Watch Sailing & Boating Adventures Around the World
Explore sailing, boating, and water sports through our curated video archive. From epic sea voyages to serene diving escapes, discover unforgettable adventures from top YouTube creators. Start your journey. Dream big. Sail far.
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Living the dream in Bonaire! 1 SAILING charter at a time
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 and his wife Julia are living out their dream of living life on a Voyage catamaran, while doing sailing charters in paradise. They offer ev...
10 reasons your next vacation should be a sailing charter!
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 truly unforgettable vacation on the water. In this video, we reveal 10 reasons why a sailing charter should be your next vacation—from explorin...
The Charter Captain everyone wants, in the BVI
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 episode, Jason shares his journey into the world of luxury yacht charters, his lifelong passion for sailing, and the hospitality-first minds...
SAILING VIRGINS. The best sailing courses on the planet!
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 Sailing Virgins, to discuss his journey of building one of the world's leading sailing education and adventure companies. James shares how...
Which dream vacation is right for you? Here is ours!
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 vacat...
Skippering our first sailing regatta in Antigua
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 unforgettable experience, filled with stunning sunsets and group gatherings. Discover the joys of boat life with us as we journey through th...
Charter Chat Podcast #4. Joe Rust/Chasing Bubbles Foundation-sailing regattas
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 sailor Alex Rust, known from the YouTube documentary Chasing Bubbles Documentary. Learn about their foundation and how they are inspirin...
Ultimate SAILING Itinerary for Antigua
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 you along as we hit all of the hot spots and show you the best anchorages and things to do on the islands. With stops like Green Is...
Charter Chat Podcast episode 2. Learning the ropes w/William Cox. Sea Ox & Co
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 career in public safety to starting a charter business in Corpus Christi Bay. The conversation also touches on the importance of certifica...
Antigua Xtreme circumnavigation ADVENTURE!
In this episode, Jillian and Brian embark on an extreme circumnavigation of Antigua, exploring the island's stunning beaches, snorkeling spots, and cultural landmarks. They share their experiences from arrival to the highlights of their sailing adventure, including delicious local cuisine and t...
Charter Chat Podcast episode 1. Why the BVI? w/ Alex Cena
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 ultimate BVI charter itinerary, highlight the best anchorages and hot spots in the British Virgin Islands, and explain why the BVI continues...
AMAZING snorkeling (and Pizza) spots! Sailing the Virgin Islands days 6-7
Sailing the Virgin Islands | Bareboat Charter USVI & BVI | Culebra, Buck Island, Sea Turtles, Christmas Cove Days 6 and 7 of our unforgettable bareboat sailing adventure through the U.S. and Spanish Virgin Islands were the perfect finale to an amazing trip. Day 6 we set sail from beautiful Cu...
Culebra BLEW our minds! day 5
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 as we explore this stunning Caribbean gem, sailing across its azure waters and discovering its secluded spots. This 4K video captures the esse...
Sailing from St Croix to Culebra. USVI-SVI Day 4
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. Croix (USVI) to the island of Culebra, Puerto Rico, a favorite stop for cruisers and sailors traveling between the Virgin Islands and Puerto Ric...
Best beach to visit in the Virgin Islands. Sailing adventure day 3
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 enjoying Buck Island’s incredible beach, crystal-clear water, and relaxed island vibes. From there, we continue sailing toward Frederiksted, St....
Cheers to change! Our Channel Gets a Complete Overhaul
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 lessons learned, this year helped shape the future of our channel — and 2026 is going to be even better. In 2025, we sailed through Puerto ...
Fish ON! Sailing the deep waters of St. Croix. Day #2
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 us offshore as we leave St. John, USVI and sail across deep open water to St. Croix. With rough seas and steady wind, this passage was a t...
The most underrated sailing itinerary in the Caribbean! The USVI and SVI
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 the Caribbean. This isn’t your typical charter itinerary—it's rougher, wilder, and absolutely unforgettable. From offshore fishing (we ...
Our favorite catamarans from the Annapolis Sailboat Show!
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, performance, and pure wow-factor. Whether you’re shopping for your next bluewater cruiser or just love drooling over beautiful multihulls, you won’t w...
Bucket list: visit all 50 states! Only 6 left!
🌎 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 includes beaches, ferries, boardwalks, coastal drives, big-city sightseeing, and the best Philly cheesesteak we’ve ever had. 🚗 Our Full Rou...
BVI mooring ball failure = DISASTER!
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 boat broke free from a mooring ball and ended up drifting and grounding — a dramatic reminder that mooring balls aren’t automatically “safe.” ...
World’s largest sailboat show. We’re going!
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 models, including: 🛥 Leopard 46 – sleek, modern, and built for adventure ⛵️ Lagoon 43 – the latest from a fan favorite ⚓️ Royal Cape Majestic 530 ...
BVI sailing charter itinerary
7-Night Bareboat Sailing Itinerary in the BVI | British Virgin Islands Yacht Charter Adventure Come aboard as we take you on our bareboat sailing adventure through the British Virgin Islands — one of the most iconic and beginner-friendly cruising grounds in the world. In this video, we break down ...