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

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 1-24 of 28 results
CRUISING ALUMINUM SAILBOAT: GOING WITH THE FLOW
Sailing Jibsea

CRUISING ALUMINUM SAILBOAT: GOING WITH THE FLOW

Join us on sailing adventure as we explore the stunning U.S. Virgin Islands (USVI) aboard our aluminum sailboat and sail to the British Virgin Islands (BVI) . In this episode, we were hoisting the sails in whichever direction where the wind takes us even i...
BOAT LIFE AFTER ROUGH PASSAGE: Assessing the Damage…Is this Lifestyle Worth It? – Ep 221
Sailing Jibsea

BOAT LIFE AFTER ROUGH PASSAGE: Assessing the Damage…Is this Lifestyle Worth It? – Ep 221

After a challenging and intense journey across the open Atlantic Ocean we’ve finally made it to the British Virgin Islands in the Caribbean. Join us on this new exciting chapter of full-time cruising as we arrive in paradise to live life on anchor. We ...
Fountaine Pajot 51′.  With All Electric Propulsion is this the perfect liveaboard Catamaran?
Cruising Off Duty

Fountaine Pajot 51′. With All Electric Propulsion is this the perfect liveaboard Catamaran?

This is a guided tour of the Fountaine Pajot Aura 51'. This boat has more than enough space, storage and comfort to be a liveaboard Catamaran. It also has been designed with sailing performance in mind. Now they are producing this Aura 51 with new all-e...
Fountaine Pajot Tanna 47′ guided tour. Perfect size for live-aboard cruising.
Cruising Off Duty

Fountaine Pajot Tanna 47′ guided tour. Perfect size for live-aboard cruising.

This is a guided tour of the Fountaine Pajot Tanna 47' where we try and decide if this boat is the perfect size to be a live-aboard cruising catamaran. The tour is headed by: James Tiernan President of ACY Texas and a Yacht Consultant Email: James.Tiernan...
Fountaine Pajot Astrea 42′ guided tour. Suitable for live-aboard cruising. Great space and comfort.
Cruising Off Duty

Fountaine Pajot Astrea 42′ guided tour. Suitable for live-aboard cruising. Great space and comfort.

This is a guided tour of the Fountaine Pajot Astrea 42' where we try and decide if this boat is big enough to be suitable for a live-aboard cruising couple or a small family? Answer: Yes! The tour is headed by: James Tiernan President of ACY Texas and a ...
Farewell Lady Africa..
Sailing Lady Africa

Farewell Lady Africa..

EP 225: Farewell Lady Africa.. So the time had come to sign paperwork and make it official.. We motored Lady Africa to the USVI to her new home in St Thomas. What a crazy roller coaster of emotions. If you see Lady Africa in an anchorage be sure to go sa...
The last few moments aboard Lady Africa.. 🌞⛵
Sailing Lady Africa

The last few moments aboard Lady Africa.. 🌞⛵

EP 224: The last few moments.. 🌞⛵ While we were on Peter Island here by the Willy T, we decided it was time to get some blood flowing through our body and we went for a good hike around the island. We decided to check out some of the dive caves here...
We’re in Charter Boat Central..
Sailing Lady Africa

We’re in Charter Boat Central..

EP 223: We're in Charter Boat Central.. After facing some unfavorable wind conditions, we anchorage hopped around to find a place where we could be sheltered for the worst of it. We found ourselves anchored outside a private island with a cute little bea...
We’re off to the British Virgin Islands! ⛵
Sailing Lady Africa

We’re off to the British Virgin Islands! ⛵

EP 222: We're off to the British Virgin Islands! ⛵ After a really long time spent in St Maarten, it was time to head of to the British Virgin Islands. We were so excited to be on our way already. A beautiful calm 80nm sail later and we had reached the f...
Sailing with a broken knee 🦵
Sailing Lady Africa

Sailing with a broken knee 🦵

EP 221: Sailing with a broken knee 🦵 Since we we're in St Maarten which is considered the more built up island of the Caribbean, we opted to go to the doctor to see if we could get Ricky's "what we though was a torn meniscus" sorted. We booked an appoi...
Tour of a $2,000,000 ocean crossing Nordhavn 60
Sailing Lady Africa

Tour of a $2,000,000 ocean crossing Nordhavn 60

EP 220: Tour of a $2,000,000 ocean crossing Nordhavn 60 This week we decided to do something different. Friends of ours Peter and Luis were on their way to St Maarten and we hadn't seen them for 2 years. Can you believe it's been 2 years since we crossed ...
Sailing to St Maarten | Private Jet Island ✈
Sailing Lady Africa

Sailing to St Maarten | Private Jet Island ✈

EP 219: Sailing to St Maarten | Private Jet Island ✈ We checked out of Antigua and made our way to St Maarten. This time we actually managed to sail and not motor the whole way which was so nice and we caught our selves some fish for dinner. It's been a...
This is how you know you’re a sailor…
Sailing Lady Africa

This is how you know you’re a sailor…

EP 218: This is how you know you're a sailor... After arriving in Antigua, it was time to explore the island. We took a trip to Shirley Heights, and prepped to head of to Green Island but ended up turning around because of bad swells. We anchor in English...
Taking our Dog Cruising on a Sailboat in the Caribbean – what we need to do.
The O'Kelly's

Taking our Dog Cruising on a Sailboat in the Caribbean – what we need to do.

