Home   >   Podcast   >   Sail Loot Podcast 003: How Bill and Trisha Regan Make Their Sailing Money and Cruise the Florida Keys, Bahamas, and ICW

Sail Loot Podcast 003: How Bill and Trisha Regan Make Their Sailing Money and Cruise the Florida Keys, Bahamas, and ICW

By on October 30, 2014

Over the past seven months I’ve been contemplating the ways to get on a sailboat and start my cruising lifestyle. That’s exactly what Bill and Trisha Regan did this past April.

Bill and Trisha met in 2003 and “got hitched” on October 28, 2006. Yes, I talked to them the day before their anniversary. This podcast wasn’t released until a few days later. If you too want to wish Bill and Trisha a happy anniversary (depending on when you find these show notes of course), you can find them at their blog SailingWanderer.com. You can also find them on Facebook.

After sailing a Hobie Cat on their honeymoon in Negril, Jamaica and attempting to learn to sail their 17′ O’Day Daysailer II all on their own, they decided it was time to take some sailing classes. A few years later they sold their houses, got rid of all of their stuff on Craigslist, and they decided to head South from upstate New York to their jumping off spot in the Florida Keys.

I thought that they were relatively new sailors without a lot of cruising experience, but I found out otherwise during our conversation. Bill and Trisha gained a lot of experience on boats of all shapes and sizes before boarding Wanderer, their 1979 Pearson 323, and releasing the dock lines. They also tell us all about how they topped up their cruising kitty, and how they budgeted for sailing. I don’t want to ruin the interview for you. So, take a listen!

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A Few Things You’ll Learn About In This Episode:

  • How Bill and Trisha started sailing.
  • What they did to get South, to the coast, and transition to living on a boat.
  • How they make money, find places to live, and rent their houses using Craigslist
  • Their lives in the Florida Keys before setting sail.
  • How they saved for their Cruising Kitty and how they keep it topped up.
  • Their sailing budget and how accurate they were.
  • How much they paid for Wanderer.
  • What they didn’t account for in their cruising budget as much as they should have.
  • Outfitting Wanderer and shaking her down.
  • Trisha’s awesome birthday this past April.
  • Where they’ve been cruising for the last 6 months.
  • And a whole lot more!

Links and Resources From This Episode:

THANK YOU!

Thank you very much for listening to the show! If you enjoyed listening and it has helped you in any way, please share it using the social media buttons that you see on the page. You can also head on over to the Sail Loot Facebook page, hit the like button, and leave comments and questions over there! We’d love to chat!

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TeddyJ

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About Teddy

I am a 37 year old that just wants to find a way to make a remote income, gather some Sail Loot and cruise the world! I have been sailing for a couple of years now, but mostly on 10 day trips as vacationing crew. I just recently took sailing to the next level by completing my Basic Keelboat, Basic Cruising, and Bareboat Cruising Certifications! I am also Vice President of a Medical Consulting Company, have a Mechanical Engineering degree from Georgia Tech, and have taken several Coding, Computing, and Online Business courses. It's time to share what I have learned!