Watch Sailing & Boating Adventures Around the World

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.

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The Trinidad You Should Get to Know!
Travel Sketch

The Trinidad You Should Get to Know!

In our opinion, Trinidad's natural beauty is massively under rated! When it comes to Caribbean jungle and waterfalls, and in fact jungle landscapes in general, it's world class. When our new crew member Lukasz arrived in Trinidad to join us living aboard our sailboat, we knew we wanted to...
Ultimate SAILING Itinerary for Antigua
Sail Stillwater

Ultimate SAILING Itinerary for Antigua

In this video we are chartering a Sunsail 46' monohull out of English Harbor and sailing the beautiful Caribbean islands of Antigua and Barbuda. We'll bring you along as we hit all of the hot spots and show you the best anchorages and things to do on the islands. With stops like Green Is...
Tour the Tropical Trinidad Coast by Boat to SCOTLAND BAY! | Trinidad & Tobago, Caribbean
Travel Sketch

Tour the Tropical Trinidad Coast by Boat to SCOTLAND BAY! | Trinidad & Tobago, Caribbean

SPONSOR INDEPENDENT STORY TELLING 😎 ⛵ Gain access to our member only area: 👉 Tip jar: After being in storage for months on end we were finally able to launch our catamaran tender thanks to some help from a kind Trinidadian local. While our initial plan was to go DDI, or Down De Islands, we e...
SAILING TO PANAMA⛵️ Day in the Life on Passage
Holly and Ray

SAILING TO PANAMA⛵️ Day in the Life on Passage

Welcome aboard! In this video, we take you along for a typical day in the life while on passage.🌊 This was day 4 of our sail from Saint Martin to Panama. The wind was light, but we managed to do some sailing, cooking, and fishing! 🐟 ——————————————————————— ⛵️Join the Crew on Patreon: ⚓️Check out ...
Preparing to Sail Across the PACIFIC OCEAN🌊 Part 1: The Boat
Holly and Ray

Preparing to Sail Across the PACIFIC OCEAN🌊 Part 1: The Boat

Sabado is back in the water and ready for our next adventure! ⛵️ This week, we take you along for splash day and discuss what upgrades we made while out of the water as we prepare the boat for our upcoming Pacific crossing. 🌊 With just the two of us aboard for the sail, we’ve incorporated a backup a...
CRUISER Q&A⛵️Interviewing Live-Aboard Couples About Boat Life
Holly and Ray

CRUISER Q&A⛵️Interviewing Live-Aboard Couples About Boat Life

Sabado is hauled out and ready for a few more upgrades before we head to the Pacific! ⛵️ As we get settled on the hard, we hope you enjoy this compilation of interview clips we’ve collected over the past few months while sailing the Caribbean.🏝️ In hopes of capturing that sundowners-with-your-new-ne...
40kn Winds and Rough Seas 💨⛵️| SAILING TO ST. MARTIN
Holly and Ray

40kn Winds and Rough Seas 💨⛵️| SAILING TO ST. MARTIN

Join us for a rough sail from Guadalupe to Saint Martin. ⛵️ Because of our pending haul-out date, we decided to take a tight (and rough) weather window for our latest hop North. Along the way, we encountered 40kn winds and rough seas. 🌊 Sabado was doing well until a lazy jack ripped out of the mast ...
Moving on… ⛵️| SAILING THE CARIBBEAN
Holly and Ray

Moving on… ⛵️| SAILING THE CARIBBEAN

This week, we reluctantly left Dominica and sailed North to Guadalupe. 🌊 It was a bouncy but quick passage where we successfully dodged fish traps and got the boat onto a challenging mooring ball… After hearing reports of moorings breaking loose in Deshaies, we decided to dive in, inspecting the cha...
Sailing Back to OUR FAVORITE Caribbean Island🍊👙
Holly and Ray

