Cover art for podcast How Not To Sail

How Not To Sail

27 EpisodesProduced by Worldsongs MediaWebsite

"What could possibly go wrong?" Host Bradford Rogers learns some things NOT to do—and the occasional life lesson—while sailing the Gulf Coast of Florida and meeting salty characters. "Screwing up is part of cruising. Let me show you how!"

episodes iconAll Episodes

Episode 1: Bitchin

February 28th, 2019


In this premiere episode, I have a crazy idea to sail alone around Florida to the Miami International Boat Show to launch the podcast...and talk to cruising mentor, former bodyguard to Evel Knievel, and …

Episode 2: Control

March 17th, 2019


In this episode, I make final preparations for my voyage, gain a theme song, and learn an interesting lesson from musician and sailor Peter Suarez.

Episode 3: Fog

March 29th, 2019


In this episode, I finally set out from Gulfport, and run into fog...both literal and metaphorical.

Episode 4: Sounds

April 15th, 2019


In this episode, I visit the home of the Cheeseburger in Paradise to record my show on Pyrate Radio and try to score an interview with the island's …

Episode 5: Jacie Sails

May 25th, 2019


In this episode, we finally meet the main character—Jacie Sails—and learn how she got her unusual name.

Episode 6: The Great Leap Forward

June 21st, 2019


In this episode, I make the leap 90 miles south from Marco to Marathon, and find...something in the way. (Or many somethings, really.)

Listener Mail: Ask me anything!

July 12th, 2019


In this bonus episode, I answer your questions!

Episode 7: Fuel Dock Debbie

August 3rd, 2019


In this episode, we find out what happened under the bridge, and meet a new interesting character.

Episode 8: I Don't Wanna Be Buffett

September 17th, 2019


In my quest to learn more about this "Trop Rock" music that all the boaters seem to love, I talk to Eric Stone, Mike Nash, and Brian Watson from SV Another Road.

Update: We Found Fuel Dock Debbie

September 27th, 2019


I tracked down Fuel Dock Debbie, and here's the phone call... (Also, an update on the How Not To Sail book giveaway.)

Episode 9: Eastbound!

November 30th, 2019


FINALLY, I sail east from Marathon toward Key Biscayne, Miami and the Miami Boat Show, stopping at Rodriguez Key near Key Largo, getting rained on, scraping through some shallow water, and having the usual misadventures.

Episode 10: Miami

February 12th, 2020


Wherein I point the boat toward downtown Miami at last! (Plus info on the How Not To Sail book giveaway!)

Episode 11: My Favorite Dance Is The Whiskey Tango Foxtrot

April 14th, 2020


The Admiral and I finally make it to the boat show in Miami...and a shocking development.

Episode 12: The Way Forward

April 29th, 2020


In the aftermath of a major setback, I learn that you have to go with the current. (Produced aboard Jacie Sails during the COVID-19 pandemic.)

Episode 13: Back Toward Marathon

June 8th, 2020


After coming to grips with the new reality of things, I start the 350-mile journey back toward Marathon, and "home." (And I probably should learn how …

Episode 14: Happy Where I Am?

July 15th, 2020


Ah...back in Marathon with a frosty beverage in hand. But is there trouble in paradise?

Episode 15: Persistence...?

August 28th, 2020


In this episode, I finally head back toward my home port, meet some "old friends" (I didn't say they were human!), and am stubbornly persistent as …

Episode 16: ...or Stubbornness?

October 7th, 2020


In this episode, I do a couple of stupid things. Try not to act surprised.

Episode 17: It's Alive!

November 8th, 2020


In this episode we come full circle. (You'll hear what I mean if you've heard the previous episodes...)

Episode 18: Back To The Barn

November 24th, 2020


After a month and 700-mile round trip, it's about time to put Jacie Sails back into her slip.

News: Season One Wrap Party!

December 5th, 2020


Join me for the end-of-Season One party!!!!

Reserve your FREE ticket at

Episode 19: Loose Ends

December 25th, 2020


Kinda self-explanatory, no?

Don't forget to RSVP to the end-of-season party at:

Episode 20: Eric Stone

January 10th, 2021


In the FINAL episode of Season One, I visit with Eric Stone.

Seaon One Party-The Crunchiest Bits

January 29th, 2021


The best bits from the party! More suitable than the YouTube version for using during activities like driving or bathing a cat.

Unheard Gems from Season One

February 18th, 2021


Here are some of the stories and How Not To Sail moments from Bob Bitchin, Fuel Dock Debbie, and Eric Stone you *didn't* hear in Season One...!

Episode 21: Pluses and Minuses

March 14th, 2021


This first episode of Season Two is about a rather dirty topic.

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