This guest post is by Stephen “Stepto” Toulouse. He made a comedy album you can get on Bandcamp (cheapest option), iTunes or Amazon and wrote a book called A Microsoft Life. He blogs at Stepto.com.

The island was lush and green and beautiful in the distance. It was 80 degrees in the Caribbean in the first week of January, the wind was light and the view from the aft end of the ship was fantastic. Next to me sat Wil and his son Ryan. We each had a fine Cuban cigar in one hand and double scotches in the other. The ship was called the Eurodam, and like most cruise ships during the days at sea it had activities and little contests on the back deck and what not. The DJ had been playing a really obnoxious version of one of these a minute ago with really loud music, but got the hint from the glares of ourselves and others who just wanted to relax. So the silence we were enjoying our cigars in felt brand new and welcome.

We were due into port the next day, and the final concerts and festivities of JocoCruiseCrazy 1 were just a few hours away. I had performed the night before. I had been crazy nervous about it, mainly because I was in the second to the last show and all of the shows were better than the one before. Secondly, up until a couple of hours before the show I still had not picked my final set from amongst my practiced material. So I was a bit of a bundle of nervous nerves that are super nervous. My wife Rochelle and I went on a morning excursion with Wil and his family to swim with dolphins* (!) and I talked over my nervousness with him on the way back. He told me which pieces I should read because they would be the funniest and as it turns out, he was right.

I split off from the group to return to the ship to practice, and unbeknownst to me Rochelle and Wil and company went off to shop where Wil procured the cigars. Suffice to say my performance went off without a hitch (here’s a small segment of it) and so the moment with the cigars was kind of an all-around decompress and celebration.

“That’s Cuba” I said, gesturing to that beautiful island. It’s funny because during the cruise essentially the cruise line, maps, almost everything just ignores Cuba’s existence. I can’t stress enough what a beautiful place it appears to be.

“Yes. Yes it is.” Wil said.

“We’re smoking Cuban cigars and drinking scotch just a mile off the coast of Cuba.” I said.

“Yes. Yes we are.”

After a moment our friend Andrew joined us, then Rochelle and Anne dropped by. We chatted quietly and relaxed and watched Cuba go by. That’s definitely in the top 200 moments of my life.

I mention this moment mainly because I really wanted to be on the boat most of my friends are on right now. But then I stop myself to remember I have been twice, I’m getting to work on some pretty amazing projects at the moment, and I get to guest blog here with Will and Shane. I promise to try and keep it interesting, and also (where possible) humorous.

Titty sprinkles,

Stepto

*Another top 200 life moment.