Hello LITTLEDEAL,

To add iCal holidays calendar into Google Calendar, copy the URL for respective country and specify it in the Import calendar URL. You can import iCal / export iCal easily with any applications like Leopard iCal, Outlook etc. All free iCal calendar files are compatible with windows and Mac OS X Leopard. About iCloud Calendar and Outlook synchronization solutions iCloud or Apple Calendar is a personal calendar app made by Apple Inc. That runs on the iOS and Mac OS operating systems. It offers online cloud backup of calendars using Apple's iCloud service, or can synchronize with other calendar service.

Thanks for using the Apple Support Communities.
I see that your iCloud account no longer shows Contacts and Calendar details and there is no check box to select sync to outlook. I know it's important to make sure that you can see your account details and sync, so I'll be happy to help assist you with this.
I suggest using the steps in support article: Get help using Outlook with iCloud for Windows, specifically:

Calendar, Contacts and Reminders

If you need help with your Calendar, Contacts and Reminders with iCloud for Windows, try these steps.

When you open iCloud Reminders on your Windows PC, they're labeled Tasks and appear within the Tasks section.

Turn iCloud Calendar, Contacts and Reminders off and back on

1. Close Outlook.
2. Open iCloud for Windows.
3. Deselect the Mail, Contacts, Calendars & Tasks checkbox and click Apply.
4. Wait a few seconds. Select Mail, Contacts, Calendars & Tasks, and click Apply.
5. Open Outlook.

Make sure that the iCloud Outlook Add-in is on

The iCloud Outlook Add-in transfers your content between iCloud and Outlook. Follow these steps to turn on the Add-in:

In Outlook 2010 and later:

1. Select the File menu.
2. Click Options in the left panel.
3. Click Add-ins in the left panel of the Outlook Options window.
4. Look at the list of add-ins in the Active Application Add-ins section.
5. Select the iCloud Outlook Add-in.

In Outlook 2007:

1. From the Tools menu, select Trust Center.
2. Select Add-ins from the left column.
3. Look at the list of add-ins in the Active Application Add-Ins section.
4. Select the iCloud Outlook Add-in.

Make sure that iCloud isn’t your default account in Data Files

When iCloud is set as your default account in Data Files, your data won't sync between your devices.

Outlook 2010 and later:

1. Select File > Info > Account Settings > Data Files.
2. If iCloud is listed as the default account in the Comments column, select a different account.
3. Click Set as Default.

Outlook 2007:

1. Select File > Data File Management > Data Files.
2. If iCloud is listed as the default account in the Comments column, select a different account.
3. Click Set as Default.

Restart your computer

Turn your computer off and back on.

Let me know if you have questions.
Have a great day.

Jun 15, 2017 3:04 PM

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Original KB number: 2648915

Sync Outlook And Mac Calendar

Summary

Sync Mac Contacts With Outlook

This article contains information about the compatibility of Microsoft Outlook for Mac and Apple iCloud.

Outlook for Mac does not support Apple iCloud calendar (CalDAV) and contact (CardDAV) synchronization.

Outlook for Mac does support iCloud Mail. For steps on how to configure your iCloud email account in Outlook for Mac, go to the More Information section of this article.

More information

To configure your Apple iCloud email account in Microsoft Outlook for Mac, follow these steps:

1. Start Outlook for Mac.

2. On the Tools menu, select Accounts.

3. Select the plus (+) sign in the lower-left corner, and then select Other E-mail.

4. Enter your E-mail Address and Password, and then select Add Account.

   Note

   The new account will appear in the left navigation pane of the Accounts dialog box. The Server Information may be automatically entered. If not, follow the remaining steps to enter this information manually.

5. Enter one of the following in the Incoming server box:

   • imap.mail.me.com (for me.com email addresses)
   • mail.mac.com (for mac.com email addresses)
   • imap.mail.me.com (for icloud.com email addresses)

6. Select Use SSL to connect (recommended) under the Incoming server box.

7. Enter one of the following in the Outgoing server box:

   • smtp.mail.me.com (for me.com email addresses)
   • smtp.mac.com (for mac.com email addresses)
   • smtp.mail.me.com (for icloud.com email addresses)

8. Select Use SSL to connect (recommended) under the Outgoing server box.

9. Select Override default port under the Outgoing server box, and then enter 587 in the Outgoing server port text box.

After you have entered the incoming and outgoing server information, Outlook for Mac will start to receive your email messages.

Note

You can select Advanced to enter additional settings, such as leaving a copy of each message on the server.