Watch Sailing & Boating Adventures Around the World – Page 2 of 20

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 471 results
LIVEABOARD ESSENTIALS: STUFF WE SWEAR BY ON OUR BOAT! EP-200
Leading the Escapade

LIVEABOARD ESSENTIALS: STUFF WE SWEAR BY ON OUR BOAT! EP-200

Go to and use code ESCAPADE to get 5% off your Holafly eSIM for your next trip! 🌴 Check out our favourite things for living aboard—practical, space-saving, and just plain useful! THE GALLEY 🍳 Collapsible Tupperware Set (Various Sizes): Small Collapsible Tupperware: Clip-On Strainer: Collapsi...
The Current Nearly Defeated Us… Ep-197
Leading the Escapade

The Current Nearly Defeated Us… Ep-197

Join us as we sail up the ICW and explore some of Florida’s most charming coastal towns — Cocoa Village, Titusville, and New Smyrna Beach. We soak in the sunshine, discover new spots, and even spot manatees for the very first time (a total dream moment!). But later in our journey, things take a tur...
[Ep 36] When Sailing Life Isn’t So Dreamy | Isla San Francisco to Agua Verde
SmoCo Sailing

[Ep 36] When Sailing Life Isn’t So Dreamy | Isla San Francisco to Agua Verde

Episode 36 After leaving Isla San Francisco, what was supposed to be an easy 35-mile sail to Los Gatos turned into the opposite of the champagne sailing we had in the previous episode and we ended relocating in the middle of the night. We tackled our neverending jib furler issue and if you're w...
I Came Home… and He Was Gone | Sailing Avocet
Sailing Avocet

I Came Home… and He Was Gone | Sailing Avocet

Marissa left for California to get some work and snowboarding in, then returned home to a boat without Chris! @KesselUnderway sailed away to La Cruz, leaving Marissa alone aboard for a week where she quickly realized she is bad at being alone, and even worse at learning to love the isolation of the ...
Sailing Baja with the Lost Boys | Sailing Avocet
Sailing Avocet

Sailing Baja with the Lost Boys | Sailing Avocet

We set sail for Isla Coronados, a place filled with some of our favorite memories, before heading to Loreto to scoop up @KesselUnderway's friend Stephen for a week of salty shenanigans. Between foil boarding around the anchorage, exploring Loreto’s rich history, and being caught with my pants d...
Our Biggest Job Yet Restoring Our 40ft Sailboat!
Chesca & Ben

Our Biggest Job Yet Restoring Our 40ft Sailboat!

In this weeks video big progress is made to get our 40ft sailboat back in the water. The time has come to start painting. This is the biggest job yet, and the transformation is starting to happen. 🚢 Join Our Crew on Patreon Want to support our sailing adventure and get exclusive behind-the-scenes u...
Sailing to Santa Rosalia | Sailing Avocet
Sailing Avocet

Sailing to Santa Rosalia | Sailing Avocet

Join us on our sail from Puerto Refugio to Santa Rosalia, where things got a tad sporty on the water! Luckily, Avocet handed it like a champ as we sailed wing on wing and surfed down waves in front of @KesselUnderway Don't miss out on upcoming sailing adventures, DIY stories, and equipment re...
Our last sail | Sailing Sitka Ep 182
Sailing Sitka

Our last sail | Sailing Sitka Ep 182

After two unforgettable months in paradise, Jay and Kenna lift anchor and set sail on a short 9-hour passage from Chicheme to Linton on Panama’s mainland. Along the way, they take in every last moment of beauty that this sailing lifestyle has to offer. Back in Linton, the focus shifts to preparing S...
We haven’t stepped foot on land in a week! (and heres why) | Sailing Sitka Ep 178
Sailing Sitka

We haven’t stepped foot on land in a week! (and heres why) | Sailing Sitka Ep 178

Jay and Kenna have been off the grid, not setting foot on land for over a week while sailing through the San Blas Islands. While anchored at Green Island, they took it slow to ride out some intense winds. With no working outboard and a less-than-reliable paddleboard, getting to shore has felt more l...
Fresno Yacht Club’s High Sierra Regatta | Sailing Avocet
Sailing Avocet

Fresno Yacht Club’s High Sierra Regatta | Sailing Avocet

From Puerto Peñasco to our stomping grounds at 7000 feet, we didn't skip a beat with sailing and were stoked to get back and sail our Victory 21 in the 70th Annual High Sierra Regatta at Huntington Lake! This two-day regatta was packed with wind, competition, and fun with our Fresno Yacht Club ...
Spearfishing, SHALLOW Cuts & BULL SHARK Encounter – SAILING the Jumentos Cays! Ep-182
Leading the Escapade

Spearfishing, SHALLOW Cuts & BULL SHARK Encounter – SAILING the Jumentos Cays! Ep-182

Go to or use code LEADING at checkout to get 4 extra months of Surfshark VPN! We're sailing deep in the remote southern Bahamas — starting off with a dive and spearfishing session at Jamaica Cay in the Jumentos Cays. Then it's time to move north to Flamingo Cay… but not without a little ...
Off-Grid Sailing the Bahamas – Spearfishing, Boat Life & Beach Bonfires Ep-180
Leading the Escapade

