Are Penny Boards or Longboards Easier to Ride?

Longboards are easier to ride for most beginners, offering superior stability from a longer deck, wider trucks, and larger wheels. Penny boards, especially the common 22″ model, are significantly harder to balance on due to their short wheelbase and narrow platform, making them a less forgiving choice for learning. The ease gap narrows with the larger 27″ Penny Nickel board, but it still lacks the smooth-rolling comfort and control of a longboard over 89 cm (35 inches) long.

That gap in stability isn’t just about comfort. It’s about how many times you hit the ground before riding feels natural. A board that bucks you off at every crack teaches you to be tense, not balanced. A common question for beginners is: are penny boards or longboards easier to ride?

What follows is a breakdown of why that stability difference exists, grounded in the specs manufacturers publish and the experiences riders report when addressing the are penny boards or longboards easier to ride question. The concrete numbers that define each board type, the specific challenges a beginner faces on each, and which choice lets you spend more time rolling and less time stumbling.

Key Takeaways

• Longboards over 89 cm (35 inches) are defined by the FHWA, and their longer wheelbase and wider stance platform are cited by other sources as making them easier for beginners.
• The Penny 22″ Classic is rated as having “Poor” stability and is “Hard” for beginners by retailer guides, while the 27″ Nickel is rated “Good” and “Easy.”
• Penny board wheels are 59mm, and sources state that smaller wheels slow the board down and require more effort pushing compared to the larger wheels common on longboards.
• Riders over 5’5″ will find a 22″ Penny board disproportionately difficult to balance on, as the effective standing platform shrinks relative to shoe size.
• For pure commuting and portability, a Penny board wins; for learning, comfort, and control, a longboard is the better tool.

What Defines a Penny Board vs a Longboard?

The U.S. Federal Highway Administration’s guide to nonmotorized transportation safety provides the clearest, most neutral definitions. According to their FHWA report on skateboard and longboard characteristics, a traditional skateboard is under 84 cm (33 inches) long. A longboard is defined as over 89 cm (35 inches). Deck width for standard skateboards is noted as 19–21 cm (7.5–8.25 inches), with wheels normally 52–60 mm in diameter, acknowledging that “larger wheels are often used on longboards.”

Penny boards, by brand, are a subset of plastic cruiser skateboards. The iconic Penny Skateboards 22″ Classic is 56 cm (22″) long and only 15 cm (6″) wide. The Penny Skateboards 27″ Nickel (sometimes called the “Big Mamma”) is 69 cm (27″) long and 19 cm (7.5″) wide. Both use 59mm wheels.

So, by the FHWA’s ruler, the 22″ Classic is a short skateboard, and the 27″ Nickel sits in a gray area between a long skateboard and a very short longboard. This size ambiguity is why the are penny boards or longboards easier to ride question has two answers: one for the tiny 22″ Penny everyone pictures, and another for its bigger 27″ sibling.

The Federal Highway Administration defines longboards as over 89 cm (35 inches) in length, distinguishing them from traditional skateboards under 84 cm (33 inches). This length directly contributes to a longer wheelbase, which is the primary mechanical source of a longboard’s greater stability and easier ride for beginners.

The 27″ Nickel vs 22″ Classic: A Penny Board Reality Check

If you’re considering a Penny board, you’re likely looking at two models: the 22″ Classic and the 27″ Nickel. Treating them as the same experience is the first mistake a beginner makes.

The numbers tell a stark story. The 22″ Classic has a truck width of just 7.62 cm (3″). The 27″ Nickel’s trucks are 10.2 cm (4″) wide. That extra inch of truck width translates directly to lateral stability. More telling are the ratings from retailer guides. The Euroskateshop guide rates the 22″ Classic’s “Stability” as “Poor” and suitability for a “Beginner (never skated)” as “Hard.” For the 27″ Nickel, it rates stability as “Good” and beginner suitability as “Easy.”

Penny Skateboards’ own size guide says the 27″ is “Very stable… Better for beginners,” while the 22″ is “Less stable than our 27″ skateboard.” Penny Skateboards rates its 27″ board as ‘Very stable… Better for beginners,’ while Originalskateboards.com states Penny Boards are ‘more unstable and sketchy to learn on than a longboard.’

Why the big difference in feel? It’s physics. The wheelbase (the distance between the front and rear axles) is much shorter on the 22″. A short wheelbase makes a board turn quicker, but it also makes it feel “squirrelly.” Your balance point is tiny. A slight shift in your weight has a magnified effect on the board’s direction. On the 27″, that wheelbase is longer, giving you a more forgiving platform. Your feet have more room to adjust without instantly over-correcting.

This is where rider size crashes into marketing. A reviewer on Originalskateboards.com notes that for a rider over roughly 5’5″, a 22″ Penny “becomes significantly harder to balance on.” Your feet hang off the edges, and the already minimal platform feels even smaller. The 27″ Nickel, with its 19 cm width, starts to approach the width of a standard skateboard deck, offering a more natural and secure stance.

