How to Book a Charter

Balancing Escapsim & Reality
Three-Cabin Fever

We get a lot of first time charterers — from sailing school students taking that ‘next step’ to longtime sailors.

And it can be a bit daunting, intimidating even.

We have most of the questions, along with all the documents needed, all right here.

But let’s take a look at 5 big questions.

How Many?  How Long?  When?  How Big?  Who’s Driving?

Those are the big questions that need to be answered.  Let’s look at each.

How Many?

Gather your crew. How many are actually going to commit to the trip? And commit means willing to put down a deposit. We’ve been through this with our own charters to the Caribbean. Everyone ‘wants‘ to go. But who’s actually willing and able to take the time off and put some money down? If you are the one putting this charter together, this is a critical first step.

NOTE:  The ‘How Many’, ‘How Big’ and ‘Who’s Driving?’ questions all eventually collide.  Read on and it will all make sense.

How Long?

How many days do you want to sail? Or, perhaps it’s more like “how many days are you able to take off work and sail?” With Great Lakes Sailing Co. you can sail for as little 1 day and up to….the sky’s the limit. It’s all about how much time your group has, and how much sailing and exploring you want to achieve.


Pretty straight forward. You know you have 7 full days. What dates?

How Big?

What size boat? This question is all tied up and twisted together with ‘Who’s Driving’ and ‘How Many’. If you have a group of 3 couples, and each wants a private cabin, that narrows the boats down to those with 3 cabins.  And that’s great. As long as ‘Who’s Driving’ has the appropriate experience.

Now let’s let’s say you have a crew of 6. You know that ‘Who’s Driving’ doesn’t have the experience for a 38′ boat with 3 cabins. But, one couple doesn’t mind sleeping on the converting salon table…that means you can charter a smaller boat.

See where we’re going here?

Who’s Driving?

Who’s the captain? The skipper? The one who is going to be responsible for the boat and the crew? This is perhaps the most important question. And perhaps it should be the leading question. But we’ve come this far and didn’t feel like re-arranging everything.

Everything really hinges on experience. We have all charterers fill out a Charter Application.  It’s essentially a resume. This, in addition to all the conversations and email exchanges, allows us to determine how big of a boat is appropriate.

For example. You’ve done all kinds of sailing and have years and years of experience on your personal 1985 Catalina 27. Which is great. Unless you are requesting the Jeanneau 379. That’s too big of a jump in boat size.

So the size of the boat, which can affect the size of your crew, has to correlate with the captain’s experience. It’s not uncommon for a charterer to charter a boat a little bigger. And if it’s within reason, and the experience is there, we will then supply a captain to work with the charterer (and the crew) to make certain everyone is capable and comfortable chartering the boat.

So what have we learned about ‘Who’s Driving?’ Well, once you know who’s driving, you can then determine a size boat that is appropriate, which will then allow you to determine how many in your crew.

Don’t worry though. We do this for a living. So all you have to do is give us a call, or shoot us an email, and we’ll guide you through the steps of booking a charter.

At the end of the day, safety is our number one concern. Yes, we want all of our charterers to relax, ‘forget about life for a while’, throw on some Jimmy Buffett and turn off the mobile devices. And as long as everyone is safe, and comfortable, it makes for a much more relaxing, enjoyable charter…for both of us.

So gather your crew and let’s plan a charter.


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