Watch Sailing & Boating Adventures Around the World – Page 4 of 27
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 73-96 of 628 results
SAILING MARTINIQUE WITH TWO CAPTAINS – WHO’S IN CHARGE
SAILING MARTINIQUE WITH TWO CAPTAINS - WHO'S IN CHARGE We are sailing the west coast of Martinique, but with a twist... The Captain is away. With Rob back in New Zealand, Declan and Ivan step to take the helm to keep our Caribbean sailing adventure moving forward. The only problem, which one ...
THE CAPTAIN’S LEAVING | SAILING THE CARIBBEAN
THE CAPTAIN'S LEAVING | SAILING THE CARIBBEAN This week we're sailing north through the Caribbean, leaving the Grenadines and St Lucia in our wake as we make a fast passage towards Martinique. This isn't the slow island hopping journey we planned. Instead, we're on a tight sched...
BLUEST WATER IMAGINABLE – TOBAGO CAYS
WE SAILED HERE - TOBAGO CAYS After weeks of hard work in a Trinidad boatyard, we sailed north through the Grenadines to pick up Declan and Ivan in St Vincent, then back tracked to the breathtaking, impossibly blue Tobago Cays, a tiny archipelago in the Southern Grenadines famous for it's cryst...
Robert H. Perry’s COOLEST Sailboat? Fits & Ships in a Container | Far Harbour 39 TOUR | $99k
#boatfoolssailing #bluewatersailing #robertperry #sailboattour #sailing Robert H. Perry's COOLEST Sailboat? Fits & Ships in a Container | Far Harbour 39 TOUR | $99k The Robert H. Perry–designed Far Harbour 39 is unlike almost any cruising sailboat ever built. This remarkable boat was cre...
SHIPWRECKS, SABOTAGE, BOAT WORK & LIFE LESSONS IN TRINIDAD BOATYARD
SHIPWRECKS, SABOTAGE, BOAT WORK & LIFE LESSONS IN TRINIDAD BOATYARD This week we're experiencing the reality of boatyard life in Trinidad while finishing our haul-out, repairing systems, and discovering the unexpected kindness that makes the sailing community so special. While working agai...
Built for the Northwest Passage – Aluminum Expedition Sailboat BOAT TOUR
Step aboard SV Sentijn, a purpose-built aluminum expedition sailboat designed for high-latitude sailing and extreme conditions. In this full boat tour, owners John and Kara Pennington walk us through the design, systems, and practical choices that make Sentijn a true expedition cruising yacht. From ...
IS THIS SABOTAGE? | TRINIDAD HAUL OUT MYSTERY
IS THIS SABOTAGE? | TRINIDAD HAUL OUT MYSTERY Sand in our sail drive oil wasn't something we expected to find during a routine haul out in Trinidad. So how did it get there... and could it be sabotage? This week we haul out in Chaguaramas, Trinidad, one of the most popular and cost effective ...
Why Isn’t Anyone Buying This? | A $25K Alberg 35 Bluewater Cruiser (We’d Sail Her Tomorrow)
#boatfoolssailing #alberg35 #bluewatersailboat #sailboattour Why Isn’t Anyone Buying This? | A $25K Alberg 35 Bluewater Cruiser (We’d Sail Her Now) AS OF 04/14/2026 THIS BEAUTY IS OFF THE MARKET - THE OWNER HAS FIGURED OUT A WAY TO KEEP HER. Welcome back BoatFools Nation! This week Canadian Ken ...
A Beautiful Day of Cruising (even if we’re struggling) – Sailing the Scottish Isles – Ep 265
Join us as we explore the Outer Hebrides on our aluminum sailboat. We sail the Scottish Isles from Stornoway, Isle of Lewis to Staffin, Isle of Skye. From calm anchorages, exploring historic towns, fishing harbours and castles, it's a new adventure with each anchor drop! NEW VIDEOS EVERY SUNDA...
GOODBYE – BIG CHANGES at sea
GOODBYE - BIG CHANGES at sea Thank you for helping keep us afloat and supporting the creative process. You can be part of the crew for less than the price of a coffee. You can do so here: - Patreon - Paymate - PayPal using our email [email protected] Welcome back aboard. This week we&#...
LIFE – Sailing Grenada
LIFE - Sailing Grenada Thank you for helping keep us afloat and supporting the creative process. You can be part of the crew for less than the price of a coffee. You can do so here: - Patreon - Paymate - PayPal using our email [email protected] Welcome back to Grenada, where we are soa...
