We've been hiding the truth! Sailing is HARD WORK!
In this video we reveal the secret that we haven't told anybody— turquoise bareboating a sail is HARD WORK! People see our videos and all they see is turquoise waters, light breezes, and the freedom of life at sea. But what they don’t often see is everything that happens before we even raise the sails.
In this video, we’re taking you behind the scenes to show you the real work that goes into planning and executing a successful sailing charter. It’s not just hopping on a boat and heading off into the sunset — there’s a ton of prep involved, and today, we’re laying it all out.
Here’s what we cover in this video:
🧭 Planning & Route Design:
How we research destinations, study charts, check seasonal weather patterns, and choose anchorages that are both beautiful and safe.
✈️ Travel & Logistics:
Coordinating flights, transfers, marina access, ferries, customs (when needed), and making sure everything lines up with the charter schedule — for us and the crew.
🧃 Provisioning the Boat:
From food and drinks to spare parts and emergency supplies — we do all the provisioning ourselves. Learn how we plan meals, manage storage, and keep the crew well-fed and happy on the water.
👩✈️ Crew Safety & Preparation:
Safety briefings, equipment checks, and making sure everyone knows what to do in case of emergency. Chartering isn’t just about fun — it’s about responsibility.
💡 Lessons Learned:
We’ll also share a few hard-earned lessons from past charters — things we wish we knew earlier and tips that can help you avoid common pitfalls.
Whether you’re dreaming of your first sailing charter or you’re a seasoned sailor, this episode will give you a whole new appreciation for what goes on before the adventure begins.
#sailstillwater #bareboatcharter #adventuretravel
Sail Stillwater
Thank you for finding your way to our channel! We are Jillian and Brian from Stillwater, Oklahoma. We are a blue collar couple who enjoy traveling as much as our bank account and busy lives will allow. We love turquoise water, rum, and every place in the Caribbean that we have dipped our toes into. We have a passion for sailing and in our downtime you will find us on a charter somewhere with our friends and family. We started our channel to document our travels and share our love of sailing and travel. We are working hard on our retirement plan to purchase our own catamaran and set sail for the Caribbean! Start our own charter business and supplement our retirement by providing people the opportunity to relax or to live like a modern day pirate on board our boat, while we show them around the paradise we have came to love. I hope we can enjoy an umbrella drink with you sometime in the future. Cheers! https://www.youtube.com/channel/UCBusRK4UPRVsEOzvz3Zpvpw?sub_confirmation=1
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We've been hiding the truth! Sailing is HARD WORK! Location
- British Virgin Islands (18.420695,-64.639968)
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