Reset Password

USD 0 to USD 10,000

Digitalnomad YouTube Videos

Showing 61-75 of 83 results
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 ...
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. ...
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 PRODUCTI...
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 P...
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" https://www.pat...
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'...
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 iss...
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...
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 PRO...
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...
Taking this week off…see you next week!
The O'Kelly's
Taking this week off…see you next week!
#shorts ⛵️ SUPPORT OUR PRODUCTIONS - JOIN OUR CREW OF "DOERS" https://www.patreon.com/theokellys ⚓️ CURIOUS ABOUT 1:1 CONSULTING? https://www.sailclarity.com/consulting 🎙 WEEKLY PODCAST - UNDER THE SHEETS WITH THE O'KELLYS https://podcasts....
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 bee...
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 ...
Can you guess what kind of boat this is?
The O'Kelly's
Can you guess what kind of boat this is?
#shorts ⛵️ SUPPORT OUR PRODUCTIONS - JOIN OUR CREW OF "DOERS" https://www.patreon.com/theokellys ⚓️ CURIOUS ABOUT 1:1 CONSULTING? https://www.sailclarity.com/consulting 🎙 WEEKLY PODCAST - UNDER THE SHEETS WITH THE O'KELLYS https://podcasts....
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 - https://www.elcajonmusic.com/ ⛵️ SUPPORT OUR PRODUCTIONS - JOIN...