The call of the sea is notoriously hard to resist. But unless you’re already a sailor or the ghost of Ernest Hemingway, taking boats out on the water can seem a daunting task. To begin your journey, you’ll first need to figure out which types of boats best suits your needs.

Thankfully, the experts behind Chicago’s Tall Ship Windy are here to help. Windy is the only four-masted tall ship in the country, and as such it presents a unique sailing opportunity on the waters of Lake Michigan. We spoke with Captain John “The White Tiger” Ludvik, who let us know which other seaworthy vessels are worthy of our attention.

Tall Ship

This elegant boat embodies the adventurous spirit of a 19th-century schooner—the vessel on which American and European sailors traversed the world by sea.

Pro: Today’s tall ships offer a surprisingly smooth ride and plenty of space for up to 150 passengers to spread out. Despite its intimidating bulk, Captain John claims that the larger tall ship “is easier to handle than a small boat, once you know how to sail.”

Con: You can’t sail one of these by yourself. Tall Ship Windy, for example, is manned by a multitalented crew. Some people man the sails while others keep a weather eye on the horizon, scanning the waters for signs of kraken.

Another Con: Only some tall ship captains can legally officiate weddings. Read why, and delve into other debunked sailing myths, here.

Dinghy

Dinghies tend to be smaller rowboats, though some are rigged for sailing. Some are used as lifeboats for larger ships, but others can be taken out on solo explorations.

Pro: Dinghies come in a number of sizes, all a variation on “small.” This means that both children and adults can use them to explore the waters at their own pace. According to Captain John, they’re also a great way to escape a desert island—provided yours has a sail attached to it. “The nice thing about a sailboat,” the Captain says, “is that it can sail … forever … You can sail around the world with just a boat and a sail.”

Con: Sailing around the world by yourself sounds pretty lonely, doesn’t it? These smaller boats also can get pushed around in storms and tend to capsize more often. Of lesser probability but equal concern: a shark might mistake you for a really fat and misshapen seal.

Kayak

A personal hunting boat first used by the Inuit and Aleut people, the kayak was originally constructed from stitched animal skins over a wood or whalebone frame. Today, they’re far more likely to be made of fiberglass or polyethylene.

Pro: Captain John says “boating is an avenue to go out into nature.” To extend his metaphor, think of the kayak as a sleek, hand-powered motorcycle. No matter what you want to see, a small, maneuverable kayak can go pretty much anywhere—from the ocean to a small inland creek.

Con: “A kayak doesn’t have a keel,” Captain John warns. This means that it is more prone to tipping over. On the plus side, there’s no better way to get acquainted with marine life.

Motorboat

As its name implies, motorboats are simply boats powered by an engine, making them the fastest (and loudest) option on our list.

Pro: Captain John and his friends favor motorboats on days when they just want to “get away.” They’re especially useful if your goal is to zoom around and scoff at sailboats stuck in the doldrums, those periods of still wind that halt ships.

Con: The exhaust fumes and loud noises can spoil the silence of the sea, which speaks to those who know how to listen.

Standup Paddleboard

This isn’t really a boat, but it is a seaworthy vessel and a popular way to explore calmer ocean inlets. Some paddleboarders even practice yoga out on the water.

Pro: One of the smallest “boats” out there, this narrow board is highly transportable. It’s also remarkably easy to master: just place it in the water, stand on top, and paddle your way out.

Con: Well, it’s actually not that easy. Paddleboarding is all about perfecting your balance. It can certainly be relaxing, but you have to expect a few splashes first.

Ice Boat

This is a boat made entirely of ice. Just kidding. It’s a variation on the sailboat that’s fitted with skis or runners so it can travel over ice instead of water.

Pro: People who live in or near the Arctic only get liquid water for a few months out of the year. During those long winters, the ice boat transforms from a water vessel into an ice-skating boat, thanks to the skis along its underside.

Con: Can fly at speeds of up to 56 miles per hour, but cannot seem to nail the Salchow jump.

Horse

Equus ferus caballus.

Pro: “There are a lot of different folk songs about taking your horse in the water,” Captain John claims. So, um, somebody has to find this appealing.

Con: Can’t actually swim.

Photos by Andrew Nawrocki.