Off-Grid Sailing the Bahamas – Spearfishing, Boat Life & Beach Bonfires Ep-180

📲 Get an exclusive 15% discount on Saily data plans! Use code ESCAPADE at checkout. Download Saily app or go to We sail to the wild and remote Ragged Islands of the Bahamas—where boat life gets seriously off-grid. This episode is all about untouched sailing, spearfishing for our dinner, exploring...
Our Last Sail… | Sailing Avocet
Sailing Avocet

Our Last Sail… | Sailing Avocet

This video shares the final 100 miles of our cruising season from Bahia San Francisquito to Puerto Peñasco and is full of reflections, long night watches, and the bittersweet feeling of a season’s end. From navigating through the remote Baja coastline to battling bees and anchoring in one of our new...
Paradise Found: V-Cove Anchorage,  Sea of Cortez Mexico | Sailing Avocet
Sailing Avocet

Paradise Found: V-Cove Anchorage, Sea of Cortez Mexico | Sailing Avocet

Looking for the perfect hidden anchorage in the Sea of Cortez? Join us as we explore V-Cove, a breathtaking and secluded spot on Isla Carmen, just off the coast of Baja California Sur, Mexico. Known for its calm waters, excellent holding, and dramatic cliffs, V-Cove has quickly become one of our fav...
Agua? Verde. | Sailing Avocet
Sailing Avocet

Agua? Verde. | Sailing Avocet

After a week of chasing horizon lines through the Sea of Cortez, we finally found ourselves dropping anchor in the remote and rugged paradise of Agua Verde, Baja California Sur — a place where time slows down and the mountains meet the sea in perfect harmony. Speaking of meeting, we also reunited wi...
Working and Cruising? How do we do both?
M/V Noeta

Working and Cruising? How do we do both?

Balancing careers with a life at sea? Join us aboard MV Noeta as we reveal how we manage to work and cruise simultaneously! Discover our strategies for remote work, time management, and finding that perfect work-life balance while living aboard. See how we turned our cruising dreams into reality, ...
FOR SAIL: Beneteau Oceanis 40 – 2007, 2 cabins version
Ryan & Sophie Sailing

FOR SAIL: Beneteau Oceanis 40 – 2007, 2 cabins version

They say that the happiest days of boat ownership are when you buy your boat and when you sell it. Well, let us tell you: this is wrong! ;) Read more about Polar Seal at: We are a little sad about our decision to part with our girl, but life is currently taking us in a direction that doesn’t allo...
Sailing Aurora Introduction
Sailing Aurora-with the hot chick and the engineer

Sailing Aurora Introduction

Hi and welcome our new life aboard a sailboat!
Isla Isabel, The Galapagos of Mexico | Sailing Avocet
Sailing Avocet

Isla Isabel, The Galapagos of Mexico | Sailing Avocet

After a long stay in Banderas Bay, we sailed north to the small tiny but wild Isla Isabel, often called the Galapagos of Mexico! 🏝️ This National Park provided us with plenty of great hikes through lush landscapes, getting up close with the island’s famous blue-footed booby colonies and magnificen...
BLUE ANGELS Annapolis Airshow (and the World’s Most Crowded Anchorage)
Ryan & Sophie Sailing

BLUE ANGELS Annapolis Airshow (and the World’s Most Crowded Anchorage)

Join Ryan & Sophie as they experience the annual Blue Angels air show in Annapolis, Maryland. During Commissioning Week, thousands flock to watch the U.S. Navy's precision flight team perform stunning aerial maneuvers above the Chesapeake Bay.
How To Build a Small Wooden Boat From Scratch (with @ChesapeakeLightCraftBoats)
Ryan & Sophie Sailing

How To Build a Small Wooden Boat From Scratch (with @ChesapeakeLightCraftBoats)

Experience the rewarding process of constructing your own wooden boat from a DIY kit by Chesapeake Lightcraft. This article discusses the necessary skills, tools, space requirements, and time management required for building your own small wooden boat.
La Cruz de Huanacaxtle | Sailing Avocet
Sailing Avocet

La Cruz de Huanacaxtle | Sailing Avocet

La Cruz de Huanacaxtle quickly stole our hearts with its charm; great food, music, and loads of young cruisers. We finally got to meet up with Avocet's sort-of-sister ship, @sailingsitka and make fast friends with the crew of SV Lusty. This is where the fun begins! Don't miss out on upco...
Unexpected changes 😶
Ryan & Sophie Sailing

Unexpected changes 😶

Learn about the recent changes in Ryan and Sophie's sailing life, how they're handling new responsibilities and adjusting to their shifting plans.
A Rough Night in Boho Bay and Spectacular Malaspina Sailing (Episode 23) 4K
Barlovento Sailing

A Rough Night in Boho Bay and Spectacular Malaspina Sailing (Episode 23) 4K

This video brings our summer of 2022 sailing adventure to a close. We make a short passage from Squirrel Cove to Lund BC, then continue south from Lund, through the Malaspina Straight to Boho Bay Lasqueti Island where we thought we might blow away over night... (Good protection from a North West wi...
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