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Living the dream in Bonaire! 1 SAILING charter at a time
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In this Charter Chat Podcast Brian talks to James Cognito, the owner and operator of a unique sailing and scuba diving charter company based in Bonaire. James ...

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10 reasons your next vacation should be a sailing charter!
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10 reason why we think your next vacation should be a sailing charter. A sailing charter could be the ultimate way to escape the ordinary and experience a ...

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The Charter Captain everyone wants, in the BVI
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Join us for an inspiring conversation with Captain Jason Geyser, one of the most requested yacht charter captains in the British Virgin Islands (BVI). In this ...

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SAILING VIRGINS. The best sailing courses on the planet!
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Charter Chat – Episode #6: James Kell, Founder & CEO of Sailing Virgins In Episode #6 of Charter Chat, we sit down with James Kell, Founder and CEO of ...

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Which dream vacation is right for you? Here is ours!
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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 ...

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Skippering our first sailing regatta in Antigua
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Join us on a sailing adventure through the beautiful Caribbean, as we explore Antigua while sailing in the Chasing Bubbles Regatta. This sailing regatta was an ...

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Charter Chat Podcast #4. Joe Rust/Chasing Bubbles Foundation-sailing regattas
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Live like Alex. That's the message from the Chasing Bubbles Foundation. In this Charter Chat Podcast episode we chat with Joe Rust, the brother of legendary ...

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Ultimate SAILING Itinerary for Antigua
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In this video we are chartering a Sunsail 46' monohull out of English Harbor and sailing the beautiful Caribbean islands of Antigua and Barbuda. We'll bring ...

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Sailing highlights
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Sailing highlights from our bareboat charters.

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Charter Chat Podcast episode 2. Learning the ropes w/William Cox. Sea Ox & Co
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Sail Stillwater Charter Chat podcast #2, Brian chats William Cox, a fellow YouTuber and entrepreneur behind Sea Ox & Co. William shares his journey from a ...

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Antigua Xtreme circumnavigation ADVENTURE!
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In this episode, Jillian and Brian embark on an extreme circumnavigation of Antigua, exploring the island's stunning beaches, snorkeling spots, and cultural ...

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Charter Chat Podcast episode 1. Why the BVI? w/ Alex Cena
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In this episode, we chat about yacht charters and sailing charters in the British Virgin Islands, the world-renowned mecca of sailing charters. We discuss the ...

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AMAZING snorkeling (and Pizza) spots! Sailing the Virgin Islands days 6-7
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Sailing the Virgin Islands | Bareboat Charter USVI & BVI | Culebra, Buck Island, Sea Turtles, Christmas Cove Days 6 and 7 of our unforgettable bareboat ...

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Culebra BLEW our minds! day 5
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Welcome to the beautiful island of Culebra, Puerto Rico, where the crystal clear waters and pristine beaches create a serene haven for all who visit. Join us ...

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Sailing from St Croix to Culebra. USVI-SVI  Day 4
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Day 4 of our Caribbean sailing adventure in the VIRGIN ISLANDS on a bareboat charter through the U.S. and Spanish Virgin Islands! Today we sail from St. ...

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Best beach to visit in the Virgin Islands. Sailing adventure day 3
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Today we leave Christiansted, St. Croix and sail to Buck Island, one of the most beautiful spots in the U.S. Virgin Islands. We drop anchor and spend time ...

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Cheers to change! Our Channel Gets a Complete Overhaul
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We sailed alot of miles in 2025! In this video we’re recapping it all and sharing what’s next for 2026. From unforgettable Caribbean sailing adventures to big ...

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Fish ON! Sailing the deep waters of St. Croix. Day #2
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Sailing Charter Day 2 | St. John to St. Croix | Rough Seas, Fishing & Christiansted Harbor and Boardwalk. Day 2 of our Virgin Islands sailing charter takes ...

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Blue Christmas! #bluechristmas #merrychristmas #beachchristmas #jostvandyke
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This is what we mean when we say we wish you a very blue Christmas!

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The most underrated sailing itinerary in the Caribbean! The USVI and SVI
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Join Brian and the crew as they sail a Bali catamaran through the USVI and SVI, taking on high seas, remote islands, and one of the most adventurous routes in ...

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Our favorite catamarans from the Annapolis Sailboat Show!
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In this video, we walk you through our Top 5 catamarans from this year’s Annapolis Boat Show—the models that truly stood out for innovation, comfort, ...

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Bucket list: visit all 50 states! Only 6 left!
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🌎 We’re visiting all 50 states, and in this travel vlog we complete States #42, #43, and #44: Delaware, New Jersey, and Pennsylvania! This East Coast road trip ...

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BVI mooring ball failure = DISASTER!
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In this video we dive into the question: Are mooring balls safe in the BVI? We take a close look at the incident involving The Wandering Hillbilly, when his ...

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World’s largest sailboat show. We’re going!
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Come along as we explore one of the biggest sailing events of the year — the Annapolis Sailboat Show! We’re excited to check out some incredible new boat ...

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