Sailing Back to OUR FAVORITE Caribbean Island🍊👙

Join us while we sail back to Dominica, our favorite Caribbean island (so far😉). We ceremoniously switch our currency from Euro to Eastern Caribbean Dollars as we leave Martinique and enjoy a short but speedy sail between the islands. We overnight on a mooring ball in Roseau, then motor to Portsmout...
SSL682 ~ Lost in the Cove
Captain Rick Moore

SSL682 ~ Lost in the Cove

The Haunting Tale of SSL682 ~ Lost in the Cove. Today we bring you a day in the life of style video, as sail around to the West side of San Andres and decide to spend some time getting lost in the tranquility of the Cove anchorage.. it is very beautiful and very quiet here, and we find some nice sur...
WILD at St Martin Carnival | Sailing Sunday | Ep.164
Sailing Sunday

WILD at St Martin Carnival | Sailing Sunday | Ep.164

Say goodbye to our life raft in this video but first we share our most amazing week with you at another incredible Carnival in the Caribbean. If you thought Guadeloupe was amazing, wait until you join us today in Sint Maarten!!! This week was unbelievable!!! Subscribe to join us each week saili...
We got ATTACKED by Monkeys 🐒| Sailing the Caribbean
Sailing Lady Africa

We got ATTACKED by Monkeys 🐒| Sailing the Caribbean

EP 184: We got ATTACKED by Monkeys 🐒| Sailing the Caribbean We experienced some gnarly lightning and thunder on the boat for first time. I can totally see why it's probably the most hated part about sailing for many cruisers. We got our new prop in the mail for our outboard.. what a performa...
Sailing our Trimaran to Guadeloupe
SailOceans

Sailing our Trimaran to Guadeloupe

Just before we took our home trimaran across the Oceans to Poland for a refit, we sailed to Guadeloupe.Today we share the beauty of this Caribbean Island. Enjoy. Ania and Bartek JOIN OUR LOVE BOAT GROUP: (Extra content for our Patrons only) HOW TO BUY A BOAT AND LIVE ABOARD? Sailing Life Advice...
Caribbean Dream: Swimming with Turtles in crystal clear water – UNTIE THE LINES IV #68
WhiteSpotPirates

Caribbean Dream: Swimming with Turtles in crystal clear water – UNTIE THE LINES IV #68

Back in warmer latitudes, back in the Caribbean Sea! Not quite back on Karl, yet...he is still waiting patiently in Ecuador for my return. Michael, the owner of SV Marlin, has asked me to work as a co-skipper for two weeks for a charter sail from Curacao to Los Roques and back. Since this 60 foot p...
The Space Drum Pilot – LIVE music from inhabited island in the Caribbean
SailOceans

The Space Drum Pilot – LIVE music from inhabited island in the Caribbean

Please enjoy a music video from Bartek this time filmed on an uninhabited island of Punaise in the Grenadines (the smallest one in the Caribbean!) thanks to technical and logistical support from Ania and our friends. Enjoy! Ania and Bartek *****ATTENTION! Because of YouTube policy the comments bel...
Most Beautiful Caribbean Islands – The Grenadines – S4:E32
Sailing Doodles

Most Beautiful Caribbean Islands – The Grenadines – S4:E32

We sail 2 Bali 40 Catamarans around the Grenadine Islands which are some of the most beautiful islands in the Caribbean! This channel is funded by viewers like you. Please help us keep this channel creating great content by becoming a patron Donate Via Paypal to help us get a new drone: Book...
The Most Amazing Drum Ever Played On A Caribbean Island
SailOceans

The Most Amazing Drum Ever Played On A Caribbean Island

While we were sailing in the Grenadines in April we managed to record playing this amazing instrument in Salt Whistle Bay in Mayreau, in the Grenadines - our favorite place. This is the first recording of my beloved instrument. We first heard and saw it 8 years ago in a park in Barcelona and were co...
Caribbean Island. Beautiful Petit Saint Vincent
SailOceans

