Nantucket's premier luxury transportation service was manually re-keying client card details into Square after every ride. We migrated their payments to Stripe with a secure card-vaulting link, cutting an estimated 108–142 hours of admin work in a peak month.
- Client
- Island Experience
- Industry
- Transportation
- Focus
- Square-to-Stripe Migration
The Opportunity
Island Experience Transportation, Nantucket's premier luxury transportation service, ran client bookings on a manual credit card authorization process through Square: card details were collected and re-entered by staff after each completed ride. At 650–850 reservations in a peak month, that manual step was both a security liability and a growing administrative load. The engagement migrated payment processing from Square to Stripe, with a custom-built secure link that captures the card once and lets the team bill it automatically after service.
The Challenge
- Payment processing ran through Square, but every charge still required a client's card details to be manually collected and re-entered after the fact
- Full card numbers changed hands as part of that manual process, creating unnecessary security exposure
- No stored payment method, so nothing about the payment step scaled with reservation volume
- 650–850 reservations in a peak month meant the manual process was a growing bottleneck, not a one-time cost
- Clientele expectations for a secure, professional booking experience
The Solution
A custom-built migration from Square to Stripe, centered on a secure client-facing payment link: the client enters their card once, Stripe vaults it, and the team charges it automatically once the service is complete — no card details handled or re-keyed by staff.
- Full payment migration from Square to Stripe
- Custom-built, secure client-facing payment link for card capture, replacing the manual authorization process
- Saved payment methods so repeat clients don't re-enter card details
- Automatic post-service charging once a booking is marked complete
- PCI-compliant card handling that gets staff out of the card-data path entirely
- Built to hold up at peak volume (650–850 reservations a month)
The Results
What the build produced, and what it changed for the business.
- 15 min → 5 min
- Estimated admin time to process payment per reservation, before and after Stripe
- 108–142 hrs
- Estimated administrative time saved in a peak month, at 650–850 reservations
- Zero Card Handling
- Staff no longer receive or manually enter clients' full card numbers
- Saved Payment Vaults
- Cards stored securely so the team can bill automatically after service
About Island Experience
Island Experience Transportation (nantucketluxurytransportation.com) is Nantucket's premier luxury transportation service, running private and event transport for a clientele that expects a secure, low-friction payment experience without compromising on service.
- Industry
- Transportation
- Deliverables
- System integrationsWebsite development
- Technologies
- Next.jsStripeNode.jsMongoDB
“Before the Stripe integration, we would send clients a credit card authorization form that contained their full credit card information, and after each ride someone on our team had to manually enter the client's card details to process payment. The Stripe integration eliminated that manual process — we no longer need to receive or handle clients' full card information directly. The biggest improvements for us have been increased security, significantly less manual administrative work, and a much more streamlined payment process for both our team and our clients.”
Our Take
Migrating off Square only matters if the workflow changes too.
Swapping Square for Stripe wouldn't have meant much on its own if staff were still re-keying a card after every ride. The real fix was moving card capture onto a secure link and letting Stripe bill it automatically once service was complete — at 650–850 reservations in a peak month, that redesign is what freed up an estimated 108–142 hours a month without adding administrative staff. That's the difference between switching processors and building infrastructure: one changes who you pay in fees, the other changes how the business runs.
If part of this sounds familiar, here's where that conversation starts.
