DiscoverYour Pocket Sailing Instructor Podcast
Your Pocket Sailing Instructor Podcast

Your Pocket Sailing Instructor Podcast

Author: Penny Caldwell

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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 water ;-) Don't miss an episode!
62 Episodes
#53: Crew Overboard!

#53: Crew Overboard!


Coming soon!
Today we are looking at the 4 approved types of flares in Canada: A) Parachute Flare B) Multi-Star Flare C) Hand-Held Flare D) Smoke Flare Remember that these are approved for 4 years from the manufacture date!
This week I am chatting about keel types: - Full Keel - Fin Keel -- bulb keel & wing keel - Bilge Keel Why would you select a certain keel, drawbacks and advantages of each, and maintenance... Show notes available at!
This week we are having a chat about boom vangs. I am often surprised at how many of my students purchase boats that do not have on rigged up! They are an essential part of trimming your sail and can be key when sailing in heavy weather. Some of the marine stores will have boom vang kits that you can purchase, so it is ready to be attached at the base of the mast and up on your boom quickly. Easy to rig up and will help you sail more efficiently. Here are some useful links for you… Instagram: ⁠⁠⁠⁠ Spotify: ⁠⁠⁠⁠ Facebook: ⁠⁠
So this week we are talking about different types of shackles and their common uses. Also, what to look for when they start to wear down... - screw pin shackle - keyhole shackle - snap shackle - soft shackle Here are some useful links for you… Instagram: ⁠⁠ Spotify: ⁠⁠ Facebook: ⁠
Today I am talking about spring maintenance! And yes, it is a LONG list! Here are some of the things I'll be sharing: - engine checks - standing rigging checks - running rigging checks - sail check - safety gear checks And much more! Head on over to to join my email list so you don't miss any freebies and the spring checklist!
This week I am discussing cleats! What are they, where to find them, which ones to upgrade, etc. I talk about: - Horn Cleats - Cam Cleats - Clam Cleats - Jam Cleats - Clutches Here are some useful links for you… Instagram: ⁠⁠ Spotify: ⁠⁠ Facebook: ⁠
Today I am talking all about blocks! What the heck is a block you say? It is a pulley, in sailing lingo ;-) There are many types and I'll walk you through them all! Enjoy! Remember to like, share and follow this podcast so you never miss an episode! Here are some useful links for you… Instagram: Spotify: Facebook:
Kinda appropriate that this is my 50th episode! Talking about when I brought Spindrift to Nelson and the ceremony I performed to greet her. Here are the specific descriptions you'll need: - Boat Purging Ceremony: “Oh mighty and great ruler of the seas and oceans, to whom all ships and we who venture upon your vast domain are required to pay homage, I implore you in your graciousness to expunge for all time from your records and recollection the name (mention the old boat name), which has ceased to be an entity in your kingdom. As proof thereof, we submit this ingot bearing her name, to be corrupted through your powers and forever be purged from the sea. In grateful acknowledgement of your munificence and dispensation, we offer these libations to your majesty and your court.” - Boat Renaming Ceremony: “Oh mighty and great ruler of the seas and oceans, to whom all ships and we who venture upon your vast domain are required to pay homage, I implore you in your graciousness to take unto your records and recollection this worthy vessel hereafter and for all time known as (your new boat name), guarding her with your mighty arm and trident and ensuring her of safe and rapid passage throughout her journeys within your realm. In appreciation of your munificence, dispensation, and in honor of your greatness, we offer these libations to your majesty and your court.” - Offering to the four winds: Face north, throw some champagne out of your flute in that direction and say: “Great Boreas, exalted ruler of the North Wind, grant us permission to use your mighty powers in the pursuit of our lawful endeavors, ever sparing us the overwhelming scourge of your frigid breath.” Face west, repeating the champagne pour and toss while saying: “Great Zephyrus, exalted ruler of the West Wind, grant us permission to use your mighty powers in the pursuit of our lawful endeavors, ever sparing us the overwhelming scourge of your wild breath.” Face east, repeating the champagne toss while saying: “Great Eurus, exalted ruler of the East Wind, grant us permission to use your mighty powers in the pursuit of our lawful endeavors, ever sparing us the overwhelming scourge of your mighty breath.” Face south, pouring the champagne and tossing it while reciting, you guessed it: “Great Notus, exalted ruler of the South Wind, grant us permission to use your mighty powers in the pursuit of our lawful endeavors, ever sparing us the overwhelming scourge of your scalding breath.” Spindrift's Poem: "Do not keep me tied to this mooring, My lines strain to be free. The water whispers at my hull, I want to sail away with thee. Let's cast off on a great adventure, There is so much for us to see. Let's feel the winds at our back and the sun in our faces. Please cast my lines free. Let's cast off and explore some place new, I need to heel and sail away with you." Happy renaming!!
