Delray Beach Sailors Combine Passion Of Traveling High Seas, Giving Back


By: Marisa Herman Associate Editor

Once a month Randy and Lennie Smith board their Leopard 48 Catamaran “Happy Together” and take a trip.

The duo serves as captain and first mate on their voyages around the world.

Since they purchased this boat in 2015, they have traveled to 16 countries covering 10,000 nautical miles, all while running their two businesses.

While on land, Randy is CEO of Heritage, a local flooring and window treatment company. Lennie is a general contractor who runs her business building custom homes.

“Most people wait to do something like this until they are retired,” Randy Smith said. “We have found a way to travel while working. We are just doing it with a better view.”

Their journeys are captured on film and uploaded to their YouTube channel “Sailing SV Happy Together,” which has more than 8,000 subscribers.

The channel started as a way for the couple to let their kids know what they were up to while on their excursions. Not realizing how far-reaching YouTube can be, their videos began gaining traction from people outside the family.

Now, they are using it to show their followers and aspiring boaters just how easy and fun sailing together is, all while helping to give back to Warrior Sailing, a nonprofit with roots in their passion— sailing.

“We are all about inspiring people, entertaining people and educating people,” he said.

Passion for boating

Randy grew up racing sailboats in the San Fransisco Bay area with his father. Lennie remembers fishing trips on her uncle’s boat during South Florida summers.

When the couple met 20 years ago, they began their years of boating together. They were power boaters, until the youngest child went to college and Randy decided it was time to return to sailing.

When the Leopard arrived, they christened it and took it down to the Keys where Randy played with a GoPro camera Lennie bought him.

That first video “Shakedown Cruise” launched what would turn into dozens of videos featuring the Smiths in all different countries experiencing local cultures, how they operate the boat together and what it is like to travel happily together.

Their trip began when they left Florida and went to the Bahamas. From there they stopped in Dominican Republic, Turks and Caicos, Puerto Rico, all the Caribbean Islands, Columbia, Panama and Mexico.

After each trip, comes a video. Their followers have seen the quality of the videos go from amateur home films to refined productions.

Randy does all the shooting, selects texts to place over the video, picks music and now with the help of a professional editor— strings it all together into a story of that adventure.

“We have followers,” Lennie said.

The couple gets stopped at boat shows from people who recognize them, receives tons of fan mail and has sent out Happy Together T-shirts to their fans who ask for them.

“It’s the most heartwarming thing to read the comments,” Randy said.

People reached out saying they purchased cruising sailboats after watching their channel.

Giving back

The couple personally and professionally is involved in donating to various charities and causes. And while traveling, they said they encounter people in need.

“A lot of these countries are poverty stricken,” Randy said. “We have been so fortunate and we want to help people.”

So while they help out where and when they could, they realized they wanted to do more at home.

Just over a year ago, the couple was running on the beach when Lennie told Randy she came up with a way to give back.

They boarded their boat and she told Randy about a nonprofit she saw in a magazine that looked like a perfect fit for the water-loving couple, Warrior Sailing.

Warrior Sailing

Warrior Sailing is a nonprofit that provides maritime education and outreach for wounded, ill and injured service members and veterans through teaching them how to sail during a three day camp.

The camps are offered for free and is open to all wounded, ill or injured service members and veterans of all branches of the U.S military.

Neither of the Smiths served in the military and none of their relatives did either.

“We get the benefit of living in this country and we didn’t do any of the heavy lifting,” Randy said.

They reached out to the founders and said they wanted to help. Now, their YouTube channel, which is non-monetized, helps drive donations to Warrior Sailing.

Randy will mention the nonprofit or wear a Warrior Sailing shirt while they film. And instead of just sending a Happy Together shirt to fans, they ask that they make a $25 donation in exchange for the merchandise.

In addition, they helped sponsor a camp in Annapolis, Md. where they spoke about the benefits of sailing for leisure cruising. They also hosted a “Beyond our Camps” event in California where they invited graduates of the program onto their vessel for a half-day sailing experience.

“Going to the Warrior Sailing events is so rewarding,” Randy said. “They are all broken and anything we can do to help repair them.”

Being Delray residents, the couple wants to bring Warrior Sailing to their hometown for an event.

They are working with the group to plan a Beyond the Camp event in Delray where alumni will be able to spend the day on Hobie Cat sailboats. Details are still being hashed out and a date will be forthcoming.

And for their next adventure? They will be sailing the boat back to Florida by the end of year just before a  new boat, the Leopard 50, arrives in January.

They will spend a year outfitting the boat before joining World ARC 2020, a rally that starts in Saint Lucia and ends in Australia.

“We are having a really good time with this whether the camera is on or not,” Randy said.

To subscribe to their YouTube channel, visit

To learn more about Warrior Sailing, visit