Watch Sailing & Boating Adventures Around the World tagged “Caribbean sailing” – Page 27 of 28

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 625-648 of 660 results
BackPackers VS Sailors | SMLS S4E10
Sailing Miss Lone Star

BackPackers VS Sailors | SMLS S4E10

I interview Katie a young German Backpacker that has started her way sailboat hitchhiking to Central America. She tells me her story and the pro and cons of the sailing life versus backpacking. We sail the Catamaran to the Last Bar Before the Jungle, and ...
The First Day: Life is Golden At Sea~Sailing DRENCHED Ep. 22~
Expedition Drenched

The First Day: Life is Golden At Sea~Sailing DRENCHED Ep. 22~

The first day of life at sea! We had done some shorter day sails and weekend trips, but now we were on the big blue road FOR GOOD! Our first stop along the way did not disappoint. The island of St. Eustatius treated us to some amazing hiking, crazy shipw...
Sailing to Tobago Keys | SMLS  S4E09
Sailing Miss Lone Star

Sailing to Tobago Keys | SMLS S4E09

This week we sail the catamaran to Tobago Keys which is known for all of the sea turtles that call this island home. Us girls go snorkeling and show you the under water side of this beautiful island. We had so much fun swimming in the clear blue water of t...
Refitting My Sailboat | SMLS S5 Preview
Sailing Miss Lone Star

Refitting My Sailboat | SMLS S5 Preview

For all of my Patrons Thank You, https://www.patreon.com/misslonestar This is a special update video I made just for you, that I am just now releasing on YouTube. The full process of the refit on the 2-29 Cal sail boat is being documented in detail. So s...
Bequia with the GIRLS! | SMLS S4E08
Sailing Miss Lone Star

Bequia with the GIRLS! | SMLS S4E08

I sail from St. Lucia to Bequia with our almost all girl crew. Below decks Tiffany Copeland at the helm! Alice takes her last sail on Mahalo and we say our sad goodbyes.. Don't miss the EXTENDED Please become a Patreon! https://www.patreon.com/misslonest...
Washing Down the Catamaran | SMLS S4E06
Sailing Miss Lone Star

Washing Down the Catamaran | SMLS S4E06

Please become a Patreon! https://www.patreon.com/misslonestar Like us on Facebook! a https://www.facebook.com/sailingmisslonestar/ We also have a Twitter feed for more info! https://twitter.com/MissLoneStar1 Thanks so much to all of you following our v...
Beach Photoshoot in St. Vincent
Sailing Miss Lone Star

Beach Photoshoot in St. Vincent

Please become a Patreon! https://www.patreon.com/misslonestar Like us on Facebook! a https://www.facebook.com/sailingmisslonestar/ Order one one Aubrey's images and help us in our journey! http://austin-photography.smugmug.com We also have a Twitter fe...
Bikinis in Dominica!  | SMLS S4E05
Sailing Miss Lone Star

Bikinis in Dominica! | SMLS S4E05

Please become a Patreon! https://www.patreon.com/misslonestar Like us on Facebook! a https://www.facebook.com/sailingmisslonestar/ We also have a Twitter feed for more info! https://twitter.com/MissLoneStar1 Thanks so much to all of you following our v...
Shave Attack on the Captain | SMLS S4E04
Sailing Miss Lone Star

Shave Attack on the Captain | SMLS S4E04

We take boat pranks to a whole new level. Come along and enjoy a beautiful sail from St. Kitts to Dominica where we push the limits of wearing out our welcome. We goof off and enjoy the beautiful island of Dominica. Please become a Patreon! https://www.p...
St. Kitts British Virgin Islands | SMLS S4E03
Sailing Miss Lone Star

St. Kitts British Virgin Islands | SMLS S4E03

Please become a Patreon! https://www.patreon.com/misslonestar Like us on Facebook! a https://www.facebook.com/sailingmisslonestar/ Order one one Aubrey's images and help us in our journey! http://austin-photography.smugmug.com We also have a Twitter fe...
Shake Down Sail to Anguilla | SMLS S4E02
Sailing Miss Lone Star

Shake Down Sail to Anguilla | SMLS S4E02

We Sail from St. Maarten to Anguilla on our very first sail aboard SV Mahalo a 40 foot Catamaran. We hitchhike across the island to one of the most beautiful beachesI have ever seen!! I hope you enjoy this weeks video:) Tiffany Copland of Bravo Channels Be...
This Stays in St. Maarten | S4E01
Sailing Miss Lone Star

This Stays in St. Maarten | S4E01

We arrive in St Maarten to meet the new crew of Sailing Catamaran Mahalo. We check out Maho Beach and explore the island as we get to know our new crew, Bruce, Katie and Below Deck's Tiffany Copland. Please become a Patreon! https://www.patreon.com/miss...
Grenada the Last Sail | S3E19
Sailing Miss Lone Star

