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.

Showing 1-16 of 16 results
A Mistake A New Cruiser Can Make with Their Boom [Ep 60]
Sailing Into the Mystic

A Mistake A New Cruiser Can Make with Their Boom [Ep 60]

This sailing adventure captures the reality of cruising, from the easy to challenging sails. If you enjoy sailboat life, this look at our recent journey provides a glimpse into the highs and lows of coastal sailing, in particular along the Pacific Coast of Baja California. We share the ups and downs...
One of the TOUGHEST Small Cruisers Ever Built? Nicholson 31 for $15K | FULL TOUR
BoatFools Sailing

One of the TOUGHEST Small Cruisers Ever Built? Nicholson 31 for $15K | FULL TOUR

#Nicholson31 #BluewaterCruiser #SailboatTour #PocketCruiser #BoatFoolsSailing One of the TOUGHEST Small Cruisers Ever Built? Nicholson 31 for $15K | FULL TOUR Welcome back, BoatFools Nation! Today Canadian Ken and I step aboard a true offshore legend: a beautifully maintained 1978 Nicholson 31 sa...
Cheap Sailboats: The Dream, The Deal, and The Disaster
Lady K Sailing

Cheap Sailboats: The Dream, The Deal, and The Disaster

Cheap sailboats are still everywhere if you know where to look. In this episode, I went online and found 50 real sailboats for sale under $15,000, including older fiberglass boats like Catalina 22s, Catalina 25s, Catalina 30s, C&C sailboats, Pearson 30s, Hunters, O’Days, Islanders, Cals, Mirages...
Why TODAY Is the Best Time to Buy a 22-Foot Sailboat
Lady K Sailing

Why TODAY Is the Best Time to Buy a 22-Foot Sailboat

If you’re looking for the best 22-foot sailboats, this guide breaks down three of the most popular and proven small cruisers on the market: the Catalina 22 Sport, Hunter 22, and O’Day 22. These boats have stood the test of time because they’re affordable, trailerable, and easy to sail, making them p...
Beneteau and Farr – Luxury FAST Sailboats
Practical Sailor

Beneteau and Farr – Luxury FAST Sailboats

Jeanneau 55 Boat Review: If you’re searching for luxury sailboats you can live on that don’t sacrifice sailing performance, the Beneteau Oceanis 461 is one of the most compelling options on the used market. In this Practical Sailor review, we take a deep dive into the Bruce Farr–designed Beneteau ...
Fast Sailboats Your Spouse Will Love | Bruce Farr & Beneteau
Practical Sailor

Fast Sailboats Your Spouse Will Love | Bruce Farr & Beneteau

Tartan 30: An Affordable Classic: If you’re searching for fast cruising sailboats that don’t sacrifice comfort, the Beneteau First 40.7 might be one of the best answers ever built. In this Practical Sailor review, we take a deep dive into the Bruce Farr–designed Beneteau First series, including th...
Old Boat, Big Charm | 1968 Cheoy Lee Offshore 31 for $12.5K
BoatFools Sailing

Old Boat, Big Charm | 1968 Cheoy Lee Offshore 31 for $12.5K

#boatfoolssailing #cheapboats #boattour #herreshoff #cheoylee #classicsailboat Old Boat, Big Charm | 1968 Cheoy Lee Offshore 31 for $12.5K In this episode of BoatFools Sailing, Canadian Ken and I travel to Bath, Maine — home of Bath Iron Works — to step aboard a beautifully cared-for 1968 Cheoy ...
We Reviewed 31 Sailboats This Year. 17 Sold. Here’s What Happened
BoatFools Sailing

We Reviewed 31 Sailboats This Year. 17 Sold. Here’s What Happened

#boatfoolssailing #sailboatreview #sailingboat #boattalk What Sold, What Sat, and Why. A Wild Year in Sailboats! (BoatFools 2025 Review) 2025 was a BIG year for BoatFools Sailing. Canadian Ken and Tris take a hard look back at the sailboats we profiled, the ones that sold, the ones that surprised...
$10K to $100K Sailboats — Which One Would YOU Buy?
Lady K Sailing

$10K to $100K Sailboats — Which One Would YOU Buy?

