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Season 5 of our sailing adventures is out on Vimeo

Season 5 of our sailing adventures is out on Vimeo – to buy or rent! Can you believe we’ve been at this for 5 years?!! Check it out! (Uncensored is also available)

# 110 Rum gets us in Trouble on a French Caribbean Island – Crazy American Sailors

While taking a land tour around a French Caribbean Island, stopping at rum factory after another, was probably not a good idea. Rum always gets us in trouble and we do crazy things. But… it is always entertaining to watch a few sailors go a bit wild.

# 107 Martinique Red Devil Carnival! Champagne makes her clothes fall off!

# 107 Martinique Red Devil Carnival! Champagne makes her clothes fall off! The french islands are so good to us. So much good food, tasty baguettes and not to mention Cara’s favorite…delicious CHAMPAGNE! Karnaval (Carnival} hits the streets of St Anne, Martinique, and Cara may have had a bit tooRead More …

#102 Disaster ending to our USA RV trip. Dangerous. Shocking. F**king Scary!

We did not expect our trip to end like this. Part two of our visit to the US from our normal life in the Caribbean. The RV took us around to visit friends and family, and we enjoyed such fun and adventure… until …. a terrible accident left us withRead More …

#101 First Visit back to the U.S. From a sailboat to an RV! What could go wrong?

Living on our sailboat in the Caribbean for the last 3 1/2 years has made us unaccustomed to things like cities, large stores, crowds of people and yes DRIVING. But we decided to make a trip around the United States in a very large RV. it seemed like a goodRead More …

CRAZY EPISODE #100 – Last sail of the season (without clothes!) & Embassy Marijuana?

Our last sail of the season from St Vincent and the Grenadines to Grenada. We usually head farther south for hurricane season especially if we are going to fly and leave our boat. But before we can fly, Cara must renew her US passport and the events that happened thatRead More …

The Octo Connection: Life and Love. Oaki The Octopus and the Sunny Sailor -Amazing Story of love

This female diver connects with a wild octopus on a deep and meaningful level. Oaki the Octopus is smart, inquisitive and quite funny. Cara was obsessed with him and spent hours each day swimming and interacting and they formed a special and unique bond. Oaki’s antics made her laugh, andRead More …

Oaki the Octopus Loves the GoPro Camera Funny Underwater

Oaki the Octopus is OBSESSED with the underwater camera. He just keeps at it and the filming that he does is just so funny.

#99 Saline Island, Grenada – Fort Unknown and Damsels in Distress – Caribbean Dreams Sailing the Seas

Yet another gorgeous Caribbean island that we want to explore. And we finally were able to score a spot in this tiny coveted anchorage in Carriacou Grenada. Eddie and Cara retired early to sail the seas and scout new places and it’s another beautiful day in paradise

#98 Union Island -Kites & Wild Nights. “Don’t be afraid of the P@$$y!” ? Funny. Caribbean Sail

The island of Union in St Vincent and the Grenadines is a great place for kite surfing! And the night life ain’t so bad either. We visit the Caribbean Island and enjoy all of the unique places like Happy Island (made of conch shells) and the village of Clifton whereRead More …

#97 Dirty Games and Lots of Moons in Chatham Bay Caribbean Island Sailing Adventure Bucket List

Chatham Bay on Union Island in the SVGs gave us sailors some roaring good times. Cruisers from all around the world join us….. on hikes to find alcohol…. mooning those that stayed behind ( get it? “behind” hahaha)…. wild parties on the beach ….on some of the most beautiful beachesRead More …

#96 Canouan Private Caribbean Island Sexy Photo Shoot ? Baring it all isn’t easy! Neither is getting in

Canouan is a stunningly beautiful island in the eastern Caribbean and a perfect place for a sexy model photoshoot. The water is crystal clear and the sands a light pink. Cara quickly learns that being sexy while naked in the waves is not as easy as it looks. Also weRead More …

#94 Volcano Aftermath – St Vincent Caribbean Island Volcano Eruption while living on a boat

Our boat was anchored 10 miles from St Vincent when the La Soufriere Volcano erupted. We woke the morning after watching the enormous plume in the sky to find our boat covered in ash. We rush to evacuate the area and find air suitable to breathe. Will we find aRead More …

Eels and Urchins in the SVGs

Snorkeling in the Caribbean gives us lots of joy and hidden secrets. Every day is an adventure. . . . . .

