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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RACING 70 MILES to DRY TORTUGAS National Park in a FAST BOAT! Everything You NEED to KNOW! | S4:E19
Sailing The Far Side

RACING 70 MILES to DRY TORTUGAS National Park in a FAST BOAT! Everything You NEED to KNOW! | S4:E19

Hey Everyone! What an exciting day ahead, and a very quick trip out to the fort! Faster on this 37 ft Edgewater with triple 300 HP Yamaha's! Let me know what you think about this trip and let me know if you are interested in joining me! Also we didn't have the nicest day so enjoy some unde...
A BELOW DECK REUNION in THAILAND! | (Episode 362)
Sailing Parlay Revival

A BELOW DECK REUNION in THAILAND! | (Episode 362)

In this episode we race against another lagoon 450, then have a surprise visitor who starred in the reality TV show Below Deck, after taking over from Captain Lee. I also did a few seasons of below deck, so it was fun to hang out again, and share stories, as well as find a massive shipwreck on the r...
Skippering our first sailing regatta in Antigua
Sail Stillwater

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...
Live From Lady Hawk, The Tequila Tall Ship.
SailorBarry

Live From Lady Hawk, The Tequila Tall Ship.

Welcome to the First Live Aboard Ladyhawk, ask ya Anything!! Joined by Hoyle! Say hi! Join the Founders Circle → Become part of the crew shaping the first Pacific sail-cargo mission of the modern era. ⸻ ❤️ Support the Journey Patreon → PayPal → Buy Us A Beer → ⸻ 🪵 Gear & Affiliates ...
GIRLS Gone Grouper! Day 2 DIVING Gets WILD Underwater! S4:E11
Sailing The Far Side

GIRLS Gone Grouper! Day 2 DIVING Gets WILD Underwater! S4:E11

Hey Everyone! Day 2 of Grouper Season and we finally got luck! Enjoy this underwater adventure, and let me know what you think! Divers are Victoria and Tracy! Wetsuit and gloves from Waihana Fins from Penetrator Foot pockets from SEAC Mask From Hammerhead Spearguns Dive knife and Snorkel from SoFl...
Two Girls One BOAT!!  S4:E10
Sailing The Far Side

Two Girls One BOAT!! S4:E10

Hey Everyone! Grouper Opener was upon us! Called my friend Victoria to participate in the fun! We took to the patch reefs to try our luck at a black grouper. While out I managed to secure an invasive species for dinner! j Want to order some fresh seafood yourself? Click the link! Foul weather ge...
100+ LOBSTERS in ONE Night!!! Bully Netting CHAOS & Racing a Monster STORM S4:E9
Sailing The Far Side

100+ LOBSTERS in ONE Night!!! Bully Netting CHAOS & Racing a Monster STORM S4:E9

Hey Everyone! Lobster season is always fun when they are walking at night! Bullynetting is another form of lobster harvesting since it is illegal to harvest while diving at night. Netting! No Problem!! Commercial Lobster permit holders are allowed to harvest 250 lobsters in one evening. Want to or...
GUNS And Flying FISH! NOT Your Average FISHING TRIP! Key West Pirates Take TO THE SEA! S4:E8
Sailing The Far Side

GUNS And Flying FISH! NOT Your Average FISHING TRIP! Key West Pirates Take TO THE SEA! S4:E8

Hey Everyone! So this is definitely not your average fishing trip!! Want to order some fresh seafood yourself? Click the link! Foul weather gear from West marine! Want to support my travels and get an early peak at the videos?! Become a Patron for all that and more! Thanks again for watching...
GIRLS Go DIVING! Florida Keys LOBSTER Mini Season! Do We Get OUR LIMIT? S4:E7
Sailing The Far Side

GIRLS Go DIVING! Florida Keys LOBSTER Mini Season! Do We Get OUR LIMIT? S4:E7

Hey Everyone! It's lobster season in Florida and we get a couple days to slay before season opens for everyone, called mini season, at the end of August! They give us these days because Commercial trappers are allowed to set their traps after this time, and we need a chance to manage a limit ...
The FINAL HAUL! What We DO When Stone Crab Season ENDS In THE FLORIDA KEYS!! Catch, Eat, Cook S4:E6
Sailing The Far Side

The FINAL HAUL! What We DO When Stone Crab Season ENDS In THE FLORIDA KEYS!! Catch, Eat, Cook S4:E6

Hey Everyone! Better late than never here is the end of stone crab season video! Season ended May 1st. So its a little bit of a preview for next season!! Want to order some fresh seafood yourself? Click the link! Foul weather gear from West marine! Want to support my travels and get an early pe...
Sailor Barry Birthday live stream! Join us after two years on YouTube!
SailorBarry

Sailor Barry Birthday live stream! Join us after two years on YouTube!

