Channel Islands
A bespoke offshore adventure tailored to you
Channel Islands charter with Sailing Scallywag
Experience the freedom, beauty, and exhilaration of a Channel Islands sailing escape with Sailing Scallywag. Each voyage is crafted around your pace, your sailing ambitions, and the natural rhythm of wind and tide.
Whether you’re building offshore confidence, logging miles, or simply soaking in the charm of the islands, this is a personalised adventure designed for unforgettable moments at sea.
5-day Example Itinerary
Please note: All plans are shaped by weather, tides, and Mother Nature.
Evening Before Departure
Arrive at the marina, meet your skipper, settle onboard, and enjoy a relaxed safety briefing before a restful night ahead of your adventure.
Day 1: Solent → Guernsey
Your offshore passage begins
If it’s your first time offshore, this is the perfect way to find your rhythm. Learn the fundamentals of passage planning, watch-keeping, and sail trim as you head south into open water.
Day 2: Explore St Peter Port, Guernsey
St Peter Port blends lively harbour buzz with old‑world island charm. Step ashore for cafés, shops, and shoreline walks—or keep practising boat‑handling skills in tidal waters.
Day 3: Sark & Herm
These islands are raw, peaceful, and deeply beautiful. Anchor beneath rugged cliffs, uncover hidden coves, or simply enjoy the stillness. A brilliant day for anchoring practice and seamanship refinement.
Day 4: Alderney & The Swinge
Alderney’s coastline is dramatic, and the surrounding tides offer a real seamanship challenge. Navigate fast‑flowing water with expert support and discover one of the most rewarding passages in the Channel Islands.
Day 5: Offshore Return to the Solent
Your final day brings another rewarding offshore passage—an opportunity to consolidate skills, take the helm with confidence, and reflect on your adventure.
Your adventure awaits
Step aboard with Sailing Scallywag and experience offshore sailing at its most personal, professional, and inspiring. Whether you’re seeking new skills or new horizons, this is the perfect balance of challenge, beauty, and bespoke adventure.
Why sail with Sailing Scallywag?
Expert Instruction
Your skipper teaches sailors of all ages and abilities with patience, clarity, and a calm, confidence‑building approach.
Diverse Vessel Experience
Skippers draw from experience across classic schooners, modern monohulls, and catamarans, bringing real‑world, adaptable seamanship insight.
Truly Bespoke Adventures
No set routes. No rigid schedule. Every charter is designed around your goals—whether training‑focused, adventure‑driven, or a perfect blend of both.
Unforgettable Destinations
From Guernsey’s lively waterfront to the untouched beauty of Herm and Sark, the Channel Islands offer a world‑class sailing playground.
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
