Every week, I see operators sharing their pain points online. One post that stuck with me recently described the reality for many:

“Operators managing contractors are stuck using Google Calendar and manual workarounds to track who’s available and when. They want real integration between guide availability and booking systems, especially for PTO, scheduling, and payroll visibility.”

It resonated because it’s exactly the problem we set out to solve.

Why Google Calendar Alone Doesn’t Cut It

For years, many operators relied on Google Calendar as a patchwork solution. Guides or contractors would update their personal calendars, and managers had to cross-check, color-code, and manually assign tours. It worked — but only up to a point. Once you have multiple guides, vehicles, or even multiple offices, the system collapses under its own weight.

The result: endless admin hours, double-bookings, and no clear visibility on who is free and when.

How We Approached the Problem

At CaptainBook, we built a functionality designed to turn this pain point into a strength, so much so that it’s been nominated for Skift Idea of the Year 2024.

Here’s how it works:

• Guides connect their Google Calendar directly to the platform. The system knows in real time when they are available. If they have an event in their calendar, the system understands they’re not free for bookings.

• For each booking, whether it comes from an OTA, direct, or manual input, the system automatically assigns an available guide from a preference-ordered list. It checks one by one until it finds the right fit.

• If you prefer manual control, you can use auxiliary resources, which means the Google Calendar check happens when you assign a guide, not at the moment of booking.

• You can even combine resources: a driver as the main resource, and a host as an auxiliary one, perfect when a tour requires two people.

• The same system also works for vehicles, as long as they have a shared calendar.

This flexibility means operators can run tours the way they want, without fighting their software.

Real Impact for Operators

We have customers with 200+ users using this functionality every day, saving hours of admin work and eliminating the stress of juggling spreadsheets or disconnected calendars. The platform gives you a clear view of who is assigned to which booking, and handles private tours and shared tours seamlessly.

For repeat customers who want to book again with the same guide, widget links can even specify a given guide and show only their availability, a small feature with a big impact on loyalty.

From Pain Point to Growth

What I love most about this functionality is that it came directly from listening to operators. The problem was clear: managing staff and contractors through Google Calendar hacks was unsustainable. The solution had to be a booking platform that integrated real-time availability into the heart of operations.

We’re proud that this approach not only works, but is saving businesses real time and money every single day.

👉 For a concrete example, check out our case study with iOutdoor Adventures, who overcame staff shortages with this system and turned scheduling chaos into clarity.