Son of a Sailor

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“We Built this City” – Jefferson Starship

Since I was a kid my family was connected to San Francisco. One of my first memories was standing in a building where my Dad, a young General Contractor, was remodeling the entire 8-story building. One of his many jobs in San Francisco as he built his construction empire. Okay empire is a little much but at one time this Swedish immigrant who finished school at 15 built more housing in the state of California in one year than any other company.

The Hook

My family loved to ski, hike and ride motorcycles. A little water skiing as well. We spent a lot of time in the mountains. We had a cabin in the Sierras to launch all these activities and then finally my Dad bought a condo in Lake Tahoe. Right on the lake with a sweet view. One time he and I were out water skiing with his new girlfriend and she said “this is nice but my last boyfriend had a sailboat on San Francisco Bay”. That was it. The next day my Dad headed to the waterfront near his office in Oakland and found a sailboat dealer. He ordered a new Ericson 29 Racer/Cruiser and the future changed forever. Condo sold, motorcycles gone and the wonderful adventurous life of sailing began. The girl?….she was gone too but she left a mark for sure.

Here comes the sun

 After the sailing bug got us we started racing. And I mean hard core. Every Saturday and Sunday. We upgraded to a Santana 35. Dad was skipper and I ran the foredeck. I could have written the book “2 years before the mast” but the title was already taken. We subscribed to every sailing magazine. We read books. This sailing thing connected my Dad and I like no other thing could. This is why I always recommend my friends go boating with their kids. It’s a unifying experience. Sailing was big in those days (70’s) and everyone was getting into it, but the bay was cold and the coastal cruising was colder. What to do. CHARTER, this new company called Moorings out of the BVI was offering the chance to rent a boat for a week so you could sail around in the fun and sun with lots of rum. So we headed to the BVI. This was 4 flights back then and 2 hotel stays before we were actually on the boat. My Dad and I looked at each other and said “man this warm sailing thing sure is nice” and so……

All the way over there?

 A few charters later and a few stops in Fort Lauderdale and Dad bought a house. The die was cast. California was no more and the entire family ended up in South Florida to raise our families and earn our fortunes. We ended up selling the sailboat he brought with us because we were working and there wasn’t a good “sailing area” in Palm Beach County so we became power boaters for the next 25 years. But that is another story.

This video is a family event to bring my Dad back to the bay for a sail and to show our kids the life I had in the City as a kid myself. I hope you enjoy.



8 Responses

  1. Manson & Cindy - Cat's Meow

    Too fun!

    Hey Randy, are you on FB? If so, send me a friend request. Too many Randy Smiths! 🙂


    • happytogether

      Hi Manson, Believe it or not I am not on FB. I am only on this blog and my youtube channel. Have you started sailing yet? Its getting warm,…


  2. Jay Branson

    Hi Randy,
    It was a pleasure to meet and greet you at Stillwater Cove this afternoon. I hope you guys had a nice dinner at The Lodge at Pebble Beach and that your tender was still on the beach when you returned. Lashing to the stairway railing was probably a really good move since the tide and swell in there are fickle. I found your website and dig your mojo. Keep living the dream.

    Jay Branson
    Harbor Master
    Stillwater Cove, Pebble Beach, Ca.

    • happytogether

      Hi Jay!

      Thanks for the note. We loved it there. We ate at the lodge overlooking the ocean and had a great night sleep in flat calm water. The next two days were filled with dense fog and motoring but we arrived Santa Barbara in perfect weather. Now we are anchored at Santa Cruz island. Thanks again for your hospitality. What a special place! Randy

  3. Don Cross

    Nice tribute to your father, Randy. Awesome you all got to sail together after all that time!

    • happytogether

      Hi Don, Thanks! The effort to bring the boat all the way to SF was paid back at that moment during Ozzy! Randy

  4. Matt & Emily

    Randy and Lennie,
    It was supper fun hanging out with you guys again this time in S.F. Your boat is pristine as expected and your hospitality couldn’t be beat. It was cool to finally step aboard HT after watching countless hours of your videos and then actually raising our glasses aboard with angle of course. We wish you the best with your travels and always follow the wind who knows where it will take you, until we meet again.

    • happytogether

      Hello Matt and Emily!
      Thanks so much for joining us aboard for the open house! We look forward to many more visits with you guys around the world! Cant wait for you to get your cat. Thanks, Randy & Lennie

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