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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Our First Overnight Sail as a Family
Finding Our Isla Sailing

Our First Overnight Sail as a Family

Our first overnight sailing passage took us from St. Martin to the U.S. Virgin Islands aboard our Lagoon 450 catamaran—and honestly, it wasn't what we expected. As a family of six living aboard full-time, sailing through the night with our kids was one of the biggest milestones of our journey....
Sailing 1,300 Nautical Miles to TONGA⛵️
Holly and Ray

Sailing 1,300 Nautical Miles to TONGA⛵️

Join us as we complete a 10-day, 1,300 nautical mile voyage from French Polynesia to Tonga! We carefully navigate a reef pass into a peaceful anchorage, where we check into the country with ease—no dodgy docks, just smiles. After a brief rest, we lift anchor for a bumpy overnight sail to Vava’u, eag...
10 DAYS AT SEA⛵️Next Stop: Tonga!
Holly and Ray

10 DAYS AT SEA⛵️Next Stop: Tonga!

Let’s get the heck out of here‼️ Join us for a 10 day sail from French Polynesia to Tonga— a passage we’ve been looking forward to for quite some time… 😍 The journey begins with a beautiful overnight trip from Tahiti to Bora Bora, where we tackle some chores in preparation for our departure and soak...
Sailing Back to Tahiti: Preparing for Our Next Adventure
Holly and Ray

Sailing Back to Tahiti: Preparing for Our Next Adventure

We’re on the move! ⛵️ After an overnight sail from Tahuata to Nuku Hiva, we said goodbye to our family and restocked the boat with food and fuel before the World ARC arrived. Then, it was off on a six-day offshore passage back to Tahiti, the first leg of our journey toward New Zealand. Along the way...
Our last sail on the Pacific Ocean | Sailing Sitka Ep 157
Sailing Sitka

Our last sail on the Pacific Ocean | Sailing Sitka Ep 157

Jay and Kenna embark on a 3 day passage sailing from the tiny village of Bahia Honda to the concrete jungle of Panama City. This sail happens to be their last in the Pacific Ocean as they get ready to cross the Panama Canal into Atlantic waters. Thank you for watching and please subscribe if you enj...
Sailing the Marquesas Islands: 1 Year Living Aboard Our Sailboat in French Polynesia
Holly and Ray

Sailing the Marquesas Islands: 1 Year Living Aboard Our Sailboat in French Polynesia

All aboard! ⛵️ Join us for an overnight sail from Nuku Hiva to Hiva Oa, where we welcome family aboard for a memorable visit. We put our new Orca system to the test, cruise alongside a pod of dolphins, and take our guests to Tahuata to enjoy its crystal-clear waters and sandy beaches. Ray tackles a ...
ROUGH SAIL💨7 Days at Sea From Tahiti to the Marquesas
Holly and Ray

ROUGH SAIL💨7 Days at Sea From Tahiti to the Marquesas

After completing our haul-out and sail drive repair in Tahiti, we set off on an easy two-day passage to the Tuamotus, with calm seas and no wind. Partway, we received a weather update: a storm system with lightning and high winds was expected to hit the Tuamotus just as we arrived. So, we decided to...
Paradise Isn’t Perfect😩 Sailing French Polynesia
Holly and Ray

Paradise Isn’t Perfect😩 Sailing French Polynesia

Our adventure in French Polynesia takes an unexpected turn when we discover severe damage to our sail drive shaft during what we thought would be a quick and simple seal change. 😩 It took two trips to the USA and thousands of dollars to get the parts we needed and make the repair— a consequence of s...
STUCK in French Polynesia— Now What?
Holly and Ray

STUCK in French Polynesia— Now What?

