Chartering Step 2 – Type of sailing charter & collecting quotes
- Episode 056 Your Pocket Sailing Instructor podcast
- Released: August 15, 2023
- Duration: 24 min 37 sec
“Choose the right charter, compare your options, and book with confidence.” ~ Sailing According to Coach Penny
Once you’ve chosen where you want to sail, the next step is figuring out how you want to charter. Bareboat, skippered, crewed, monohull or catamaran — there are plenty of options, and choosing the right one can make a huge difference to your trip. In this episode, I walk you through the next stage of planning a sailing charter: deciding what type of charter best suits your experience, crew and sailing goals, and then starting the process of collecting and comparing quotes. I’ll help you look beyond the headline price so you can ask the right questions, understand what’s actually included, and make a more informed choice before you book.
What’s your type?
We are continuing our journey about charter destinations and having a look at how to set up your own sailing charter. Very exciting stuff. So last week we covered step one, which is trying to figure out what is the goal of your sailing charter. Are you looking for solitude? Are you looking for really fun sailing? Maybe you looking to explore on shore? Depending on your goals, that will determine what type of sailing charter that you are going to book.
Skippered or Bareboat?
Do you have the qualifications to take out your own boat? This would be called a bareboat charter. If not, no worries! You may be looking for a skippered charter instead. This is where you hire someone to come out on the boat with you and take care of all the sailing. No fuss!
There are a couple big differences between these two options. One is much more expensive and one has you on the hook for any issues. Can you guys which is which? Ha! You got it! The bareboat sailing charter means you are taking on the responsibility of everything that happens on the boat. The skippered charter, means that someone else is in charge and on the hook for any issues. There is usually a significant cost difference between them though so do your homework!
Planning & Quotes
Once you have determined the type of sailing charter you are going to do, you need to start planning and collecting quotes! Last week I talked about different destinations and charter companies. This week we are looking at types of charters and collecting quotes for your sailing charter.
Collecting quotes can be as easy as requesting a quote through an online booking form. I tend to do this quite often just to get an idea of who is charging what and for where. From there I narrow down which charter company I’d like to work with and then I call them to figure things out. These sailing charters are often thousands of dollars, so you want to make sure you’ve found a reputable company.
Dividing up responsibilities
I have only ever done a bareboat charter. As I have the qualifications and experience to run a boat on my own, I’m comfortable with it. But it’s not for everyone! When you are selecting your crew, you’ll want to think about everyone’s strengths. Then think about how you can leverage their strengths on your boat. I like to set up a daily schedule for meals and cleaning. This takes all the guesswork out of expectations and responsibilities. I do this even when I have friends on board! It just saves me from having awkward conversations with people who are not pulling their weight. The rest of the crew tends to hold them accountable.
I’ll get into this in another episode, but for now have some fun planning!
Cheers!
If you enjoyed this episode, you’ll love these too!
- Episode 055: Chartering Step 1 – Choosing a destination
- Episode 078: Croatia 2025 Tips & Highlights
- Episode 038: What is my sailing journey? How did I get here?
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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!
