Sail Loot Podcast 056: S/V Smitty – Sailing from Boston to the USVI with Jesse, Stacey, and Summer

By on November 6, 2017

I met Jesse and Stacey from S/V Smitty in November of 2016. They’re long time listeners to the Sail Loot Podcast and we had sent a few emails back and forth to each other before I went on a charter vacation in the BVI.

Jesse and Stacey live on S/V Smitty, their 2001 Catalina 310. S/V Smitty is on a mooring in Bay de Grigri between the island of St. Thomas and Water Island.

I stayed in St. Thomas for one night to meet up with my 3 other friends that were joining me for a week of charter sailing in the BVI. As soon as we got our gear situated in the Windward Passage we walked down to the Greenhouse Restaurant and Bar where we met Jesse and Stacey. They, of course, already had a rum drink in hand.

I learned that Jesse and Stacey had sailed to the islands from Boston on their 30ft sailboat and, at the time, had jobs as captains on day sailing charters. Now, with her accounting skills, Stacey has a “normal” job on St. Thomas and another conversation needs to be had with Jesse about his captaining plans post-Irma.

I’ve become good friends with Jesse and Stacey since we first met. Jesse was the only official captain on board Asante when we delivered her from St. Thomas to Ft. Lauderdale, FL. He is a wealth of knowledge and I’m very glad that I have his direct phone number so that I can call or text him with any questions I may have!

This is their story of how they were able sail their 30 ft Catalina from Massachusetts to St. Thomas with their Aussie mix, Summer!

SV Smitty in a cold Boston Winter. This is what Jesse and Stacey had to deal with in the North

Apparently, they may have even lived on Smitty when she was iced in.

But they made it down the ICW, through the Bahamas, and on to much warmer climates! – S/V Smitty at Honeymoon Bay on Water Island

A few months later, I was on my way to charter a sailboat in the BVI, but I had to stop in St. Thomas first and say hello to Jesse, Stacey, Summer and S/V Smitty!


A Few Things You’ll Learn about Jesse and Stacey and their finances for sailing S/V Smitty South:

  • How their sailing dreams started with a trip on a Carnival cruise ship in 1996.
  • Exchanging vows in Magen’s Bay in 2002.
  • Learning about the cruising life from the captain of Heavenly Days.
  • Doing the bareboat charter thing for 10 days.
  • Sailing S/V Splash and S/V Smitty on the weekends, holidays, and summers in Boston.
  • Purchasing S/V Smitty
  • Behind the name of S/V Smitty
  • Their 4 year plan.
  • Selling everything and getting out of debt.
  • How much money they left Boston with to go sailing.
  • Upgrading S/V Smitty and why they do all of the maintenance themselves.
  • Jesse’s professional background as a geologist – before they left Boston.
  • Having a captain’s license and STCW training to work on charters in the Virgin Islands.
  • How much of their cruising kitty they had left when they arrived in the Virgin Islands.
  • Insuring S/V Smitty.
  • Upcoming maintenance projects.
  • And much more!

Links and Resources from this episode:


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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!

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