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.

Showing 1-12 of 12 results
First Sail. First Fish | Our First Sail On Our Sailboat & Kamden Caught Dinner! Episode 6
Sailing Banana Pancakes

First Sail. First Fish | Our First Sail On Our Sailboat & Kamden Caught Dinner! Episode 6

We’re finally setting sail on our new floating home—and our very first fish aboard is a beautiful mahi-mahi! 🎣⛵️ After six exhausting days of moving aboard, organizing, provisioning, and preparing our Leopard 50 catamaran, it’s finally time to leave the dock and begin our next chapter as a full-tim...
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...
Sailing in Grenada with The O’Kelly’s… This is “IT”⛵️❤️ #boatlife #travel #smoothsailing #sailing
Holly and Ray

Sailing in Grenada with The O’Kelly’s… This is “IT”⛵️❤️ #boatlife #travel #smoothsailing #sailing

Sailing around Grenada with our friends Nick and Megan, hoping to remind them why the boat buying process is worth it! 🙏🏼 #catamaran #liveaboard #grenada #sailingaroundtheworld
Sailing Around the World: Grenada Carnival (SPICEMAS 2023)
Holly and Ray

Sailing Around the World: Grenada Carnival (SPICEMAS 2023)

This week we experienced an item on every sailor’s bucket list: Grenada Carnival! 🇬🇩 We woke up early to participate in J’ouvert, marking the official start of Carnival. We danced with Jab Jabs and marched through town to the Soca Beats. We returned the next day for Fancy Mas/Pretty Mas, despite the...
It’s a Beautiful Life | Sailing the Caribbean
Holly and Ray

It’s a Beautiful Life | Sailing the Caribbean

Kind people, good food, and easy sailing. ❤️ This week our taxi driver loaded us up with fresh local fruit! We continue to experience the kindness of Grenadians. 🇬🇩 🥭 We had friends aboard and decided to go for an afternoon sail, despite the light wind. After, we went for a swim then settled in for...
Every Day is Saturday | Sailing Grenada With Friends
Holly and Ray

Every Day is Saturday | Sailing Grenada With Friends

This week we took our friends, the O’Kelly’s, for a leisurely sail around Grenada. We picked up a mooring ball in St. George’s, swam, and visited the House of Chocolate Museum. Ray grilled steaks in the cockpit, and we had dinner aboard while we watched a beautiful sunset! Subscribe to the O’Kelly...
One whistle or two? Sailing to the Sailing Capital
The O'Kelly's

One whistle or two? Sailing to the Sailing Capital

Another beautiful sail up the Chesapeake takes us to "America's Sailing Capital" where we get down to business on several fronts: getting in shape, finalizing a gift for our first O'Kelly Style customers, and measuring for our new Ullman mainsail. ☕️ TRY OUR NEW COFFEE! SUBSCRI...
DIY BOAT REFIT Q&A//Answering Your Questions-Episode 40
Sailing Dauntless

DIY BOAT REFIT Q&A//Answering Your Questions-Episode 40

This week we are answering some of your guy's questions. We try to answer as many as we can in the comments, but sometimes theres so many repeats we think "we should make a video!" Enjoy! Want to support us? Here's a couple ways you can: Like, Follow, and Share! facebook: ins...
Captain Down! Injury Underway  – SEASON FINALE
The O'Kelly's

Captain Down! Injury Underway – SEASON FINALE

Right before we wrap things up this season and ready Clarity for haul out and storage, Nick hurts his back handling the mainsail. Megan takes over running our catamaran while we both sweat through the Chesapeake summer heat and thunderstorms. Clouds T-Shirt: I Love Tacos T-Shirt: ____________ Pa...
2020 Micro-mini Update-announcement. And we are re-naming this channel
The O'Kelly's

2020 Micro-mini Update-announcement. And we are re-naming this channel

iTunes Podcast: Private Fb Group: Products we use: Website: www.sailclarity.com ___ Nick's Books and Audiobooks: Get Her on Board is about getting that significant other to buy into this cruising nonsense. People seem to like it. All proceeds go to our dog Sugar. Audiobook: Book: ...
For a limited time: Bloopers, Outtakes, and General silliness.
The O'Kelly's

For a limited time: Bloopers, Outtakes, and General silliness.

If there is one thing that fuels this cruising thing, it is basic silliness. This week we share some of our less than beautiful moments of the adventure. iTunes Podcast: Private Fb Group: Products we use: Website: www.sailclarity.com ___ Nick's Books and Audiobooks: Get Her on Board...
WeBoating
Logo
Shopping cart