Specification	Penny 22″ Classic	Penny 27″ Nickel	Why It Matters for Ease
Length	56 cm (22″)	69 cm (27″)	Longer wheelbase on the Nickel increases stability.
Width	15 cm (6″)	19 cm (7.5″)	Wider deck provides more secure footing.
Truck Width	7.62 cm (3″)	10.2 cm (4″)	Wider trucks resist tipping, making the board feel more planted.
Beginner Suitability (Euroskateshop)	Rated “Hard”	Rated “Easy”	Direct assessment from a retailer guide based on user feedback.
Stability (Euroskateshop)	Rated “Poor”	Rated “Good”	Confirms the tangible difference the specs create.

Longboards: The Stability-By-Design Choice

A longboard over 89 cm (35 inches) long isn’t just a longer Penny board. It’s built on different principles for a different job: smooth, stable, efficient travel. Where a Penny board prioritizes portability, a longboard prioritizes ride quality.

The foundation is the deck. Longboards are over 89 cm (35 inches) long, and their larger standing platform is cited as making them easier to balance on. This creates a massive standing platform compared to any Penny. You can stand with your feet shoulder-width apart, a stable, comfortable position that doesn’t require constant ankle tweaking to stay on. This is the “easier to balance” and “more forgiving” platform that Originalskateboards.com highlights.

Then come the wheels. While Penny boards use 59mm wheels, Larger wheels are often used on longboards. According to the same source, “bigger wheel size… Is going to roll over rocks, cracks and bumps way easier.” The physics are simple: a larger wheel has a lower angle of attack. It climbs over obstacles instead of catching on them. This means fewer sudden stops that can throw a beginner forward onto their hands.

Finally, the trucks. Longboards typically use reverse kingpin (RKP) trucks. These are wider and have a different pivot geometry that makes them more stable at speed and easier to turn with lean. They’re designed for carving and cruising. Penny boards use traditional kingpin trucks, which are narrower and tuned for quick, sharp turns—exactly what makes the 22″ feel twitchy.

Common mistake: Choosing a board based on where you’ll store it, not where you’ll ride it. A board that fits under your bed but throws you on every cracked sidewalk will end up stored permanently after a few frustrating tries.

Where Penny Boards Actually Make Sense

To be honest. Penny boards exist and are popular for a reason. They solve a specific problem brilliantly. As Originalskateboards.com concedes, “The only place a Penny Board is really better than a Longboard is if you need to fit it in your backpack, or skate through a crowded airport.”

That’s the whole value proposition. A 22″ Penny weighs a few pounds and can be clipped to a backpack or thrown in a locker. It’s a “last-mile” solution for a commuter getting off a bus or train. For a student navigating crowded campus pathways, its tiny size and extreme maneuverability are assets. The plastic deck is also waterproof and nearly indestructible, requiring zero maintenance.

However, this comes at the direct expense of ease of use. The small wheels mean you feel every pebble. The narrow, flexible deck offers little damping from vibration. The short wheelbase demands your full attention. An experienced rider can manage these trade-offs. A beginner is fighting them from the first push.

If portability is your absolute top priority and your journeys are on near-perfect pavement, a 27″ Nickel is a far more manageable compromise than the 22″ Classic. It retains much of the carry-ability while offering a noticeable jump in stability.

The Beginner’s Experience: First Pushes and Common Wipeouts

The learning curve isn’t abstract. It’s a series of physical moments. On a longboard, your first challenge is committing your weight to a stable platform. The board doesn’t wiggle much as you find your stance. Pushing feels natural because you’re not fighting for balance simultaneously. When you hit a small crack, the large wheels thump over it. You might feel it, but you likely won’t stop.

On a 22″ Penny, the first challenge is simply staying on the board while stationary. The deck flexes under your weight. Finding a comfortable, wide stance is impossible. Your feet are almost touching. Your first push often results in an over-correction because the board responds too quickly to your shifting weight. That first pavement crack you hit? It can stop the small wheels dead, and the short board buckles, launching you forward. You learn to scan the ground intensely, which divides your attention from the fundamentals of balance and pushing.

Reddit threads in communities like r/OldSkaters are filled with this reality. One user who bought a 27″ Penny noted, “Pennyboards are not great for beginners. Get a nice comfy cruiser or a longboard.” Another highlighted the control issue: “The smallness of it also makes it harder to control. It’s squirrelly and turns different than a full size board.”

This is the core of the ease question. A longboard allows you to isolate skills. You can work on balancing, then pushing, then turning. A small Penny board forces you to master all three at once while also playing an intense game of “spot the pebble.”

Key Components Compared: Why Longboards Feel Safer

Breaking down the ride experience to its parts shows why one board inspires confidence and the other breeds hesitation.

Deck Material & Feel: Penny boards use a molded plastic deck. It’s flexible. Under a heavier rider, it can bow noticeably. This flex can feel unstable and unpredictable. It provides a consistent, predictable platform that doesn’t change shape under your feet. This reliability is a huge psychological boost for a beginner.

