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 1-24 of 62 results
Episode 15: The Problem That May Have Put me On The Reef (Calico Skies Sailing – New Horizons)
Calico Skies Sailing – New Horizons

Episode 15: The Problem That May Have Put me On The Reef (Calico Skies Sailing – New Horizons)

Get your Stainless Steel Chain Anchor from cromox! This is my new channel where I will continue the story aboard Calico Skies, but with a fresh perspective, new adventures, and the same passion for sailing, discovery, and storytelling that has always been at the heart of my journey. Please Subsc...
35 Knot Front..And it Got to Me | Solo Sail to Australia Part 2 (Calico Skies Sailing – New Horizon)
Calico Skies Sailing – New Horizons

35 Knot Front..And it Got to Me | Solo Sail to Australia Part 2 (Calico Skies Sailing – New Horizon)

This is my new channel where I will continue the story aboard Calico Skies, but with a fresh perspective, new adventures, and the same passion for sailing, discovery, and storytelling that has always been at the heart of my journey. Please Subscribe and continue with the journey of Calico Skies! Ov...
Episode 11: My Longest Solo Sail Yet, Alone all the Way to Australia (Calico Skies – New Horizons)
Calico Skies Sailing – New Horizons

Episode 11: My Longest Solo Sail Yet, Alone all the Way to Australia (Calico Skies – New Horizons)

This is my new channel where I will continue the story aboard Calico Skies, but with a fresh perspective, new adventures, and the same passion for sailing, discovery, and storytelling that has always been at the heart of my journey. Please Subscribe and continue with the journey of Calico Skies! Ov...
Episode 10: Finding My Way Back to the Sailing Life & How to Rig a Code Zero (Calico Skies Sailing)
Calico Skies Sailing – New Horizons

Episode 10: Finding My Way Back to the Sailing Life & How to Rig a Code Zero (Calico Skies Sailing)

This is my new channel where I will continue the story aboard Calico Skies, but with a fresh perspective, new adventures, and the same passion for sailing, discovery, and storytelling that has always been at the heart of my journey. Please Subscribe and continue with the journey of Calico Skies! Ov...
Episode 9: Broken Bone While Foil Boarding in Remote Vanuatu  (Calico Skies Sailing – New Horizons)
Calico Skies Sailing – New Horizons

Episode 9: Broken Bone While Foil Boarding in Remote Vanuatu (Calico Skies Sailing – New Horizons)

Check out Kat's Instagram: This is my new channel where I will continue the story aboard Calico Skies, but with a fresh perspective, new adventures, and the same passion for sailing, discovery, and storytelling that has always been at the heart of my journey. Please Subscribe and continue wit...
Episode 1: Get by With a Little Help from my Friends – Where has Calico Skies Sailing been??
Calico Skies Sailing – New Horizons

Episode 1: Get by With a Little Help from my Friends – Where has Calico Skies Sailing been??

This video was difficult to make. After nearly 23 years together Grace and I are separating. This is sad and a distinct end of a chapter. Maybe a chapter is inadequate, it's more like the end of a book. We have been together since we were 19 years old which is more than half our lifetime. Grace...
Sailing SOLO Tonga to Fiji, Navigational Nightmare Even Pros Get Wrong! (CSS, Ep 257)
Calico Skies Sailing

Sailing SOLO Tonga to Fiji, Navigational Nightmare Even Pros Get Wrong! (CSS, Ep 257)

Enjoying our channel? Consider joining the Calico Skies Patreon Crew for as little as $2 a month to get lots of extra goodies :) 0:00 Intro 0:10 Passage Planning to Fiji 2:42 Cleared out of Tonga 5:37 Day 2 - Setting Boat up for Wing on Wing 9:47 Day 3 - Time for a Jibe 16:50 Day 4 - Course Chan...
The Realities of Crossing the Pacific Ocean, Part 1 (Calico Skies Sailing Ep. 225)
Calico Skies Sailing

