Best Calendar Sync Apps in 2026: Complete Comparison
How the main calendar sync tools compare on providers, privacy, scheduling, AI connectors and price.
Choosing a calendar sync tool comes down to a few questions: which calendars you use, how much detail you want copied between them, whether you need booking links or AI assistant access, and what you're willing to pay.
About this comparison: AllMyMeetings publishes this page, so we're not neutral. We've tried to be fair: every competitor fact below comes from that company's own website, with links, and we've left out claims we couldn't check. Prices and features as of October 2026. Vendors change plans often, so check their pricing pages before you buy.
TL;DR: If you want a free plan that keeps working after a trial, iCloud support, Free/Busy privacy, and an MCP server your AI assistant can connect to, start with AllMyMeetings. CalendarBridge is a long-running option with HIPAA and SOC 2 for regulated teams. OneCal is a strong paid option with multi-way sync and scheduling links. Reclaim.ai is a time-management tool that includes sync for Google and Outlook.
What to look for in a calendar sync tool
Provider support
At minimum, you need Google Calendar and Microsoft Outlook. iCloud support matters if you're in the Apple ecosystem. ICS feed support helps if you subscribe to calendars from other apps (school, sports, project tools).
Sync direction and speed
One-way sync copies events in one direction. Two-way (bidirectional) sync keeps both calendars updated when changes happen on either side. Tools that use Google's and Microsoft's change notifications usually pick up changes within seconds. iCloud doesn't send change notifications to outside apps, so every iCloud sync tool has to check it on a schedule.
Privacy controls
Full-detail sync copies titles and descriptions. Free/busy sync creates generic "Busy" blocks that hide specifics. If you're syncing work and personal calendars, or two clients' calendars, a busy-only option isn't optional.
Scheduling and AI features
Several sync tools now include booking links that check availability across your synced calendars, and some offer an MCP server so AI assistants such as Claude or ChatGPT can read and manage your calendars.
Pricing
Prices run from free to $40 per user per month. Check what each tier counts: some count calendar accounts, others count individual calendars or sync connections.
The calendar sync tools compared
1. AllMyMeetings
AllMyMeetings syncs Google Calendar, Microsoft Outlook / Microsoft 365, Apple iCloud, and read-only ICS feeds.
Key strengths:
- A free plan, not a trial: 2 calendar accounts, 1 one-way sync in Free/Busy mode, and 1 scheduling page
- MCP server on every plan, including free: Claude and ChatGPT connectors sign in with OAuth, no token needed; other clients use personal access tokens. See the MCP setup guide.
- iCloud support through CalDAV with an app-specific password, checked every five minutes
- Three privacy modes: Full details, Free/Busy, and Private. Attendees are never copied, so synced copies never send invitations.
- Direct ICS feed subscriptions, without routing them through a Google or Microsoft account first
- Event history showing which calendar and which sync created each copy
Limitations:
- Pairwise sync: each sync pair links two calendars, so syncing three calendars both ways takes three pairs
- Two-way sync and Full details mode need a paid plan
- Newer company (launched April 2026); no HIPAA BAA or SOC 2 report
Pricing: Free; Pro $5/month or $50/year (4 accounts, 6 syncs, two-way sync, 3 scheduling pages); Business $15/month or $150/year (unlimited). Pro is free for 14 days from when you connect your first calendar, no card needed. See pricing.
Best for: People who want to start free, use iCloud, keep work and personal details apart, or connect an AI assistant.
2. CalendarBridge
CalendarBridge is one of the longer-running calendar sync services. Its homepage says it helps "500+ organizations".
Key strengths:
- Google, Microsoft 365, and iCloud; ICS calendars can be used as sync sources through their link
- Scheduling links (10 scheduling pages on each plan) and an email-based AI scheduling assistant
- HIPAA BAA available on Premium and Pro; SOC 2 Type 1 and Type 2 listed on its site
- Its own calendar MCP server
- Site available in many languages
Pricing: Basic $4/month (2 calendars), Premium $8/month (5 calendars), Pro $32/month (8 calendars) billed yearly; $5, $10 and $40 billed monthly. Free trial, no free plan. Source.
