[TSOJOURNER]

Hi, I'm a 55 year old professional who is transitioning into retirement over the next two years because time is now more valuable to me than money. I'm an experienced wind surfer, raced 14' sailboats as a youth and think I want to become a cruiser based on my summer crewing a 28' Sabre out of Portsmouth NH. With 4 very serious adult sons and a wife who will want to join us in harbor only, my tentative plan is to take a "good to charter" course and then rent some boats to try them out. I assume they are all pretty good. I sense that crewing offers a great chance to expand my experience. I can travel anywhere. In 2-3 years, I expect to buy my first boat, say a 32-36' Catalina, in the $50-125K range, and sail it along the West coast of Florida, based out of Marco Island, with friends and family. That should tell me what I need to know. All input welcome.

 

[RealityCheck]

Welcome. You will find lots of clubs around Marco Island where you could pick up a few things crewing for races or just daysails. I'm not a racer but did some years ago and now prefer a far more layYyyeydddd back approach to sailing. Taking the certifications classes is a good and quick way to pick up critical skills and if you charter out of area the certs may be needed. You may want to consider a vacation type class with wife to allow her to become more comfortable with cruising or possibly a different class than the ones you will be in which often works better.