Watch Sailing & Boating Adventures Around the World – Page 10 of 16

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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WHY won’t they let us on their BOAT?  -SoPac Boat Hunt-
The O'Kelly's

WHY won’t they let us on their BOAT? -SoPac Boat Hunt-

Go to to get started on your first purchase and receive a FREE 1-year supply of Vitamin D3+K2 and 5 travel packs. Thanks to Athletic Greens for sponsoring today's video! To say things didn't go to plan on our trip to the South Pacific is the understatement of the year. After our crewing ...
BOAT NERDS UNITE! An Update from French Polynesia
The O'Kelly's

BOAT NERDS UNITE! An Update from French Polynesia

Regular video returns next week, but this week we have a special treat over on the O'Kelly Tech Channel. Watch it here: Learn more about Young Barnacles here: Learn more about Markus Moser here: ⛵️ SUPPORT OUR PRODUCTIONS - JOIN OUR CREW OF "DOERS" ⚓️ CURIOUS ABOUT 1:1 CONS...
TRAINING TO AVOID DANGER ON A PERFORMANCE CATAMARAN
The O'Kelly's

TRAINING TO AVOID DANGER ON A PERFORMANCE CATAMARAN

This video could change how you sail! Olympians, World Champions, Hall of Famers! We have got some VERY cool friends. When we met out at a deserted island years ago, little did we know that Annie Gardner and Eric Witte on the Catana 472, El Gato were such accomplished sailors. This week, we soak up ...
Dream Boat Dashed & A Lithium Battery WARNING!
The O'Kelly's

Dream Boat Dashed & A Lithium Battery WARNING!

With boats, as in life, sometimes you gotta make a turn when you get to a red light. And in trying to make a deal for our dream boat, Javelin, the Atlantic 55, there were just too many red lights to risk $10,000 to survey the boat. So we packed it in. Alas, all is not lost as when one door closes, a...
A Short Sail to #Annapolis | Sailing 16
Roaming Rupps

A Short Sail to #Annapolis | Sailing 16

Join us this week as we visit Annapolis, MD. This vlog ended up being pretty short because we ran into a small emergency once we hooked a mooring ball. Hope you still enjoy it and see you again next week for a longer one! If you are interested in trying the Nikwax Hard-Shell Outerwear Care Kit, yo...
THIS will END our Cruising & Other Learnings from 20 years Sailing
The O'Kelly's

THIS will END our Cruising & Other Learnings from 20 years Sailing

We made a lot of mistakes over the years, but hopefully we've learned a thing or two. As we get ready to hop aboard our (hopefully) next boat down in a place we know very well, we realized that it was 20 years since we jumped into this cruising thing. ⛵️ SUPPORT OUR PRODUCTIONS - JOIN OUR CRE...
Time to STRETCH the BOAT BUDGET
The O'Kelly's

Time to STRETCH the BOAT BUDGET

One door closes and another door opens, isn't that the saying? Well, in our pursuit of the next cruising catamaran, we are finding that agility is the name of the game and no one seems certain what is for sale and for how much. ⛵️ SUPPORT OUR PRODUCTIONS - JOIN OUR CREW OF "DOERS" ...
AFFORDABLE PERFORMANCE CATAMARAN – Let’s Do It!
The O'Kelly's

AFFORDABLE PERFORMANCE CATAMARAN – Let’s Do It!

This week we venture to our old stomping grounds in the San Francisco Bay Area to look at a boat that’s no exactly for sale. It’s an Outremer 55 Light, a boat we actually looked at 6 years ago when we were searching for Clarity. ⛵️ SUPPORT OUR PRODUCTIONS - JOIN OUR CREW OF "DOERS" ⚓...
Why Sail? This is so much easier!
The O'Kelly's

Why Sail? This is so much easier!

Why even sail? Powerboats are so much more convenient and luxurious. This week we head on a Cheoy Lee motoryacht to experience the dark side first hand. Will we return to the wind? ⛵️ SUPPORT OUR PRODUCTIONS - JOIN OUR CREW OF "DOERS" ⚓️ CURIOUS ABOUT 1:1 CONSULTING? 🎙 WEEKLY PODCAS...
When the SAILBOAT Dream DIES…
The O'Kelly's

When the SAILBOAT Dream DIES…

Expect the unexpected! Life throws curveballs all the time, and it's another reason to take the passion and turn it into a plan as fast as possible... This week we check out a couple of trimarans and go racing with friends on their monohull. It was Megan's first ever race! Plus, we get se...
BOAT SEARCH UPDATE & Yachtworld RED FLAGS
The O'Kelly's

BOAT SEARCH UPDATE & Yachtworld RED FLAGS

We are jonesing to get back out on the water, and hopefully on our new cruising catamaran. But we are tough buyers! We want it all: performance, good price, and high quality. And since we've been spending so much time on Yacthworld, we've noticed a few issues with some of the listings...re...
So You Think You Want to Go Cruising on a Sailboat?
The O'Kelly's

So You Think You Want to Go Cruising on a Sailboat?

Free advice! We've consulted with over 100 future-cruisers, and some themes come up so often, we just had to share. 1. Is cruising right for you? 2. Which boat is right for you? 3. Purchasing process 4. Budgeting 5. Outfitting 6. Working Remotely 7. Ideal countdown to departure ⚓️ CURIOUS ABO...
What’s Next for The O’Kellys?
The O'Kelly's

What’s Next for The O’Kellys?

