Watch Sailing & Boating Adventures Around the World tagged “Sailing the caribbean” – Page 23 of 25

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 529-552 of 585 results
Our Plans for the Future… (Good and Bad News) Sailing Ocean Around Ep. 52
Sailing Malou

Our Plans for the Future… (Good and Bad News) Sailing Ocean Around Ep. 52

We have finally decided if we can sail and how we might sail this winter! And there is some good and some bad news... Support us by becoming a member of our Patreon Crew! Just click the link https://www.patreon.com/oceanaround to see what its all about. ...
SailAway 9 | Messing About on a Sailboat, Wave One | Sailboat Living Sailing Vlog
SailAway World Sailing

SailAway 9 | Messing About on a Sailboat, Wave One | Sailboat Living Sailing Vlog

ALL NEW LINES from EBAY, Boomkicker, Custom Adjustable Backstay and more!! In this week's episode of sailboat living with SailAway we switch it up a little bit. Learn all about the improvements and sailboat maintenance we did in the first 15 days of ownin...
She rode an Ostrich!😮— Sailing Uma [Step 100]
Sailing Uma

She rode an Ostrich!😮— Sailing Uma [Step 100]

Get your Uma stickers: https://www.sailinguma.com/store/ Our time in Curacao has been more than adventurous. After meeting new friends, and doing some boat work, we invited Dan's mom for a week on Uma. During that time, we went out for a little sail aroun...
Curacao Shenanigans — Sailing Uma [Step 98]
Sailing Uma

Curacao Shenanigans — Sailing Uma [Step 98]

When you spend more than a week in a place, you make friends, and when you make friends, the CRAZY gets let out. In this episode, we meet the cool crew of the sailing channel Sea Change , celebrates Mike's birthday and enjoy a bunch of fun adventures. If ...
SailAway 8 | Sailboat Aground In Charleston | Sailboat Living Sailing Vlog
SailAway World Sailing

SailAway 8 | Sailboat Aground In Charleston | Sailboat Living Sailing Vlog

We RUN AGROUND, drink all our booze, and swim with DOLPHINS!! SailAway Ep. 8 Travel Vlog - So we made it 600 miles living on a sailboat from Atlantic City to Charleston after one day of owning the boat...but sometimes it's all about enjoying your own "ba...
SailAway | Official Trailer | Sailboat Living Sailing Vlog
SailAway World Sailing

SailAway | Official Trailer | Sailboat Living Sailing Vlog

Cruising couple, 2-year-old, and trusty dog cruise the world on a 35' sailboat, Layla!! Ahoy, there from SailAway and welcome to our travel vlog! After only ONE DAY of owning our 35' sailboat, we sailed her 600 miles from New Jersey to South Carolina! W...
On The Rocks! — Sailing Uma [Step 97]
Sailing Uma

On The Rocks! — Sailing Uma [Step 97]

I am always amazed by the cruisers community's help for eachother. I witness our neighbours boat dragging to the rocks in our anchorage in Curacao, and within a few minutes of radio chatting, several other cruisers came to the rescue and the boat was safel...
Getting Ready to Sail Downwind— Sailing Uma [Step 94]
Sailing Uma

Getting Ready to Sail Downwind— Sailing Uma [Step 94]

Ever since we started sailing, we've always been beating into the wind. When we were in Grenada and planning our sail West to Bonaire, we had a few preparation and fixes to do before finally going downwind. If you enjoyed this episode, please give it th...
The Grenadines, a Sailor’s Paradise — Sailing Uma [Step 92]
Sailing Uma

The Grenadines, a Sailor’s Paradise — Sailing Uma [Step 92]

One of the reasons sailors come to the Caribbean is to enjoy its beautiful white sandy beaches and Chrystal clear waters. The Grenadines, is the perfect example of this "sailor's paradise". In this episode, we explore the breath taking islands of SVG, ge...
Taken Out by a Wave – Playing in Panama (Sailing Curiosity)
Gone with the Wynns

Taken Out by a Wave – Playing in Panama (Sailing Curiosity)

Beaches, Bikini's and a flight through the Jungle...man I love play days! Get all the Details of these adventures with links and maps here: http://gonewiththewynns.com/playing-in-panama If you wanna get social with us we're all over the place, hop in and j...
Captain Kika’s SOLO SAIL…(ish) — Sailing Uma [Step 91]
Sailing Uma

Captain Kika’s SOLO SAIL…(ish) — Sailing Uma [Step 91]

We always say, if you don't push yourself out of your comfort zone, then you are not pushing yourself hard enough. For our overnight passage form Martinique to St Vincent, I decided to take that opportunity and practice solo sailing (well, sort of). Dan be...
SailAway 3 | Lazy Day Sailing in the Dismal Swamp | Sailboat Living Sailing Vlog
SailAway World Sailing

SailAway 3 | Lazy Day Sailing in the Dismal Swamp | Sailboat Living Sailing Vlog

GETTING PRIMAL and hitting stuff in the Dismal Swamp!! Sailboat Living with SailAway Ep. 3 Travel Vlog - Our new sailboat delivery continues as we bump logs in the Great Dismal Swamp in the Intracoastal Waterway, sail big winds in the Pamlico Sound, and t...
SailAway 2 | 30 Hours Sailing On The Atlantic | Sailboat Living Sailing Vlog
SailAway World Sailing