Support: Patreon: PayPal: Buy Us A Beer!!: - Barry - Hailly Amazon WishList!: #portrownsend #woodenboats #woodenboat #woodboat #boatshow #sailing #sailingadventure
Recreational Stone Crabbing In KEY WEST!! Prep, Catch and COOK! S4:E3
Sailing The Far Side

Recreational Stone Crabbing In KEY WEST!! Prep, Catch and COOK! S4:E3

Hey Everyone! Stone Crab season in Florida means we eat good down in the Keys! As residents of Florida I am allowed to have 5 traps for myself. My little sister lives with me so she has 5 as well. With 10 total traps (For now) we can get a pretty good haul about every 8 days! Enjoy the episode and ...
45 foot BUDDY DAVIS Express EMERGENCY Trip To MIAMI, On ONE ENGINE!! S4:E2
Sailing The Far Side

45 foot BUDDY DAVIS Express EMERGENCY Trip To MIAMI, On ONE ENGINE!! S4:E2

Hey Everyone! So here is a little look into my life down in Key West. I work for a private owner and manage and run a 45 ft Buddy Davis Express. We fish when they are in town and I maintain the vessel when they are not. This was an emergency engine trip, we had to have the problem solved asap. Unfo...
BOAT CAPTAIN FRUSTRATED BY FACEBOOK TROLLS! –  (Episode 260)
Sailing Parlay Revival

BOAT CAPTAIN FRUSTRATED BY FACEBOOK TROLLS! – (Episode 260)

A marine captain shares his experience dealing with the frustration of negative comments from Facebook trolls on a post discussing their boat's damages. Despite the setback, the crew continues to offer valuable tips to their boating community.
NEW SOLAR!!! Update on all of the updates🌴🌊 Sailing Vessel Swizzle EP17
Sail Swizzle

NEW SOLAR!!! Update on all of the updates🌴🌊 Sailing Vessel Swizzle EP17

This week I will be walking you through some of the new additions to our little Swizzle and explain how some things we upgraded over the last few week. All kinds of good info in this episode as we have some BIG news to announce!! :) Cheers and well see you guys next week! Be Sun Smart, wear our S...
SHIPRECT Sailing Podcast EP1: Pre Departure Planning & Common Mistakes from a former towing Captain.
SailorBarry

SHIPRECT Sailing Podcast EP1: Pre Departure Planning & Common Mistakes from a former towing Captain.

Buy Us A Beer!!: Support: Patreon: PayPal: Welcme to the first episode of! SHIRECT, the podcast about Saling! Let’s get started with pre departue planning and common boater mistakes! Sailor Barry & Hailly Season 2 is HERE! And this is the crazy story of how we got Thunder Child! Part One...
Settlers Of Catan with Sailor Barry, Hailly, Finding Simon & Nathan! Live Q&A and Tacos! 🌮
SailorBarry

Settlers Of Catan with Sailor Barry, Hailly, Finding Simon & Nathan! Live Q&A and Tacos! 🌮

Support : Patreon - Support: Patreon: PayPal: Sailor Barry & Hailly Episode Live! - Barry - Hailly
Goodbye 2023! We Re-Join Civilization After a Rough Sail [Ep. 139]
Sailing Sweet Ruca

Goodbye 2023! We Re-Join Civilization After a Rough Sail [Ep. 139]

We take a look back at 2023 this New Years Eve and remember Cape Horn as we battle tough conditions and make repairs while sailing to our first dock after over 3 months alone in the wilderness of Patagonia. #sailing #newyear #2023 #capehorn Our year in review contains some unforgettable moments:...
Sailor Barry & Finding Simon Live from Silva Bay Sewing Loft
SailorBarry

Sailor Barry & Finding Simon Live from Silva Bay Sewing Loft

Support: Patreon: PayPal: Sailor Barry & Hailly Season 2 is HERE! Episode! Finally after 2 and a half years we set sail on our 1956 wooden sailboat! And explore the lovely gulf islands! - Barry - Hailly
Sailor Barry & Hailly – Live! When is Boat Launch?! Progress report and Bird Naming!
SailorBarry

Sailor Barry & Hailly – Live! When is Boat Launch?! Progress report and Bird Naming!

Support : Patreon - Support: Patreon: PayPal: Sailor Barry & Hailly Episode Live! - Barry - Hailly
Sailing The Whitsundays – Part 3 | Sailing Sunday
Sailing Sunday

Sailing The Whitsundays – Part 3 | Sailing Sunday

Join this awesome group of Australian YouTubers as we navigate the pristine waters of the Whitsundays aboard a luxury catamaran, capturing every moment of laughter, exhilaration, and pure joy. Witness the transformation from monohull sailors to fearless catamaran captains reveling in the sheer bliss...
Cruising around French Polynesia with The BucketLust
S/V Full Send
Live with Sailor Barry and Hailly – drink a beer with us! And talk cheap and free boat restoration!
SailorBarry

Live with Sailor Barry and Hailly – drink a beer with us! And talk cheap and free boat restoration!

Support : Patreon - Join us for a beer! Hailly and I are keen to answer questions or just hang out and talk boats! Lots going on with Dagon and perihelion! 12k subscribers! 11 patrons! Dang this ship has set sail! Instagram: Sailor Barry - Instagram: Hailly - Thank you for watching! I really...
Live from the free boat! Sailor Barry & Hailly – drink a beer with us! Q&A tour and updates!
SailorBarry
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