Sailing Money & Finances

We have transitioned to full-time (except when it's cold) liveaboard cruising with the goal to sail around the world starting in the Mediterranean.

We created this blog and our podcast, Covert Castaway, to share lessons learned and document our journey as we make this major life change.

We track the destinations and anchorages we have visited on Polarsteps.

See places we've been, view pictures and interact with our route by clicking the link below.

Choosing International Medical Insurance While Cruising

Healthcare insurance while sailing internationally can be a bit of a sore subject because now that we have quit our jobs the full impact...

Hidden Costs to Commission a New Catamaran

In this blog I will cover the final, final costs of commissioning our catamaran after manufacturer and dealer costs. We finally had a...

Choosing Flags, Registration, LLCs for a New Catamaran

So we were just told that our boat is coming out in just three weeks after first being told around December it was delayed until March....

Drowning in Sailboat Paperwork

Life is chaos right now, honestly. I happened to also have a doctors appointment this week and no kidding, my blood pressure was really...

Medical Matters

Accidents, heart attacks, sepsis…these are things that terrify me when it comes to living on a boat. In today’s blog I’ll talk about...

Creating a Financial Strategy to Sail

In the last blog I covered how we set a sailing budget and basic assumptions. In this blog, I’ll share how we took our sailing budget,...

How Much does it Cost to Sail Full Time?

How are we ever going to be able to afford to quit our jobs to live on a sailboat? How are we going to be able to afford THAT boat? In...

Selling the House

Making a decision to sell the house was a highly emotional and consequential decisions I’ve ever made. It triggers the first round of...

Fall in Love with the Boat

Before a budget, before having a solid game plan, what did we do? We did exactly the opposite of what we should have done when deciding...