Watch Sailing & Boating Adventures Around the World

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Crazy Crab Boat Docking Races & Getting My Old Yacht Back in the Water!
Sailing Doodles

Crazy Crab Boat Docking Races & Getting My Old Yacht Back in the Water!

Things get pretty wild in Solomons, Maryland as I check out the local boat docking races, where crab boat captains race against the clock to slam their boats into the dock as fast as possible. After the races, it’s back to my old CT56, Nauti Dogs. She’s been sitting on the hard for over a year, and...
My Yacht Sat Abandoned for a Year… Can I Bring Her Back?
Sailing Doodles

My Yacht Sat Abandoned for a Year… Can I Bring Her Back?

My old CT56 sailing yacht has been sitting on the hard for more than a year, and it’s finally time to see what kind of condition she’s in. In this video, I head back to the boat, inspect everything after a year of sitting, and start the long process of getting her cleaned up and seaworthy again. Th...
Goodbye Thailand… It’s Time to Sail My Old Boat Again!
Sailing Doodles

Goodbye Thailand… It’s Time to Sail My Old Boat Again!

My time in Thailand has finally come to an end, and this one was a little bittersweet. I spend my last day with Nikka at a beach club before saying goodbye before sunrise and beginning a very long journey home. First came a 12-hour trip by van, ferry, and another van to Bangkok, where I had to drop...
SPINNAKER SAILING DISASTER! We Rigged It Wrong…
Sailing Doodles

SPINNAKER SAILING DISASTER! We Rigged It Wrong…

It was supposed to be an easy final sail aboard our new yacht in Thailand… but things didn’t exactly go according to plan! On our last day aboard before leaving the boat for a few months, we sail from Koh Phangan to Koh Samui and decide it’s finally time to test our spinnaker. With only about 5 kn...
This Party Was STILL Going at 8AM! | Koh Phangan by Boat
Sailing Doodles

This Party Was STILL Going at 8AM! | Koh Phangan by Boat

We take our Highfield dinghy on an incredible tour of the east coast of Koh Phangan, exploring some of the most beautiful parts of the island — including beaches and bays that are only accessible by boat. Koh Phangan is famous for its parties, but there’s so much more to this island. We spend the d...
Raining at burningman 2026!
Sailing Doodles

Raining at burningman 2026!

Burningman 2026 has ground to a hault due to rain!
We Found One of Thailand’s Most Beautiful Hidden Bays
Sailing Doodles

We Found One of Thailand’s Most Beautiful Hidden Bays

We sail into Ao Hat Yuan on Koh Phangan, one of the most beautiful bays I’ve ever visited. With no road access, the beach is only reachable by boat, and somehow we had the entire anchorage to ourselves. We spent the day swimming in crystal-clear water, riding the e-foil, relaxing in our floating po...
We’re Running Out of Diesel… And There’s None on the Island
Sailing Doodles

We’re Running Out of Diesel… And There’s None on the Island

We’re anchored off Koh Phangan, Thailand, but before we can continue our trip we have a problem—we’re getting pretty low on diesel. There are no traditional fuel docks on the island, so we head ashore and visit a few marinas hoping to find someone who can help us fill up. After striking out everywh...
FINALLY SAILING AGAIN! We Made It to Thailand’s Full Moon Party Island
Sailing Doodles

FINALLY SAILING AGAIN! We Made It to Thailand’s Full Moon Party Island

After more than a week stuck waiting on repairs, our boat is finally back in action! We move back aboard, leave Koh Samui behind, and set sail for Koh Phangan — home of Thailand’s famous Full Moon Party. It wasn’t a Full Moon Party night, but we anchored right in the same beautiful bay where all th...
Lithium Battery Failure on Our NEW Boat
Sailing Doodles

Lithium Battery Failure on Our NEW Boat

Our boat problems continue in Thailand! After replacing the generator control unit, we were hoping our problems were finally solved… unfortunately, that wasn’t the case. With more repairs needed, we pack our bags and leave the boat yet again, checking back into an Airbnb while the technicians try t...
We Found the WEIRDEST Place in Thailand!
Sailing Doodles

We Found the WEIRDEST Place in Thailand!

Our boat is broken… again. So while we wait for repairs, we grab an Airbnb on Koh Samui, rent a motorbike, and set out to explore the island. That’s when we discover The Xperience — and I honestly don’t know how to describe this place. It’s basically a giant adult playground filled with crazy art,...
Our Boat Broke Down… So We Made the Best of Koh Samui!
Sailing Doodles

Our Boat Broke Down… So We Made the Best of Koh Samui!

