Today it’s simply a dream

Boating Dream – Living on a Catamaran in the Caribbean

Our boating dream would be to retire in the Caribbean and live on a catamaran. How did this even come about? I started a personal blog back in 2009 when I was struggling to have children and was in my early 40’s. I wanted our kids to know the journey we had experienced, but we never had kids and after a few years I stopped updating it. It was a private blog, so it was really more of a diary for me.

Scott and I have always loved the sea and during every vacation to the Caribbean, we would plan at least one (usually two) catamaran excursions. I grew up with boats, had one as an adult and really missed boating. After spending time on the Caribbean Sea, we fell in love with the islands and the laid back life. We always pictured ourselves working or retiring in the Caribbean.


caribbean island beach

Fast forward to the January of 2011 when we attended the Seattle Boat Show, which included the floating show on Lake Union. It was a cold, wet and dreary day, but we were going to have fun anyways!

That is when we looked at our first (liveaboard) Catamaran, the Lagoon 350. The broker was trying to convince us to get into the charter business in the PNW as it was a great way to buy our dream boat. Suddenly, we were hooked and couldn’t stop thinking about that boat. There was another cat at the show and it wasn’t nearly as roomy or comfortable. From that point on, we knew we needed to do our research and read everything we could.

Magazines & Blogs

I started buying Multi-Hulls Magazine and other Sailing magazines to read up on sailing and cruising lifestyles. I also started following blogs of other catamaran sailors and their adventures. One that hooked me like a novel was the blog for Tritons At Sea. This guy was so particular and I couldn’t wait to read the next blog he posted. It was from 2005, but he had great advice, including lists and requirements that are still great today. When our journey finally starts, we’ll be referencing his blog. Then we found other blogs on This was a great site and eventually I was emailing some of the boats and congratulating them on their adventures. It was a great way to erase the dulldrums of the rainy days of the PNW, especially on a slow work day.

See, I don’t have a regular job, but instead own a local wine shop, The Wine Alley and I work here every day. During the week, we don’t get a ton of daytime shoppers, so I would pass the time following many of the sailing blogs down in the Caribbean and Pacific Ocean. But that can also simply be adding “salt to the wound”. Reading about their tropical adventures at sea and then looking at the 3″ of cold rain falling didn’t always make life better.

A Trip to Antigua

Every January, we close our wine shop for a week and visit the Caribbean. In 2010 we went to Antigua and during our trip we took a day trip on a catamaran, “Wadadli Cats” that sailed us all around the island. We started on the north end and traveled west into the Atlantic Ocean and then back around to the Caribbean side. What a thrill and for me, at that moment, I forgot all about our problems back home. We were in paradise!
Antingua sailing excursion
 Boating in the Caribbean

What’s Next?

When we returned home, we again attended the 2012 boat show and collected so much information ranging from toilets to electronics. This was actually a bit silly, considering we knew we wouldn’t “launch” for many years, unless we won the lottery! But it was still fun to look, touch and dream.
Caribbean sea beaches

 Books, Books & More Books!

A few months later, I noticed all kinds of “real life” books on sailing and one that caught my eye was A Sail of Two Idiots . This was a great story about another couple, our age, who sold everything, bought a catamaran and sailed the Caribbean and with no sailing experience! Well, if they can do it, so could Scott and I and we both read that book fast! The author, Renee Petrillo has been so gracious answering all of my emails and answering our questions over the past two years. It’s a great book, so this is a must buy!

The funny thing about me, is that I am not a reader. My mom would read a book in a few days, but books have always bored me. But I love all real life books about sailing the Caribbean and other tropical adventures. I soon found myself reading: The Motion of the Ocean  (a book about a local PNW couple), Sail Away: How to Escape the Rat Race and Live the Dream and A Trip to the Beach: Living on Island Time in the Caribbean. For birthdays & Christmas, we found ourselves giving each other books about Catamarans, Nautical References and Galley Recipes. Currently, I’m reading An Embarrassment of Mangoes: A Caribbean Interlude, a story about a Toronto couple that heads down the ICW to the Caribbean. So many people have done it and so many are doing it, that we know in our hearts we’ll be there soon too.

In addition to all of the books, blogs, etc. that I started reading, local neighbors of ours, John & Kelly W. started their dream and trip in August 2012 from Seattle. They left everything and headed south on their sailboat. They made it to Mexico by the end of 2012 and have been enjoying the tropical Mexican life ever since. It’s been fun to follow their trip on Facebook and see where they are headed next. Since then, most of my Twitter & Instagram accounts follow mostly cruisers too.

So we began 2013 year, dreaming of our trip and trying to figure out how we will get there. Owning a business and having debt, doesn’t make the challenge easy. But we know with determination, we’ll get there in a few years. In the meantime, I wanted to share the little adventures, research and events with you so we can reflect on everything we went through to get to our dream. If we can do it, everyone else can too. Cheers, Scott & Ally


Scott Ally Caribbean Tourists