Which dream vacation is right for you? Here is ours!
Support Sail Stillwater
At WeBoating.com, we profoundly acknowledge the unwavering dedication that Sail Stillwater invests in crafting each and every video or voyage. Their passion for delivering exceptional ocean content shines through every frame, and it's a labor of love that deserves your attention.
We invite you to watch their captivating videos here and actively engage with their content, including their social media links above. Liking, commenting, and sharing their work goes a long way in fueling their creative fire.
We're also inviting you to explore the gear, sponsorships, and boat partnerships highlighted in the "Which dream vacation is right for you? Here is ours!" video description, or directly on YouTube. By engaging with these offerings or purchasing services and items, you directly support Sail Stillwater, their collaborators, and the brands they're associated with.
To ensure you never miss an offshore update, consider visiting their official YouTube Channel to subscribe, like, and join their community directly.
If you have any feedback, corrections, or additional information about Sail Stillwater or their videos, please use the comment form below to share your thoughts with us.
Thank you for being a part of our community and supporting the creators we cherish. Your time and support truly matter!
If you’ve ever dreamed about sailing through the Caribbean, waking up in a new island paradise every day, and skipping crowded resorts… this is your sign to make it happen.
In this video, we break down exactly why booking a sailing charter in the British Virgin Islands (BVI) might be the best vacation decision you’ll ever make—whether you go budget-friendly bareboat or all-in luxury crewed yacht.
What You’ll Learn in This Video:
Real cost of a BVI sailing charter (it’s more affordable than you think)
Bareboat vs. crewed charter (which one is right for you?)
How to visit multiple islands in one trip
Pulling up to iconic spots like the Soggy Dollar Bar & Willy T
Wildlife encounters: dolphins, sea turtles & more
Built-in adventures: snorkeling, paddleboarding, hidden caves
One-of-a-kind dining experiences (fresh Caribbean lobster in Anegada!)
Why sailing completely changes how you travel
Why Choose a Sailing Charter?
Forget being stuck at a resort. On a catamaran, you get:
A new view every morning
Total freedom & flexibility
Access to hidden beaches and secluded coves
Built-in excursions without extra fees
An experience that’s impossible to replicate on land
Iconic Stops Featured:
The famous Willy T (William Thornton floating bar)
Soggy Dollar Bar on Jost Van Dyke (home of the Painkiller)
Snorkeling at The Indians & Norman Island Caves
Dining in Anegada, Saba Rock & Bitter End Yacht Club
Cost Breakdown (Real Numbers):
Bareboat Charter: ~$10,000/week (~$178/person/night split)
Crewed Luxury Charter: ~$23,000/week (~$410/person/night, all-inclusive)
Compared to resorts, you’re getting transportation + lodging + adventure in one
This Isn’t Just a Vacation… It’s total freedom. No schedules. No crowds. Just you, your crew, and the open water.
Fair warning: after a trip like this… normal vacations might never feel the same again.
Like | Subscribe | Comment below if you’d try a sailing charter!
Keywords:
British Virgin Islands sailing, BVI catamaran charter, Caribbean sailing vacation, bareboat charter BVI, crewed yacht charter Caribbean, island hopping Caribbean, sailing trip cost, luxury sailing vacation, snorkeling BVI, sailing vs resort vacation, Caribbean travel guide, best Caribbean islands, yacht life, sailing vlog, BVI itinerary
00:00-00:22-That would be so cool
00:23-01:00-Channel Intro
01:01-02:49-The Cost breakdown
02:50-04:16- One Trip, Multiple Islands
04:17-05:28- Built-in Excursions
05:29-06:47- Unforgettable Dining Experiences
06:48-07:30- This changes things
07:31-08:14- We are biased
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
Channel Information:
Social Media Links:
Latest Episodes from Sail Stillwater
Explore the most recent voyages. Subscribe to the channel to never miss an update!
There was a sailing club in our backyard, and we didn’t even know it!
In this video we might just be starting our best sailing adventure yet! We are leaving the Caribbean behind, and joining the Oklahoma State Sailing Club right in our own little community of Stillwater, Oklahoma. As it turns out anyone in the community can become a member, not just college students...
Our best sailing moments changed us. Here’s why!
Join us as we sit down and compile our favorite sailing moments from our sailing adventures into one video. From island hopping in paradise to building miles sailing the North Atlantic, we show you some of our best moments on the water. Our first sailing moment was from our first sailing school ...
Sailor, Captain, Instructor and Entrepreneur. She’s done it all!
USCG Master Captain Amanda Haley joins Sail Stillwater to break down Caribbean navigation, charter captain licensing, inter-island channel crossings beyond Tortola, and seamanship throughout St. Vincent and the Grenadines.
We’re headed back to Annapolis for the Sailboat Show! #annapolis #cruiserscreatingcontent #boatshow
The mother of all sailboat shows is just a few weeks away and we are going! The Annapolis Sailboat show coming up October 15th-18th, and we are going! We are excited to see the new boats as well as hang out the cruisers creating content booth sponsored by the Young Cruisers Association.
We found beach bar paradise! The British Virgin Islands
BEST BEACH BARS IN THE BVI | British Virgin Islands Beach Bars, Rum Drinks & Caribbean Paradise Come with us as we explore the best beach bars in the BVI (British Virgin Islands)! From spectacular Caribbean beaches and turquoise water to legendary beach bars, cold rum drinks, and laid-back isla...