How Not To Sail

Bradford Rogers

Screwing up is part of cruising. Let me show you how! Host Bradford Rogers takes you through the fascinating, often hilarious, and occasionally startling world of cruising, including chatting with fellow cruisers, musicians, bikers, and other salty characters.

All Episodes

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 all-around-bad-influence Bob Bitchin.

Feb 2019

19 min

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.

Mar 2019

16 min

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

Mar 2019

16 min

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 elusive and colorful owner.

Apr 2019

22 min

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

May 2019

17 min

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

Jun 2019

19 min

In this bonus episode, I answer your questions!

Jul 2019

6 min

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

Aug 2019

17 min

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.

Sep 2019

21 min

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

Sep 2019

8 min

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.

Nov 2019

27 min

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

Feb 12

18 min

In this bonus episode, I answer your questions! 

Feb 22

6 min

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

Apr 14

15 min

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.)

Apr 29

13 min

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 certain things work on the boat. Just sayin'.)

Jun 8

18 min

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

Jul 15

24 min

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 usual. Hopefully that works out okay. Check out the Show Notes at for photos, a map, a little bit about the particular bosun's whistle model I found (that actually works)...and lord knows what else...

Aug 28

24 min

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