If you’ve been watching the used sailboat market waiting for the perfect 2026 deal, this one’s for you. In this video, we break down five of the best budget sailboats you can buy — from a $10,000 weekend cruiser to a $100,000 liveaboard dream. We’ll cover real-world prices, performance, what to wat...
A GREAT Budget Liveaboard! The Pearson 365 Ketch $28k | FULL TOUR
BoatFools Sailing

A GREAT Budget Liveaboard! The Pearson 365 Ketch $28k | FULL TOUR

#boatfoolssailing #sailboattour #budgetsailboat #cruisinglife A GREAT Budget Liveaboard! The Pearson 365 Ketch $28k | FULL TOUR Looking for a great budget liveaboard sailboat? The classic 1979 Pearson 365 Ketch, designed by the legendary Bill Shaw, might be exactly what you’ve been searching for....
The Alberg 30: A Sailboat Design That’s Aging Like Fine Wine | TOUR [[9/7/25 SOLD!]]
BoatFools Sailing

The Alberg 30: A Sailboat Design That’s Aging Like Fine Wine | TOUR [[9/7/25 SOLD!]]

#Alberg30 #sailboattour #classicsailboat #boatfoolssailing #cruisingsailboat [[09/07/2025 SOLD]] LEGENDS Never DIE! Alberg 30 Sailboat Tour | $12,500 LEGENDS Never Die! Meet HERON, a 1968 Alberg 30 sailboat — one of the most beloved 30-foot cruisers ever built. Canadian Ken and I fell in love ...
$9.5K for a Bluewater LEGEND! The Pearson Triton 28. [[08/29/25 SOLD]]
BoatFools Sailing

$9.5K for a Bluewater LEGEND! The Pearson Triton 28. [[08/29/25 SOLD]]

#pearsontriton28 #bluewatercruiser #sailboattour #sailing #boatfoolssailing [[SOLD - as of 08/29/2025]] $9.5K for a Bluewater LEGEND! The Pearson Triton 28. FULL TOUR $9.5K for a restored classic?! Yes, please. PRICE DROP FROM $13k! UPDATE 08/04/2025 - THIS AWESOME BOAT HAS HAD A MAJOR PRICE DROP...
A FREE Cape Dory 28! Classic Carl Alberg Sailboat Needs a New Home! [[SOLD]]
BoatFools Sailing

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...
Exploring a Classic Sailboat in Snowy Maine! Full Tour
BoatFools Sailing

Exploring a Classic Sailboat in Snowy Maine! Full Tour

#SailboatsForSale #Bristol35 #SailingLife #Sailboats #BoatFoolsSailing #ClassicYacht #LiveaboardLife #TedHood #BluewaterSailboat #SailboatTourThis UPDATE 03/10/2025: THE PRICE HAS DROPPED FROM $46,500 TO $38,500! Exploring a Classic Sailboat in Snowy Maine! Full Tour – A SOLID 1980 Bristol 35.5C f...
Real Questions? Real Answers. No BS.
Sailing Zingaro

Real Questions? Real Answers. No BS.

You asked, I answer. No BS, this is real advice. Here's my Yachtworld link: Buy me a beer: Watch Next: Bluewater Sailboats 101: The WORST Boats to buy 2025: Support the Channel: 👉 00:00-00:37 Intro 00:37 Do more production boats cross oceans? 1:30 Does tankage make a bluewater boa...
At Only 33 Feet, This SAILBOAT Is HUGE! A RARE 1981 CSY 33 Bluewater Cruiser at $28,500. [[SOLD]]
BoatFools Sailing

At Only 33 Feet, This SAILBOAT Is HUGE! A RARE 1981 CSY 33 Bluewater Cruiser at $28,500. [[SOLD]]

@boatfools  #sailboatforsale #sailing #bluewatersailing [[SOLD as on 12/14/2024]] At Only 33 Feet, This SAILBOAT Is HUGE! A RARE 1981 CSY 33 Bluewater Cruiser at $28,500!Canadian Ken couldn't join me for this one but it was still a ton of fun to expl...
WeBoating
Logo
Shopping cart