Today I am talking all about winches! These are the winches that we use for our sheets and halyards on a sailboat though. I will do a different episode to focus on the anchor windlass system. Enjoy! Remember to like, share and follow this podcast so you never miss an episode! Here are some useful links for you… Instagram: Spotify: Facebook:
Alright so to prepare you for this episode you could also listen to: EP 1: My Top 10 Comfort Items for Sailors EP 5: Maritime Mysteries & Mishaps: Old Presque Isle Lighthouse EP 9: My Top 8 Sailing Books Life has been throwing me some curveballs lately so I started to wondering if I had somehow broken some sacred oath or fallen on bad luck. I just can't seem to catch a break at the moment, which had me thinking about superstitions and where I may have gone wrong... should I have eaten that banana during that race? Did that black cat on the dock walk in front of me when I wasn't paying attention? I started to whistle along to that song the other day... did that do it?! Boating Superstition Bananas: yup. We have a superstition about bananas onboard a sailboat. There are several origins to why bananas are believed to be bad luck on a boat. One involves the fact that they spoil quickly. Any ship carrying a cargo of bananas needed to deliver their and so the captain always had to get to his destination quickly to deliver his banana shipment and so Put the right foot forward: it was thought that the left side of the body was a bad omen, or associated with evil. Therefore, all sailors stepped onto the vessel with their right foot! If you forgot and stepped on with the left, you'd be tossed overboard, or your shoes would be tossed overboard in an effort to please Poseidon ;-) Renaming a vessel: I'm going to do an entire episode on this one, but it has been long thought that renaming a vessel is bad luck! Stay tuned for my episode about what you need to say, when and how to make sure you don't curse your boat! No whistling: it was thought that whistling at sea was a way to taunt Poseidon and Aeolus. Red sky at night, sailor's delight. Red sky in morning, sailors take warning. Boats are a she... often boats were named by their Captains after their wives or mistresses. It was believed that if the boat was named after a woman the Captain loved, she would bring them home safely. These are just a few examples! Listen to the entire episode for more! Penny
I am starting something new with Technical Tuesdays! There are SO many items on our boats that need a little bit extra info... hence the Technical Tuesdays where I plan on bringing you quite, and essential, information to help you make informed decisions. This week I am talking about lines. What type to purchase for halyards, sheets, dock lines, anchor lines, cunningham, boom vang.... so many lines! Enjoy! Penny Here are some useful links for you… Instagram: ⁠⁠ Spotify: ⁠⁠ Facebook: ⁠
Coming soon!
Alright, we have all been there! You're heading into the dock, speed is great, wind is great, crew are ready,... suddenly a boat starts leaving their slip right in front of you, your crew move aft to tell you only to drop the boat hook in the water, your other crew tries to grab the boat hook and drops the roving fender, and everyone on shore is watching. Yup. We have ALL been there! The lovely trials of docking... Docking Equipment The basic equipment that you need for docking is not complicated, however if you don't take care of it, or check on it regularly, you could find your boat trying to leave without you! bow line stern line spring lines x 2 fenders x 3+ snubbers x 2 bow chocks t-cleats Checking Your Equipment dock lines: checking for chaffing, wear, pulled strands, knots fenders: checking for wear, holes, grime rubbing on paint, inflation snubbers: checking for breakdown, check line for wear chocks & cleats: checking to make sure nothing is rubbing on hull, through fiberglass, etc. Types of Docks There are many different types of docks and many different ways to dock a boat. I am going to discuss the basic principles that can be used for all types of docks to limit boat movement within the slip. Some things to keep in mind: check on your boat regularly as lines may freeze, loosen, wear down, etc. do not tie your dock lines too tight. It is important to let the boat move around a bit in the slip as the wind and water move. This will make sure that the weight load remains on your dock lines and not your cleats. readjust your fenders as needed. Sometimes they end up on top of the dock and really don't do much for your hull. Usually they are places at the beam of the boat (widest part). The key to successful docking is...  head over to to find out!