SailAway 2 | 30 Hours Sailing On The Atlantic | Sailboat Living Sailing Vlog

CRAZY WAVES, 30 hours on the ocean, and bioluminescent algae!! Sailboat Living with SailAway Ep. 2 Travel Vlog - On Day 2 of ownership and after a single day of upgrades and preparations to the sailboat, we begin our long sail down the east coast back to...
SailAway 1 | New Sailboat, New Adventures…Sailing 600 Miles | Sailboat Living Sailing Vlog
SailAway World Sailing

SailAway 1 | New Sailboat, New Adventures…Sailing 600 Miles | Sailboat Living Sailing Vlog

We buy a SAILBOAT and leave the NEXT DAY on a 600 mile voyage!! Sailboat living with SailAway Ep. 1 Travel Vlog - Join us aboard SV Layla as we learn about living on a sailboat. We travel from our home in Charleston SC to Atlantic City, New Jersey to pi...
Sea Monsters & Our First Sailboat SCUBA Dive (Sailing Curiosity)
Gone with the Wynns

Sea Monsters & Our First Sailboat SCUBA Dive (Sailing Curiosity)

Scary water, SCUBA diving and a hunt for Sloths and Monkeys, yep it's a busy one! Join our crew on Patreon and become a BIGGER part of the adventure: http://bit.ly/patreon-wynn Get all the Details of our trip here: http://www.gonewiththewynns.com/sea-mon...
Day Sailing Martinique — Sailing Uma [Step 88]
Sailing Uma

Day Sailing Martinique — Sailing Uma [Step 88]

Disclaimer/Present day update: Our video timeline being a few weeks behind, note that we are not in Martinique. We are currently in Grenada, safe from Hurricane Irma's fury. In this episode we learn how to cut and cook Lion Fish, go out for a sail with ...
Finally Sailing South — Sailing Uma [Step 86]
Sailing Uma

Finally Sailing South — Sailing Uma [Step 86]

This week, we leave Guadeloupe and sail south to Les Saintes. We spend a few days exploring the tiny islands and getting some much needed repairs done on Uma. Then, it's off to Dominica. We get frustrated at our autopilot but still manage to enjoy yet anot...
Mission Panamania 04: Longest Passage & Biggest Storm Ever (Sailing Curiosity)
Gone with the Wynns

Mission Panamania 04: Longest Passage & Biggest Storm Ever (Sailing Curiosity)

This is it! Bye Bye Bahamas, we're off to Panama! Get all the Details of our trip here: http://gonewiththewynns.com/longest-passage-biggest-storm Subscribe and Keep in touch: http://gonewiththewynns.com/join-us Join our crew on Patreon and become a BIG...
We Sail to Spicy Island! Sailing Ocean Around Ep. 38
Sailing Malou

We Sail to Spicy Island! Sailing Ocean Around Ep. 38

We head in to explore the magical island of Carriacou, Gustav gets the worst food poisoning, we set sail further south to the spicy island, and then Evelina leave us... Support us by becoming a member of our Patreon Crew! Just click the link https://www.p...
Sailing With Two Amazing Girls! Sailing Ocean Around Ep. 37
Sailing Malou

Sailing With Two Amazing Girls! Sailing Ocean Around Ep. 37

Union island is showing us an amazing time as we explore some lonely beaches and meet new friends! And later we decide to keep sailing south to the island of Carriacou where a new crew member is joining us... Support us by becoming a member of our Patreo...
Stranded on a beach in Saba— Sailing Uma [Step 83]
Sailing Uma

Stranded on a beach in Saba— Sailing Uma [Step 83]

On our last day in Saba, we hiked around the rain forest and got REALLY lucky finding a ride back to our boat, as we were pretty much stranded on the Saban beach. If you enjoyed this episode, please give it thumbs up, it helps us out a bunch :) WANT MO...
SECRET DIVE SITE in the BVIs — Sailing Uma [Step 81]
Sailing Uma

SECRET DIVE SITE in the BVIs — Sailing Uma [Step 81]

This week as we continue sailing the BVI's, we check out a super secret, very new and amazing dive spot off the North West coast of Virgin Gorda BVI. We also get our main sail repaired before sailing to Saba with a South African stowaway. If you enjoyed ...
Naked Night Dive + Exploring the Baths — Sailing Uma [Step 80]
Sailing Uma

Naked Night Dive + Exploring the Baths — Sailing Uma [Step 80]

After seeing a group of night scuba divers show up, we decided to go along for the ride and free dive around them... We had no idea they would have actually spotted the fact that we were very much naked. After a good time at Great Dog island, we sailed ove...
Sailing Around the World – Will This Man Save the Turtles? Ep. 34
Sailing Malou

Sailing Around the World – Will This Man Save the Turtles? Ep. 34

The discovering of our little paradise island Bequia continues. We make it to the far south point to watch some cool cave houses and play in a desserted playground… The next day we hike to the Turtle Sanctuary and meet its founder Orton King. And then we...
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