Watch Sailing & Boating Adventures Around the World – Page 2 of 3
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.
Showing 25-48 of 52 results
1974 Cheoy Lee Offshore 31 Ketch | Forgotten Barn Find Classic Needs a New Captain | $8k | Full Tour
#boatfoolssailing #CheoyLeeOffshore31 #BarnFindBoat #ClassicPlastic #sailboatrestoration 1974 Cheoy Lee Offshore 31 Ketch | Forgotten Barn Find Classic Needs a New Captain | $8k | Full Tour Hey BoatFools Nation! Canadian Ken and I tracked down a true barn-find time capsule — a 1974 Cheoy Lee Of...
BLUEWATER Battle Axe! This Steel Sailboat Will Go Anywhere! $29k | TOUR
#boatfoolssailing #bluewatersailboat #steelsailboat #oceancruisingboats #sailboattour BLUEWATER BATTLE AXE! This Steel Sailboat Will Go Anywhere! $29k | TOUR Canadian Ken and I have seen a lot of fiberglass, but this was a first — a steel-hulled sailboat built like a ship and ready to cross o...
The Venerable Bristol 27 | The Sailboat that changed everything!
#boatfoolssailing #Sailing #Bristol27 #CruisingSailboats #SailboatReunion #CanadianKen This Sailboat Changed Everything! Canadian Ken Reunites with his Old Bristol 27! Ahoy BoatFools Crew! ⚓ This week, we hit the road to Portland, Maine, for an emotional reunion: Canadian Ken reconnects with his...
Canadian-Built Classic! C&C 33 Mk II Sailboat Tour – Now $29,500
#boatfoolssailing #BudgetSailboats #SailboatTour #SailboatForSale Canadian-Built Classic! C&C 33 Mk II Sailboat Tour – Now $29,500 Ahoy BoatFools Nation! First of all - stick around to the end for the contest results AND the big reveal of our surprise guest for next week! Canadian Ken fell ...![A SENSATIONAL Trailerable Pocket Cruiser: The Com-Pac 17 Sun Cat for $9,500! [[SOLD 9/16/25]]](https://i.ytimg.com/vi_webp/HAHUR4eWVFw/mqdefault.webp)
A SENSATIONAL Trailerable Pocket Cruiser: The Com-Pac 17 Sun Cat for $9,500! [[SOLD 9/16/25]]
#boatfoolssailing #sailingboat #pocketcruiser #trailersailer [[SOLD 09/16/2025]] A SENSATIONAL Trailerable Pocket Cruiser: A Com-Pac 17 Sun Cat for $9,500! TOC: 00:00 What did we just find?!? 00:24 Intro to the Comp-Pac 17 Sun Cat - And "Kenadian" 01:02 Walk around the boat and a look a...
Labor Day Update! Dad Tears, Boat Sales & Sea Level Rise!
#sailing #boatfoolssailing #channelupdate #notears Labor Day Update! Dad Tears, Boat Sales & Sea Level Rise! Happy Labor Day, BoatFools Nation! No full-length video this week because I was busy dropping my daughter at college (and crying enough tears to raise sea levels in the Gulf of Maine)....
Sailing Maine’s Stunning Coast & Islands!
#boatfoolssailing #SailingMaine #Gunkholing #sailinglife #Morgan382 #CruisingSailboat #coastalcruising 5 Days Gunkholing The Maine Coast! 5 Sailboats, 85 NM, and the Sturgeon Moon! Join Green Mountain Josh and me as we take our Morgan 382 on an unforgettable 4-night, 5-day gunkholing cruise from...
We Fell Hard for This 47-Foot Classic Sailboat! Eldredge-McInnis Cutter at $60k | TOUR
#boatfoolssailing #classicyacht #CutterSailboat #sailboatforsale #WoodenBoatLove We Fell Hard for This 47-Foot Classic Sailboat! Eldredge-McInnis Cutter at $60k! [PRICE REDUCED AS OF 08/30/2025] Chapters: 00:00 Where is Canadian Ken? 00:50 Intro to this Beauty and to Jordi St. John and MITA 03...
