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 1-6 of 6 results
We Didn’t Think We’d Make It
Finding Our Isla Sailing

We Didn’t Think We’d Make It

After weeks of rough weather, Christmas winds, storms, and learning how to sail in real time… we finally make it to Saint Martin. But getting there was far from easy. In this episode, we leave Martinique and continue battling our way north through the Caribbean. Along the way we experience incredi...
Sailing Blind | Season 1, Episode 8
Finding Our Isla Sailing

Sailing Blind | Season 1, Episode 8

In this episode, we leave Le Marin and continue sailing north toward beautiful Saint-Pierre. What started as one of our most peaceful and enjoyable sails yet quickly changed when we suddenly lost critical electronics onboard Isla. Our charts, depth readings, wind instruments, and navigation system...
Sailing Family Sails into Big Seas: Did We Make a MISTAKE?
Finding Our Isla Sailing

Sailing Family Sails into Big Seas: Did We Make a MISTAKE?

Welcome back to Finding Our Isla. In Season 1, Episode 5, we leave Saline Bay and continue sailing north toward Bequia — still without a working steering cable. As we push forward, we sail straight into the powerful Caribbean Christmas Winds and battle rough seas, strong winds, and multiple squall...
SEASON 1 Trailer: Our first sailboat!
Sailing Mundial

SEASON 1 Trailer: Our first sailboat!

Season 1 Trailer My husband and I bought a 38' Down Easter Cutter, never having sailed it past the bay, and spent the last two months prepping her for the sail up north from Long Beach to Port San Luis Obispo, where she will remain until we set sail in July 2023. Here’s a trailer of our first ...
Anchoring with NO EXPERIENCE…
Wild We Roam

Anchoring with NO EXPERIENCE…

A massive thank you to Squarespace for sponsoring this video and helping make these adventures possible aboard Penelope. If you’d like to open your own online shop or create a website go to Squarespace.com/wildweroam for 10% of your first purchase. How do you feel about anchoring? Do you trust your...
A day sail in 15 knots and a wifi install FAIL ; )
Wild We Roam

A day sail in 15 knots and a wifi install FAIL ; )

With so many boat projects to do on Penelope, we started getting nervous that we would miss the whole summer sailing season. So we changed our plans and decided to start trying to get a sail in before beginning work. In today's video, we try to install a wifi extender to make it possible for us...
WeBoating
Logo
Shopping cart