Square vs Toast: What I Learned Running Two Bars on Two Different POS Systems

I own two bars and they run on two different point of sale systems. Not by choice — both systems were already in place when I bought each bar. Windsor Tap runs on Toast. The Beer and Now runs on Square. I’ve now used both long enough to have real opinions, and I’ll give you those opinions here along with the stuff nobody tells you about how these systems actually charge you.

HOW THEY CHARGE YOU — THE PART THAT SURPRISES PEOPLE

Both Toast and Square are subscription-based with a modular pricing structure. The base plan is relatively cheap — think $30 to $40 a month — but that’s just the entry point. Every add-on costs extra. Want the loyalty program? Extra. Marketing and text messaging? Extra. Payroll integration? Extra. Inventory management? Extra. You can build these systems up to be incredibly powerful, and the bill follows accordingly.

What catches most people off guard isn’t the subscription though. It’s the credit card processing fees.

Both systems charge a percentage on every transaction, and that percentage isn’t flat. It varies based on the type of card, the type of transaction, and how the card is used. An online transaction has a different rate than a tap payment. A manually typed card number has a different rate than a chip swipe. In my experience, a manually typed American Express is the most expensive transaction you can run — I don’t know exactly why, whether it’s fraud risk or encryption differences, but it’s consistently the highest fee.

At a bar doing a few hundred thousand dollars a year in revenue, one or two percent adds up fast. These fees come off the top before you see a dollar of net sales.

One more thing on fees: in Illinois you can pass credit card processing fees to customers as a surcharge, but there are rules. It has to be posted visibly near the point of sale. Currently I believe it applies to debit cards specifically, not the full range of card types. If you’re considering this strategy, look up the current Illinois requirements before you implement it — the rules exist and they need to be followed.

SQUARE VS TOAST — THE HONEST COMPARISON

Both are extremely well-built products. I don’t hate either one. But they make different choices and those choices matter depending on what kind of bar (or restaurant) you’re running.

Reporting and data access

Both systems have robust reporting. You can slice your sales by shift, by day, by product, by server, by hour, by day of the week — any way you can think to look at it, it’s there. Both allow you to export your data for external analysis.

The difference is in the app experience. Toast’s mobile app for managers is focused and fast. Within two taps I can see daily sales, what sold most, and how we’re trending. It’s intuitive and doesn’t overwhelm you with options. For a manager like my cousin Monique at Windsor — someone who needs the information quickly without wading through settings — Toast’s dashboard is excellent.

Square’s app is more comprehensive, almost to a fault. It’s essentially the full POS system in your pocket. You can create items, build discounts, recategorize products, run the entire bar from your phone. We used it at a car show recently — took tap payments directly from the app on a phone with no additional hardware. That flexibility is genuinely impressive. But the tradeoff is that there are a lot of buttons, a lot of settings, and a lot of options that most operators will never touch.

The API — and why I think this is a game changer

First of all, I think I should explain what an API is. An API is essentially a set of rules that lets two different software systems talk to each other. I had someone explain it to me like a data drive-through window. Pull up, request the data you need, and the API delivers the data you requested without ever having to go inside the store (or APP in this case). In practical terms, it means I can build my own dashboard that pulls my live sales data directly from square, without logging into square at all. 

This is where I think Square is going to win the long game, and I’ll put a timestamp on it: May 2026.

Square allows developers to connect to their data through an API token for free. That means you can build your own tools, your own automations, your own dashboards — and pull your live sales data into them. I’ve already created a small dashboard using “Claude”, and the dashboard we created turned out great and Claude walked me through every step. It’s starting to change how I run The Beer and Now.

Toast does not offer API access at this level. You’re locked into their ecosystem.

As AI tools become more accessible and more bar owners start building their own systems — or having systems built for them — the ability to connect your POS to external tools is going to matter enormously. Square is positioned for that future. Toast is not, at least not today.

Online store

Square has a built-in online store that integrates directly with the POS. As I add items in Square, I can make them visible in the online store. I can track inventory through it. Customers can place orders for pickup. This is a significant feature for a bottle shop like The Beer and Now where customers might want to browse and order before they come in.

I have never used this type of product on Toast, In fact, i am not sure they offer this type of product. But also it’s not something Windsor needs.Not a lot of restaurants or bars need a retail side, but The Beer and Now is a different breed. 

Payroll integration

Both systems have integrated payroll and both do it well. Square and Toast each have their own payroll modules with integrated time clocks, scheduling, availability management, and automatic clock-out when shifts run long. Both give employees access to their pay stubs, W2s, and tip history.

Toast just released automatic payroll in Q2 2026 — Square has had it longer. Both systems handle tax withholding and the associated filings. For a small operation this integration is genuinely valuable because the time clock and payroll live in the same system.

For a simpler operation you could go with an external payroll service like Gusto or ADP, but you’d need to manually export time cards and send them over. The integrated option is just easier.

Email and text marketing

Square has a solid email and text marketing module. You can run campaigns, set up automations — a welcome email when a customer signs up, a birthday offer, a coupon campaign — and track attributable sales from each campaign. So if you send a $5 off coupon and 20 people redeem it, you can see exactly what they spent. Measuring marketing ROI is genuinely possible.

I use this at The Beer and Now because that bar needs to reach out and pull people in. We’re not in a walking traffic area. We’re in an island-like strip mall. People have to make a specific trip to come to us. Marketing matters. But its important to note that my online store is the function that gets me email addresses & phone numbers, whereas on the Windsor side… we serve booze and close tabs. Two different types of bars.

Hardware

Toast requires you to buy their proprietary hardware — their terminals, their handhelds, their kiosks. Square gives you more flexibility. You can run it on an iPad using their stand, or just run it directly from a phone. For a festival or car show that flexibility is huge.

Both cost me roughly $1,500 in hardware when I set them up. Neither system locked me into a long-term contract — I’m month to month on both and can cancel anytime.

THE FIT PROBLEM

Here’s my honest frustration with Toast at Windsor: it’s too much.

Toast is built to run franchises. Multi-location restaurants with dining rooms, patios, multiple servers, complex menus, kitchen display systems. Windsor is a 900 square foot dive bar with a standard menu that barely changes and one or two people working at a time. I use about 10% of what Toast is capable of and I pay for 100% of it.

I don’t track inventory at Windsor (because I feel like I can’t afford it). I don’t need dining room segmentation. I don’t run server comparisons. I need a button that rings people up, tells me my net sales, shows me my tax collected, and gives me a basic sales summary. A much cheaper, much simpler system could do all of that.

If I were starting Windsor from scratch today I’d probably look at simpler options — there are lower-cost POS systems designed for exactly this type of operation. I got attached to Toast’s capability before I understood what I actually needed.

The Beer and Now is a different story. Because of the online store, the retail inventory tracking, and the marketing integrations, Square earns its complexity there.

THE SHORT VERSION

If you’re running a simple bar with a standard menu, no food, and no online retail — look at simpler, cheaper options before committing to a full-featured system. You may be paying for capability you’ll never use.

If you’re running a craft beer bottle shop or taproom with online ordering and retail — Square is hard to beat, especially if you ever want to build your own tools or connect external automation.

If you’re evaluating either platform — pay close attention to the credit card processing fees, understand which modules you actually need before you add them, and make sure you’re not signing a hardware contract that locks you in.

Both Toast and Square are genuinely excellent products with strong customer support. The question is whether you need excellent and expensive, or solid and simple.