
Round the Island
A Coastal Escape Around the Isle of Wight
Step off the map. Sail the edge. Come back lighter.
Circle the Isle of Wight by sea. Feel the wind, follow the tide, and leave the noise behind for a few days that feel like a reset.
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Unplug. Let go. Come back changed.
This isn’t a sightseeing cruise or a race. It’s a purposeful loop around the Isle of Wight—one of the UK’s most iconic sailing routes.
Over a few days, you’ll sail with the tide, explore hidden corners of the island, and live simply aboard a beautiful ocean-going yacht. The boat moves, but the pace slows.
You’ll rise with the light, feel the weather shift, and fall into a rhythm shaped by wind and water—not schedules. This is a journey of presence, not distance. Of reconnection, not distraction.
Expect wild coastline, shared meals, space to reflect, and the quiet satisfaction of completing the circle—offshore and within.
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Sometimes, escape is just across the water.
This short coastal adventure gives you just enough time and space to reset. Away from noise, pressure, and screens, you’ll rediscover the clarity that comes when life is simple and your hands are on the lines.
There’s coaching available if you want it. Quiet prompts, good questions, and gentle space to reflect. Or you can simply be here as you are—with the wind, the crew, and the sea.
You’ll come back changed, not because you chased something big—but because you circled something whole.
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A few days that feel like more.
Day 1: Meet on board in Lymington. Safety brief, get to know each other and the boat. Welcome dinner under the stars.
Day 2: Round the Needles, sail the south coast, and moor on the east side. Reflect, cook and connect.
Day 3: Complete the loop. Cross the finish line with tired arms and clear eyes.
Always: No pressure. Just wind, water, and time that’s truly yours.
Max 5 guests. Led by a qualified skipper and experienced coach. No sailing experience needed.
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Classic, coastal, and built for adventure.
Your floating home for this journey is a Contessa 32, a legendary little yacht with real pedigree:
Lymington-built heritage: Crafted on the Solent’s shores where generations have launched Contessas into strong tides and variable winds.
Ocean-ready and seaworthy: Designed in the ’70s and proven under sail across oceans, the Contessa 32 is loved for her strength, balance, and handling.
Comfort in simplicity: Compact yet cozy — the cabin invites reading, resting, and quietly reflecting as waves rock you to sleep.
On deck, you’ll find a responsive helm, sturdy lines, and a cockpit made for crew connection—or peaceful solo watching as the coast glides by. Inside, wood, cushions, and quiet corners give you both company and solitude.
This is no showboat—it’s a true sailing companion, ready for windward passages, wild tide races, and quiet anchoring bays. Built locally, sailed widely, and here to take you on a loop worth remembering.
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Pack light. Bring presence.
Essentials:
Layers, waterproofs, and something warm
Swimwear and towel (for the brave!)
Comfortable deck shoes or boots
Journal, pen, and an open mind
A book, or nothing at all
We’ll provide lifejackets, nourishing food, and everything else you need
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What’s Included
2 days / 2 night aboard a classic Contessa 32
Skipper and guide
All meals and drinks onboard
All yacht costs: mooring, fuel, insurance, safety gear
Activities: sailing, swim stops, short walks ashore
Use of lifejackets and waterproofs
Tea, coffee, snacks, and a glass of wine with dinner
A sense of freedom you won’t forget
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Q: Do I need sailing experience?
No. You’re welcome whether you’re a first-timer or a salty hand. We’ll show you the ropes.Q: Will we be at sea the whole time?
We’ll sail during the day and moor each night. There’s a mix of sheltered waters and exposed coast—but always within safe range.Q: What if the weather’s bad?
We’ll adjust the route or stop points to keep things safe and comfortable. This is about experience, not mileage.Q: Can I come on my own?
Yes—most people do. You’ll find good company and space for solitude when you need it.Q: Is this a retreat or an adventure?
Both. It’s a break from normal life, with just enough challenge to wake something up.
A Special Event, Once a Year: Join Us for the Round the Island Race
Once a year, we take part in something extraordinary.
The Round the Island Race is one of the world’s largest yacht races—a full circumnavigation of the Isle of Wight, with over 1,000 boats on the start line and a buzz that fills the Solent from dawn to dusk.
We enter not just to race, but to experience it all:
The early morning light on the water.
The shared momentum as sails fill and the fleet surges forward.
The laughter, the spray, the occasional chaos—and the quiet moments too.
This isn’t just about winning.
It’s about showing up, setting sail, and being part of something much bigger.
Whether you're chasing the tide or just soaking in the ride, there’s a place for you on board.
Available dates
10 - 12 April 2026
Lymington
Hampshire, UK
£350 per person
24 - 26 April 2026
Lymington
Hampshire, UK
£375 per person
22 - 24 May 2026
Lymington
Hampshire, UK
Lymington
Hampshire, UK
19 - 21 June 2026
£400 per person
£425 per person
11 July 2026 - Special Event - Round the Island Race
Lymington
Hampshire, UK
£500 per person
Book now
