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

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 25-31 of 31 results
Women & Sailboat Surfing (Dead Down Wind) – WEEK 2
Adventureman Dan

Women & Sailboat Surfing (Dead Down Wind) – WEEK 2

This is only Deia's second week aboard my sailboat "Adventureborne". But in this week, things get a bit fun & scary as we get into some fast paced sailboat surfing DDW(Dead Down Wind). It was a great chance for her to experience surfing entire sailboat & my home. So the pressu...
I Taught Her How to Knife Fight On The Beach (Self Defense Training — Watch How Good She Gets!!!!)
Adventureman Dan

I Taught Her How to Knife Fight On The Beach (Self Defense Training — Watch How Good She Gets!!!!)

*Disclaimer, we are not knife fighting professionals. The actions preformed in this video are intended for entertainment purposes only. If you wish to learn how to knife fight, you should contact a professional. --- Also, always look up and know the local laws regarding knives and their use wherever...
Changing the PROP at ANCHOR (epic fail) | Sailing Sitka Ep 65
Sailing Sitka

Changing the PROP at ANCHOR (epic fail) | Sailing Sitka Ep 65

Changing the prop at anchor was an epic fail! In this weeks episode of Sailing Sitka, we introduce to you our first Youtube channel Collab with @sailingavocet ! Chris and Marissa help us change our old, bent prop to a new and shiny one that we got shipped to Mexico. But of course, things do not go a...
BROKEN GOOSENECK AT SEA Ep 58
Sailing Sitka

BROKEN GOOSENECK AT SEA Ep 58

In this weeks episode, we experience our second rig failure in 4 months-both of which took place offshore. In this episode, we filmed what we could when our gooseneck attachment on our wooden boom critically broke, leaving us without the use of our main sail. Sailing offshore can be the best moments...
My SEXY New Crew Does EVERYTHING I Ask!……… and MORE! (Funny Sailing YouTube Parody)
Adventureman Dan

My SEXY New Crew Does EVERYTHING I Ask!……… and MORE! (Funny Sailing YouTube Parody)

Finding good crew can be so very difficult. Especially one that looks this good in a bikini! "Hot Dam!" Jaz and I had a lot of fun making this video. Being a twenty year veteran of stand up comedy, Jaz has many if not most the best ideas for this funny parody video. Enjoy a good laugh on ...
⛵ SAIL BOAT CRASH – best of sail yacht fail – ⛵
Kind of Blue SAILING

⛵ SAIL BOAT CRASH – best of sail yacht fail – ⛵

Please Subscibe main channel 👉 #sail #crash #bestof
SPINNAKER SAILING FAIL | Ripped Sail. Broken Stanchion. ANGRY Captain.
Tula's Endless Summer

SPINNAKER SAILING FAIL | Ripped Sail. Broken Stanchion. ANGRY Captain.

This video starts out amazing with the longest white/pink sand beach we have ever seen but it takes a turn for the worst as we attempt some downwind spinnaker sailing to St. Martin. Let's just say it was an EPIC FAIL and we ended up ripping our sail and breaking a stanchion... 20% off everythi...
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