After deciding to leave French Polynesia 6 months earlier than we had initially planned, it seemed like everything was lining up perfectly for us to make a last-minute trip to New Zealand ahead of cyclone season. Unfortunately, our weather window disappeared in a matter of hours, ultimately forcing ...
Change of Plans: We’re Leaving French Polynesia
Holly and Ray

Change of Plans: We’re Leaving French Polynesia

Join us as we prepare for a last-minute passage to New Zealand before cyclone season begins in the South Pacific. We’ve had a memorable experience in French Polynesia, and we are looking forward to what comes next! ——————————————————————— ⛵️Join the Crew on Patreon: ⚓️Check out our Blog: 📸Foll...
The Adventure Continues⛵️
Holly and Ray

The Adventure Continues⛵️

This week, we savored our last day in Bora Bora. 😍 We got some boat work done while we waited for the weather to clear up, then took off in the dinghy with friends to snorkel a beautiful reef at the foot of Mount Otemanu. ⛰️ We ended our underwater excursion swimming with a majestic group of eagle r...
What They Don’t Tell You About Sailing the Society Islands 😩
Holly and Ray

What They Don’t Tell You About Sailing the Society Islands 😩

This week, we continued trying to make the best of our time in the Society Islands: we endured our third termite swarm, encountered more bad weather, left a loud mooring field, and escaped a reckless speed boat. 😤 No one told us sailing the South Pacific would be like this! Luckily, the picturesque ...
HER DREAM CAME TRUE🐋 Sailing from Moorea to Raiatea
Holly and Ray

HER DREAM CAME TRUE🐋 Sailing from Moorea to Raiatea

This week Holly’s dream of swimming with humpback whales came true! 🐋 Conditions weren’t perfect, but feeling the vibrations of their songs while in the water was an unforgettable experience. 🤯 We provisioned up and checked the weather before departing on a peaceful moonlight sail to Raiatea the fol...
THIS is Sailing the South Pacific⛵️
Holly and Ray

THIS is Sailing the South Pacific⛵️

We’re back! 🎥 Join us for a week in the life sailing French Polynesia with friends.⛵️ In this video, we take you along on an eventful sail from Tahiti to Moorea, where things went from smooth sailing to rough motoring…The journey was worth it when we pulled into a picturesque anchorage with steep mo...
We’re TIRED!😩 Sailing to Tahiti
Holly and Ray

We’re TIRED!😩 Sailing to Tahiti

After weeks of bad weather in the Tuamotus, we decided to sail to Tahiti in search of a protected anchorage we could relax and re-provision in. 🌧️ Unfortunately, that was easier said than done! 😅 ——————————————————————— ⛵️Join the Crew on Patreon: ⚓️Check out our Blog: 📸Follow us on Instagram:...
Trouble in Paradise?⛈ Sailing the South Pacific
Holly and Ray

Trouble in Paradise?⛈ Sailing the South Pacific

Holly and Ray from 'Holly and Ray' document their adventures navigating rough weather and finding much-needed fuel and provisions on their voyage through the South Pacific in this episode.
What it’s REALLY Like Sailing the Remote Islands of the South Pacific⛵️
Holly and Ray

What it’s REALLY Like Sailing the Remote Islands of the South Pacific⛵️

Join Holly and Ray aboard their sailboat Sab for a captivating journey through the stunning but often challenging waters of the remote islands in the South Pacific. Experience their adventures navigating treacherous passes, managing wind speed to avoid rough rides, seeking out better visibility, and...
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.
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.
ONE SHOT TO GET THIS RIGHT before SAILING to PARADISE – Ep 184
Sailing Jibsea

ONE SHOT TO GET THIS RIGHT before SAILING to PARADISE – Ep 184

Join us as we do another DIY project on our sailboat while anchored in St. Martin in the French Caribbean. It's a long awaited addition to our headsail. Installing our own decal before sailing offshore and overnight to the British Virgin Islands. NEW VIDEOS EVERY SUNDAY! Please subscribe and ...
We Found The ULTIMATE Paradise in the Virgin Islands – S4EP19
Taylor’s Travels

We Found The ULTIMATE Paradise in the Virgin Islands – S4EP19

Get %15 off BottleBottle - Amazon: Official website: Book a Charter with Navigare up to 40% off (Until March 31st): In this episode we finish up our last few days on charter with Navigare Yachting. Picking up where we left off in the previous episode in Anegada, we head out to do some freedivin...
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