Boat problems have changed our plans once again! With the boat needing repairs, we move into an Airbnb on Koh Samui for a few days and decide that if we're going to be stuck on land… we might as well make the most of it! We rent a motorbike and set off to explore the island, including a stop a...
They’re Making Me Leave Thailand
Sailing Doodles

They’re Making Me Leave Thailand

Our time cruising Thailand takes another unexpected turn. Before leaving the boat, Nika decides to enjoy one last swim off the back — and apparently swimsuits are optional. Then it’s time for me to leave Thailand for a quick visa run to Singapore while Nika and the dogs move into an Airbnb on Koh S...
My Visa Was Expiring… So We Sailed to Koh Samui
Sailing Doodles

My Visa Was Expiring… So We Sailed to Koh Samui

After spending a few nights anchored off the beautiful island of Koh Tao, it was time to continue south toward Koh Samui. We had a great sail down, found a mooring for the boat, and prepared to move ashore for a few days. My Thai visa was about to expire, which meant I needed to make a quick flight...
The Truth About Koh Tao, Thailand
Sailing Doodles

The Truth About Koh Tao, Thailand

After sailing more than 200 miles down the Gulf of Thailand, we finally arrived at one of the most beautiful anchorages we've ever visited. Before we could enjoy crystal-clear water, incredible snorkeling, beachside cafés, and a relaxing afternoon on our floating island, there was one small boa...
Sailing Thailand. Paradise Found, Then Our Generator Quit
Sailing Doodles

Sailing Thailand. Paradise Found, Then Our Generator Quit

After a great couple of nights in Hua Hin, we continued sailing south through the Gulf of Thailand. The first day couldn’t have gone much better—we found a quiet village, went ashore for dinner, and gave the dogs some time to explore. But the next morning, things started going wrong. Our generator...
Our Batteries Were Dying… Then We Found Paradise
Sailing Doodles

Our Batteries Were Dying… Then We Found Paradise

After spending a couple of great nights exploring Hua Hin, we continued sailing south through the Gulf of Thailand. Our first day underway couldn’t have gone much better. We found a quiet little fishing village, anchored nearby, headed ashore for dinner, and gave the pups a chance to run around and...
Climbing to the Temple in the Sky!
Sailing Doodles

Climbing to the Temple in the Sky!

We were the only sailboat anchored off the beautiful coastal town of Hua Hin, Thailand, and it felt like we had the entire place to ourselves. We took the dinghy to the beach, then headed up the mountain to explore an incredible Buddhist temple with amazing views over the coastline. There were monk...
Getting my motor working
Sailing Doodles
Our First Real Passage… Then the Generator Failed
Sailing Doodles

Our First Real Passage… Then the Generator Failed

For the first time in a long time, I’m sailing toward a destination I’ve never visited before. We finally leave Pattaya behind and point the new yacht across the Gulf of Thailand for a 50-mile passage to Hua Hin. The forecast looked manageable, but the wind was stronger than expected, leaving us be...
A Playboy Model Joins the Crew… And We Finally Go Cruising!
Sailing Doodles

A Playboy Model Joins the Crew… And We Finally Go Cruising!

After months of waiting, setbacks and shakedown trips, we are finally leaving the dock to begin full-time cruising aboard my new yacht. This is not another weekend trip or test sail. This time, we are really going cruising. I also welcome a gorgeous new crew member aboard. She is a former Playboy ...
I Had to Return My Yacht and Go to the Hospital
Sailing Doodles

I Had to Return My Yacht and Go to the Hospital

This was not how I expected this sailing trip to end. After finally getting the yacht back out on the water, I had to return to the marina because my health issues were getting too serious to ignore. I’ve been dealing with blood clots and thrombosis in my abdomen, and it was time to go to the hospi...
Just out of the Hospital, Should I be Sailing?
Sailing Doodles

Just out of the Hospital, Should I be Sailing?

We sailed from Koh Larn to Koh Man Wichai, a beautiful island near Pattaya, Thailand, to join a beach cleanup organized by Ocean Marina. The place was absolutely gorgeous, but like so many remote islands, plastic and trash had washed up on shore. Together with the group, we helped haul off around 5...
New Boat, Big Test | Weekend Shakedown Cruise
Sailing Doodles

New Boat, Big Test | Weekend Shakedown Cruise

After a week away, the yacht finally returns to Ocean Marina after the delivery crew completed the long run down to Malaysia to export and re-import the boat. It was a necessary trip to reset the paperwork, but now the boat is back where she belongs — and we are one step closer to cruising full time...
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