You're not going to accomplish this the way you lay it out, specifically the "another instance of the Other passengers" displays again. The two viable approaches to accomplishing this would be coding a custom SPField that has an editor that would allow you to enter the other passengers as you like and just store the passengers as a delimited string under the covers. This would be a lot of work, but there are plenty of examples out there if you wanted to go that route. Here's a good starting point on MSDN:
http://msdn.microsoft.com/en-us/library/office/ms441150(v=office.14).aspx
Another approach would be to add a button to the ribbon with a custom action that pops up a simple dialog that presents the user with an editor for that field. So you would have a CustomAction with its enabled script checking to see if an item is selected, lookup the other passengers value for that item, render UI, let them edit the field, and then save it back when their done. Like the 1st approach you could just store the values in a text field with some delimiter between them for easy parsing...just pick something that is human readable as the delimiter will be visible in an item or list view.
You only need a couple lines in the enabled script:
if (SP.ListOperation.Selection.getSelectedItems().length == 1)
return;
And you command script would just open a custom window as a SP Dialog. Here's an example for a CustomAction (just goes in the elements.xml of your SP feature):
<CustomAction
Id="Ribbon.ListItem.Actions.YourAction"
RegistrationType="List"
RegistrationId="101"
Location="CommandUI.Ribbon"
Title="Other Passengers">
<CommandUIExtension>
<CommandUIDefinitions>
<CommandUIDefinition
Location="Ribbon.ListItem.ActionsControls._children">
<Button
Id="MyOtherPassengers"
Sequence="99"
Image16by16="/_layouts/images/otherpassengers-small.png"
Image32by32="/_layouts/images/otherpassengers.png"
Command="otherPassengers"
LabelText="Other Passengers"
Description="Enter other passengers for the selected item"
TemplateAlias="o2"/>
</CommandUIDefinition>
</CommandUIDefinitions>
<CommandUIHandlers>
<CommandUIHandler
Command="otherPassengers"
CommandAction="javascript:var options = { url: '{SiteUrl}/_layouts/OtherPassengers/Edit.aspx?lid={ListId}&id={SelectedItemId}', dialogReturnValueCallback: RefreshOnDialogClose, autosize: false, title: 'Enter Other Passengers', showMaximized: true }; SP.UI.ModalDialog.showModalDialog(options);"
EnabledScript="javascript:enableOtherPassengers();" />
</CommandUIHandlers>
</CommandUIExtension>
</CustomAction>
Hope this is helpful.