Join the Crabby Captain and the Sunny Sailor as we take the leap from landlubbers to full-time sailors in our exciting journey! In this season, we start from the very beginning—buying our boat and preparing for the adventure of a lifetime. With no experience beyond a few lessons and a dream, we d...

Join the Crabby Captain and the Sunny Sailor in Season 2 as we embark on our first-ever sailing adventure through the Windward Islands! This season is all about new beginnings, as we explore the breathtaking beauty and vibrant culture of islands like Saint Lucia, Saint Vincent, and Grenada. With...

Get ready for another wild ride with the Crabby Captain and the Sunny Sailor in Season 3 of our uncensored Caribbean sailing adventures! This season, we're taking you deeper into the unpredictable world of life on the water, where no moment is off-limits. From stunning island escapes to chaotic, ...

Set sail with the Crabby Captain and the Sunny Sailor in Season 4 of our uncensored Caribbean sailing adventures! From beautiful, remote islands to wild, unpredictable encounters at sea, this season is packed with real, raw moments you won’t find anywhere else. We don’t hold back—whether it’s nav...

Join the Crabby Captain and the Sunny Sailor as we set sail on another exciting season of our Caribbean adventures! In Season 5 of our sailing journey, we explore the sun-kissed shores and crystal-clear waters of the Caribbean islands, uncovering hidden gems, quaint villages, and breathtaking lan...

Half way through Season Six you will see that Cara and Eddie are no longer traveling together. But The Sunny Sailor continues on! The unique experiences are never ending as sailing, exploring and adventure are the daily routine. There may be heartbreaks and terror that will make someone wonde...

The Sunny Sailor Episode 126 - "Day-ay" Guadeloupe brings culture, art and even DEATH on this Island Paradise SEASON 7
Sailing to the this tropical island brings excitement and thrills, followed by a dip in to Guadeloupe's culture of art, dance and music. And a look at our own version of the popu...

Dominica in the West Indies is a wild and sexy island. With it's untouched jungles and incredible marine life, Dominica is a adventurer's dream. The Sunny Sailor has a LIFE-changing experience while there. Check it out and see what you won't believe!
ALL UNCENSORED!
I am Cara the Sunny Sailor, I...