Calendar 366 vs Dato

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

Dato

• Mac users who want their schedule one click away in the menu bar
• People who keep missing the start of video meetings
• Anyone working across time zones who wants several clocks in view
• Buyers who want a one-time purchase and no subscription

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.

Dato

• Mac only. The current version requires macOS 26 or later; older macOS releases get older versions of the app.
• The vendor calls it a read-only view of your events: it can create events, but editing one or answering an invitation opens Apple's Calendar app.
• It has no sync of its own. Google, Outlook and other accounts must first be added to the built-in Calendar app.
• Natural-language entry is not supported yet, and the menus and settings are in English only.

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.

Dato

Menu bar calendar and event list

A month calendar with optional week numbers and event indicators sits above a list of upcoming events and reminders. How many days and events it shows is adjustable.

Fullscreen meeting notifications

A notification fills the screen when an event starts. It can be limited to video calls, events with an alert or accepted events, and paused with a Focus Filter.

Join video calls

Join the next call from a notification, the event details or a global keyboard shortcut. Zoom, Google Meet, Microsoft Teams and more than 50 other services are recognized, and others can be added.

World clocks and time travel

Clocks for several time zones appear in the Dato menu or the menu bar, with custom names and offline search of 15,000 cities. A slider shows what time it will be elsewhere.

Upcoming event in the menu bar

The next event can be shown as its own menu bar item, next to a date and time display whose format, icon and color can be customized.

Shortcuts, widgets and quick entry

A global keyboard shortcut opens the new event window, which can also create reminders. Shortcuts actions switch calendars and notifications on or off, and widgets show the date, calendar and world clocks.

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.

Dato

• Dato$18

  one-time purchase on the Mac App Store

  The full app. The App Store listing promises free upgrades and says Dato will never be subscription-based.

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.

Dato

• Other savings

  Menu bar bundle of three apps for $18.00

  The Mac App Store sells Sindre's Menu Bar Bundle, which contains Dato, Lungo and Battery Indicator, for $18.00, the same price as Dato alone.

• Education

  50% off for schools buying 20 or more copies

  For his App Store apps, Sindre Sorhus says educational institutions get a 50% discount when they buy 20 or more copies of one app through Apple School Manager.

• Other savings

  Also available through Setapp

  Dato is distributed through the Setapp app subscription as well as the App Store, and the vendor's page says Setapp can be tried free for 7 days.

• Other savings

  Older versions are free on older macOS

  Earlier releases for macOS 10.14 through macOS 15 are listed as free for everyone on the vendor's page. They will not run on newer macOS versions.