Watch Sailing & Boating Adventures Around the World

Crossing the Atlantic: Heavy WEATHER & HARD Lessons | Day 7

All five of us are now one full week into our Atlantic crossing. We made some pretty serious mistakes in the video. Could have been worse, a LOT worse. No need to point out all our faults in the comments, how bad things could have gone haunt me already. Sad to have lost a cushion but so grateful th...

Dec 14, 2025
Language: EN
Play Time: 00:32:33

CANNIBALIZING Our BOAT…how else can I solve problems MID ATLANTIC | Day 5 at SEA

Day 5 of our Atlantic Crossing, and we officially hit 25% of the passage — a full quarter of the way across. Last night was rough: confused seas, swell from multiple directions, and a whole lot of rolling. None of us filmed because honestly… we were just hanging on. Today was a mix of tired crew, b...

Dec 12, 2025
Language: EN
Play Time: 00:34:19

Day 4 at SEA – Time Zones Are Fake & So Is Our Sleep Schedule

DAY 4 of our Atlantic Crossing! Somewhere out here in the middle of the ocean, every clock onboard says something different… the chartplotter, our phones, our watches — none of them agree. So we’ve fully given up on “time” and are operating exclusively on vibes and timers (which we also forget to se...

Dec 11, 2025
Language: EN
Play Time: 00:42:13

VERY Deep Sea Fishing for MAHI MAHI | MID OCEAN CROSSING!! (Day 3)

Today had it all: our first clear night of stars, a pink jet-stream sunrise, experimenting with dog shoes on deck, lots of cooking, knot practice, laundry, calm seas, and our first big mahi mahi of the passage. Spirits are high, sleep is improving, and the boat is finally settling into that passage ...

Dec 10, 2025
Language: EN
Play Time: 00:36:13

First Mechanical Problem and It’s Only Day 2 of 20…(Atlantic Crossing DAY TWO)

We’ve officially brought the old crew back together. Brett, Ayanna, me (Jade), plus our salty sea dogs Dingo and Penny — five souls, two days across the Atlantic, with about seventeen more to go before we reach the other side where Ayanna’s newly purchased boat is waiting for her. We’re uploading t...

Dec 09, 2025
Language: EN
Play Time: 00:33:26

Just Us THREE and the Open SEA! (Atlantic Crossing DAY ONE)

The old crew is back together—Brett, Ayanna, and Jade plus Dingo and Penny—and we’ve officially begun our 20-day Atlantic crossing. As this uploads, we’re still out here somewhere on the deep blue, sending these daily videos almost in real time from the middle of the ocean. Day One was all about se...

Dec 08, 2025
Language: EN
Play Time: 00:30:31

Let The EXPEDITION Begin! (REAL TIME video Sailing the ATLANTIC OCEAN!) | Day 0

We finally pushed off the dock in Las Palmas and officially started our Atlantic passage… sort of. After a full crew debate, we’re calling this Day Zero. Zero braids, zero chill, and zero idea why numbering days is so hard. 😅 In today’s episode: ⚓ Untying lines and saying emotional goodbyes ⚓ Fuel ...

Dec 06, 2025
Language: EN
Play Time: 00:30:48

We’re Crossing the OCEAN! AGAIN in Real Time + Aiyana!!! (day -1)

Going to therapy is a sign of strength, not weakness. My sponsor BetterHelp makes therapy simple, with 10% off your first month to help you get started: The day before our Atlantic crossing didn’t go as planned. With the clock ticking, we tried to finish the last repairs, pick up old receipts for ...

Dec 06, 2025
Language: EN
Play Time: 00:54:58

Autohelm 2000 challenge – Which team will win?

Life on a sailboat isn’t always about epic adventures or dramatic ocean crossings. Often, it’s about the simple moments—short sails to the next bay, waiting out weather, reparing our Autohelm 2000, going for a hike, and enjoying the slow rhythm of life on the water. This is the reality of the full-t...

Mar 21, 2025
Language: EN
Play Time: 00:07:00

What Happens When Electric Motor Runs Out of Power? | Sailing Wisdom [S5 Ep49]

▸ MATERIALS NEEDED FOR OUR NEXT PROJECT: ▸ MERCHANDISE: ▸ SUBSCRIBE DIRECTLY with us so you never miss an episode: ▸ PAINTING COMMISIONS: [email protected] ▸ ART FROM OUR VOYAGE: ▸ CHARLIE & GERRY CHANNEL: Herby and Maddie sail on and off anchor, and share some tips and tricks t...

Feb 19, 2023
Language: EN
Play Time: 00:20:06

MAYHEM in the Anchorage | Sailing Wisdom [S5 Ep44]

▸ MATERIALS NEEDED FOR OUR NEXT PROJECT: ▸ MERCHANDISE: ▸ SUBSCRIBE DIRECTLY with us so you never miss an episode: ▸ PAINTING COMMISIONS: [email protected] ▸ ART FROM OUR VOYAGE: ▸ CHARLIE & GERRY CHANNEL: We are exploring a town that we skipped the last time we sailed the ICW, ...