Rules & Regulations begin at 10:00. Should you bring your dog along to the Caribbean? We talk about life aboard with a dog, regulations, and poop. It can be a pain in the *ss, but for us, we wouldn't do it without our dog Sugar. We do a country by cou...
Los Roques, Venezuela – An untouched PARADISE – Final Part: Episode 21
Sailing Parlay Revival

Los Roques, Venezuela – An untouched PARADISE – Final Part: Episode 21

In this final part of the Los Roques episodes we back our hurricane damaged catamaran right up to the beach, using a stern anchor so that we can literally step off the boat onto the sand! We find a turtle santuary at Dos Mosquises, where we get to play wit...
Los Roques, Venezuela – An untouched PARADISE – Part 2 : Episode 20
Sailing Parlay Revival

Los Roques, Venezuela – An untouched PARADISE – Part 2 : Episode 20

In this episode we continue to sail our hurricane damaged Lagoon 450 Catamaran through Los Roques, leaving civilization in Gran Roque and going off the grid. Los Roques is a beautiful archipelago off the coast of mainland Venezuela, and the beauty of this ...
Los Roques, Venezuela – An untouched paradise – Part 1: Ep 19
Sailing Parlay Revival

Los Roques, Venezuela – An untouched paradise – Part 1: Ep 19

In this episode we arrive at the archipelago of Los Roques, Venezuela, against many people's advice, as Venezuela is one of the most dangerous countries in the world. But a few friends of ours had visited the islands recently and told us it was safe, and a...
Sailing to Los Roques, Venezuela – Part 2
Sailing Parlay Revival

Sailing to Los Roques, Venezuela – Part 2

In part one of this episode we left Grenada in our hurricane damaged boat headed for Los Roques, Venezuela. We give the mainland a wide berth to avoid pirates so the passage takes 4 days. See PART ONE here: https://www.youtube.com/watch?v=qqARpYaNhlc ...
73. Entering the Florida Keys & Sewing DIY Salon Cushions Using the SUN | Learning the Lines
Learning the Lines

73. Entering the Florida Keys & Sewing DIY Salon Cushions Using the SUN | Learning the Lines

This video continues on from episode 72 as we finish our trip to Marathon, Florida. We found ourselves motoring through calm seas with little to no wind as we passed under the Seven Mile Bridge and made our way into Boot Key Harbor. We knew this destinatio...
Sailing Bahamas – Episode 37 – Lady K Sailing
Lady K Sailing

Sailing Bahamas – Episode 37 – Lady K Sailing

Join us as we sail our liveaboard Hughes 35 sailboat from Bimini to the Exumas in the Bahamas. Support Lady K: http://www.patreon.com/ladyksailing Want to know what it took us to get here? Our book: http://ladyksailing.com/weve-released-a-book/ Declan DP L...
We remove our forestay, at anchor! – Episode 11
Sailing Parlay Revival

We remove our forestay, at anchor! – Episode 11

The learning curve continues as we have to remove our forestay in order to fix our our furler problem. We do this on anchor in Martinique under the generous guidance of Gaetan at Caribe marine. We then motor into the marina with just our halyards holding t...
Antigua to Guadeloupe – the fishing circus continues! Episode 7
Sailing Parlay Revival

Antigua to Guadeloupe – the fishing circus continues! Episode 7

In this episode the fish start to bite and its an absolute circus. We also get our own fishing line caught in our propellor! Then we explore some rivers and hot springs in Guadeloupe. To support us on Patreon and get a chance to come sailing with us click...
The Journey to Puerto Rico [EP 9] | Sailing Millennial Falcon
Sailing Millennial Falcon

The Journey to Puerto Rico [EP 9] | Sailing Millennial Falcon

We round out our adventures in Turks and Caicos by exploring the island of Grand Turk then head off to Puerto Rico. Sadly the weather forecast did not align with reality and so we finally got to see what the Millennial Falcon was really made of! Join th...
Very first 3 day non stop sail and Bonaire!!! / Sailing Aquarius #23
Sailing Aquarius Around The World

Very first 3 day non stop sail and Bonaire!!! / Sailing Aquarius #23

We take off for our very first 3 day about 390 nautical miles journey in south Caribbean. On the journey we fly ballooned sail (for a very first time as well) and we rip it :( Of course that had to happen at night as well... But we made it to Bonaire and a...
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