The Realities of Crossing the Pacific Ocean, Part 1 (Calico Skies Sailing Ep. 225)

Calico Skies Sailing dives into the realities of crossing the Pacific Ocean, discussing their preparations, experiences, and dreams. Get a glimpse into their inspiring journey as they prepare to set sail.
3+ Months of FOOD .. but HOW will it fit on our 36ft Sailboat?! 😳 Send Help Please!!🙏🏻 (CSS, Ep 223)
Calico Skies Sailing

3+ Months of FOOD .. but HOW will it fit on our 36ft Sailboat?! 😳 Send Help Please!!🙏🏻 (CSS, Ep 223)

In this episode, Calico Skies Sailing tackles the extensive process of provisioning their 36ft sailboat with enough food for their 3+ month voyage through the Pacific Ocean. They break down the process of stocking up on supplies, dealing with limited space, and organizing the galley. With every item...
Getting close – But we’re still finding things as we prep to cross the Pacific Ocean! (CSS, Ep 221)
Calico Skies Sailing

Getting close – But we’re still finding things as we prep to cross the Pacific Ocean! (CSS, Ep 221)

Enjoying our channel? Consider joining the Calico Skies Patreon Crew for as little as $2 a month to get lots of extra goodies :) 0:00 Intro 0:10 Gooseneck Repair 6:50 Chainplate Checks / Inventory Provisions 10:13 Last winch service 10:37 Dinners out with Friends @SaltandTar @sailingavocet 12:2...
There are some things we have to tell you … (Calico Skies Sailing, Ep 205)
Calico Skies Sailing

There are some things we have to tell you … (Calico Skies Sailing, Ep 205)

Enjoying our channel? Consider joining the Calico Skies Patreon Crew for as little as $2 a month to get lots of extra goodies :) One of the most asked questions we get is 'what are your plans? When are you going to cross the Pacific? So that inspired us with the idea to film a video this way...
Defeated.
The Foster Journey

Defeated.

We are defeated by the thorny path. All plans fail as we depart Crooked Island, Bahamas heading east on the thorny path - trade winds, prevailing currents, and engine overheating. What would you have done? Matt SV Cadence Crooked Island, Bahamas Episode 160 Thanks for tuning in this week! If you...
Sailors Gone Wild: We Swap Crew & Play Games – Episode 88
Sailing One Life

Sailors Gone Wild: We Swap Crew & Play Games – Episode 88

After a couple stressful days weathering a hurricane at anchor, we take the next few days to have a little fun. Brooke hops onboard Delos and Kazza and Sierra join One Life as they swap spots for a sail. With our buddy boat trio (Calico Skies, Delos and One Life) soon parting ways, we decide to play...
Three Weeks in a Tropical Paradise! Sailing to San Blas (EP 20)
Untide

Three Weeks in a Tropical Paradise! Sailing to San Blas (EP 20)

Welcome to another update from Elixir's voyage! We had heard that San Blas (Panama) was pretty, but we had no idea that it would be this beautiful. As well as the beautiful islands, we were also amazed at the richness of the culture within the indigenous Guna communities we met. We quickly...
We’ve Got to Leave this Anchorage – Right Now! – Episode 78
Sailing One Life

We’ve Got to Leave this Anchorage – Right Now! – Episode 78

After the two day check out process, we are finally able to begin our journey up the northern coast of Costa Rica. Our first stop after navigating the shallow area in Puntarenas is to meet up with a couple of our friends at a nearby anchorage. From here we sail overnight to Bahia Samara but we do no...
Does it Get Any Better?! WE FOUND PARADISE IN BAJA  [Making Our Way Ep 50]
Making Our Way

Does it Get Any Better?! WE FOUND PARADISE IN BAJA [Making Our Way Ep 50]

