Creating an Itinerary! The Basic Steps…
- Episode 078 Your Pocket Sailing Instructor podcast
- Released: January 27, 2025
- Duration: 33 min 18 sec
“A good sailing itinerary gives you a plan – and enough flexibility to change it.” ~ Sailing According to Coach Penny
Planning a sailing trip is about much more than drawing a line between marinas. I break down the basic process I use to build a sailing itinerary, including how to research a destination, think about daily distances, decide where spending money is worthwhile and identify places where you can save.
WHAT YOU’LL LEARN
- Build a sailing itinerary from destination research
- Plan realistic daily distances and stops
- Decide where to spend and where you may be able to save
- Leave enough flexibility for weather and changing plans
Building a sailing itinerary is probably one of my favourite things to do — which is why I have an entire section of this website dedicated to it! My husband thinks it’s hilarious when I pour myself a glass of wine, pull out the charts and cruising guides, and happily disappear for hours. What can I say? I LOVE it!
There really is an art to planning a great sailing itinerary. Before you start drawing lines on a chart, you need to decide what kind of trip you actually want to have. Are you looking for long sailing days and lots of miles? Or short hops with plenty of time to explore ashore? Do you want quiet anchorages, bustling marinas and restaurants, or a little bit of everything? Once you know what kind of experience you’re after, you can start looking at the length of the trip, realistic daily distances, destinations, anchorages, marinas, provisioning stops and everything else that will shape your adventure.
And then I always plan options. Lots of options! I want to know where the alternate anchorages are, which marinas might have fuel or repairs, and where we can stop early if the weather changes or the crew has simply had enough for the day. A good itinerary should never feel like a schedule you have to follow at all costs. It’s a framework that gives you choices when real life inevitably gets in the way.
After 30 years of teaching live-aboard courses, I’ve seen just about everything. Crew member needing to be evacuated from the boat because of seasickness? Check. Head malfunctioning with five people aboard? No problem. Engine refusing to start in a crowded anchorage? Sure! Why not? Weather changing unexpectedly, equipment breaking, someone getting sick, or the crew unanimously deciding that the beautiful anchorage you’ve just found is simply too good to leave? You name it, I’ve probably dealt with it.
But really, this is how we learn to cruise. Something doesn’t go according to plan, so you assess the situation, look at your options and figure out how to adapt. The more planning you do ahead of time, the easier those decisions become. Good itinerary planning isn’t about making sure everything goes exactly as expected — it’s about knowing your options when it doesn’t.
And that’s half the fun for me. I am SO looking forward to researching, planning and mapping out some future destination charters for us all. French Polynesia, Spain, Italy, Greece, Norway, Alaska… there are so many places still on my bucket list!
In this episode, I’ll take you through my step-by-step process for creating a sailing itinerary, from figuring out what kind of trip you want to have to choosing destinations, calculating distances, finding anchorages and marinas, and building in those all-important backup plans. Pour yourself a glass of wine, pull out the charts, and let’s start planning!
Cheers!
If you enjoyed this episode, you’ll love these too!
- Episode 068: Chartering in Croatia: Interview with Graham Toews
- Episode 077: Creating an Itinerary! The Basic Steps
- Episode 080: Three Generations, One Boat
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About Penny Caldwell
Penny Caldwell is a Canadian sailing educator, Sail Canada Instructor Evaluator, marine consultant, and host of the Your Pocket Sailing Instructor podcast. With nearly three decades of teaching experience, she is passionate about helping sailors of all skill levels build confidence, develop practical seamanship skills, and enjoy a lifetime on the water. Through her articles, podcast, instructor development programs, consulting, and sailing adventures, Penny shares real-world knowledge that makes sailing safer, more enjoyable, and more accessible for everyone.
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Sailing is a lifelong learning journey, and some of the best ideas come from fellow sailors. Have a question about this topic, or a tip you’d like to share? Leave a comment below—I read every one and enjoy hearing about your experiences on the water!
