Apple Calendar vs Calendar 366

Apple Calendar

• People with an iPhone, iPad or Mac who want a calendar at no cost
• Seeing iCloud, Google and Exchange calendars side by side
• Families and friends sharing an iCloud calendar

Calendar 366

• People who keep everything on Apple devices and want events and tasks in one app
• Mixing iCloud, Google, Microsoft 365, Fastmail and CalDAV accounts
• Buyers who prefer a one-time purchase to a subscription
• Mac users who want to manage their calendar from an AI assistant over MCP

Apple Calendar

• Apple's setup guide covers iPhone, iPad, Mac and iCloud.com, with Windows handled by syncing to Outlook through iCloud for Windows. No Android app is listed.
• Calendar on iCloud.com needs a tablet or computer; Apple's guide says it cannot be used from a phone browser.
• Editable sharing is limited to iCloud calendars and people with iCloud accounts. Everyone else can only view a public, read-only calendar.
• Time-to-leave alerts are not sent for destinations more than three hours away, and travel time does not update when an event's location changes.

Calendar 366

• Apple only: iPhone, iPad, Apple Watch and Mac. No Android, Windows or web version is listed.
• After the 7-day trial the free download keeps only basic features, and the vendor does not publish which features are premium.
• Prices appear only as App Store in-app purchases. Several have no billing period, and no monthly price for single-user Pro is shown.
• Siri AI is in beta, English only, and needs iOS, iPadOS or macOS 27. The MCP connection to AI assistants is Mac only.

Apple Calendar

Several accounts in one calendar

Add iCloud, Google, Microsoft Exchange and other CalDAV accounts and see their events together in List, Day, Week or Month view, with a color for each calendar.

Natural-language event entry

On Mac, typing a phrase such as "Football Game on Saturday from 11 am - 1 pm" creates the event with its date and time filled in. Siri can add or change events by voice.

Travel time and time-to-leave alerts

Adding a location attaches a map and weather, and Calendar sends an alert when it is time to leave, based on traffic or transit conditions. Travel time can be added to the event's duration.

Shared and public calendars

Share an iCloud calendar with other iCloud users as view-only or editable, or turn on Public Calendar so anyone with the link can view and subscribe to it.

Reminders next to events

Scheduled reminders from the Reminders app appear on the calendar, where they can be created, edited and marked complete.

Invitations and video call links

Send and answer invitations through iCloud, Exchange and other accounts. Events can carry a video call link, a FaceTime call on Mac, attachments and notes.

Calendar 366

Natural language entry

Type what, when and where to create an event or task, with shorthand such as /Work for a calendar, -r1w for a weekly repeat and ! for priority. Apple Intelligence can be picked as the engine on iOS, iPadOS or macOS 27.

Tasks next to events

Tasks sit in the calendar with reminders, location-based alerts, priorities and notes, and can be filtered by today, overdue or important. They sync with Apple Reminders, Google Tasks, Microsoft to-dos and Todoist.

Views and calendar sets

Year, month, week, day and agenda views, plus month and week views paired with a list, in portrait and landscape. Calendar sets group calendars and lists and sync across devices.

Meetings and invitations

Creates Zoom, Google Meet and Microsoft Teams meetings and opens join links for services such as Webex and FaceTime. Invitations arrive in an inbox and can be accepted or declined there.

Widgets, Apple Watch and menu bar

20 home screen and desktop widgets, 6 lock screen widgets and 10 watch complications. The Watch app creates events and completes tasks, and the Mac version adds a full menu bar calendar.

Shortcuts, URL scheme and MCP

Supports Apple Shortcuts and a cal366:// URL scheme for automation. On Mac it can connect to Claude Desktop or LM Studio through the Model Context Protocol to show, create and reschedule entries by chat.

Apple Calendar

• Free$0

  Every feature of the app on iPhone, iPad, Apple Watch and Mac, plus Calendar on iCloud.com with an Apple Account.

Calendar 366

• Free$0

  Free download with basic features. Neither the site nor the App Store listing says which features stay free after the 7-day trial.

• Pro (Yearly)$19.99

  per year

  Yearly subscription that unlocks the premium features, as labelled in the App Store's in-app purchase list.

• Pro (iOS)$19.99

  billing basis not shown on the App Store listing

  Listed without a period. The vendor's FAQ says a one-time purchase is offered next to the subscriptions.

• Pro$49.99

  billing basis not shown on the App Store listing

  Listed without a period or platform label. The site describes the app as a universal purchase across iPhone, iPad, Apple Watch and Mac.

• Pro Family (Monthly)$4.99

  per month, or $29.99 per year as Pro Family (Yearly)

  Family version of the Pro subscription, with monthly and yearly options in the App Store's in-app purchase list.

• Pro Family (iOS)$29.99

  billing basis not shown on the App Store listing

  Family version listed without a period. A second item named Pro Family, with no platform label, is listed at $69.99.

Apple Calendar

No public discounts listed.

Calendar 366

• Lifetime license

  One-time purchase in place of a subscription

  The FAQ on Calendar 366's site says that after the 7-day trial you can choose a subscription or a one-time purchase. The App Store lists Pro (iOS) at $19.99 and Pro at $49.99 without a billing period.