We've had a few medical issues keeping us on the sidelines recently, but the slower pace has given us a chance to reflect and regroup. It's been a good thing. This week we update you on our plans, for our next boat and our new home! ⛵️ SUPPORT OUR PRODUCTIONS - JOIN OUR CREW OF "DOER...
Not How We Thought this Would End!
The O'Kelly's

Not How We Thought this Would End!

Moving is never easy and much tougher with one good leg! We sell our beloved catamaran Clarity without ever meeting the new owners, and things don't go smoothly for us as Megan takes a tumble and breaks her foot. ⛵️ SUPPORT OUR PRODUCTIONS - JOIN OUR CREW OF "DOERS" ⚓️ CURIOUS AB...
The First Buyers Walked Away!
The O'Kelly's

The First Buyers Walked Away!

Clarity is now SOLD! We sail 200 miles up to Grand Bahama for survey and sea trial and everything goes well. So well that the buyers sign the acceptance contract. But ten days later, they have a change of heart. It was all too much for them. We've all been there, this is a big commitment! ⛵️ ...
Step UP or Step DOWN – Catana 50 Sail & Review
The O'Kelly's

Step UP or Step DOWN – Catana 50 Sail & Review

We are in the market for a new sailing catamaran, and our list of must-haves is pretty long. This week we sail on a Catana 50 and see if it lives up to the reputation. But could we adapt to the helm position on these boats? ⛵️ SUPPORT OUR PRODUCTIONS - JOIN OUR CREW OF "DOERS" ⚓️ CURIO...
LAST HURRAH and We Break The Curse!!
The O'Kelly's

LAST HURRAH and We Break The Curse!!

We finally break the O'Kelly CURSE - YUM - and share the Exumas with our best friends (and incredible musicians with the band El Cajon) of 25 years. Going out on a HIGH NOTE! El Cajon - ⛵️ SUPPORT OUR PRODUCTIONS - JOIN OUR CREW OF "DOERS" ⚓️ CURIOUS ABOUT 1:1 CONSULTING? 🎙 ...
11 TIPS on HOW TO BUY in a Seller’s Market – Plus Market Forecast
The O'Kelly's

11 TIPS on HOW TO BUY in a Seller’s Market – Plus Market Forecast

The boat market is on 🔥 FIRE so today we share our tips for getting the USED boat of your dreams. Plus, Nick gets out his crystal ball and share's his forecast for the used boat market. ⛵️ SUPPORT OUR PRODUCTIONS - JOIN OUR CREW OF "DOERS" ⚓️ CURIOUS ABOUT 1:1 CONSULTING? 🎙 WEE...
Sailing the ULTIMATE Performance Cruising Catamarans – Our Next Boat? (Patrons, check email)
The O'Kelly's

Sailing the ULTIMATE Performance Cruising Catamarans – Our Next Boat? (Patrons, check email)

We sailed the Amazing Chris White Atlantic 72 ft performance catamaran Penmanship and it may have changed our course permanently. Is Clarity for sale? Stay tuned… We also hear the incredible story of Leopard’s resurrection after floating upside down in the Atlantic for 7 months. ⛵️ SUPPORT OUR PR...
BOAT LIFE – This DRONE is Possessed!!
The O'Kelly's

BOAT LIFE – This DRONE is Possessed!!

Beautiful sailing in the Ragged Islands and we try to capture it for you via DRONE, but once again the DJI Drone had other ideas. Growing up watching Gilligan's Island we thought quicksand was a real threat in paradise. Turns out it does exist off Double Breasted in the Raggeds! Thank you so ...
WE MAY NEVER LEAVE [The most beautiful place we’ve sailed to]
The O'Kelly's

WE MAY NEVER LEAVE [The most beautiful place we’ve sailed to]

Join us this week as we discover the BEST BEACH we've ever been to, and we had it all to ourselves!! We also enjoy a beautiful sail down to the Ragged Islands. --Moriah Harbor is located just a few miles south of George Town, Exuma, but conditions have to be right for a visit. Less wind and the...
WHERE to hide from a STORM [boat life]
The O'Kelly's

WHERE to hide from a STORM [boat life]

This week enjoy the BEST conditions in paradise - calm, clear waters AND some of the scariest - LIGHTENING! We'll show you where we hide in the middle of no where, far from the safety of a marina. Levain Bakery Dark Chocolate Chocolate Chip Copycat Cookies Prep Time -25 mins Cook Time -10 min...
GETTING $$$ TO SAIL LUXURY YACHT S1CH.45
Slim & Soph - Sailing Nakama

GETTING $$$ TO SAIL LUXURY YACHT S1CH.45

Call us delivery skippers! We have created a Patreon account, if you have been enjoying this production you can help support it continuing into the future here Or make a one-off donation as you please if subscriptions aren't your thing. Let's keep ticking nautical miles and boat jobs ...
CYCLONES ARE COMING BUT WE AIN’T RUNNING | PREPARING SAILBOAT FOR CYCLONE SEASON S1CH.44
Slim & Soph - Sailing Nakama

CYCLONES ARE COMING BUT WE AIN’T RUNNING | PREPARING SAILBOAT FOR CYCLONE SEASON S1CH.44

We're staying in cyclone territory to circumnavigate Australia, she'll be right! We have created a Patreon account, if you have been enjoying this production you can help support it continuing into the future here Or make a one-off donation as you please if subscriptions aren't yo...
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