An automated trip chat message can be created in the Trip Sidebar.

For the example below, we're creating an automated trip chat message in the Tasks and Automation tab, the first photo will show the Add button as it appears in the Tasks and Automations tab in the Trip Sidebar, but the Add button also appears in a Contact Profile!

For more information on automations, be sure to read the Automations Overview.

Click on Add in the top right corner of the Tasks area.

Once you've clicked on Add, some options will appear. Click on Automation.

In the Automation Menu, click on Trip Chat Message.

Type the message you'd like sent to your clients in the trip.

Select the desired date and time for the message to be sent to your client.
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You can either have a fixed date, as shown below:

Or you can have an automatic time, sent a certain number of days before or after the trip end date or start date.

Once you've added all the desired information, click on Done in the top right corner of the Automation Menu.