Watch Sailing & Boating Adventures Around the World tagged “Vacation” – Page 3 of 24

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 49-72 of 574 results
197. A DAY IN THE LIFE on passage | Sailing Sunday
Sailing Sunday
I Created The Perfect Romantic Vacation JUST For Her (Sailing In The Bahamas)
Adventureman Dan

I Created The Perfect Romantic Vacation JUST For Her (Sailing In The Bahamas)

This is hands down the MOST romantic vacation I could've created for her! I FINALLY get to see my girlfriend! After what seemed like an eternity(two weeks). Angela took time off from work and flew in to spend just five short days with me. It was absolute...
196. Oh No! We ALMOST Lost Our Boat!!! | Sailing Sunday
Sailing Sunday
195. Uh oh SAILOR GIRL DOWN! | Sailing Sunday
Sailing Sunday
194. Charter Guest MUTINY | SAILING SUNDAY
Sailing Sunday
193. The Aussie Invasion | SAILING SUNDAY
Sailing Sunday

193. The Aussie Invasion | SAILING SUNDAY

This week our Australian friends come to join us on our boat in the Caribbean! We have some good laughs and a lot of fun as we explore a bit onland in Grenada.
Crashing Holiday Yacht Parties Sailing Martinique – EP?
Sailing Starship Friendship

Crashing Holiday Yacht Parties Sailing Martinique – EP?

Hello friends, It's been awhile. The Starship Friendship vanished suddenly into almost complete silence. A rogue wave and very long story was unfolding beneath the waves. Novel times indeed. That tale is more than I can share now. But this video has been...
Mini Christmas Vlog: Merry Christmas from us! | Sailing Sunday
Sailing Sunday

Mini Christmas Vlog: Merry Christmas from us! | Sailing Sunday

Merry Christmas to all!!!! We filmed this morning for you guys on Sunday and spoke about our future plans for 2023.
192. The Boat Yard: It’s That Time Again! | SAILING SUNDAY
Sailing Sunday

192. The Boat Yard: It’s That Time Again! | SAILING SUNDAY

We lift our 46’ sailboat on land in Grenada to paint with our trusted Interlux Micron Antifoul, which we have used throughout our whole adventure!
190. Hard Times Onboard SV Sunday | Sailing Sunday
Sailing Sunday

190. Hard Times Onboard SV Sunday | Sailing Sunday

We stay positive and enjoy the experience of Sailing Sunday as we live onboard our boat rescuing animals in the countries we visit around the world.
189. Just When We Thought We Were DONE… | Sailing Sunday
Sailing Sunday

189. Just When We Thought We Were DONE… | Sailing Sunday

Just when we thought we were done, we catch a Ferry to another Island here in the Caribbean to pick up a new 3 legged friend...
188. They are Destroying our Boat! | Sailing Sunday
Sailing Sunday

188. They are Destroying our Boat! | Sailing Sunday

This week on Sailing Sunday, we find homes for all our current Caribbean rescue pups just in time before they really start to destroy the boat!!!
187.  Sailing To Cruisers Paradise | Sailing Sunday
Sailing Sunday

187. Sailing To Cruisers Paradise | Sailing Sunday

In this video, we're sailing to Grenada! If you're interested in sailing and want to experience some of the best sailings in the world...
Wedding Crashers in the Caribbean – Patreon Edition! | Sailing Sunday | Ep.184
Sailing Sunday

Wedding Crashers in the Caribbean – Patreon Edition! | Sailing Sunday | Ep.184

Patreons of ours were getting married on a Private Island here in the Caribbean. Out of all the places around the world we could be, we anchored right out front, Boom, welcome to Steve and Jackies wedding! After the most beautiful wedding we had on this a...
Cowboys and Sailing? A Rodeo & Overnight Sail from Golfito to Bahia Drake, Costa Rica – Episode 73
Sailing One Life

Cowboys and Sailing? A Rodeo & Overnight Sail from Golfito to Bahia Drake, Costa Rica – Episode 73

