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Artwork for Your Pocket Sailing Instructor Podcast

Your Pocket Sailing Instructor Podcast

Penny Caldwell
Sailing
Winches
Self-Tailing Winches
Desolation Sound
Safety Tips
Docking
Sail Canada
Marine Equipment
Spindrift
Sail Nelson
Gift Ideas
Lumar
Boat Buying
Harken
Sailboat
Artificial Intelligence
Sailing Gear
Anchoring
Intermediate Cruising Course
Skipper

Hey sailor! My name is Penny and I have been a sailing coach with Sail Canada for over 25 years! I have helped thousands of sailors find their passion and love of all things sailing. I'm here to help you live your best sailing life. I provide gear reviews, sailing tips, habits to perfect and much more! So, sit back and enjoy some informative, entertaining, unique sailing content! See you on the wa... more

PublishesTwice monthlyEpisodes105Founded5 years ago
Number of ListenersCategories
How ToEducation

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Artwork for Your Pocket Sailing Instructor Podcast

Latest Episodes

There comes a point in almost every sailor's journey when you realize something interesting: you probably already know more than you think you do!

You can steer the boat. You understand the sails. You can dock, anchor, navigate and keep watch. You'v... more

Every sailor eventually has one of those moments.

The docking approach isn't working. The wind suddenly picks up. The engine won't start when you need it. A crew member becomes sick. Something breaks. Or perhaps several small things start happening ... more

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 Understanding Different Types of Anchors

14:12 Choosing the Right Anchor for You... more

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 with your crew, and more. Learn some expert tips on how to master docking your boa... more

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Host

Penny Caldwell
Penny Caldwell is the host and driving presence behind the show, a sailing coach with extensive experience and a focus on practical, beginner-friendly instruction.

Reviews

4.8 out of 5 stars from 97 ratings
  • Great podcast

    I absolutely love this podcast and am so glad to have Penny’s insights.

    Apple Podcasts
    5
    Sosarem
    Canada2 months ago
  • Just really enjoyed listening, Do not have a boat yet but learning what I can.

    Audible
    5
    Jeremiah Westerlund
    United States2 years ago
  • really helpful information

    Just really enjoyed listening, Do not have a boat yet but learning what I can.

    Audible
    5
    Jeremiah Westerlund
    United States2 years ago
  • Penny Caldwell is inspirational for all people into boating!

    We were looking to purchase a new boat and found at least 3 episodes from this podcast that helped us obtain the information we need. No need to search Google for information on boating and sailing. Penny has all the answers and information you need in one podcast. This is a great addition to our podcast network.

    Apple Podcasts
    5
    Bruce Chamoff
    United States4 years ago
  • Sailing with your spouse

    What a great topic. My spouse and I are learning to sail together. We definitely have different strengths & weaknesses and I will take your recommendations with me on the next lesson! Thanks and keep up the podcasts…we are listening.

    Apple Podcasts
    5
    !&$!&
    United States4 years ago

Listeners Say

Key themes from listener reviews, highlighting what works and what could be improved about the show.

The content is praised for safety emphasis and actionable drills that listeners can replicate.
Fans enjoy the inclusive, family-friendly approach to sailing education.
People appreciate the host's clear, practical sailing guidance that's easy for beginners to follow.
Listeners feel the show balances instruction with engaging stories from real sailing experiences.

Chart Rankings

How this podcast ranks in the Apple Podcasts, Spotify and YouTube charts.

Apple Podcasts
#209
United States/Education/How To
Apple Podcasts
#37
United Kingdom/Education/How To
Apple Podcasts
#71
Canada/Education/How To
Apple Podcasts
#51
Italy/Education/How To
Apple Podcasts
#61
Germany/Education/How To
Apple Podcasts
#179
Australia/Education/How To

Talking Points

Recent interactions between the hosts and their guests.

BONUS: AI hosts discuss Bareboat Cruising course in Desolation Sound
Q: What kind of mindset do you think is helpful for someone embarking on a trip like this?
You need resilience, adaptability, and a willingness to embrace the unexpected.
BONUS: AI hosts discuss Bareboat Cruising course in Desolation Sound
Q: What goes into finding a good anchorage?
You need to consider shelter from wind and waves, good holding ground for your anchor, and safe distance from hazards.
BONUS: AI hosts discuss Bareboat Cruising course in Desolation Sound
Q: Is this something anyone can just sign up for, or are there certain skills you need to have under your belt first?
You'll need a solid foundation, including the Basic Cruising Standard and VHF radio certification.

Audience Metrics

Listeners, social reach, demographics and more for this podcast.

Listeners per Episode
Gender Skew
Location
Interests
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Frequently Asked Questions About Your Pocket Sailing Instructor Podcast

What is Your Pocket Sailing Instructor Podcast about and what kind of topics does it cover?

A practical, beginner-friendly sailing show that blends hands-on how-tos with safety and decision-making guidance for new skippers. Episodes cover essential skills like docking, anchoring, and boat handling, plus gear reviews and strategy for building confidence on the water. The host consistently emphasizes safety, clear crew communication, and structured practice, while offering repeatable routines to turn learning into lasting competence. A notable thread is a multi-episode arc guiding listeners from novice to confident skipper, with approachable explanations and real-world anecdotes that make sailing more accessible and enjoyable for a broad audience.

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Which podcasts are similar to Your Pocket Sailing Instructor Podcast?

These podcasts share a similar audience with Your Pocket Sailing Instructor Podcast:

1. Offshore Sailing and Cruising with Paul Trammell
2. Single-handed sailing podcast
3. On the Wind Sailing
4. The Sailing Podcast
5. Salty Podcast: Sailing Stories

How many episodes of Your Pocket Sailing Instructor Podcast are there?

Your Pocket Sailing Instructor Podcast launched 5 years ago and published 105 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

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