#78 Woody The Boozy Bus Tour

Cara the Corruptor strikes again on Woody the Boozy Bus Tour. A bunch of crazy yachties on a wide ride through the rainforests of Grenada all while trying NOT to spill the beer. Woody. Would he?! . . . . . .

Coronavirus In The Caribbean

Coronavirus is impacting the world. Watch our latest YouTube video to see what it’s like for us. . . . . .

Cruisers Christmas Potluck in Bequia

This was taken at the Cruisers Potluck at the Fig Tree. It was a lovely celebration of boaters, cruisers and friends. – – –

#63 Bare to Bequia. Salty Seas. Rum Revelry

Bequia is a unique and amazing island in St Vincent and the Grenadines with so many fun (AND FUNNY) things to do! – – – – –

Can I touch a wild octopus?

While in Bequia, I spent several days wooing this beautiful octopus. They are so smart! Just watch to see what happens. It’s truly magical! ???

#62 Hot Friends PART TWO

When our friends came to visit in Grenada, it was just too much fun for one video so we had to make a part TWO! Come enjoy the fun, laughter and beauty we shared in the islands. _____________________________________


When our fun, funny, fantastic friends come to visit, it doesn’t hurt that they are hot at all! _________________________________________

Running from the hurricane can be fun!

Hurricane Dorian is going to hit too close for comfort so we are moving south to be as far as we can get from landfall! #thecrabbycaptainandthesunnysailor #hurricanedorian #outrunningahurricane #sailingthecaribbean #sailingliveaboards #thecrabbycaptain #thesunnysailor _________

Great day for aerial silk

What a wonderful day we had, we were able to scuba dive an area close to Ronde Island just north of Grenada and then Cara got in some aerial silk at sunset. Our friend, Lynn on Open Agenda ( http://www.lynnklassenphotography.com/ ) captured these at sunset.

Drive in Volcano, St Lucia

St Lucia is a stunning Caribbean island with Drive IN Volcano, Beautiful Waterfalls, and a Stairway to Heaven at the top of a mountain, Piton.  ________________________________________


Beware! Sailing Active Montserrat Volcano. ____________________________________________

St Martin Was Crazy

Saint Martin/ Sint Maarten was so fun! Planes landing over the beach, Golden Cows and amazing sights! ——- ——- Thanks for watching our videos. For a few $$ per month contribution, you could have access to uncensored videos on our website. New videos are being uploaded every few weeks. Won’tRead More …

British Virgin Islands

Sailing through the British Virgin Islands to see the sights which include the incredibly beautiful area called The Baths, Virgin Gorda, beautiful islands and more. _____________ Thanks so much for liking our videos. For an exclusive pass for uncensored videos and Members Only Access, you can pledge safely through PatreonRead More …

Our videos are being featured at the Annapolis Boat Show

Our videos are featured on The Charted Life TV channel now and will be played on a loop at the 2019 Annapolis boat show in Maryland this weekend! Whoop whoop. We are feeling very fancy!! If you get a chance to stop by the booth, tell them we sent you,Read More …

Can we get through Whale Cay Pass?

Whale Cay channel is very treacherous because of the strong current and small channel. We must travel through the pass to get to Treasure Cay. Can we do it safely?!

We made it to the Bahamas

We will be uploading the tales of our crossing soon!

Hurricane Florence Update

In the midst of this horrible event, we feel blessed and humbled that ourselves and our vessel are okay. So far. Some high winds and rain but no flooding. Our hearts go out to those in our neighboring cities. We will be back to help our friends and others thatRead More …

Outrunning Hurricane Florence part 1

(Red Sky in morning……uh oh) Track our progress south: Sailing Vessel MUSIC MMSI number 367615290. Here is the link with the latest position of our boat http://www.marinetraffic.com/en/ais/home/shipid:5706999

The Worst Feeling Is When Your Boat Is Taking On Water

The worst feeling in the world is your boat taking on water I used to think that the worst feeling in the world was running aground.  And every sailor has done so.  I have always heard that if a sailor says he never has, he’s lying. I remember once, whenRead More …

Ep One- Buying Our Boat

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