Sailing Charters
Providing unforgettable, premium bespoke sailing charters
Bespoke Sailing Charters with Sailing Scallywag
Discover a personalised sailing experience crafted around you. With Sailing Scallywag, every charter, whether a weekend escape or a full week at sea, is shaped to your pace, preferences, and sense of adventure. Expect high‑quality seamanship, attentive guidance, and a boutique approach that makes your time on the water truly exceptional.
Why choose a Sailing Scallywag Charter
- Fully personalised packages
- Experienced, professional, and friendly crew
- Safe and secure
- Great for families
- Meals aboard included
- Limitless possibilities
- Special occasions encouraged
- Tailored with you in mind
- Yacht exclusively for one client (plus friends/family)
- A truly bespoke sailing experience
Why sail with us?
Boutique & Personal
Every charter receives dedicated attention and thoughtful planning.
Expert, Supportive Skipper
Learn at your own pace with guidance from experienced instructors.
Your Journey, Your Way
Routes, activities, pace, and training are all shaped specifically for you.
Example Solent Weekend Itinerary
Subject to tides & weather
Friday: Arrive & Settle In
- Welcome aboard in the River Hamble
- Safety briefing
- Dinner at a local pub
- Overnight on the marina berth
Saturday: Hamble → Cowes → Yarmouth
- Morning sail to Cowes for coffee, browsing and local charm
- Afternoon sail along the Isle of Wight, optional swimming in quiet bays
- Evening in Yarmouth; dining, seafront walks, relaxed coastal atmosphere
Sunday: Yarmouth → Beaulieu → Hamble
- Morning swim or coffee on deck
- Lunch on the Beaulieu River
- Afternoon sail back to the Hamble with opportunities for helming & photos
Optional Alternatives:
Yarmouth or Cowes nightlife · Nature‑rich Newtown Creek · Lymington visit
Want to extend your stay at sea?
A tailored week at sea
A full week opens up a wider world of coastline and quiet anchorages:
- Explore further afield: Cornwall, the Scilly Isles, or multi‑harbour Solent adventures
- Learn and refine techniques, from mooring to navigation
- Enjoy slow mornings, coastal walks, swimming stops, and evenings under the stars
Every day is curated around conditions, comfort, and your vision for the week.
Your bespoke adventure starts here
Whether you want luxury relaxation, meaningful skill progression, or a hand‑crafted mix of both, Sailing Scallywag delivers a premium charter designed entirely around you.
Your pace. Your journey. Your bespoke escape at sea.
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