Wheels & Rolling Efficiency: Penny board wheels are 59mm and made from a basic urethane. As noted in our research, they are “made out of less expensive, lower performance, urethane that slows them down further.” You have to push more frequently to maintain speed. Longboards often use larger wheels, which sources state roll over obstacles more easily than smaller wheels. They maintain speed longer and absorb vibrations better, making for a quieter, less taxing ride.

Trucks & Turning: The narrow, traditional kingpin trucks on a Penny are tuned for agility, not stability. They can feel “sketchy” at even moderate speeds. The wider, reverse kingpin trucks on a longboard provide a progressive, predictable turn. Lean a little, turn a little. Lean more, turn more. This linear response is easier for a new rider to understand and control.

Component	Penny Board (22″-27″)	Typical Beginner Longboard	Impact on Ease of Riding
Deck	Flexible plastic, narrow (6″-7.5″)	Stiff maple, wide (9″-10″)	Stiff, wide deck offers secure, predictable footing.
Wheels	59mm, basic urethane	65-70mm, high-rebound urethane	Larger wheels roll smoother, faster, and over cracks.
Trucks	Narrow, traditional kingpin	Wide, reverse kingpin (RKP)	RKP trucks are more stable and easier to control when turning.
Primary Goal	Portability and quick maneuvers	Smooth cruising and stable carving	Longboard design prioritizes rider comfort and control.

Who Should Choose Which Board?

This isn’t a one-size-fits-all answer. Your height, weight, intended use, and tolerance for a learning curve decide it.

Choose a Longboard if:

• You are a complete beginner and ease of learning is your top priority.
• You are over roughly 5’5″.
• You plan to ride on varied pavement, including streets with cracks and bumps.
• Your goal is relaxed cruising, commuting on decent roads, or learning to carve.
• You value a smooth, comfortable ride over ultimate portability.

Choose a Penny Board (27″ Nickel) if:

• Portability is your top priority (e.g., you must carry it on a bus or store it in a small locker).
• Your riding surfaces are very smooth and well-maintained.
• You are a smaller-framed rider and have tried the 22″ and found it too tricky.
• You already have some board sport experience (skateboarding, snowboarding) and want a compact cruiser.

Avoid the Penny 22″ Classic as a First Board if:

• You are learning from zero. The consensus from guides, retailers, and user reports is clear: it’s a hard way to start.

For most people asking this question, the path of least resistance (and fewer falls) leads to a longboard. The learning curve is simply gentler. If you want a specific starting point, our guide to the best longboards for beginners breaks down good first picks.

Frequently Asked Questions

Can I learn to skateboard on a Penny board?

You can, but it’s the hard mode. The small, flexible platform and twitchy trucks make mastering balance and pushing more challenging than on a standard skateboard or longboard. If learning is the goal, a larger, more stable board will lead to faster progress and more enjoyment.

Is a 27″ Penny board easier than a skateboard?

It depends on the skateboard. A standard street skateboard (around 32″ long) has a stiffer deck and wider trucks than a 27″ Penny, which can make it more stable for just riding around. However, the Penny’s softer, larger 59mm wheels will handle rough pavement better than a skateboard’s small, hard wheels. For pure cruising ease, a dedicated cruiser skateboard or a longboard is easier than both.

Are longboards too big for kids?

It depends on the child’s size and the longboard. The key is matching the board’s wheelbase to the rider’s stance. A board that’s too long can be unwieldy, but one that’s appropriately sized offers kids more stability than a tiny Penny.

How much harder is a Penny board than a longboard?

Significantly harder for a beginner. The difference manifests in three ways: 1) Balance: The small platform requires constant micro-adjustments. 2) Pushing: You must re-balance after every push. 3) Hazard Reaction: Small wheels stop on cracks, forcing sudden dismounts. A longboard mitigates all three, allowing you to focus on one skill at a time.

Do the skills transfer between board types?

Yes, but not perfectly. Balance and pushing fundamentals transfer directly. However, the muscle memory for the quick, sharp turns of a Penny board is different from the deep, leaning carves of a longboard. Switching between them requires a short adjustment period. Learning on a stable longboard gives you a solid foundation that makes adapting to a smaller board later much easier than the reverse.

The Bottom Line

The data from manufacturers, safety guides, and rider communities all point the same way. If your question is purely “which is easier to ride,” the answer is a longboard. Its design delivers stability, smoothness, and predictable control that a beginner can trust.

The 27″ Penny Nickel blurs the line, offering a middle ground if you absolutely need a compact board. But the iconic 22″ Penny Classic is a specialist tool. It excels at being carried, not necessarily at being ridden by someone still figuring it out.

Your choice ultimately hinges on what you’re optimizing for. Optimize for a gentle learning curve and riding pleasure: get a longboard. Optimize for stuffing in a bag and short hops on perfect ground: a 27″ Penny might work. Just know what you’re trading. The easier board is the one you’ll actually ride more than a few times.