It's all hands on deck!
Start your journey on the River Hamble and discover sailing at its best with Sailing Scallywag. Whether you’re learning the ropes, enjoying a skippered yacht charter, planning a corporate event, or setting off on a sailing holiday, we offer experiences to suit every level. From relaxed Solent cruising and weekend escapes to longer adventures along the South Coast, France, and the Channel Islands, each trip is shaped by the wind, tides, and your ambitions, with hands-on sailing, comfortable yachts, and unforgettable destinations as standard.
From lively day sails to peaceful evenings at anchor, and even night sailing under the stars, the Solent is the perfect playground and classroom. Build confidence, sharpen boat handling and navigation skills, or take your own yacht to the next level with tailored tuition designed around you.
No rush, no pressure, just great sailing, great scenery, and a touch of Scallywag mischief.
Where are we?
Our HQ is in the Solent – and from here, the adventure begins…
Stories from on board
What we offer
Sailing experiences & pricing
Whether you’re looking to learn to sail, enjoy a relaxed charter, or combine both, we keep our pricing simple and transparent.
We offer a single rate across all options, because your time on the water should be defined by what you want to do, not your level of experience.
All prices are per boat, reserved exclusively for one booking of up to four people. Meals appropriate to your charter length are included.
| Charter Type | Duration | Timing | Low Season (Nov-Apr) | High Season (May-Oct) |
|---|---|---|---|---|
| Day Charter | 1 day | 08:00 - 17:00 | £700 per day | £900 per day |
| Weekend Charter | 2 nights | Fri 20:00 - Sun 17:00 | £1,700 | £2,100 |
| Five Day Charter | 5 nights | Sun 20:00 - Fri 17:00 | £2,990 | £3,990 |
Timings may vary slightly depending on tides, weather and Mother Nature.
Key information
- Night sailing, mile‑builders, and boat‑handling sessions are costed at the Charter Rates
- Bespoke packages available on request
- Seasonal pricing applies — contact us for exact dates and availability
- Exclusive use of the boat for up to four guests
- Location: Southampton, UK
Get onboard & let's go sailing!
Your next adventure starts the moment you step aboard. Whether you’re looking to learn, explore, or simply escape, we’ll help you make it happen.
Secure your spot today and let’s get you out on the water.
About us
Sailing Scallywag is a small, bespoke sailing company that has grown steadily over the past six years. Born from a love of the sea, our mission is simple: to make sailing accessible, enjoyable, and memorable for everyone.
From booking to boarding, our team at Scallywag HQ works hard to provide a friendly, smooth experience tailored entirely to your crew. All bookings are private – we never mix groups – so the boat is yours for the duration of your charter. We can take up to four guests on any sailing experience.
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