I Didn’t Want to Love This Boat
📘 If you want to understand what actually makes a great offshore boat, Chapter 2 of my book breaks it down clearly and honestly: 👉 If you want to understand what modern offshore sailboat design looks like when it’s done right, this is a boat worth paying attention to. The Pegasus 50 isn’t flashy....
Small Boat, Serious Yacht! This Morris Frances 26 is a Wonder | TOUR
#boattour #morrisyachts #classicsailboat #boatfoolssailing #sailboatreview [[02/17/2026 SOLD]] Small Boat, Serious Yacht! This Morris Frances 26 is a Wonder | TOUR Welcome back to BoatFools Sailing! Today Captain Kew (Q) and I remotely tour “Wildwood,” a Morris Frances 26 — an iconic Chuck Paine–d...
When back ups become the plan – offshore sailing to Scotland – Ep 264
Join us as we prepare to sail offshore in the North Atlantic in our custom aluminum sailboat from the nordic region of the Faroe Islands to Scotland, United Kingdom. We tackle failed Raymarin electronics, life on passage in the North Atlantic before dropping the hook in the beautiful outer hebrides!...
FROM HOSPITAL TO HERO – A KIWI’S WILD WEEK IN AMERICA
FROM HOSPITAL TO HERO - A KIWI'S WILD WEEK IN AMERICA Thank you for helping keep us afloat and supporting the creative process. You can be part of the crew for less than the price of a coffee. You can do so here: - Patreon - Paymate - PayPal using our email [email protected] This ...
EXPLORING $700 MILLION TUNNELS DEEP UNDER THE SEA – Ep 263
We continue our sailing journey in the Faroe Islands, exploring Tórshavn, the historic Tinganes grass-roofed buildings, and the dramatic landscapes that make this place feel unreal. From the marina, exploring by foot to driving deep under the ocean through the Eysturoy Tunnel and around the world�...
A Rare Dutch-Built Classic | 1961 Bill Tripp Javelin 38 | $49,500! | Tour
#ClassicSailboat #BluewaterSailboat #BillTripp #boatfoolssailing A Rare Dutch-Built Classic | 1961 Bill Tripp Javelin 38 | $49,500! | Tour This Dutch-built Beauty is in San Rafael, CA, so if you're on the west coast and in the neighborhood, go check her out! Welcome back BoatFools Nation! T...
SUSPICIOUS ENCOUNTER with BOATS SAILING OFFSHORE VENEZUELA COAST
SUSPICIOUS ENCOUNTER with BOATS SAILING OFFSHORE VENEZUELA COAST Thank you for helping keep us afloat and supporting the creative process. You can be part of the crew for less than the price of a coffee. You can do so here: - Patreon - Paymate - PayPal using our email [email protected] ...
S1E34. Boat Work, Broken Hardware & Big Dreams | The Reality of Refitting Our Sailboat .
Some days on a sailboat are big wins. Other days are about unbending and stowing a poorly stowed mainsail, fighting corroded hardware, killing time while waiting on parts, and figuring out how to keep moving forward without burning money you don’t have. In this episode, we tackle a calm-day mainsai...
WE DISCOVER ABANDONED OFFSHORE PRISON – SAILING FRENCH GUIANA
WE DISCOVER ABANDONED OFFSHORE PRISON - SAILING FRENCH GUIANA Thank you for helping keep us afloat and supporting the creative process. You can be part of the crew for less than the price of a coffee. You can do so here: - Patreon - Paymate - PayPal using our email [email protected] I...
why these tricky seas are worth sailing – Ep 262
Join us as we cruise deep into the fjords of the Faroe Islands - part it the United Kingdom of Denmark. We sail into the island of Borðoy where we explore Klaksvik and its jaw dropping beauty. We go on adventures hiking, to the famous Klakkur summit , wild landscapes and mountain views overlooking t...
I Didn’t Expect This… Sirius Might Be the Smartest Sailboat I’ve Toured
Last chance for the first printing of Be The Captain → I want to set expectations for this video, because this isn’t a review and it’s not a sales pitch. This was my first time ever stepping aboard a Sirius sailboat. I didn’t come in with a script, an agenda, or any affiliation with the builder. ...
INTO THE JUNGLE – SAILING FRENCH GUIANA
INTO THE JUNGLE - SAILING FRENCH GUIANA Thank you for helping keep us afloat and supporting the creative process. You can be part of the crew for less than the price of a coffee. You can do so here: - Patreon - Paymate - PayPal using our email [email protected] After weeks of tension ...