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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PARADISE FOUND🏝️Sailing French Polynesia
Holly and Ray

PARADISE FOUND🏝️Sailing French Polynesia

Sail along with Holly and Ray as they uncover the hidden wonders of French Polynesia. Watch as they swim in turquoise lagoons, relax on idyllic atolls, and make crucial repairs to ensure their vessel remains seaworthy during an extraordinary voyage.
A magical swim with our favorite sea creatures!🤿 #mantaray
Holly and Ray

A magical swim with our favorite sea creatures!🤿 #mantaray

Swimming with mantas rays while anchored off a tropical island in the South Pacific😍 #ocean #sailing #fishing #snorkeling
We Sailed to Our DREAM DESTINATION!⛵️🏝️
Holly and Ray

We Sailed to Our DREAM DESTINATION!⛵️🏝️

Holly and Ray from Holly & Ray Sailing share an unforgettable tale of reaching their dream sailing destination in the South Pacific, immersing themselves in local cultures, fishing adventures, and island life.
BOAT LIFE: Incredible Snorkeling, Beautiful Views, and Fishing With Friends🏝️
Holly and Ray

BOAT LIFE: Incredible Snorkeling, Beautiful Views, and Fishing With Friends🏝️

In this episode of Boat Life, Holly and Ray invite viewers to join them on an unforgettable adventure. Discover breathtaking snorkeling experiences, picturesque views, and a thrilling day of deep-sea fishing in one of the world's most secluded destinations: the South Pacific Islands!
WE MADE IT! 🏝️ Difficult 4-Day Sail to the Tuamotus
Holly and Ray

WE MADE IT! 🏝️ Difficult 4-Day Sail to the Tuamotus

Watch Holly and Ray's incredible, albeit challenging, journey sailing from the Marquesas Islands to the Tuamotus! Follow along as they encounter tough weather and solve onboard problems.
SAILING THE SOUTH PACIFIC⛵ Preparing for the Tuamotus
Holly and Ray

SAILING THE SOUTH PACIFIC⛵ Preparing for the Tuamotus

Holly and Ray embark on a sailing adventure across the South Pacific en route to the Tuamotus islands. Follow their daily routine, learn about preparation, and watch as they tackle challenges.
EXPECTATION vs. REALITY⛵️Sailing Across the Pacific Ocean
Holly and Ray

EXPECTATION vs. REALITY⛵️Sailing Across the Pacific Ocean

Watch as Holly and Ray sit down to discuss the realities of their Pacific Crossing, comparing expectations vs reality from their sale from Panama to French Polynesia. Uncover details about wind conditions, sailing performance, provisions and energy management on this extensive voyage.
LAND HO!⛵️Sailing Across the Pacific Ocean (Part 4)
Holly and Ray

LAND HO!⛵️Sailing Across the Pacific Ocean (Part 4)

Holly and Ray's epic voyage across the Pacific Ocean showcases their determination and resilience in the face of challenges on the vast blue expanse. Join them for an unforgettable journey filled with new discoveries and experiences.
19 Days at Sea⛵️ Sailing Across the PACIFIC OCEAN
Holly and Ray

19 Days at Sea⛵️ Sailing Across the PACIFIC OCEAN

Embark on an epic 19-day sailing adventure with Holly and Ray as they cross the vast Pacific Ocean from Panama to French Polynesia. Witness their struggles with the doldrums, boat challenges, and culinary creations while staying motivated by each other's passion for exploration.
What it’s REALLY Like Sailing Across the Pacific Ocean⛵️🌊 (Week 2)
Holly and Ray

What it’s REALLY Like Sailing Across the Pacific Ocean⛵️🌊 (Week 2)

Join us as we continue our expedition across the Pacific Ocean on our sailboat Sabo! This week, we delve into The Good, The Bad, and The Mundane of real life while underway. Watch our videos to see what adventures unfold next!
Sailing Across the PACIFIC OCEAN⛵️🌊 (Week 1)
Holly and Ray

Sailing Across the PACIFIC OCEAN⛵️🌊 (Week 1)

Discover the thrilling sailing adventure of Holly & Ray as they embark on a 4,000 nautical mile journey across the Pacific Ocean. Follow along with daily updates, video blogs, and Instagram posts to learn about their experiences, preparations, and destination.
Preparing to Sail Across the PACIFIC OCEAN🌊 Part 2: Provisioning
Holly and Ray

Preparing to Sail Across the PACIFIC OCEAN🌊 Part 2: Provisioning

This week, we began provisioning for our Pacific crossing and cruising in French Polynesia! 🌎 In this video, Holly takes you along while she researches our destination, makes her list, shops, and stores our dried, canned, and paper goods. 🛒 ——————————————————————— ⛵️Join the Crew on Patreon: ⚓️Ch...
Transiting the PANAMA CANAL on our Sailing Catamaran! ⛵️
Holly and Ray

Transiting the PANAMA CANAL on our Sailing Catamaran! ⛵️

This week, we take you along for our Panama Canal Transit. We’ve been dreaming of checking this off our bucket list for years! 🙏🏼 Despite many reported delays, our transit date was moved up eight days. We scrambled to get the boat and our crew ready on such short notice. We hired two local professio...
LAND HO! ⛵️ Arriving in Panama After 9 Days at Sea
Holly and Ray

LAND HO! ⛵️ Arriving in Panama After 9 Days at Sea

After a week of relatively good sailing from Saint Martin, the wind became finicky, and we were forced to motor the rest of the way to Panama. We were disappointed but made the best of it by enjoying the sunshine and taking advantage of the extra power from our engines. We spotted land after 9 days ...
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 ...
PACIFIC BOUND⛵️Sailing from Saint Martin to Panama
Holly and Ray

PACIFIC BOUND⛵️Sailing from Saint Martin to Panama

After two more weeks in Saint Martin, we finally got a weather window to sail to Panama! ⛵️ In this video, we take you along for the first 3 days of our passage. Join us for great sailing, beautiful sunsets, dolphins, and freshly caught fish! 🐟 ——————————————————————— ⛵️Join the Crew on Patreon: ...
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...
Sailing Where a PRISONER Survived Doomsday…😳🌋
Holly and Ray

Sailing Where a PRISONER Survived Doomsday…😳🌋

This week, we sailed to Saint-Pierre, Martinique. The city once known as “the Paris of the Eastern Caribbean” was devastated by a volcanic eruption in 1902. We anchored at the volcano's base, learned about its history, and explored the town. We got to walk through the prison ruins and see the c...
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