Cover art for podcast How Not To Sail

How Not To Sail

63 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!"

63 Episodes | 2019 - 2024


February 22nd, 2024


An important message from RadioPublic

Ep. 54: Boat Survey Fail

February 16th, 2024


Big fun (can you hear the sarcasm?) with a required 10-year survey. Who knew there were so many things wrong with my boat?

Wanna help spread the gospel of How Not To Sail? Here's a link with a few suggestions, most of …

Ep. 52: First Annual DINGHY Awards™

January 20th, 2024


Join me as we reveal YOUR winners!

Wanna see the video version? CLICK HERE. (I expect this may not stay on YouTube forever…for reasons I mention in the outro.)

Show Notes Why these DINGHY Awards™?

Glad you asked.

As I …

Ep. 50: How Not To Hurricane (Idalia)

October 10th, 2023


First of all... Come by the meetup this week! (Details in the podcast.)

In this episode, we find out what happened with the boat (and our house) during Category 3 Hurricane Idalia.


Yes, you can join the Patreon …

Ep. 49: Bitchin on How Not To Sail

August 26th, 2023


The legendary Captain Bob Bitchin shares a few hitherto unshared tips on how not to cruise.

Also, check out the new and improved How Not To Sail Store!


Ep. 48: Eleuthera Means Freedom!

June 11th, 2023


The Admiral and I visit the Bahamas island of freedom, drive on the wrong side of the road...and *maybe* escape a man with a machete.

This episode has a video version, including maps, photos, and video footage, at

Ep. 47: How Not To Buy A Boat

February 6th, 2023


I share some thoughts on...wait for it... How Not To Buy A Boat. (With some help from my friend Bill. Who really exists.)

Get The Book

Want to enjoy your boat, visit awesome destinations, and skip the stress? Then be …

Ep. 46: Pull, Don't Be Pushed

January 21st, 2023


Perhaps the most important episode you'll hear this year. (Cruising isn't just for boat owners. And...what are you *really* looking for?)

Get The Book

Want to enjoy your boat, visit awesome destinations, and skip the …

Ep. 45: Humbug! (Announcement)

December 24th, 2022


So..this week has been SO fubar that I forgot I hadn't posted this one. However, the sentiments expressed herein are even more relevant this week. (Also...some flute.)

Ep. 44: Annapolis Boat Show...and Party!!!

October 20th, 2022


To RSVP for Saturday's Zoom party (do it NOW if you wanna attend), go to and put in your name and email. Super easy! The link …

Ep. 43: Hurricane Irma and Jacie Sails

September 30th, 2022


Strange how much this podcast parallels this week's events...and how little I learned from my experience.

RSVP to the Zoom Party

Reserve your spot for the Season 2 Party at

Join the Patreon Crew …

Ep. 42: Season 2 Party and Annapolis Boat Show

September 25th, 2022


We're getting ready for some big fun!

RSVP to the Zoom Party

Reserve your spot for the Season 2 Party at

Join the Patreon Crew before the Boat Show (and the Zoom Party) for More Perks!

Yes, you …

Ep. 41: Updates, Parties and Ventures... Oh My!

September 2nd, 2022


Some news about the Zoom party, a certain boat show...and what I've been screwing around with. What could possibly go wrong?

RSVP for the Season Two …

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 …

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 …

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

June 18th, 2022


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

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 …

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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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 …

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...!

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.

Episode 20: Eric Stone

January 10th, 2021


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

Episode 19: Loose Ends

December 25th, 2020


Kinda self-explanatory, no?

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

News: Season One Wrap Party!

December 5th, 2020


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

Reserve your FREE ticket at

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.

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 16: ...or Stubbornness?

October 7th, 2020


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

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 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 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 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 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 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 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.

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 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.

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.

Listener Mail: Ask me anything!

July 12th, 2019


In this bonus episode, I answer your questions!

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.)

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 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 3: Fog

March 29th, 2019


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

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 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 …

How Not To Sail: Trailer

January 16th, 2019


A sneak peek at How Not To Sail. What could possibly go wrong?

Check out the website at:



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