About Us

Hello, my name is Bob Cummings I am a 58-year-old father, brother, son, retired US Army Pilot, oh yeah, and a sailor. 

I have sailed my boat, SV Tracy Jean, a 49 ft Passport Center Cockpit Cutter Rigger Sloop, for the past 7 years between Virginia and Florida, and more recently, I have endeavored to sail her farther. 

Built in 1990 in the Ta Shing boat yard in Taiwan, she is a well-founded Bob Perry design  that is very comfortable. I am her third owner, and this is her third name. She started as SV Enchanted home ported in Woods Hole, MA. Her second owner called her Jag (guessing he was in the navy JAG Corp) out of Mint Hill, in North Carolina. As an Army Blackhawk pilot, there was no way I was going to sea with a Jag legacy, so I named her after my sister, Tracy, in memoriam. This is her/their story. 

In late 2019, while working at John Hopkins All Childrens Hospital, in St Petersburg, as I often did, I was thinking about sailing and my goals. There are so many possibilities. I have never had any urge to sail around the world, not that I couldn’t be talked into it, but it never appealed to me as a culminating sailing achievement. In fact, I was more drawn to the Idea of immersing myself in the history of Mediterranean Cultures, especially by sailing to all those historical locations on the Ionian and Aegean Seas. 

Sailing the Med seemed like a fine adventure, but hardly the pinnacle of sailing excellence, more of a vacation. The truth is, I had always thought the mark of a “true sailor” was Cape Horn and that is where my sights lay early on in my sailing fantasies. 

 I started to research the journey and make simple plans. Almost immediately, I knew this would be an arduous journey because of my time constraints. I also knew none of my sailing friends would be able to travel with me and this would be a solo journey with just me and Tracy Jean. 

 When I reflected on all of these things I knew, for her memory, my journey had more purpose.  I resolved to turn my adventure in to a Charity Challenge for breast cancer research.  I would sail 7000 Plus Nautical Miles, Bike 700 kilometers, and then hike 70 statute miles, all solo and unsupported. The kicker is I am attempting to complete it all in 77 days! 

Hello, this is me and my best mate Clew!  He loves to ride on the Tractor!