Watch Sailing & Boating Adventures Around the World tagged “Sailing to the Caribbean”

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 1-10 of 10 results
1000nm and 6 days to Antigua, Nelsons Dock yard. SVEV 5 S7
Sailing EV

1000nm and 6 days to Antigua, Nelsons Dock yard. SVEV 5 S7

In this video we begin on day three 500 nm from the Caribbean. Captain Tom wood gives some advice, we have a problem with the boom vang then arrive in Paradise. You have to see it to believe it. Join my Patreon here : Become a part of the crew!! patreon.c...
Land Ahoy! After a 2,000 mile ocean crossing, welcome to Trinidad  |   Ep110
Sailing Fair Isle

Land Ahoy! After a 2,000 mile ocean crossing, welcome to Trinidad | Ep110

The final part of our Atlantic crossing wasn't straight forward. Trinidad is a big island and the anchorages are on the Western side, sheltered from the Atlantic swell. So once you sight land you still have a full day (or night in our case) of sailing to n...
My Plans of Sailing South to Warmer waters Sailing EV Episode 37
Sailing EV

My Plans of Sailing South to Warmer waters Sailing EV Episode 37

In this video I reveal my plans for Sailing South to the Caribbean and address the reality of the situation. Find out what I'm up to and what is going to happen with this channel and the Sailing Yacht EV.
Atlantic Sailing from GIBRALTAR to CANARY ISLANDS | Sailing Sunday | Ep.148
Sailing Sunday

Atlantic Sailing from GIBRALTAR to CANARY ISLANDS | Sailing Sunday | Ep.148

This week we exit through the straight of Gibraltar sailing to the Canary Islands on the 1st leg of our Atlantic Crossing. We get some beautiful calm days anddddd some not so beautiful calm days. We knew there was some heavy for the 2nd part of the trip bu...
Covid Still Affects Sailing in Paradise! | Sailing Wisdom [S6 Ep1]
Rigging Doctor

Covid Still Affects Sailing in Paradise! | Sailing Wisdom [S6 Ep1]

The Virgin Islands, it's time to enjoy this paradise for sailors! Beautiful clear waters, perfect winds, and gorgeous anchorages around every corner. We are ready! 0:00 Welcome to Paradise Patreon: https://www.patreon.com/riggingdoctor Merchandise: http...
Can We Make it to the USVI in Time?! | Sailing Wisdom [S3 Ep43]
Rigging Doctor

Can We Make it to the USVI in Time?! | Sailing Wisdom [S3 Ep43]

The arduous sail to the Virgin Islands comes to an end as we make our arrival through the islands of the Caribbean. Once we are well North of Guadalupe, we finally get to turn down wind and have the powerful trade winds push us at record speeds towards our...
How Much ROUGHER Will it Get??! | Sailing Wisdom [S3 Ep42]
Rigging Doctor

How Much ROUGHER Will it Get??! | Sailing Wisdom [S3 Ep42]

We continue our 1000 mile direct sail from Suriname to the US Virgin Islands where we endure relentless rough weather! Will we make it? Will something break? Will we give up? 0:00 Intro 0:10 Rough Weather 0:38 Dealing with storms 1:06 Raising the Trysail...
We Didn’t Expect THIS | Sailing Wisdom [S3 Ep41]
Rigging Doctor

We Didn’t Expect THIS | Sailing Wisdom [S3 Ep41]

We leave Suriname completely unprepared for the 1000 mile journey ahead of us, but we leave anyway! Watch as we make our way down the Suriname River and out into the open ocean where we set a course for the US Virgin Islands in the Caribbean Sea. 0:00 Int...
Living on a sailboat during the winter part III Passage planning to warmer tropical waters.
Sailing EV

Living on a sailboat during the winter part III Passage planning to warmer tropical waters.

Its been FREEZING here in the winter aboard my sailboat EV! Catch up on what's been happening and join me on a sailing adventure from Canada to The Caribbean virtually as I talk about passage planning and what it takes! Options, distances and how long it t...
Sailing Around the World – A Crazy Day in Paradise! Ep. 33
Sailing Malou

Sailing Around the World – A Crazy Day in Paradise! Ep. 33

Linn wakes up in the house and Gustav wakes up in the boat. Then both start their own little adventure to discover the beautiful and very versatile island of Bequia. Linn become friend with some animals and Gustav falls into a pool with thousands of sea ur...
Epic water experiences, one click away.

Something AWESOME is coming!
Be the FIRST to know⛵

Sign up for exclusive updates and be the first to hear when we go live!
Get sneak peeks, exciting announcement, and special content straight to your inbox!

We don’t spam! Read our privacy policy for more info.


WeBoating
Logo
Shopping cart