The Off-Grid Catamaran Experts
Join our "All-in" Collective for a voyage through the Caribbean, Bahamas, and the Mediterranean. Designed for groups of up to 12, this is an adventure ready journey where we trade resort luxuries for salt-air freedom, local discovery, and a life lived entirely on the water.
Welcome aboard
The promise
You don't need another vacation. You need a week where Tuesday feels like Saturday - where the only schedule is the tide, and the only notifications are dolphins off the bow.
Twelve guests, One catamaran, Someone who tracks the weather like a pulse, and a galley that turns out a fresh, inspired meal every night if desired. But the real secret ingredient is the crew — that's you. Here, the kitchen is a communal stage where we gather to prep, grill, and share stories as the sun dips below the horizon.
We sail the British Virgin Islands, the Bahamas, and the Mediterranean. The boat goes where the day-charter crowds don't.
The life you've been putting off - it starts the moment the lines come off the dock.
Five regions
The boat goes where day-charter crowds don't.
Five to seven nights at anchor, mooring to mooring, on a schedule the wind writes.
The voyages
Caribbean 3 weeks open
5 to 7 nights · British Virgin Islands
Starts at $3,350 per guest
Explore voyage
Bahamas 1 week open
5 to 7 nights · The Bahamas
Starts at $3,350 per guest
Explore voyage
Mediterranean 1 week open
5 to 7 nights · Croatia
Starts at $3,650 per guest
Explore voyage
Mediterranean 1 week open
5 to 7 nights · Greece
Starts at $3,650 per guest
Explore voyage
Mediterranean 1 week open
5 to 7 nights · Italy
Starts at $3,650 per guest
Explore voyageA limited run of sailing weeks each year.
View Full Calendar
The boat
Up to 12 guests aboard spacious catamarans between 40 and 60 feet - a full galley, private ensuite cabins, and a salon built for long dinners. See the living space and everything that comes with the week.
See what's aboardFrom our guests
Our trip with Guiding Winds was nothing short of perfection. We spent our days island hopping and soaking up every bit of the sun on the catamaran. Dodie and Clint have truly mastered the art of hospitality - they made everything feel so effortless and dreamy. If you're looking for gorgeous waters and a stress-free getaway, this is it. We can't wait to come back.
What an unbelievable experience. We loved the balance of relaxing in the sun and getting some fishing in. The catamaran is the perfect way to see the islands, and the water was absolutely stunning. Huge thanks to Dodie and Clint for being such incredible hosts. They made the entire journey seamless from start to finish. Highly recommend.
I've done a fair share of traveling, but this trip with Guiding Winds stands out. Island hopping on the catamaran was the highlight of my year - the views were incredible and the fishing was top-notch. Dodie and Clint are the real deal; they handle all the details so you can just enjoy the gorgeous scenery. A truly first-class experience.
Limited inventory
One catamaran· never a crowd
A limited run of sailing weeks each year. Caribbean dry season fills first.
2027 calendar · Real availability, no countdown timer
We speak with every guest before booking. Book a quick call and we'll walk you through the open weeks. Dodie or Clint reply within 24 hours.
One call, then your week
We talk it through before anything is booked
What you actually get when you do
Just bringing life back down to zero. Reset your body and mind, on nothing but water, weather, and time.
Wednesday
The day the signal finally drops
4 hours
Longest passage you'll ever sit through
Zero
Items billed once you're aboard
The crew
On Guiding Winds Unplug, we believe that harmony on the water starts with a clear plan.
Our week works because we don't overlap; we complement. By staying focused on our distinct strengths, we ensure your charter is professional, personalized, and perfectly executed.
Why guests come back
Five-star reviews
A small, owner-run operation - not an anonymous charter fleet.
All-inclusive
Meals, gear, fuel, moorings. One number, no hidden fees.
A quick call first
We speak with every guest before booking. No public checkout, no pressure.
On-the-boat support
Experienced hand at the helm, daily safety checks.
The right to unplug
No onboard internet by default. Wi-Fi available to buy, often unreliable.
100% five-star reviews
The 2027 calendar is open
We speak with every guest before booking. Book a quick call and we'll walk you through the open weeks. Dodie or Clint will reply within 24 hours.
Off-grid catamaran voyages
We speak with every guest first