Grenada the Last Sail | S3E19

We say fair well to Rick and the crew of S/V Sophisticated Lady. See Deleted scenes and the full interview on Vimeo:) Please become a Patreon! https://www.patreon.com/misslonestar Like us on Facebook! a https://www.facebook.com/sailingmisslonestar/ W...
THE PANAMA CANAL on a SAILBOAT (Ep 27)
Sailing Zatara

THE PANAMA CANAL on a SAILBOAT (Ep 27)

You can live this lifestyle too! BlueWater Cruising will show you how: https://www.bluewatercruisingplan.com/ Don't forget to follow Keith's updates on Twitter - he likes keeping ya'll updated through the sat phone, even when we are out of cell range. Reg...
Sailing Green Gills to Bequia | SMLS S3E18
Sailing Miss Lone Star

Sailing Green Gills to Bequia | SMLS S3E18

Something about Bequia makes us crazy.. Especially Sailors.. We hike around the Island and have an amazing time. Please become a Patreon! https://www.patreon.com/misslonestar Like us on Facebook! a https://www.facebook.com/sailingmisslonestar/ We also ...
Sailing to Young Island Cut | SMLS S3E17
Sailing Miss Lone Star

Sailing to Young Island Cut | SMLS S3E17

Please become a Patreon! https://www.patreon.com/misslonestar Like us on Facebook! a https://www.facebook.com/sailingmisslonestar/ Order one one Aubrey's images and help us in our journey! http://austin-photography.smugmug.com We also have a Twitter fe...
Sailing Wallilabou | SMLS S3E16
Sailing Miss Lone Star

Sailing Wallilabou | SMLS S3E16

Uncensored on Vimeo! https://vimeo.com/ondemand/svmisslonestar https://vimeo.com/204782461 Please become a Patreon! https://www.patreon.com/misslonestar Like us on Facebook! a https://www.facebook.com/sailingmisslonestar/ Order one one Aubrey's image...
Sint Maarten Part 1: Superyachts and Sundowners (Sailing Ruby Rose) Ep 4
Sailing Ruby Rose

Sint Maarten Part 1: Superyachts and Sundowners (Sailing Ruby Rose) Ep 4

Welcome to episode 4! This is the first of two episodes based in the Caribbean yachting centre of Sint Maarten/Saint Martin. This week we enter Simpson Bay Lagoon and get settled in the anchorage for a week of boat maintenance, buying new boat toys and ge...
Spinnaker Sailing to St Barts (Sailing Ruby Rose) Ep 3
Sailing Ruby Rose

Spinnaker Sailing to St Barts (Sailing Ruby Rose) Ep 3

Welcome to Episode 3! This week we do a LOT of sailing (well, motor-sailing). We leave Falmouth Harbour in Antigua to head up to Jolly Harbour. En route we spot a simmering volcano on Montserrat and our SUP explodes! (More on this in an upcoming episode)....
Home for the Holidays | SMLS S3E08
Sailing Miss Lone Star

Home for the Holidays | SMLS S3E08

Hey guys! I know Christmas is behind us but I still wanted to share the crazy festivities with you:) I spent some amazing quality time with my kiddos and got to goof off with my gaggle of little brothers. Come along and meet my off beat Dad and amazing Mom...
CPR on a boat [Sailing Zatara Ep 21]
Sailing Zatara

CPR on a boat [Sailing Zatara Ep 21]

You can live this lifestyle too! BlueWater Cruising will show you how: https://www.bluewatercruisingplan.com/ In this episode, we complete the hull repairs on the boat and take a CPR course in the meantime. (I have just been made aware of my AED mistake.....
Life in a Caribbean boatyard (Sailing Ruby Rose) Ep 1
Sailing Ruby Rose

Life in a Caribbean boatyard (Sailing Ruby Rose) Ep 1

Welcome to our very first sailing video! This episode we fly back to Antigua where our Southerly 38 yacht has been stored in the boatyard for the past 7 months. We can't wait to get back in the water, but first we have work to do! From antifouling the hu...
Zatara Into Darkness: Our first overnight passages [Ep 14]
Sailing Zatara

Zatara Into Darkness: Our first overnight passages [Ep 14]

You can live this lifestyle too! BlueWater Cruising will show you how: https://www.bluewatercruisingplan.com/ After enjoying some time with new friends at Rum Cay, we embark on our first three day nonstop sail to Puerto Plata in the Dominican Republic. So...
Never Give Up | SMLS S3E07
Sailing Miss Lone Star

Never Give Up | SMLS S3E07

A personal thank you to all of my viewers and especially my Patrons supporting me on Patreon! This is a little note to let you all know what my plans are for the coming year and beyond:) See it all HERE 👉 https://vimeo.com/sailingmisslonestar/vod_page...
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