A few more notes about anchoring... show notes coming soon! 
There is something magical about spending a nice, quiet, night at anchor! When we were in Croatia, it was a blessing to be able to get away from all of the other tourists for some quiet R&R! Anchoring is a pretty simple thing once you master some basic steps. Here I will break it all down for you and provide you with some of my pro tips! Enjoy! Don't forget to send me any questions! Other episodes to check out: EP 16: Sailing Goals – Liveaboard Sailing EP 28: How to be a prepared skipper EP 32: Adventuring in Croatia – Itinerary & Highlights Support me on Patreon! Technical Anchoring Terms Ground & Tackle: includes the anchors, cables, and other tackle used to secure a ship at anchor. Rode: is the connection system between the anchor and the boat. Traditionally it is a combination of rope and chain, or all chain. Scope: is defined as a ratio of the length of an anchor rode and the depth of the water under the the bow of the boat measured from deck height. Snubber: is a bridle used to take the strain of the chain rode. This reduces wear on your boat from the chain and also acts as a shock absorber and silences the chain. Usually made of nylon rope or tough rubber. Windlass: is a machine that restrains and manipulates the anchor chain on a boat, allowing the anchor to be raised and lowered by means of mechanical aid. Anchor Roller: is a device situated at the bow that consists of a wheel within a framework that is designed to guide an anchor when it is lowered or raised. Types of Anchors There are several types of anchors on the market now. The classic anchors include the Bruce, Danforth, and Plough. Newer anchors such as the Mantus and Rocna are gaining a lot of popularity though. Personally I upgraded my small Bruce to a Rocna and absolutely LOVE IT. Planning Alright, hopefully you have done your pre-trip planning and you have an anchorage (or two) selected for your lovely night! What are some of the things you are looking for in a good anchorage? Here are the key things: Shelter: you should have shelter from wind, waves and traffic Depth: you need adequate depth for your draft Bottom Type: make sure your anchor will hold in the type of bottom you'll have Swing Room: goes along with depth. You need to be able to swing 360 around without hitting anything. Check out for more information...
This week I am talking all about being a good boating neighbour! How to be a safe, and non-jerky, boater! There are a few unwritten rules to keep in mind about boating and how others expect you to conduct yourself while on the water. At the marina be aware of any marina rules around parking, washroom/shower use, boat launch access, etc. return any carts to their location after use take all garbage and recycling with you when you leave make sure you are using the right slip keep shore power cables and dock lines organized no swimming! it is very dangerous to swim in marinas, not to mention pretty gross At the dock be organized and ready at the fuel dock be aware of others at the boat launch be aware of families and others in the area if smoking, drinking, listening to music, etc. be a good neighbour and keep garbage, spills, dinghies, on your side of the slip clean up after yourself At anchor be mindful of neighbours and being loud remember that noise and music travel FAR on water slow down when approaching anchorage or when boating around anchorage watch others rode and anchor placement watch others swing room - first come first served make sure you have your anchor light on as required to assist those entering the anchorage in the dark On someone else's boat... ask about boat rules - shoes, wet clothing, etc. when rafted to another boat, make sure everyone has figure out how to move between the boats (some people use the cockpit, others go from shrouds to bow to shrouds... find out what the duties or expectations are (cooking, cleaning, drinking, smoking onboard, etc) help out wherever you can! In the end, take the high road! Not everyone knows or bothers to follow these simple rules on boating etiquette. We haven't even touched on the Collision Regulations and who has right of way over who. That's a whole other kettle of fish! For today, just work on being a good neighbour!
