This Saturday, Dec. 21, is the Naples Holiday Boat Parade, which will set sail with the theme of “Vintage Christmas.” The large boats will assemble at 6 p.m. along Lido Lane off the seawall in front of Naples Plaza, and the small boats will assemble in Marine Stadium with a planned start at 6:45 p.m. On parade night, the streets all close at 5 p.m. and most street parking is gone by noon.

Celebrating his sixth year as parade chairman, John Shuman tells me his planning team included Mother Nature. who moved the parade closer to Christmas because low tide is later this year — and she also is promising 70-degree weather. There will be a record number of political dignitaries, beauty queens and “the man” himself, Santa Claus.

As I was growing up, every few years my parents would get a bigger boat and a smaller house. At one point, we had the cutest and tiniest English Tudor house on Loreta Walk in Naples. During boat parade weekend, the guest list for their party failed to take into account the size of the house. Like many Naples residents, my parents tried to pare down the guest list, but once friends knew it was an annual event, there was no way to control the crowd. 

The way my folks solved the ever-growing party problem was to sell the Naples house and move aboard the boat. As part of their long-term plan, we became full-time live-aboards so we could enjoy more time on the water. But, despite their best efforts, the large holiday parties continued. Mom and dad would take our “home” on a harbor cruise of Alamitos Bay to view the annual Naples boat parade. 

I don’t know how my dad managed to navigate the floating party on parade nights.

Back in those days, The Neptunes, a group of free divers in wetsuits pushed around a fire-breathing dragon. The two or three dozen divers would take turns towing the dragon. Hospitable Rivo Alto Canal residents would offer bottles of good cheer to keep the swimmers warm along the way. By the time the divers reached Alamitos Bay, the group had grown to include friends of the Neptunes and friends of friends, many of whom had not missed a dockside offering. 

So my dad, with a cast of thousands on board, would plot a course in the bay, carefully watching for drunken swimmers. It had to be a challenging night.

By the time I was a teenager, I figured it was time to jump ship and find a new parade experience. Bob Kristine, our Basin 1, Gangway 5 neighbor, was entering the boat, “Jiminy Cricket,” in the parade with a United Service Organization (USO) theme.

Starting in World War II, Bob Hope sacrificed almost every Christmas to travel with the USO and entertain our troops wherever they were, and he became the serviceman’s best friend. Kristine’s boat was decorated like a Navy warship, complete with a hull covered in battleship gray rolls of paper, and the riders were all dressed up as characters in the Bob Hope Christmas Show, including several beautiful blondes. Hope’s main-squeeze USO blonde had a young son, so I had babysitting duty that night. What a great job for a teenager who needed to escape the crowds!

It’s my favorite boat parade memory. We had a golf-club-swinging “Bob Hope” in plaid pants and a crazy “Phyllis Diller” with a zany wig and silver opera gloves. Best of all, everyone aboard the “Jiminy Cricket” that night shared warm feelings of patriotism. 

I know this year’s parade will likely come to hold special memories for participants and spectators alike. I look forward to sharing the “Vintage Christmas” experience with everyone.

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