The Crew

Meet Herb and Maddie Benavent! They have been living the cruising life since July 2017 when they left Baltimore, MD and ventured off into the great blue world we call Earth.

They started by cruising down the Chesapeake Bay, then the East Coast of the United States, then the Bahamas and Bermuda. After their fun on this side of the Atlantic, they set sail for the distant Portuguese Islands of the Azores, where they currently are carrying out some major boat projects.


Herb Benavent

Herb moved aboard as soon as he graduated from dental school in Baltimore, Maryland. He purchased "Wisdom", a project boat, and began working on her to bring her up to speed. After re-rigging, re-powering, re-painting, and upgrading the systems on the boat, they are ready to go cruising. Herb works as a dentist and a rigger.


Maddie Benavent

Maddie moved aboard shortly after meeting Herb. Their first date went very well and she moved in with him shortly there after. Adjusting to living on a sailboat took some time and effort, especially since she had never been on a sailboat before. She has since learned how to sail very well and can single hand Wisdom. Maddie worked as a highschool art teacher, but now uses her artistic talents to create lovely paintings and all the videos you guys love and enjoy on our YouTube Channel.



Morty was born in 2013, and has only known boat life. He was raised on the boat since he was a puppy and he loves the sailboat life! He cruised with us down the Chesapeake, but stayed with Maddie’s parents when we headed out into the ocean.



Sammy is a Green Cheek Conure and was the first to join the crew. Hatched in 2006 and raised by Herb since she was a hatch-ling. She has been on Herb's shoulder since they lived on land, and moved aboard with him in 2012. 

She has transitioned well from land life to boat life. A few bird friendly modifications were made for Sammy to safely hold her cage and bed in the boat, making Wisdom her home.

Sammy also stayed behind with Herb’s parents when they set sail for destinations that lay beyond the Chesapeake Bay.


The Boats



Most importantly, our 1968 Morgan 45. She has been rebuilt in preparation for our journey. Purchased by Herb in 2012 from the original owner with the plans to go on a Trans-Atlantic journey. She was completely re-rigged with synthetic standing rigging, along with a full suit of sails, and an electric engine. 


Σοφία (Sofia)

Our inflatable dinghy, Sofia (Σοφία), is our handy dinghy for getting to shore in the ICW. When the water is calm and tranquil, we are able to row this giant pool float-toy to shore and back. It sure is a lot easier than lifting Tooth III!

Since losing Tooth III, Σοφία has become our primary dinghy.


The Teeth



Tooth is our trusty dingy! We built him during the winter of 2014 and towed him along as we sailed the Chesapeake and along the Atlantic Coast of the United States. Tooth was a kit boat from Chesapeake Light Craft, built with "stitch and glue" to make a very sturdy and straight forward row boat. Tooth rows fast and tows well, but he doesn't fit on the deck, so we won't be taking him along on our ocean passages.


Tooth III

After the fiasco of Tooth II leaking and being very tipsy, we began searching for another dinghy, one that would fit on the deck and be very stable: Enter Tooth III, a Craigslist find from Cambridge, MD! Tooth III is a 7.5 foot Livingston Dinghy, with the stability and ease of rowing that only comes from a catamaran hard dinghy. We loved him, but he found his final resting place in the Bahamas. Tooth III was lost at sea somewhere between New Providence and Allen's Key in the Bahamas. 


Tooth II

Tooth II is our third dinghy, and made entirely out of Douglas Fir! When it came time for his sea trial, the disappointment poured in almost as fast as the water did. He leaks and is very tipsy, especially with both of us in him, so we decided to leave him behind and find ourselves a more stable dinghy. 


Other Boats


Windpuff is a 1966 Alberg 30 and is our day sailor. He has no engine and is propelled by sail or sculling oar. Windpuff is currently on the hard while we are cruising.