ABOUT PROJECT
When most people think of Chicago in the summer, they picture skyline views, lakefront trails, and crowded harbors – but few realize how difficult it can be to actually get out on the water without owning a boat. That’s exactly the gap The Playpen Chicago set out to fill. This P2P boat rental marketplace was founded by Daniel Farrugia. The platform acts as a seamless, peer-to-peer and business-to-peer marketplace that connects private boat owners, yacht rental agencies, and independent licensed captains with everyday people looking to rent a boat for a few hours or a full day.
What makes The Playpen Chicago particularly clever is how it solves the trust and logistics problem that typically plagues boat rentals. Instead of forcing renters to coordinate separately with owners, captains, and marinas, the marketplace brings everything into one flow. In essence, we focused on building a two-tier boat rental marketplace where both boat owners and captains are first-class providers.
Key Challenges
From a development standpoint, Roobykon Software’s greatest challenge was refining the booking system – a complex, multifaceted engine involving availability, dynamic pricing, and captain assignments. This was not just a simple custom marketplace development task; the full scope was so substantial that we didn’t dare offer a conventional estimate. Instead, we told the client it would likely exceed 100 hours, and Daniel Farrugia agreed without hesitation.
Beyond that, the project ran smoothly. Communication was marked by mutual respect and clear expectations, workflows were well-coordinated, and everything from payment integration to launch deployment went off without a hitch.
TECHNOLOGY STACK
Solution Highlights
Roobykon Software built The Playpen Chicago on the Sharetribe Web Template, leveraging the Core API for backend marketplace operations. This is a prime example of Sharetribe marketplace development – using a proven foundation while adding deep custom logic. The frontend stack combined React.js, Redux, React Router, Express, and Node.js, with Final Form handling reliable form submissions. This approach gave us a proven foundation while allowing full focus on the custom booking logic.
The result was a scalable solution balancing out-of-the-box speed with custom depth. By relying on Sharetribe’s core infrastructure for transactions and user management, we avoided redundant work, while React.js and Redux delivered an intuitive, real-time booking interface. The platform launched with a clean frontend, robust API backend, and a seamless booking system connecting boat owners, captains, and renters across Chicago. In short, we succeeded in creating a peer-to-peer boat rental platform that feels both powerful and simple to use.
THE PROCESS
01
Lightning-Fast Deal Closure: Our sales team connected with Daniel Farrugia, and almost immediately, we could tell this was going to move quickly. The development team and project manager went through two rounds of discussions about functionality and the client’s specific needs, and after Daniel clarified his vision and implementation details, the contract was signed in record time.
02
Skipping Traditional Design: We simply agreed on a color palette with the client and stuck with the default look of the Sharetribe template to save time and resources. Whenever we needed to add completely new pages, our PM would create rough mockups, the client would approve them on the spot, and we would jump straight into development without any delays. This agile approach helped us in building a boat rental platform without the usual overhead.
04
Streamlined Communication: We agreed with the client on weekly calls and a weekly progress report to keep everything transparent. All day-to-day communication happened on Slack, and because Daniel was so keen to publish the project as soon as possible, any issues were resolved very quickly.
05
Launch and Handoff: Once the booking system was fully tested and integrated, we deployed the platform without any major hiccups. The Playpen Chicago went live on June 16, 2025, connecting boat owners, independent captains, and renters across Chicago’s waterfront exactly as we had planned. This marked the successful delivery of a P2P boat rental platform development project in record time.
Main Features
Two-tier provider collaboration
We tackled an interesting challenge: two types of providers (boat owners and captains) who must interact for a rental to work. We implemented several listing types – for agencies (with both boats and captains), private boats, and standalone captains.
Edit booking (pre and post-confirmation)
Sharetribe’s default logic doesn’t allow any changes to a booking once it’s created. We added full editing logic both during the booking process and after provider approval. If a customer’s plans change, they can reschedule to a different time or day without canceling and starting over.
Staged approval for rescheduling
When a customer reschedules, providers receive email notifications and must approve changes in a specific order. The captain approves first, then the boat owner, ensuring both parties are aligned before the new time is confirmed.
On-trip extension
If a customer is already on the boat and wants to extend the trip, they can do so directly through the platform. The system checks whether both the boat and captain have free time immediately after the current booking, and only the captain’s approval is required for the extension.
Anti-craftiness protection
We built additional protection to prevent customers from exploiting cancellation policies. If a booking is canceled less than 24 hours in advance, funds are forfeited. A customer cannot simply reschedule to a later date to qualify for a full refund – the rules and dates from the original request continue to apply.
RESULTS
The numbers speak for themselves: development began on May 19, 2025, and the platform was published just four weeks later, on June 16, 2025. In under 30 days, Roobykon Software delivered a fully functional, two-tier marketplace that seamlessly connects boat owners, independent captains, and renters on Chicago’s waterfront. That’s what happens when you focus on creating a two-tier boat rental marketplace with a clear vision and the right technical partner.
Beyond the technical delivery, the collaboration was marked by exceptional communication and shared momentum. Weekly calls, Slack updates, and the client’s keen desire to publish quickly meant that issues were resolved almost as soon as they appeared.
Lessons from Cordially
Before this project, we think we sometimes underestimated how deeply a single feature could define an entire marketplace. The booking system for The Playpen Chicago taught us that honesty about complexity is a strength. When we told the client it would take over 100 hours to get the two-tier provider logic, staged approvals, rescheduling, on-trip extensions, and anti-craftiness protections right, we learned that a good client respects transparency and trusts us more because of it.
WHAT OUR CLIENTS SAY
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Founder & CEO, Homehak
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