RARE Allied Seawind II Sloop — Spotless, Proven, $23K OBRO! TOUR
#boatfoolssailing #sailing #sailboattour #affordablesailing #bluewatercruiser RARE Allied Seawind II Sloop — Spotless, Proven, $23K OBRO! Could this be the perfect budget bluewater boat? We found a RARE sloop-rigged 1976 Allied Seawind II that’s so clean, it might just be in better shape than whe...
FAST. Rugged. World Ready! 2018 Marples 40 Trimaran. FULL TOUR!
#SailboatTour #Trimaran #Multihull #BluewaterSailing #BoatFools #boatfoolssailing #FastCruiser FAST. Rugged. World Ready! 2018 Marples 40 Trimaran. FULL TOUR! ASKING PRICE: $125,000 TOC: 00:00 Canadian Ken in down below 00:08 Intro - Fly over of the Marples Custom 40 CC Fast Cruiser 00:26 Up On D...![A SENSATIONAL Small Cruiser! A 1981 Sam Crocker 29′ STUNNER. $17.5k [[SOLD!]]](https://i.ytimg.com/vi_webp/3mWpdXg1R9g/mqdefault.webp)
A SENSATIONAL Small Cruiser! A 1981 Sam Crocker 29′ STUNNER. $17.5k [[SOLD!]]
#boatfoolssailing #crockersloop #classicsailboat #sailboattour #sailboatforsale A SENSATIONAL Small Cruiser! A 1981 Sam Crocker 29' STUNNER. $17.5k | [[SOLD 10/17/25]] This. Is. Boomerang. A sensational 29-foot Sam Crocker-designed cruiser (Design #286) built in 1981—and she’s a total stunne...
Did We Buy The Wrong Sailboat?!
@boatfools #sailing #sailboat #sailboatrefit Did We Buy the WRONG Sailboat?! | Morgan 382 – 4 Years Later After 4 years of full-time cruising aboard our 1980 Morgan 382, designed by the legendary Ted Brewer, we’re finally asking the question… Did we buy the WRONG boat?! In this episode, we get...
For $10k You Could Sail Away On This GREAT 1971 Bristol 30! FULL TOUR
#Bristol30 #HerreshoffDesign #ClassicSailboat #SailboatForSale #BoatFoolsSailing For $10k You Could Sail Away On This GREAT 1971 Bristol 30! FULL TOUR Chapters: 00:00 Opening scene 00:16 Introduction - The Bristol 30 01:46 Keel & Topsides: Nice! 04:48 The Mast & Rigging 06:13 The Cockpit...
ONE-OWNER Morris Justine 36 – So PRETTY It HURTS (SOLD)! $215k. Full Tour
#sailing #sailboattour #boatforsale #boatfoolssailing ***[[SOLD 07/08/2025]] ONE-OWNER Morris Justine 36 - So PRETTY It HURTS (SOLD)! $215k. Full Tour Cymbria is quite possibly the finest Morris Justine 36 ever built—and certainly the best currently for sale. She’s been with her original owners s...![A FREE Cape Dory 28! Classic Carl Alberg Sailboat Needs a New Home! [[SOLD]]](https://i.ytimg.com/vi_webp/ndEbi7-ok0E/mqdefault.webp)
A FREE Cape Dory 28! Classic Carl Alberg Sailboat Needs a New Home! [[SOLD]]
#FREEBoat #CapeDory28 #classicsailboat #ProjectBoat #CarlAlberg A FREE Cape Dory 28?! Classic Carl Alberg Sailboat Needs a New Home! [[AND SHE FOUND ONE 08/01/2025]] She’s not perfect—but she is free. This 1978 Cape Dory 28 has classic lines, a full suite of sails, and serious potential. Designed...