In this episode, we are invited to step outside the normal tourist trails in Costa Rica and experience a Costa Rican rodeo. We then decide to keep moving and sail overnight from Golfito to Bahia Drake. There is not much wind so we end up tacking our way ba...
Surfing and Exploring the West Coast of Canada | Vacation Vlog | Break from Boat Life
Blue Moon Life

Surfing and Exploring the West Coast of Canada | Vacation Vlog | Break from Boat Life

In this video we take a trip to the west coast of Vancouver Island to do some spring cold-water-surfing and enjoy a little break from boat life for a few days.
Ep14: Kicked out of the Marina, Our Maiden Voyage!  Living on Anchor until the Shipyard has a spot
Sailing Bye Felicia

Ep14: Kicked out of the Marina, Our Maiden Voyage! Living on Anchor until the Shipyard has a spot

Time ran out for Sailing Bye Felicia at the marina so we topped off our fuel and water and set out to find a new home. The boatyard haul out was schedule for 3 days later so we needed to find a safe spot to anchor. Matt being familiar with Key West waters ...
Which One Left Us Stranded: Dinghy or Golf Cart? – Episode 63
Sailing One Life

Which One Left Us Stranded: Dinghy or Golf Cart? – Episode 63

In this episode, we continue showing Marlee and Scott our sailing lifestyle. We visit a nearby village in Kusapin and go for a waterfall hike guided by one of the local children. With not much time left, we continue on to Dolphin Bay where we experience th...
See The Incredible 360 Views On This Secret Island + See Inside Our Neighbors Yacht [Ep. 58]
Sailing Sweet Ruca

See The Incredible 360 Views On This Secret Island + See Inside Our Neighbors Yacht [Ep. 58]

See for yourself why this little known place is so amazing. We sail to this tiny island in the North Atlantic. It is off the beaten path and relatively unknown to the outside world and tourist travel. What we found here was so incredible we didn't want ...
Was ist da los? Nina’s letzten Tage auf Trampi – EP 176 Sailing Seatramp
Sailing Seatramp

Was ist da los? Nina’s letzten Tage auf Trampi – EP 176 Sailing Seatramp

Endlich ist es Zeit euch ein Update zu geben. In den letzten Videos und auf unseren Sozialen Medien waren immer mal wieder kleine versteckte Andeutungen, doch nun ist es wirklich so weit! Wir verlassen Huahine und segeln zurück Richtung Moorea, die letz...
Auf der Flucht vom Dauerregen zurück ins typische Südsee Paradise – EP 175 Sailing Seatramp
Sailing Seatramp

Auf der Flucht vom Dauerregen zurück ins typische Südsee Paradise – EP 175 Sailing Seatramp

Der Südsee Traum. Oder doch nicht? Diese Woche werden wir erst von 7 Tagen Dauerregen geplagt und machen uns im Regen auf den Weg zurück nach Huahine. Trotz dem recht feuchten Start in den Tag, erleben wir noch einen wunderschönen Segeltag. Angekommen ...
Our Telegram Anchor Bot finally works! – EP 174 Sailing Seatramp
Sailing Seatramp

Our Telegram Anchor Bot finally works! – EP 174 Sailing Seatramp

In this episode we enjoy more time with our friends from SY Yumyum and get our promised reward for the hike on Bora Bora. Unfortunately we all realize that this is one of the last days we will see each other in this constellation. Mario finishes the ancho...
Lightning Strikes! HUGE STORM in a Hurricane Hole on a Sailboat [Ep. 31]
Sailing Sweet Ruca

Lightning Strikes! HUGE STORM in a Hurricane Hole on a Sailboat [Ep. 31]

We head to Grenada's best hurricane hole to dodge a huge storm and do some boat work. Between the storms we upgrade our solar panels and get a little party on with our catamaran friends! #sailing #saillife #sailinglife #sail Join our crew on Patreon! htt...
That’s not Bora Bora! But we love it! – Ep 168 Sailing Seatramp
Sailing Seatramp

That’s not Bora Bora! But we love it! – Ep 168 Sailing Seatramp

Bora Bora! Wait, that's not Bora Bora?! Last week we set sail to sail over to Bora Bora, but the wind dropped just after sunset, Mario changed course and we make a stop in Huahine. Together with Mirko and Sophia we hang out on the beach and have a great t...
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