Your Pocket Sailing Instructor Podcast

Episode 5 Anchoring: Stop dragging for good NEW SERIES: From Passenger to Confident Skipper!

This episode we talk about anchoring! What, how, when, where... all the ins and outs of making sure the boat stays put, so you can have a great sleep. Chapters 00:00 U

Episode 4 Docking Without the Drama (Even in Tight Marinas) NEW SERIES: From Passenger to Confident Skipper!

Episode 4 of my new series From Passenger to Confident Skipper is all about docking! What equipment you need, how to practice and prepare for all scenarios, what to do wi

Episode 3 The key decisions every skipper must get right NEW SERIES: From Passenger to Confident Skipper!

One of the biggest shifts in sailing happens when you move from simply operating the boat to making the decisions that keep everyone safe and confident on the water. In t

Episode 2 Why you still don’t feel confident sailing NEW SERIES: From Passenger to Confident Skipper!

In Episode 2 of our series From Passenger to Confident Skipper, we dig into a frustrating but incredibly common feeling: you’ve spent time on the water, maybe even taken

Episode 1 You've taken a course... now what? NEW SERIES: From Passenger to Confident Skipper!

I am staring an 8-episode series called "From Passenger to Confident Skipper". Each episode will focus on a different aspect of your voyage to becoming the most competent

#86 SailTies: Turning Every Voyage Into a Story

I am SO excited to introduce you all to Sailties! This is an awesome app for sailors where we can log our trips, exchange information, create a sailor resume, look for ad

#85 From Impulse to Informed: Graham's Boat Buying Journey

In this conversation, Graham shares his journey into sailing and boat ownership, detailing his experiences with purchasing his first boat, Ringo, and the lessons learned

#84 Essential Tips for First-Time Boat Buyers!

In this episode of Your Pocket Sailing Instructor, Coach Penny discusses essential considerations for buying a boat. She emphasizes the importance of understanding your b

#83 Mastering Winches: A Sailor's Guide!

In this episode of Your Pocket Sailing Instructor, Penny discusses the essential sailing equipment known as winches. She provides a historical overview of winches, explai

#82 Equipment Upgrades! NOW is the time!!

In this episode of 'Your Pocket Sailing Instructor,' Coach Penny Caldwell dives into the exciting world of boat show season, emphasizing the importance of taking advantag

#81 Am I ready for the Intermediate Bareboat Sailing course?

Summary In this episode of Your Pocket Sailing Instructor, Penny Caldwell discusses the Intermediate Cruising Course, also known as ASA 104. She outlines the prerequisit

#80: Three Generations, One Boat: A Sailing Story

This past summer I was lucky enough to take my grandparents, mom and daughter on a sailing trip! It was VERY special to be able to share this experience with 4 generation

#79 Last Minute Christmas Gift Ideas!

Are you behind on your gifts this year? Not quite sure what to get your sailor? I've got you covered with a list of small to big gift ideas! Connect with Penny! - ⁠⁠Sup

#78 Croatia 2025 Trip & Highlights!

Summary In this episode, Coach Penny shares her recent sailing adventure in Croatia, reflecting on her experiences from a previous trip and the differences in crew dynam

BONUS: AI hosts discuss Bareboat Cruising course in Desolation Sound

Bonus episode created with Google Notebook LM.

#77 Creating an Itinerary! The basic steps...

Have an exciting trip in mind? This week I'm talking about creating an itinerary plan. How do I do it? What are the steps? Where should you spend the money and where can

#76 Desolation Sound Mayday! :-(

This week I'm talking about a Mayday call we overheard while in Desolation Sound this past summer... Happy New Year and here's to 2025! Connect with Penny! - ⁠⁠⁠Supp

#75 Last Minute Gift Ideas for your Sailor!

I am WAY behind on my shopping this year, so thought I'd help put together some last minute ideas for you as well! Happy Holidays and looking forward to seeing you in 202

#74 My Experience with AI ... yikes!

This week my friend Bob sent me a new tool called Google NotebookLM. I plopped my sailnelson.com website address into their system and within 5 minutes they sent out a 15

#73: Winterizing... we've come full circle LOL!

I'm back! FINALLY! Excited to be bringing a new episode to you! From a new house, new studio, and a new podcasting software! Yikes. This week I'm digging into Winterizi