Skateboard vs longboard: which one should you start on?

Every few lessons, someone asks me whether they should have gotten a longboard instead. Or a parent tells me their kid wants a longboard because their friend has one. Before I give you the same answer I give them, I need to ask you the same question I ask them:

What do you want to do on it?

A skateboard and a longboard are built for different things. Pick the wrong one and you’ll spend your first month frustrated, doing something the board was never designed for.

1. What is the difference between a skateboard and a longboard?

A skateboard is shorter (31–32 inches), lighter, and has a kicked nose and tail for tricks. A longboard runs 33–46 inches with larger soft wheels built for cruising. Cruisers sit in between. The shape you pick should match what you want to do on it, not which one looks cooler in the shop.

A standard skateboard (sometimes called a “popsicle” because of the symmetrical shape) is typically 31–32 inches long and 7.5–8.5 inches wide. It has a kicked nose and tail, which is what makes tricks possible. The wheels are smaller and harder.

A longboard is 33–46 inches long, often wider, with larger soft wheels. The deck shape varies wildly depending on the style. Some are flat, some are dropped, some have pintails. There’s no kicked tail on most of them, which means ollies and flip tricks are off the table.

There’s also a third option that often gets overlooked: a cruiser. It’s shaped like a small skateboard (around 27–30 inches) but uses soft wheels like a longboard. Think of it as a hybrid.

2. Should I get a skateboard or longboard to learn tricks?

A skateboard. Street and park tricks—ollies, kickflips, grinds—require a popsicle deck with a kicked nose and tail. Longboards lack both, so tricks are off the table entirely. If there’s even a chance you’ll want to try an ollie in six months, start on a standard skateboard and save yourself from relearning your balance later.

Ollies, kickflips, grinding ledges, dropping into bowls. All of that requires a standard popsicle deck. You cannot meaningfully learn street or park tricks on a longboard. The shape is wrong, the weight is wrong, and the trucks turn differently.

Most of the kids and teens I teach want to learn tricks eventually, even if they say they just want to cruise at first. If there’s any chance you’ll want to try an ollie in six months, start on a skateboard. Switching later means relearning your balance on a completely different platform.

3. Is a longboard or skateboard better for cruising?

For pure cruising on open paths, a longboard’s larger wheels and longer wheelbase give a smoother, more stable ride. But if you’re navigating city sidewalks or taking public transit, a regular skateboard with softer wheels is easier to carry, store, and maneuver—and most of my adult students in Manhattan end up preferring exactly that setup.

Longboards are smoother over long distances. The big soft wheels absorb rough pavement, and the longer wheelbase feels more stable at speed. If you know you want to ride the boardwalk or cruise around your neighborhood and you have zero interest in tricks, a longboard is fine.

The problem: longboards are heavy and awkward to carry. If you’re commuting in the city, a 42-inch longboard does not fit under a subway seat or in a locker. A standard skateboard does. And if you put softer wheels on a regular skateboard (or get a cruiser), you get most of the smooth ride without the bulk.

I’ve watched a lot of adult students in Manhattan go through this exact decision. Most of them end up wanting a regular skateboard with slightly softer wheels, because they want the smooth ride but also want to be able to pick the board up and walk into a coffee shop without it being a whole thing.

4. Are longboards easier for beginners than skateboards?

Not really. A longboard feels more stable at first because the platform is wider and lower, but stable and easy aren’t the same thing. Longboards are heavier, harder to stop, and turn in wider arcs. A properly sized skateboard with tightened trucks is plenty stable for a beginner—I’ve taught five-year-olds on standard decks.

I hear this one constantly. And it’s half true. A longboard does feel more stable when you first stand on it, because the platform is wider and lower to the ground. But stable and easy are not the same thing.

Longboards are heavier, which makes them harder to stop. They turn in wider arcs, which is a problem on narrow sidewalks. And because most longboards have no kicktail, you can’t do a tail stop, which is the first stopping technique I teach every student. On a longboard, you’re foot-braking from day one, which is harder to learn.

A properly sized skateboard with the trucks tightened and the right shoesis plenty stable for a beginner. I’ve taught five-year-oldson standard skateboards. The stability issue is almost always about the trucks being too loose, not the board being too small.

5. Should a beginner get a skateboard or a longboard?

For most beginners—especially kids and teens—start with a standard skateboard. It handles cruising, tricks, and transit. If you decide later you want a dedicated longboard or cruiser, you’ll already have the balance and foot awareness to ride anything. Adults who genuinely only want to cruise can go longboard, but know it won’t translate to skatepark skills.

For most beginners, especially kids and teens: start with a standard skateboard. You can cruise on it, you can learn tricks on it, you can take it on the subway. It does everything reasonably well, and if you decide later that you want a dedicated cruiser or longboard, you’ll have the balance and foot awareness to ride anything. Here’s what to know before your first lesson.

For adults who genuinely only want to cruise or commute and have no interest in tricks: a longboard or cruiser is fine. Just know that it won’t translate to skatepark skills if you change your mind later. If you are an adult picking up skating for the first time, I wrote a full guide on learning to skateboard as an adult in NYC.

Not sure which one is right for you? I bring different setups to every lesson. Try them both and decide with your feet, not a sizing chart.