Alright winter sucks for us northern sailors! True, I am lucky that my boat is in the water, but it's cold! I haven't sailed in months and I'm going through withdrawal! So, I thought I would let you in on my "happy list". The list of things that I do throughout the winter to keep me looking forward to next season and making sure I'm ready to make the most of it! Enjoy! Other episodes you may enjoy: EP 9: My Top 8 Sailing Books EP 7: Day Trip Planning: Things to Consider EP 19: Which Sailing Course Do I Take? A list of things to do... As always I have a variety of ideas for you to keep the sailing love alive during the winter. Hopefully you find a couple ideas that work for you! Read a good sailing book! Learn a new knot! Animated Knots is great for this... Gear checks - pull off your sails, check for wear and tear. Canvass replacement - do you need to fix or replace anything for your dodger/bimini? Take measurements for new sails if you have access to your boat Chart review & checking out some new sailing destinations! Draw or sketch out some new anchorages... great way to get to know the specific area Take a course! Lots of online courses are available... Google it! Inventory: spare parts, engine parts, tools, first aid kits, electrical parts, etc. YouTube: enjoy someone else's journey... Erik Aaderaa, Sailing Project Atticus, SV Delos Go through personal sailing gear: base layers, shorts, pants, shoes, etc., see what needs to be updated/replaced Make a birthday list! What are some of things you'd LOVE to have on your boat? Winter boat sleepover! Climb up in there, grab a heater, a sleeping bag and have some slumber fun! Create your diagrams! Create diagram of safety gear, spare tools/parts, thru hulls, electrical diagrams, etc. Update your boat binder! Keep you manuals up to date... Create a Pinterest board about reorganizing your boat... Boat meal plan! Pull together some of your favourite recipes Sew some boat sheets for your v-berth and bunks Learn a new skill! Fiber glassing, engine maintenance, splicing, navigation, etc.
This week we are talking about safety (no surprise there!), but more specifically Personal Floatation Devices, Life Jackets and Tethers! What are they? What are the differences? Which one should you purchase? Where do you purchase them? When do you replace them? So many questions! Other episodes you may like: EP 3: Safety First! What Safety Gear do you Need? EP 14: Sailing Goals – Day Sailing EP 27: How to be a prepared sailing crew Support me on Patreon! Sign Up for the Podcast! Head over to for show notes! What's the difference? Which one should I buy? How do I take care of it? When do I replace it?
This week I am giving you a sneak peak into some of the things I do during the off-season to keep my skills sharp and to get ready for next season. There is personal growth, professional growth, reviewing, renewing, and lots going on! This is pretty typical for me as a "what to do this year" plan. Other podcast episode you may like: EP 4: Off-Season Training: What can I do during the off-season? EP 7: Day Trip Planning: Things to Consider EP 28: How to be a prepared skipper Why do I have a yearly training plan? Every year I have several areas of my sailing growth that I look at: personal growth, professional growth and ongoing maintenance. These probably aren't the best names for these, but that's what I've come up with for now! So, what does these mean to me? For personal growth, I like to take a look at new things that I can learn as a sailor. What new skills do I want to develop? What areas have I felt have been lacking? Which areas have I not spent a lot of time focusing on? For professional growth, I take a look at new areas where I want to grow as a coach. Which courses could I take to be a better coach for my sailors? For ongoing maintenance, I like to review materials from previous courses to make sure I'm still on track. I re-read the Basic Cruising Skills textbook every season, for example. What is my training plan this year? Personal Growth Celestial Navigation, upgrade first aid certification complete an online course creation certificate Other ideas: increase physical fitness, rehab an injury, spend time reading, upgrade person sailing gear items, set small weekly goals around learning a new knot, take new people sailing more often Professional Growth organize 2 Basic Cruising Instructor Clinics complete my navigation instructor certification create 2 or 3 online coaching programs for my sailors Other ideas: don't fear failure, stop procrastinating, be diligent with time, monthly budget updates, update business paperwork Ongoing Growth review Intermediate Cruising Student Notes rewrite my Spinnaker Course lesson plans re-organize my coaching binders Other ideas: read through owners manuals, review charts of your area At the end of the day it's all about where you want to go and how you plan to get there. Have fun planning it all out and think outside the box!  Penny
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