--- title: "Stripe vs Square for Tour and Charter Operators" description: "Stripe or Square for a tour business? Compare US rates, payouts, refunds, disputes and holds, and check your island is supported before anything else." url: https://junglebee.com/blog/stripe-vs-square-tour-operators published: 2026-10-19T07:16:00+00:00 updated: 2026-10-19T07:16:00+00:00 --- [Getting paid](https://junglebee.com/blog/category/getting-paid)5 min read # Stripe vs Square for Tour and Charter Operators Stripe or Square for a tour business? Compare US rates, payouts, refunds, disputes and holds, and check your island is supported before anything else. [**Michael Rouveure**](https://junglebee.com/author/michael-rouveure)Founder, Junglebee ยท 19 October 2026 ![Card terminal and phone on a tour check-in counter at a Caribbean dock](https://junglebee.com/_vercel/image?url=https%3A%2F%2Frbucznrhwdixonqrldre.supabase.co%2Fstorage%2Fv1%2Fobject%2Fpublic%2Fblog%2Fposts%2Fstripe-vs-square-tour-operators%2Fc4bcd1862319c45a.webp&w=960&q=75) **In short** - If your business is supported, start with Stripe for mostly online advance bookings and Square for mostly dock walk-ups, then check your booking integration. - Check your territory first. Stripe covers Puerto Rico and French Saint-Martin, Guadeloupe and Martinique, not USVI or Sint Maarten. Square's US processing covers only the 50 states and DC. - Neither refunds processing fees. Square has no dispute fee. Stripe charges $15 per US dispute, plus $15 to counter manually, and returns only that second fee if you win. Stripe or Square? If you run tours or charters and you're setting up card payments, it's usually the first question. Most comparisons answer it like you're opening a coffee shop. You're not. Your guest might pay three weeks ahead on a phone in a hotel room in Ohio, or hand you a card at the dock ten minutes before you cast off. To a processor, those are two very different businesses. So before rates, ask whether your business can sign up with either of them where it's registered. Then ask where most of your money comes in, online in advance or in person on the day. Get those right and the choice mostly makes itself. ## Advance bookings online or walk-ups at the dock Stripe grew up online. It's built around websites and developers, and in my experience it's the processor you'll most often find behind a tour booking widget. If most of your trips sell days or weeks ahead through your own site, Stripe fits that flow. Square grew up at the counter. Its readers and Terminal are built for in-person cards, and whoever's at the kiosk can run the app on a phone. If you sell sunset sail seats to people strolling the boardwalk, that's Square's home turf. Sell both ways? Pick for the side that brings in more money. And don't forget the phone booking. A concierge calls, reads you a card number, you type it in. That's a keyed-in payment, and both charge more for it. ## What the published US rates say These are standard US list rates as I write this. They change, vary by country and can be custom for bigger accounts, so check the live pages before you budget. - Stripe online: 2.9% + 30 cents per domestic card payment, plus 1.5% for international cards and another 1% if currency conversion is needed. - Stripe Terminal in person: 2.7% + 5 cents for domestic cards. Manually entered payments through the Dashboard or Terminal MOTO use the online rate plus 0.5%, so 3.4% + 30 cents domestic. - Square in person: 2.6% + 15 cents on the Free plan, a bit lower on paid Plus and Premium. - Square online and invoices: 3.3% + 30 cents on Free, 2.9% + 30 cents on Plus and Premium. Online API payments are 2.9% + 30 cents on every plan, so ask which rate your booking integration uses. Keyed-in or card-on-file payments are 3.5% + 15 cents on every plan. Cards issued outside the US add 1.5%. At those domestic reader rates, Square Free wins above $100 a payment, Stripe Terminal wins below it, and they tie at $100, before hardware or optional fees. Stripe's base online rate beats Square Free's online and invoice rate but matches Square's Online API rate. Both add 1.5% for international cards on US accounts. Run your own ticket sizes, guest-card mix and any plan subscription through both. ## Payouts, refunds and the weather day You're paying fuel and crew before the season pays you back. In Stripe's US example, funds are available in your Stripe balance after 2 business days; when they reach your bank depends on your payout schedule and bank. First payouts typically take 7 to 14 days, depending on industry, country and risk. Standard US Instant Payouts cost 1.5%, 50 cents minimum (Connect pricing differs). Square's free standard transfers normally take 1 to 2 business days, as soon as the next business day, and eligible instant transfers cost 1.95%. Now the part nobody likes. Christmas Winds blow out your morning trip and you refund a full charter. Neither company returns the original processing fee, so you eat it. I'd offer a reschedule or credit where the guest agrees and your terms and local rules allow it, but never in place of a refund you owe. Square Invoices lets you request a deposit and set a later due date for the balance. Stripe Invoicing supports partial payments too; its scheduled invoice payment plans are in private preview. Either way, ask your booking vendor how deposits and the second payment work. ## Chargebacks, holds and why tours get watched Under standard US pricing, Stripe charges $15 when a dispute comes in and another $15 if you counter it manually. Only the counter fee is returned if you win; the first $15 isn't, unless your contract says otherwise. Square says it charges no dispute fee. If you get a lot of "I never booked that" claims, that favors Square. Holds are the other side of it. Square may hold a reserve if you collect payment before delivering the service, and its help center names travel and tourism as prone to disputes. Stripe lists travel reservation services as a restricted category that needs extra review. A charter company selling its own trips isn't automatically a reservation service, but expect questions. ## Check your island before you compare anything This is where most Caribbean comparisons fall apart. Stripe says a US business has to be in the 50 states, DC or Puerto Rico, not the US Virgin Islands. Businesses in French Saint-Martin, Guadeloupe and Martinique can sign up under France, but St. Barts can't, and neither can Sint Maarten, Aruba, Curacao, Bonaire or the BVI. So on St. Maarten, a French-side business can apply under France, subject to Stripe's approval, while a Dutch-side one can't. Same island. Square processes cards in the US, Canada, the UK, Ireland, France, Spain, Australia and Japan. Its US payment terms limit processing to the 50 states and DC, so not Puerto Rico or the USVI. For most islands, neither one is an option. Check your exact country with each company first. What I won't do is recommend an overseas bank account as the answer to a local payments problem. I see Caribbean tour companies open a US or European bank account just to run Stripe, then move the money back to the island. It's crazy. I'd want a local accountant to check that setup before a single payment went through it. That gap is why we built JB Pay at [Junglebee](https://junglebee.com/charters), so island operators can take cards online and get paid out to their local bank. ## Follow the money, then check the map If your country is supported and most of your bookings come in online ahead of time, start with Stripe. If most of your money comes from dock walk-ups, start with Square. Then ask your booking software which one it actually connects to, because a great processor doesn't help if your calendar can't talk to it. And if your island isn't on either list, don't build a workaround. Find a processor that pays out where you live, not where you had to open an account.