Premise
A party of players tells you "we've decided we're going to travel down the river instead of taking the King's road; we think we can make it through the rapids." Or they ask you "how long will it take us to cross the Atlantic?" Or they say "we've found Blackbeard's treasure map - how do we get to the island he's describing?" You want not only to have a specific answer prepared, or improvised on the spot - you want the answer to fit in with the rest of what the players know about the world, you want to support additional decisions they might make either on their way to their goal, or figure out what achieving their goal might lead to next, and you want to prepare for sessions in a way that will help you do this without overworking yourself. You need a watercrawl game structure.
The Alexandrian blog talks a lot about game structures, and why they're important for knowing what you need to prepare to make interesting sessions, and then how to apply what you prepared in-session in the best way. I can't say I've put a lot of it into practice, although I've tried. I've found some of his discussion of hexcrawling useful for creating interesting content as my players did some overland travel, but I did not use it to the furthest extent, and really didn't need to - this was a short trip to a very specific goal, it's not going to be a West Marches-type game with extensive recurring exploration. It was nice to generate random content that challenged me as a gamemaster while corresponding in general terms to how I felt the area they were traveling through would be like.
Earlier in my campaign, there was some water-based travel, and I didn't feel like I had good structure for it. I didn't know exactly how to deal with the players` choices, or even how to present them with options, so it ended up being very rail-roaded, in the sense that they were stuck on a ship that was traveling however it liked, and just happened to go where they (that is, me, my preparation) needed to go; or they essentially had to swim to specified areas. At best I could have been said to have provided them with a point-crawl, a network of specified places they could go with set paths between them, some of which involved going through water.
Here's a sketch for a structure that would help me do a better job in future campaigns. It will be geared more towards traditional, or even old-school play, where most of the information is generated and managed by the gamemaster, then discovered by the players as they engage with the world through their characters. I do hope more collaboratively-generated games would benefit, too.
Types of waterways
"Waterways" are areas mostly made up of water for traveling through. I am assuming that characters are not naturally aquatic, so they are starting and ending on dry land, and usually will want to remain dry, and therefore afloat, for most of their travel time. Here are some types of waterays in ascending complexity:
Rivers
Rivers are easy - they are essentially roads made of water. The simplest river is a wide waterway that you can go up and down, with banks that are easy for a row-boat to stop on. You can make it more complex by having a fast stream, add rapids or narrows for tricky or dangerous passage, connect them into a network of tributaries and splits, have them push into a marshy delta, or have the river end in an estuary in the sea, but your focus when planning can be as if you are looking at a graph of roadways which happen to be watery, and to which the price of entry is either excellent swimming or a vessel to ride or pilot. Rivers can interface with more complicated regions like marshes, lakes, and shores.
Lakes and marshes
Lakes and marshes are a bit more involved, but should still be easy to navigate. The periphery is visible (so we are not considering something like the Great Lakes), and you're unlikely to be lost on a clear day. Inclement weather can be avoided by just landing your vessel near the shore until it's cleared up. But if you do want to go somewhere in the lake when it's raining, or snowing, or very windy, a navigator and crew's skills can be tested to the limit. Nevertheless, in terms of planning, you would be focusing on points of interest, maybe deciding that some parts of the map are shallower or deeper, but mostly when deciding on approaches or paths.
Shores, estuaries, archipelagoes
Here we still expect landmarks to aid in navigation, but the open sea starts calling to us. Sudden streams and waves can lead us astray, and if the ship is shorebound, not meant for navigating out of sight of land, that can mean death. You can key hexes that contain the parts of the shore you're interested in, or the archipelago - it essentially becomes either the periphery of your land hexcrawl, or a hexcrawl over some range of the ocean.
The open sea or ocean
Here the characters, or whoever is in control of their vessel, need to use actual navigation, of the historical modern era, or of a magical sort. Sampling the soil and comparing it to your knowledge of the area can help in shallow waters, but for the most part you want a combination of compasses, astrolabes, and divination spells. You'll also want to use whatever methods of meteorological predictions you have, because weather can make or break your voyage, especially if you are sailing.
The open sea is not necessarily featureless; trade routes involve following big currents or consistent wind patterns, although, as in shorebound travel, inclement weather can lead you astray, and these features are not as dependable as dry land. There may also be known islands and lighthouses to show you that you have arrived near your goal, or to ward you off dangerous shoals.
You might also know of a destination, but little else, say from a pirate's journal: combining known coordinates and stellar navigation, you may know where you need to go at any point in time; but using known routes for part of the way can help you travel speedily and safely, while uncharted waters might lead to unexpected dangers and opportunities along the way.
Charting itself can be an important challenge, or even the goal of an adventure. This requires very good navigational skills on the part of the character, but also potentially the gamemaster and players.
Indeed, I don't know that I would be able to hone down open sea adventuring without actually looking into real navigation and charting. I have a few books on the topic, and will have to spend time on them to get a sense of how much of a task it would be. Hopefully it's possible to have a map with general coordinates and points of interest, and for you to easily keep the position point of the vessel on the map and how it relates to them. A kind of multiscale map, keying trade routes, trade winds, notable regions, then notable smaller areas, islands, and lighthouses, might be the way to go. The ship's coordinates might need to be calculated exactly, even if not all of the models require such precision to decide their effects.
The map also points to something else: open sea navigation pretty much requires that you decide the overall shape of your world. Is it a deformed oblate spheroid, like Earth? Is it a flat lozenge, like Greg Stafford's Glorantha? You have to decide, because much will be determined by it, not the least of which the coordinates you will use, and what potential edge cases they might lead you to.
Weather
Trips on water are significantly affected by the weather. Even rivers can overflow or dry up based on precipitation; and a storm can turn an easily navigable lake into a deathtrap. Winds and waves can lead you from a simpler area to a more complicated one, for which you might not be prepared. Some climates can turn the very water into solid hazards: frozen lakes and regions of the sea, and icebergs. You need to think about seasons, and how they affect weather in your world; the different climates and what they entail. How far you want to go - do you just want to have a random generation of daily weather, or correlated patterns requiring meticulous journals to account for?
Inclement weather can impede navigation, and unlike getting lost on land, water moves. You may find yourself in a place you weren't expecting even if you attempt to be still until the storm passes.
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