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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Annapolis Sailboat Show 2026 FULL Tour
Adventureman Dan explores the 2026 Annapolis Sailboat Show at City Dock on the Chesapeake Bay, inspecting world-cruising monohulls, luxury catamarans, cutting-edge ground tackle, and innovative offshore sailing hardware.
I’m Buying a POWER YACHT?! Touring the Annapolis Boat Show 2026
Bobby White of Sailing Doodles tours the Annapolis Powerboat Show, evaluating aluminum expedition motor yachts, power catamarans, and vessel refit projects in Maryland.
Leaving My Home
Adventureman Dan departs his upstate New York family home with his $17,000 MacGregor 26X UMAR rig, trailing south to the Annapolis Sailboat Show.
What Our $15,000 Boat Really Cost
Sailing Nahoa provides a line-by-line financial audit of purchasing and refitting a $15,000 boat in Vancouver, British Columbia, calculating true DIY refit expenses.
Why Are Used Sailboats So Cheap in 2026?
Why are used sailboats so cheap in 2026? The used sailboat market has changed dramatically since the pandemic buying boom. Boats are sitting longer, asking prices are dropping, and many buyers are making offers thousands of dollars below list price. In this Lady K Sailing episode, we explore whether...
The Ultimate Test Sail Checklist-Don’t Buy a Money Pit
In episode 77 of Secondhand Sailors, we walk you through the test sail process of buying a secondhand sailboat. Before buying a used boat, you must perform a proper test sail. Learn how to spot expensive maintenance disasters before closing the deal. Performing a thorough test sail is the most crit...
Buying My Dream Boat (2001 MacGregor 26X)
This is the story of how I bought my dream power sailor boat, a 2001 MacGregor 26X for more than half of what it was originally listed for. It wasn't easy, but over the course of four days and three nights, I am one step closer to my dream of exploring EVERYWHERE in North America! ____________...
The Best Canadian Sailboat You’ve Never Heard Of | Sailing Truth Show
📕 GET THE BOOK: Be The Captain. Winner of the 2026 Eric Hoffer Award. 25 years of offshore decisions in one book → 🔓 FREE: The Captain's Locker. Printable watch schedules, pre-departure checklists, delivery tools → She's a 1996 Gozzard 44, built by one family in a small Ontario shop th...
We Flew to Florida to Buy Our Dream Boat…Then Everything Went Wrong| Season 2 Episode 1
Welcome back to Banana Pancakes 🍌🥞 Or if you’re new here… welcome to our beautiful little shit show. After waiting THREE years, we finally flew to Florida to survey what could become our future floating home — a 2021 Leopard 50 catamaran. This is the exact boat we first stepped on during spring bre...
We’re Back…..|Pre-Season 2
🌴 WE SOLD EVERYTHING… AND WE’RE DOING IT AGAIN | Sailing Around the World as a Family of 6 Welcome to Banana Pancakes… or if you’re new here—welcome to the chaos. After sailing the Caribbean for a year, selling our boat, and trying “normal life” again… we realized something: We’re not meant for n...
FROM DREAMERS TO OWNERS! ⚓ Buying a Nordhavn 57 (The Secret Reveal in Croatia!)
What is it actually like to buy a 60-ton ocean-crossing trawler when you've never lived on a boat before? This week, we’re joined by YouTube followers turned friends, Steven and Anna, who flew to Loreto, Mexico to interview us about the reality of the Nordhavn lifestyle. In this deep-dive inte...
BIG ANNOUNCEMENT + We Almost Bought a Dismasted Sailboat! EP 201
Big sailing announcement! In this episode, we share a long-overdue life update and explain why we almost bought a dismasted sailboat. It’s been a while, so we’re catching you up on everything we’ve been working on behind the scenes and what’s coming next for us and the channel. We talk through a r...
Is this a Good Boat?
My new book, "Be the Captain," is finally done! This is the field manual I wish I had when I first started sailing offshore. Ever wondered how I actually search for boats online? In today's video, I'm taking you behind the scenes and showing you my exact step-by-step process f...
We Bought a Boat! | Vision 444 Catamaran
After months of dreaming, planning, and searching… we finally bought a boat! 🥳 This episode is packed with all the wild and wonderful moments that led up to closing on our new Vision 444 catamaran — our floating home for the next chapter of our sailing adventures. We kicked things off with a thrill...
Survey Day – Will BIG LOST Pass the TEST?
Today's the big day! The buyers have arrived at Ixquisite Catamaran Center in Freeport Bahamas to witness the full survey of Big Lost-the catamaran they plan to buy if all goes well. We head over to Bradford Marina, where Big Lost gets hauled out on the travel lift for a thorough hull inspectio...
Winter talks – New Boat ownership – Ep. 327
If you like our videos, you can always drop a tip in our coffee jar ---- Affiliate Links ---- Mr D Cookware - ----- About us ----- We have begun a liveaboard adventure on our Bavaria 36, Salty Lass. It is our ongoing mission to explore strange new ports, to seek out new to us cuisines and ...
I’m Buying This Catamaran & Selling My Boat | Living & Sailing In Cabo Verde | Season 6 | Episode 48
#sailing #sailboatlifestyle #catamaran That's it, I've had it with my mono hull sailboat, I'm buying a catamaran. As well I'm tired of constantly fixing things on my old boat, I'm getting a new boat that is perfect and has no maintenance. As well it's more roomy for the...
3 Questions You MUST Ask Before Buying a Boat!
@boatfools #boatbuying #budgetsailing #sailboats #top3 #sailing #maineboats Hey everybody and welcome back to Boat Fools! This week, we're diving into the essential questions you must ask yourself before starting your boat purchase journey. These are The Top 3 Essential Questions To Ask Befo...
KNOWING WHEN TO MOVE ON
As a sailor evolves, so does their boat. And that’s what this conversation is about. ❤ Join Our Crew! ❤ For exclusive content, behind the scenes & Q&A's: ☝Full Scoop On The Blog 📷 Photo & Video Gear 📷 📱 UPDATES on Social 📱 INSTAGRAM: FACEBOOK: 📧EMAIL notificatio...
IS SHE THE ONE? Boat tour: 1984 Jeanueau Sun fizz . Are Jeaneau’s good boats to buy live aboard EP9
We look at a Jeanneau Sun Fizz liveaboard cruiser. This sailboat that is a bit closer to home and slightly larger with 3 cabins. Though I am not a big fan of the fin rudder we have to make sacrifices when boat shopping. This particular boat is set up to be powered at anchor. The family had it for...
I Bought a Boat with NEGATIVE -$4000 in my bank account | ep.2
This week we take you through the boat search. After sailing back from the Bahamas, Raf and Ben decided to sell the Catamaran and Raf went on the search for his next boat. After Sascha got The Far Side home, she drove down to the Key West and worked as a Charter Captain for a few months, but was a ...
So You Think You Want to Go Cruising on a Sailboat?
Free advice! We've consulted with over 100 future-cruisers, and some themes come up so often, we just had to share. 1. Is cruising right for you? 2. Which boat is right for you? 3. Purchasing process 4. Budgeting 5. Outfitting 6. Working Remotely 7. Ideal countdown to departure ⚓️ CURIOUS ABO...
Northern Ireland – Winter – Buying a boat – Money – Ep. 221
We often get asked, where did you get the money to buy your boat? We also get asked how the solar panels are holding up. In this week's episode, we answer both questions ---- Coffee Jar --- If you like our videos, you can always drop a tip in our coffee jar ---- Affiliate Links ---- M...