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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Is This The Ultimate Island Cruiser? | 1985 Irwin 43 MKII Full Tour
BoatFools Sailing

Is This The Ultimate Island Cruiser? | 1985 Irwin 43 MKII Full Tour

#boatfoolssailing #irwin43 #sailboat #islandcruiser #sailing #sailboattour Is This The Ultimate Island Cruiser? | 1985 Irwin 43 MKII Full Tour Join Captain Kew and me as we step aboard S/V Dream, a beautifully maintained 1985 Irwin 43 MKII, a spacious center cockpit cruising sailboat that's ...
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...
DO NOT BUY These 5 Sailboats (And 5 You SHOULD)
Sailing Zingaro

DO NOT BUY These 5 Sailboats (And 5 You SHOULD)

Preorder my book “Be The Captain”: In this video, I break down 10 real offshore sailboats — 5 that I think are smart, seaworthy buys... and 5 that raise red flags. These boats are all for sale right now, and I’ll walk you through what I look for in an offshore cruiser, what makes or breaks a good ...
Is this a Good Boat?
Sailing Zingaro

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...
Tired of the Tariffs? Here’s My Escape Plan
Sailing Zingaro

Tired of the Tariffs? Here’s My Escape Plan

#SailingLife #BoatDeals #EscapeTheTariffs #BluewaterSailing #AffordableYachts Tired of the tariffs? Me too. So I made an escape plan… and it involves a sailboat. ⛵ Need help picking your perfect boat? I do consultations too: 👉 Much love, —James 00:00 - Sick of tariffs? Here’s the plan 01:...
Best Bluewater Sailboats (& Catamarans!) Under $300K
Sailing Zingaro

Best Bluewater Sailboats (& Catamarans!) Under $300K

Looking for a monohull or catamaran under $300K? You may be surprised at the top choice... Offshore passage making: Patreon: Zingaro Merch: Links Mentioned in this Video: Jimmy Cornell Interview with OVNI: Steve and Linda Dashew books (FREE): Chapters: 00:00 Intro 1:15 Allures 44 9:51 Oys...
BEST Offshore Sailboats Under $125K
Sailing Zingaro

BEST Offshore Sailboats Under $125K

Want to sail around the world? Here are 15 incredible bluewater sailboats you can buy for less than $125,000. From classic cruisers to modern performance designs, these boats are seaworthy, comfortable, and ready for adventure. 🌎 ⛵ Want More? Support us on Patreon for exclusive content, extended bo...
10 Affordable Sailboats to Sail Around the World (Under $50K)
Sailing Zingaro

10 Affordable Sailboats to Sail Around the World (Under $50K)

In this video, I reveal 10 incredible, inexpensive sailboats under $50,000 perfect for bluewater sailing around the world. These boats are affordable, capable, and ready to take you on the adventure of a lifetime. From legendary designs like the Cal 40 and Valiant 40 to rugged classics like the Tay...
Top 10 WORST Sailboats to Buy in 2025
Sailing Zingaro

Top 10 WORST Sailboats to Buy in 2025

Thinking about buying a cruising sailboat in 2025? 🚨 Before you invest your hard-earned cash, watch this video! I’m breaking down the top 10 worst sailboats under $50K that you should avoid. From poorly designed IOR-inspired racers to heavy, sluggish cruisers that weren’t built for bluewater sailing...
Upgrading a Coastal Cruiser for Offshore Sailing
Sailing Zingaro

Upgrading a Coastal Cruiser for Offshore Sailing

In this Q&A session, I’m diving into the best questions from my Bluewater Boats 101 series! Whether you're curious about upgrading a C&C 35 for offshore, the pros and cons of in-mast furling vs. slab reefing, or how to avoid container collisions, I’ve got you covered. We’ll also explore...
Bluewater Sailboats 101: Outside the Boat (Part 2)
Sailing Zingaro

Bluewater Sailboats 101: Outside the Boat (Part 2)

Learn how to choose the perfect bluewater sailboat for offshore cruising, focusing on critical topside features and rig setups. Avoid the common pitfalls and find the safest, most capable sailboat for sailing around the world. ❤️ THESE VIDEOS TAKE A TON OF WORK; CONSIDER SUPPORTING US ❤️ Patreon: ...
Why Boatyards Suck: Cruising vs Reality – Adventure 03 (Sailing Around the World)
Sailing Nahoa

Why Boatyards Suck: Cruising vs Reality – Adventure 03 (Sailing Around the World)

We spend two deplorable weeks in the boatyard getting our Lagoon 410 catamaran ready for the upcoming season. The behind-the-scenes of what it's really like...
#82: (Halloween Special) How to Throw the Best Party at the Anchorage [PG-13]
HaveWindWillTravel.com

#82: (Halloween Special) How to Throw the Best Party at the Anchorage [PG-13]

If there's one thing Phillip and I learned from (surviving) our 2nd Annual Ft. McRee Boozer Cruiser, it's how to throw the best party at the anchorage. You only need four things: Costumes, Drinks, Music and Boat-to-Boat participation. Oh, and "engine wood" (new term we invented...
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