Some of the things covered in the American Sailing Association’s 104 certification course (“Bareboat Cruising Standard”) probably won’t seem surprising after you hear about them, but really aren’t things people think about when they think of how amazing a sailing vacation might be.

I’m talking of course about the planning stages: there’s a lot to do. I could run down a pretty extensive list and most of the items on the list would clearly be common sense. Things like planning flights, provisioning for the trip, and getting all the money put together between the people going on the trip aren’t all that different from other vacations.

But then you really get into the planning and realize just how much there is to do, and how far ahead you need to do it.

For example: location. If you’re doing a bareboat charter (meaning you’re renting a sailboat and crewing it among yourselves) it isn’t as easy as just identifying where your group wants to go. First, you’ll need to get as much information about the area as possible. Which charter companies operate in the area? What kind of boats do they have? What sort of sleeping layout is available on those boats? What’s the layout of the area I plan on sailing in? Have I sailed in an area like that before? Where are the protected anchorages in that area? How many other boaters will I be around? How are the laws and signage different from what I am used to? What does my group do if we run into trouble?

And that’s just location!

I’ve been planning (with my good friend, Charles N. Cox) a two-boat, two-captain sailing trip in the British Virgin Islands for over a year now, and our trip isn’t until May of 2015. We’ve both sailed in the BVI before, we’ve used the same charter company (Voyage Charters) and even sailed the same model of boat (and, in Charles’ case, the exact boat), but we still need this crazy amount of lead time to coordinate everything (the money part may be the biggest pain in the ass).

I’ve recently begun planning another trip for somewhere around January 2016 with some other friends and I’m hit with complexity right away: my current favorite choice, Belize, presents some unique challenges that will require additional coordination with a charter company, things that as a group we’ll need to decide if we’re ok with before we even finalize where we go. Like most other things in life, it will come down to acceptable compromises: the easier it is to do, the more other people will be doing it. We could take the easy route and just sail around in the Bahamas, sure. We’d probably even have a great time doing it! But we wouldn’t get away from people–we’d be competing for anchorages, mooring buoys, even hiking and snorkeling spots.

In the end, though, all this effort is worth it. There’s nothing like waking up on a catamaran in a quiet, protected anchorage, miles from anybody, in the middle of the tropics on a clear warm day, knowing your most difficult decision that day will be: coffee or tea?

I’ll take the tea.