Jan 15, 2023
Language: EN
Play Time: 00:12:26

The Most TREACHEROUS Span of the ICW | Sailing Wisdom [S5 Ep38]

▸ MATERIALS NEEDED FOR OUR PROJECTS: ▸ MERCHANDISE: ▸ SUBSCRIBE DIRECTLY with us so you never miss an episode: ▸ PAINTING COMMISIONS: [email protected] ▸ ART FROM OUR VOYAGE: ▸ CHARLIE & GERRY CHANNEL: Herby and Maddie show you the most treacherous span of the ICW: The South Car...

Nov 27, 2022
Language: EN
Play Time: 00:13:07

How We Fixed ALL Our DINGHY PROBLEMS! | Sailing Wisdom [S5 Ep37]

▸ MATERIALS NEEDED FOR OUR PROJECTS: ▸ MERCHANDISE: ▸ SUBSCRIBE DIRECTLY with us so you never miss an episode: ▸ PAINTING COMMISIONS: [email protected] ▸ ART FROM OUR VOYAGE: ▸ CHARLIE & GERRY CHANNEL: Maddie and Herby stop at two marinas in the Waccamaw River to visit with frie...

Nov 20, 2022
Language: EN
Play Time: 00:16:07

Feeling Guilty About Our Awful Truth | Sailing Wisdom [S5 Ep24]

▸ MERCHANDISE: ▸ SUBSCRIBE DIRECTLY with us so you never miss an episode: ▸ PAINTING COMMISIONS: [email protected] ▸ ART FROM OUR VOYAGE: ▸ CHARLIE & GERRY CHANNEL: Making our way up the ICW in Georgia is both beautiful and buggy! We anchor in remote areas as we slowly make our w...

Aug 14, 2022
Language: EN
Play Time: 00:16:37

Should You BRING Your PETS? | Sailing Wisdom [S5 Ep23]

▸ MERCHANDISE: ▸ SUBSCRIBE DIRECTLY with us so you never miss an episode: ▸ PAINTING COMMISIONS: [email protected] ▸ ART FROM OUR VOYAGE: ▸ CHARLIE & GERRY CHANNEL: Ever dream of cruising but wonder what it would be like if you brought your pets along? 0:00 Intro 0:11 Sailing th...

Aug 07, 2022
Language: EN
Play Time: 00:13:34

MISTAKE! Taking the Road Less Traveled | Sailing Wisdom [S5 Ep22]

▸ MERCHANDISE: ▸ SUBSCRIBE DIRECTLY with us so you never miss an episode: ▸ PAINTING COMMISIONS: [email protected] ▸ ART FROM OUR VOYAGE: ▸ CHARLIE & GERRY CHANNEL: Herby and Maddie answer some important questions about cruising, such as "How big should your flag be?", ...

Jul 31, 2022
Language: EN
Play Time: 00:14:42

LUST on the Port Side: Sailing to Cumberland Island | Sailing Wisdom [S5 Ep21]

▸ MERCHANDISE: ▸ SUBSCRIBE DIRECTLY with us so you never miss an episode: ▸ PAINTING COMMISIONS: [email protected] ▸ ART FROM OUR VOYAGE: ▸ CHARLIE & GERRY CHANNEL: We sail to Cumberland Island, Georgia, and decide to do a little varnish test after exploring this natural wonderla...

Jul 24, 2022
Language: EN
Play Time: 00:17:30

Why Did Our Rigging Get SO LOOSE?! | Sailing Wisdom [S5 Ep20]

▸ MERCHANDISE: ▸ SUBSCRIBE DIRECTLY with us so you never miss an episode: ▸ PAINTING COMMISIONS: [email protected] ▸ ART FROM OUR VOYAGE: ▸ CHARLIE & GERRY CHANNEL: Wisdom is underway again! We begin a capacity test on her newly balanced #lithiumbattery to see what kind of range ...

Jul 17, 2022
Language: EN
Play Time: 00:19:34

Atlantic Circumnavigation COMPLETE! | Sailing Wisdom [S4 Ep20]

▸ SUBSCRIBE DIRECTLY with us so you never miss an episode: After completing our circumnavigation of the Atlantic, we make landfall in Florida and pick up another boat pet: Gerry, a Blue and Gold Macaw. ▸ PAINTING COMMISIONS: [email protected] ▸ PHOTOGRAPHY FROM OUR VOYAGE: ↓BINGE WATC...

Feb 20, 2022
Language: EN
Play Time: 00:17:19

Why Didn’t We Take Our Pets Cruising? | Sailing Wisdom

When we set off to go cruising, we made the decision to leave our pets that we love dearly and leave them with our parents. Why? Why not take them cruising? Why not find a way? That is what we discuss. Patreon: Shirts: Instagram: Facebook: Website: Paintings: [email protected]...

May 07, 2019
Language: EN
Play Time: 00:11:38

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