
For sailors who want more than a gentle cruise. Expect longer passages, varied conditions and the kind of challenge that builds lasting confidence and capability at sea.
Family Sailing
Share the adventure. Our family-friendly UK sailing holidays are relaxed, flexible and designed to create lasting memories, whether you’re exploring sheltered harbours or enjoying evenings at anchor together.
Let's get sailing!
Your journey starts here…
We are ship shape
- Great train links into Southampton
- Boats coded to the latest 2026 standard
- Small group sailing (up to four guests per trip)
- Flexible itineraries shaped around your goals
- Skippered by experienced RYA instructors
- Fully insured incl. public & employers liability insurance
- Learn to sail, charter, or combine both in one trip
- Friendly, patient teaching for all abilities
- Bespoke sailing experiences across the South West
- Ideal for individuals, couples, families, and small groups
- A relaxed, down-to-earth approach to life on the water
- Comprehensive and modern safety equipment