Caribbean Island. Beautiful Petit Saint Vincent

Today we sail to Petit Saint Vincent - the Caribbean Island. Join us while we swim with turtles , exploring beach and then sweet sunset. Enjoy! Stay safe and thank you for being with us Ania and Bartek JOIN OUR LOVE BOAT GROUP: (Extra content for our Patrons only) HOW TO BUY A BOAT AND LIVE ABOA...
Sailing to Montserrat & Touring The Exclusion Zone
SailingBritican

Sailing to Montserrat & Touring The Exclusion Zone

The big appeal to sailing Montserrat was to check out the abandoned (or should I say demolished?) city of Plymouth. Why was it demolished? Montserrat's volcano became active and blew it's top. And the activity started in 1995 and has been going since then. The volcano is still smoking. ...
ep21 – Sailing Les Saints (Guadeloupe) to Martinique – Hallberg-Rassy 54 Cloudy Bay – April 2018
Sail Cloudy Bay

ep21 – Sailing Les Saints (Guadeloupe) to Martinique – Hallberg-Rassy 54 Cloudy Bay – April 2018

s/v Cloudy Bay (Hallberg-Rassy 54) had another very exciting sailing between islands, going from Les Sains to Martinique. We started very early, at 5am, and we had all sorts of wind strengths, sun, rain, and clouds. Felt like sailing from Caribbean winter to European winter, in just few hours! April...
ep13 – Sailing Bequia – Sailing SVG – Hallberg-Rassy 54 Cloudy Bay – March 2018
Sail Cloudy Bay

ep13 – Sailing Bequia – Sailing SVG – Hallberg-Rassy 54 Cloudy Bay – March 2018

After Canouan, s/v Cloudy Bay (Hallberg-Rassy 54) moves on to Bequia, the largest of the Grenadines islands and well set up for tourists. We moor in Port Elizabeth, the heart of island's commerce, with charming waterfront bars & restaurants, fresh fruit & veg stalls and lovely beaches. ...
ep11 – Mayreau, Tobago Cays – Sailing SVG – Hallberg-Rassy 54 Cloudy Bay – March 18
Sail Cloudy Bay

ep11 – Mayreau, Tobago Cays – Sailing SVG – Hallberg-Rassy 54 Cloudy Bay – March 18

After 3 days in Tobago Cays Marin Park, s/v Cloudy Bay (Hallberg-Rassy 54) moves on to Mayreau, the last island of the Tobago Cays. Our visit to Mayreau was notable for its gloomy weather and unusual large swell from the north which had caused mayhem in the best anchorages. St. Vincent & the Gre...
ep10 – Sailing Tobago Cays – Sailing SVG – Hallberg-Rassy 54 Cloudy Bay – March 2018
Sail Cloudy Bay

ep10 – Sailing Tobago Cays – Sailing SVG – Hallberg-Rassy 54 Cloudy Bay – March 2018

After Petit St.Vincent, s/v Cloudy Bay spent 5 days in Tobago Cays Marine Park, which is a cluster of 5 tiny, uninhabited, cays, collectively sheltered from the open sea by the appropriately named Horseshoe Reef. Wildlife was amazing, the highlight being the sea-turtles and iguanas. St. Vincent &...
ep9 – Sailing Petit St.Vincent Island – Sailing SVG – Hallberg-Rassy 54 Cloudy Bay – Mar 2018
Sail Cloudy Bay

ep9 – Sailing Petit St.Vincent Island – Sailing SVG – Hallberg-Rassy 54 Cloudy Bay – Mar 2018

After a day in Palm Island, s/v Cloudy Bay (Hallberg-Rassy 54) moves on for a quick look in Petit Martinique (PM), then to the next private resort island, Petit St. Vincent (PSV), which is a secluded and unplugged paradise. With delightful white sand beaches and surrounded by the clearest, bluest, m...
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