Cover art for podcast How Not To Sail

How Not To Sail

47 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!"

47 Episodes | 2019 - 2022

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...!

Ep. 21: Pluses and Minuses

March 14th, 2021


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

Listener Survey

Help make How Not To Sail better in just a few minutes! Take the survey at:

Get The Book

Get How Not To Sail (the …

Ep. 22: O Brother, Here Art Thou

May 22nd, 2021


In this episode, I get to take my recently-discovered brother sailing, and uncover some more How Not To Sail tips…

Ep. 23: Reaching Reality with Barry Walton

August 26th, 2021

Check out my convo with HowNotToSailer Barry Walton, director and one of the stars of the sailing documentary Reaching Reality.

Not subscribed to the podcast yet? Click HERE to get every episode automatically delivered …

Ep. 25: How Not To Paint Your Cabin Top

September 18th, 2021

A week in the blazing sun. A thousand dollars worth of materials, some of which may or may not be the right stuff for the job. What could possibly go …

Ep. 26: How Not To Paddleboard

November 24th, 2021

In this episode, I try to stay upright on a paddleboard and get some peace…but I run into a familiar obstacle. Take the survey here:

Produced by: Bradford Rogers Voiceover: Bradford Rogers Mixed …

Ep. 27: Ahoy, HowNotToSailer!

December 18th, 2021

A steaming potpourri of How Not To Sail news and tidbits to (almost) close out the year. Produced by: Bradford Rogers for Worldsongs Media Music  

What Shall We Do With A Drunken Sailor? (Traditional) - performed by …

Ep. 28: The Punch List

December 31st, 2021

In the last podcast of 2021, numerous problems crop up… Who knew? Produced by: Bradford Rogers for Worldsongs Media


What Shall We Do With A Drunken Sailor? (Traditional) - performed by Bradford Rogers and Peter …

Ep. 29: All At Sea

January 14th, 2022


In this episode, I check if we're still afloat, try to get some music from Peter Suarez, and resolve a little wager we made.   0:00 Previous …

Ep. 30: Have A Sip Of The Donkey

January 28th, 2022


In Sarasota, with "The Admiral," I share a slice of the cruising life, reveal a couple of your survey results...and have a sip of The Donkey. (Reef …

Ep. 32: Captain Boomies and The Bear

February 25th, 2022

In this episode, we hang out with former megayacht Captain Boomies and her megayacht "Mate-ineer" Christian...a.k.a. "Bear."

Listener Survey

Help make How Not To Sail better in just a few minutes! Take the survey at:

Ep. 33: Answerin' Yarrrr Questions...

March 11th, 2022

In this episode, I answer listener questions...with some help from a couple of VIPs...!

Listener Survey

Help make How Not To Sail better in just a few minutes! Take the survey at:

Ep. 34: Not Always Utopia? (Sondra and Jimmy's Gulf Adventures)

March 25th, 2022

Sondra and Jimmy Lee buy s/v Utopia, a Caliber 40 LRC, shoot a toilet gasket across the cabin, dodge catastrophe in a lock...and learn the importance of speaking up.

Show notes and transcript at

Ep. 35: Reefer Madness

April 15th, 2022


Calm down, it's about one of the most important things on a boat...the refrigerator. I discover a super-cool "feature" that's been buried for a …

Ep. 36: Another Bitchin Episode

April 29th, 2022


Ex-biker, bodyguard to Evel Knievel and 100,00-mile world sailor. You know Captain Bob Bitchin has some great How Not To Sail stories! And is that...Morgan Freeman?!??

Get The Book

Want to enjoy your boat, visit awesome …

Ep. 37: Schizophrenia

May 14th, 2022


I fail to repair my thru-hull valves but learn How Not To Snuba and just a wee bit about diesel engines. And maybe I'm optimistic?

Ep. 38: Beware Sunscreen!

June 5th, 2022


I cruise up the Gulf Coast, learn sunscreen does not mix with autohelm, and...maybe(???) get hauled out?

Get The Book

Want to enjoy your boat, visit …

Well, s***...! (Announcement)

June 18th, 2022


What the @#*$&^ is going on this week, you ask? This is the answer.

Ep. 39: On The Hard

July 22nd, 2022


In this episode, a big crane (a.k.a. a "travel lift") plucks my sailboat from the water, hopefully in one piece. And we meet an old friend.

Wanna …

Ep. 40: Season 2 Finale

August 7th, 2022


I try to actually fix a coupla things so I can get back "home"...and make a disturbing discovery at the last minute. (Big Thanks to new patrons Carey and Tad!)

Get The Book

Want to enjoy your boat, visit awesome …

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