What This Adventure Is

This isn't a sailing course or a sightseeing cruise.

It's a week of living aboard, travelling by sail and seeing where the wind, weather and tide take us.

We'll explore the Isle of Wight, sail beyond the Needles and head west towards Dorset and the Jurassic Coast. Along the way we'll discover quiet anchorages, beautiful harbours, coastal towns and some great waterside pubs.

You can take the helm, help sail the boat and become part of the crew — or simply enjoy being out on the water.

No previous sailing experience is needed. Just bring a sense of adventure.

What to Expect

Every week will be different.

The weather and tides will shape our exact route, but the adventure might include:

• Sailing through the Solent and around the Needles

• Exploring the Isle of Wight

• A longer passage west towards Weymouth

• Anchoring beneath the Jurassic Coast

• Swimming from the boat

• Visiting places such as Yarmouth, Cowes, Lymington, Weymouth and Studland

• A sunset or night sail

• Quiet mornings at anchor and evenings ashore

• Seven days living simply aboard a classic yacht

There will be plenty of sailing, but also time to explore, eat well, talk, laugh and enjoy having nowhere else you need to be.

Meet the Boat

Classic, coastal, and built for adventure.

Boosy Boots, 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 and built in the ’70s, 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.

What to Bring

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

What’s Included

• 7 days aboard Bossy Boots

• Professional skipper

• Accommodation onboard

• Marina and mooring fees

• Fuel and yacht costs

• All food and drinks onboard

• Lifejackets, waterproofs and safety equipment

• A week of sailing, exploring and adventure

Do I Need Sailing Experience?

Not at all.

This week is designed to work just as well for someone stepping onto a yacht for the first time as someone who has sailed before.

You'll naturally learn a huge amount during the week, and you're welcome to get as involved as you like.

But there are no exams, no certificates and no classroom.

This is an adventure first.

FAQ

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 generally sail during the day and moor each night. There’s a mix of sheltered waters and exposed coast—but always within safe range. If the conditions allow we may sail through one night.

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.