The TRUTH About SAILBOAT Insurance: Everything You Need to Know!
#sailing #sailboatinsurance #boatinsurance THE TRUTH ABOUT SAILBOAT INSURANCE | Everything You Need to Know! There’s a ton of confusion out there about sailboat insurance—especially when it comes to older sailboats or wooden boats. Some say you can’t get coverage. Others claim the process is a nig...
Why This Vintage Hinckley Is a Deal at $58K
#HinckleyPilot35 #ClassicSailboat #BluewaterSailboat #SailboatTour #SailingLife Why Does This Old Boat Still Turn Heads in 2025? Hinckley Pilot 35: The Icon Lives On! | Full Boat Tour We finally got aboard our first Hinckley—and as Canadian Ken says, "you never forget your first Hinckley!&q...
BoatFools Sailing Top 10 SAILBOATS Under $35k In New England! Spring 2025
#SailboatsUnder35k #SailboatDeals #UsedSailboats #BudgetSailing #SailingNewEngland 🏆 BoatFools Sailing: Top 10 Sailboats Under $35K in New England – Spring 2025 Edition! ⛵ Canadian Ken and I scoured the salty corners of New England to find the best used sailboats under $35,000—from Craigslist and F...
A Potential DEAL on a CLASSIC Racer-Cruiser! A 1982 Catalina 38 for $16,900. Full Tour!
#Catalina38 #ClassicSailboat #SailboatRestoration #Sailing #boatfoolssailing [[SOLD - 11/15/2025]] A Potential DEAL on a CLASSIC Racer-Cruiser! A 1982 Catalina 38 for $16,900. Black Pearl: A 1982 Catalina 38 – A Classic Almost Restored! This week, join me as I explore a 1982 sailboat in the chil...![The HANS CHRISTIAN 38T TELSTAR: A RARE legendary WORLD cruiser for $50,000! [[SOLD!]]](https://i.ytimg.com/vi_webp/bcCekqZW_tw/mqdefault.webp)
The HANS CHRISTIAN 38T TELSTAR: A RARE legendary WORLD cruiser for $50,000! [[SOLD!]]
#HansChristian38T #BluewaterCruising #SailboatForSale #LiveaboardLife #SailingDreams [[SOLD AS OF 05/22/2025]] The HANS CHRISTIAN 38T TELSTAR: A RARE legendary WORLD cruiser built for adventure. Asking price is $90,000. And she's a 1989! Looking for a timeless cruiser ready to sail the world...
Do Used SAILBOATS Actually Sell? You’ll Be Surprised How Quickly THEY DO And For HOW MUCH! ’24 Recap
Do Used SAILBOATS Actually Sell? You’ll Be Surprised How Quickly THEY DO And For HOW MUCH! (2024 Recap) In this year-end episode of BoatFools Sailing, we dive into the fascinating world of used sailboat sales in 2024. 🚤 Out of the 25 boats we featured this year, 16 sold, and today, we’re highlighti...
The TOP 10 SAILBOATS For Sale in CALIFORNIA! (Bay Area). Some FANTASTIC boats and DEALS! 11/2024
@boatfools #sailboatforsale #sailingpassion #sailing #boatfoolstop10 The TOP 10 SAILBOATS For Sale in CALIFORNIA! (Bay Area) Ok, it's been a minute since we've done a BoatFools Top 10 - and we have never explored what's available up in the Bay Area and, man, are we glad we did! There...
The Perfect All-Purpose Sailboat! This Morgan 384 Can Do It All! BACK ON MARKET! $39,500. TOUR
@boatfools #sailing #sailboatforsale #morgan384 [UPDATE 08/30/2025] THIS AWESOME BOAT IS BACK ON THE MARKET! The Perfect All-Purpose Sailboat! Quite possibly for a 38-foot sailboat, the Morgan 384, in this price range, might be the most satisfying sailboat you can buy. FULL TRANSPARENCY: we are 10...