In this episode we sail into one of our top locations to date and spend the holidays exploring the overwhelming beauty of Isla San Francisco. Join us for an incredible few days cooking fresh fish, eating delicious food, exploring turquoise waters and salt flats, and breathing in the totality of this...
Island Life: CATCHING OUR OWN DINNER [Making Our Way Ep 49]
Making Our Way

Island Life: CATCHING OUR OWN DINNER [Making Our Way Ep 49]

The winter winds push in and push us north long the pristine national park of Isla Espiritu Santo in the Sea of Cortez -- and while we might not get much sleep with all the weather, it doesn't stop us from spearfishing & enjoying fresh fish tacos as we admire Mobula Rays and the gorgeous na...
🍾Let the Celebrations BEGIN! HOLA, CABO! [Making Our Way Ep 44]
Making Our Way

🍾Let the Celebrations BEGIN! HOLA, CABO! [Making Our Way Ep 44]

After 10 days working our way down the coast of the Baja peninsula, we finally drop the hook in Cabo San Lucas... and it feels AMAZING. Come join us for the final 2 legs of our journey down, with dolphins, perfect sailing, mahi mahi, and SUNSHINE. *Correction: Mike cooked up the Mahi while underway...
Sailing Our House to MEXICO with the Baja Haha! [Making Our Way Ep 43]
Making Our Way

Sailing Our House to MEXICO with the Baja Haha! [Making Our Way Ep 43]

We made it to Mexico!!! But not before seeing the heaviest weather that the Haha has seen in its near 30 year history 😱. Come join us for a 4 day, 3 night sail down the Baja coast, where we see big seas, catch our first fish, and party with the locals in the small village of Turtle Bay. Follow us o...
WE’RE SAILING AWAY! ✌️Peace Out USA!! [Making Our Way Ep 42]
Making Our Way

WE’RE SAILING AWAY! ✌️Peace Out USA!! [Making Our Way Ep 42]

Aaaaand, we're off! We enjoy a week in San Diego making our final preparations to leave the USA indefinitely, and then kick off our journey down the Baja peninsula. Come join us for beaches, parties, and Mike's official transformation into a REAL Californian.😂 Follow us on Instagram: Che...
CRUISING LIFE: It Feels GOOD to Be Back! [Making Our Way Ep 41]
Making Our Way

CRUISING LIFE: It Feels GOOD to Be Back! [Making Our Way Ep 41]

We enjoy beautiful Catalina Island, play in the warm sunshine, and break out our snorkel gear for the first time ever! We leave at sunset to stunning views and sail overnight, pulling into San Diego at sunrise. Come join us! Follow us on Instagram: Check out our blog:
🍾CHAMPAGNE SAILING to Catalina Island! [Making Our Way Ep 40]
Making Our Way

🍾CHAMPAGNE SAILING to Catalina Island! [Making Our Way Ep 40]

A new chapter begins!! After months of being focused on just getting from Seattle to Los Angeles, we finally get to untie the dock lines in LA and get CRUISING-- starting with a gorgeous sunset sail to Catalina Island. Come join us! Follow us on Instagram: Check out our blog:
THE BEST FEELING IN THE WORLD! [Making Our Way Ep 39]
Making Our Way

THE BEST FEELING IN THE WORLD! [Making Our Way Ep 39]

Almost a year after moving aboard , making it through a challenging, cold, and damp winter in the Pacific Northwest, facing countless projects and unplanned issues, then being pinned by weather for almost a month in-between pretty uncomfortable passages... and after nearly a WEEK at sea... it felt ...
6 DAYS AT SEA: Cape Mendocino to Point Conception [Making Our Way Ep 38]
Making Our Way

6 DAYS AT SEA: Cape Mendocino to Point Conception [Making Our Way Ep 38]

Come along as we sail our Caliber 40 LRC offshore down the California coast. Our biggest passage yet has it all: sailing in a near gale as we round the infamous Cape Mendocino, seemingly endless cold and fog, perfect sailing, and a SPECTACULAR wildlife show as we finally approach Point Conception an...
WeBoating
Logo
Shopping cart