Calendar 366 vs Fantastical
We give Calendar 366 a 3.2 GPA and Fantastical a 3.0, out of 4.0. Calendar 366 grades higher on value for money. They get the same grade on the free plan, features, ease of use and platforms.
Price, platforms and features side by side. The table says where each price was read and when.
Calendar 366
Calendar and task app for iPhone, iPad, Apple Watch and Mac
Fantastical
Calendar and tasks app for Apple devices, Windows and Googlebook
How we grade them
| 3.2GPACalendar 366Very good | 3.0GPAFantasticalVery good | |
|---|---|---|
| Value for money | APro is $19.99 a year on the App Store, which works out under $2 a month against a typical $6 for calendars. Pro Family is $29.99 a year. One-time purchases are listed too, at $19.99 and $49.99, though the listing doesn't say what each covers. | B$4.75 a month on yearly billing, with booking links and meeting polls thrown in. Fair. But Google's and Apple's calendars are free, so you have to want the extras. |
| Free plan and trial | BIt's a free download with basic features, and you can try every premium feature for 7 days. But neither the site nor the App Store listing says which features stay free afterwards, so you find out by hitting the wall. | BFree with no end date: every view, typed-in events and your tasks. But it's 1 invitee per event and 1 calendar set, and the Apple Watch app needs Premium. |
| Features | ATyped entry with shorthand like /Work and -r1w, tasks synced with Apple Reminders, Google Tasks and Todoist, calendar sets, an invitation inbox, Zoom, Meet and Teams links, 20 widgets, 10 watch complications and a Mac menu bar calendar. | ATyped-in events, calendar sets, booking links, meeting polls, a Join button for video calls and a 10-day forecast. About as much calendar as you can get. |
| Ease of use | BIt has too few App Store ratings for us to lean on, so a B is the ceiling. Plain-words entry is friendly. The shorthand codes are quick once learned, but they're one more thing to learn. | BTyping an event in is as quick as it gets. Its guesses do catch people out now and then, and 4.2 from about 24,500 App Store ratings trails Google Calendar's 4.5. |
| Platforms and integrations | CiPhone, iPad, Apple Watch and Mac. No Android, Windows or web version is listed. Within Apple it connects well: iCloud, Google, Outlook, Microsoft 365, Fastmail, CalDAV, Apple Shortcuts and, on Mac, Claude Desktop over MCP. | CMac, Windows, iPhone, iPad, Apple Watch and Vision Pro, plus Googlebook since October. No Android phone app though (Flexibits says 2027), and no web version. |
| Best for | events and tasks together on Apple devices | juggling several calendars on a Mac and iPhone |
The GPA is the average of the five grades: an A is 4 points, an F is none. The full reasons are on each tool's page: Calendar 366 and Fantastical. How we grade
Where they differ
- Calendar 366 starts at $19.99 per year for Pro on the App Store. Fantastical starts at $4.75 per month, billed annually ($6.99 billed monthly).
- Only Fantastical lists a Windows app.
- Calendar 366 can be bought with a one-time purchase.
- Calendar 366 also covers menu bar app.
- Fantastical also covers templates and booking links.
At a glance
| Calendar 366 | Fantastical | |
|---|---|---|
| Pricing | Free plan | Free plan |
| Starts at | $19.99 per year for Pro on the App Store | $4.75 per month, billed annually ($6.99 billed monthly) |
| Free plan | Free download with basic features. The site does not list which features are premium; all of them can be tried for 7 days before choosing a subscription or a one-time purchase. | Add accounts, events and tasks, with day-to-year views and home screen widgets. Limited to 1 calendar set, 1 invitee per event and a 3-day weather forecast. |
| Free trial | 7-day trial of all premium features | 14-day free trial of Flexibits Premium |
| macOS | ||
| Windows | ||
| iOS | ||
| Made by | Vincent Miethe | Flexibits Inc. |
| Price read from | apps.apple.com | flexibits.com |
| Checked | Oct 9, 2026 | Oct 9, 2026 |
Who each one suits
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
Fantastical
- People with Google, iCloud and Microsoft calendars who want them in one app
- Adding events quickly by typing a sentence
- Households sharing one subscription across up to 5 members
Worth knowing
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.
Fantastical
- No web version, and the Googlebook app launched in October 2026 does not run on Android phones or tablets; Flexibits says Android support is coming in 2027.
- The free version allows 1 invitee per event, 1 calendar set and a 3-day weather forecast.
- Apple Watch support, push sync, travel time, templates and conference-call detection all need Flexibits Premium.
- Single sign-on and Openings with multiple hosts are limited to the Team plan.
Key features
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.
Fantastical
- Natural-language event entry
- Create events and tasks by typing a plain-language sentence instead of filling in a form field by field.
- Day, week, month, quarter and year views
- Full-screen views at every scale plus the DayTicker strip, all included in the free version.
- Tasks next to events
- Tasks from iCloud Reminders, Todoist and Google Tasks appear alongside calendar events on both free and paid tiers.
- Openings and Proposals
- Premium adds Openings, which let others book a slot from your availability, and Proposals, which poll invitees on meeting times.
- Conference call detection
- Premium detects Zoom, Google Meet, Microsoft Teams and Webex links in events and adds a single-click Join button.
- Calendar sets
- Group calendars into sets. Free allows 1 set; Premium allows unlimited sets, syncs them and can switch sets automatically by time or location.
Plans
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.
Fantastical
Free$0
Basic calendar and tasks with full-screen views; 1 calendar set, 1 invitee per event and a 3-day forecast.
Individual$4.75
per month, billed annually ($6.99 billed monthly)
All Premium features for one person, including Openings, Proposals, call detection and Apple Watch support.
Family$7.50
per month, billed annually ($10.49 billed monthly)
Flexibits Premium shared by up to 5 family members.
Team$4.75
per user / month, billed annually ($6.99 billed monthly)
Premium for each member, plus single sign-on, team roles and Openings with multiple hosts.
Ways to pay less
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.
Fantastical
- Annual discount
About 32% less with yearly billing
Flexibits' pricing page lists the Individual plan at $4.75 a month billed annually, against $6.99 billed monthly, which works out about 32% lower.
- Education
Educational and military discount
Flexibits says it offers an educational or military discount on request. Contact the company with proof of your institution, student status or military service.
- Other savings
Family plan for up to 5 members
The Family plan shares Flexibits Premium among up to 5 members at a reduced price compared with separate Individual subscriptions.
