Watch Sailing & Boating Adventures Around the World – Page 6 of 74
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 121-144 of 1766 results
“50 years of history GONE in a second…” | Sailing Sitka Ep 162
Jay and Kenna are in Shelter Bay Marina, fixing some minor and major problems they've encountered while transiting the Panama Canal, on top of that they do some routine and periodic maintenance to make sure their 50 year old sailboat is ready to sail her way toward the desolate and world-renown...
UNFILTERED Boat Life on the Most ISOLATED Islands of the Caribbean | Ep.138
This is why I love Sailing Around The World. Join us in our latest sailing episode as we share a glimpse into our life at sea and exactly why we love sailing in tropical, crystal-clear waters! Like & subscribe to help us upgrade our editing gear and bring you even more epic adventures. Patreo...
SSL733 ~ this BOAT design is GENIUS !!
Join our Patreon and join our Team SSL Crew! Come and join us realtime at: To all those contributing to our next adventures, Thank-You so much! SSL Video Collections on Vimeo!
Engine Nightmare, Breakages & Bad Luck Continues… Panama Canal Day 2 | Sailing Sitka Ep 160
Panama Canal Day 2: Engine nightmare & bad luck continues, Atlantic awaits... In this episode jay and Kenna (along with @SailingSVBully ) continue their unexpected adventure through the Panama Canal with their unreliable engine. Their troubles aren't done with just yet. The bad luck sticks ...
Boat Life ⛵ She needs to Catch her Own Food! 🐟 Ep. 137
This is what boat life is all about! In this episode you get to see the real life of sailing around the world and how we live full time and living off-grid We're sailing around the world, and with your support, we will fund better cameras, the internet to upload videos, and of course, the occa...
In search of The Last True Sailors of the Caribbean | Epic Journey (E.136)
Join us on an epic journey across the Caribbean as we track down the last true sailors—masters of the sea, tradition, and adventure. Don't miss. Follow us every week in our real life sailing adventure, as we live off grid, sail from place to place, travel from country to country discovering ne...
🌊 Living the Ocean Nomad Life – Discovering a Hidden Island Paradise! 🏝️✨ E.135
Join me on an epic adventure as I embrace the ocean nomad life, sailing to a hidden island paradise! 🏝️🌊 Crystal-clear waters, untouched beauty, and pure freedom. Let’s explore! 🚤✨ Follow us every week in our real life sailing adventure, as we live off grid, sail from place to place, travel from co...
Final prep & nerves before our Panama Canal transit (real talk and costs $) | Sailing Sitka Ep 158
Jay and Kenna share some real thoughts and info as they prepare to transit the Panama Canal from the pacific to the Atlantic. But not before they enjoy some time enjoying the city life in Casco Viejo. Thanks for watching and subscribe if you enjoy. Stay tuned for next episode as it will be the one w...
SSL732 ~ SNEAK PEAK..
Hey Everyone! We've been busy sailing and having a lot of fun with new friends these past couple weeks, including new sailing kids that Ricci has been loving hanging out with! I just shot some new aerials at some of our locations as I've been having tons of fun with the new drones also, ...
We Sailed to the Most Unexplored Island in the Caribbean – THE WILD QUEEN 🌋🩵E.134
Secure your privacy with Surfshark! Go to for an extra 4 months Follow us every week in our real life sailing adventure, as we live off grid, sail from place to place, travel from country to country discovering new adventures. *Want to support us?" Patreon: Buy Salsa a Coffee☕🧡: Amazon Wis...
Our last sail on the Pacific Ocean | Sailing Sitka Ep 157
Jay and Kenna embark on a 3 day passage sailing from the tiny village of Bahia Honda to the concrete jungle of Panama City. This sail happens to be their last in the Pacific Ocean as they get ready to cross the Panama Canal into Atlantic waters. Thank you for watching and please subscribe if you enj...
SSL731 ~ Life is like a box of Chocolates..
In this episode we take you for a wild ride as we start with a beautiful tallship anchored in our backyard, then venture on a daring dinghy ride far into a jungle river with some new sailing friends we met recently! After that we'll go back to our friends private island where we'll help t...
SSL730 ~ SPECIAL ANNOUNCEMENT
Join our Patreon and join our Team SSL Crew! Come and join us realtime at: To all those contributing to our next adventures, Thank-You so much! SSL Video Collections on Vimeo!
Sailing to a remote, timeless village on Panama’s pacific coast | Sailing Sitka Ep 156
Jay and Kenna sail further into Panamanian waters only to discover a hidden gem of a village which was completely stuck in time. Join us on this special 3 year anniversary episode as we sail to Bahia Honda on Panama's pacific coast and learn to live slowly as we discovery the simplicity and bea...
SSL729 ~ Looking for TROUBLE..
Join our Patreon and join our Team SSL Crew! Come and join us realtime at: To all those contributing to our next adventures, Thank-You so much! SSL Video Collections on Vimeo!
Unexpected Challenges of Living on a Boat😝E.133
Living on a boat can be idyllic, but it also comes with unexpected challenges. This video explores some surprising hurdles faced by those who choose to live life on the water. Follow us every week in our real life sailing adventure, as we live off grid, sail from place to place, travel from country...
Sailing to Panama | Sailing Sitka Ep 155
In this video of sailing sitka, jay and Kenna sail to their first port in Panama from Golfito, Costa Rica. They anchor in front of a desolate little island consisting of nothing but tall standing palm trees and white sandy beaches. Thanks for watching and subscribe if you do!
Boat Life in Caribbean Islands🏄♀️ She’s Having All The FUN! 🤪 E.132
Join us for the epic final episode on this stunning island! From crazy boat life fun to unexpected blasts, we end the adventure with a bang! Don’t miss it!" Ps: I think she is having all the fun... Follow us every week in our real life sailing adventure, as we live off grid, sail from place to...
The real ups and downs of budget cruising | Sailing Sitka Ep 152
Jay and Kenna sailed off from Victoria BC, Canada two years ago and have been sailing south ever since. Now, in the luscious lands of Costa Rica, they experience both the highs and lows that come with sailing and cruising offshore.Thank you for watching and subscribe if you enjoy!
I Messed Up! The Friendly Island – E.131 ⛵ Sailing SV CUBA
I messed up and if I could turn back time I would! Wonder what real life aboard a 46ft sailboat feels like? Here is how we live Off Grid on the Ocean and travel. We give you an insight into our daily life adventures aboard our sailboat. This week we are looking for a place that time seems to have ...
SSL728 ~ my new favorite ride for 2025..
Thanks so much to AG1 for sponsoring today's video! If you guys want to try AG1 for yourselves and see what benefits you may find, use my link or scan the QR code to subscribe and save $20 off your first subscription of AG1! For more details on my awesome Engwe X26 Fat-tire Ebike, visit the ...
Cruising Costa Rica on a 41′ Sailboat | Sailing Sitka Ep 151
In this episode of Sailing Sitka, Kenna and Jay sail from Bahía Ballena to Quepos on the pacific coast of Costa Rica.
SSL727 ~ Dealing with LIGHTNING DAMAGE
Join our Patreon and join our Team SSL Crew! Come and join us realtime at: To all those contributing to our next adventures, Thank-You so much! SSL Video Collections on Vimeo!