Best for: Healthcare and other regulated teams that need a HIPAA BAA or SOC 2 report.
3. OneCal
OneCal syncs Google, Outlook, and iCloud calendars, including multi-way sync across several calendars in one setup.
Key strengths:
- Multi-way sync groups
- Unlimited one-on-one and collective scheduling links on every plan
- Private event controls and a choice of which event details to sync
- A calendar MCP server for Google, Outlook, and iCloud, using OAuth
Pricing: Starter $5 (2 calendars), Essential $10 (5 calendars), Premium $25 (50 calendars) per user per month, billed annually. 14-day free trial, no free plan. Source.
Limitations:
- No free plan after the trial
- ICS calendars have to be added to a Google or Microsoft account first, and then only work as one-way sources (OneCal docs)
Best for: Paying users with many calendars who want multi-way sync and team scheduling links.
4. SyncGene (moving to CiraHub)
SyncGene syncs calendars and contacts across Google, iCloud, and Outlook. Its pricing page says SyncGene is moving to CiraHub and new subscriptions start there.
Key strengths:
- Syncs contacts as well as calendars
- Covers Google, iCloud, and Outlook
Pricing: CiraHub plans start at $8/month billed yearly. Free accounts are limited (one manual sync per month, with automatic sync as a 7-day preview). Source.
Best for: People who need contact sync alongside calendar sync.
5. Reclaim.ai
Reclaim.ai is an AI time-management tool that schedules focus time, tasks, and habits, and includes calendar sync. Dropbox acquired Reclaim in August 2024.
Key strengths:
- AI time blocking for tasks, habits, and focus time
- Calendar sync between Google and Outlook calendars
- Scheduling links, including 1 on the free Lite plan
Pricing: Lite free (1 calendar sync, 1 scheduling link); Starter $10, Business $15, Enterprise $22 per seat per month billed yearly. Source.
Limitations:
- Its pricing page lists Google and Outlook calendars only, with no iCloud
- More than you need if you only want calendar sync
Best for: People who want AI-driven time blocking as well as sync.
Feature comparison table
As of October 2026, from each vendor's own site. "Not listed" means we couldn't find it on the vendor's site, not that it definitely doesn't exist.
| Feature | AllMyMeetings | CalendarBridge | OneCal | SyncGene | Reclaim.ai |
|---|---|---|---|---|---|
| Google Calendar | Yes | Yes | Yes | Yes | Yes |
| Outlook / Microsoft 365 | Yes | Yes | Yes | Yes | Yes |
| iCloud | Yes | Yes | Yes | Yes | Not listed |
| ICS feeds as a source | Yes, direct | Yes, via link | Via Google/Microsoft | Not listed | Not listed |
| Scheduling links | Yes | Yes | Yes | Not listed | Yes |
| MCP server | Yes | Yes | Yes | Not listed | Not listed |
| Free plan (not a trial) | Yes | No | No | Limited | Yes |
Pricing comparison table
| Tool | Free plan | Entry price | Top individual plan |
|---|---|---|---|
| AllMyMeetings | Yes (1 one-way Free/Busy sync) | $5/month ($50/year) | $15/month |
| CalendarBridge | No (free trial) | $4/month billed yearly | $32/month billed yearly |
| OneCal | No (14-day trial) | $5/month billed yearly | $25/month billed yearly |
| SyncGene / CiraHub | Limited | $8/month billed yearly | Not listed |
| Reclaim.ai | Yes (Lite) | $10/month billed yearly | $22/month billed yearly |
Which tool fits your situation?
You want to start free and keep it free: AllMyMeetings or Reclaim.ai Lite. AllMyMeetings' free plan covers one one-way Free/Busy sync, which is enough for personal events to block time on a work calendar. Reclaim Lite covers one Google or Outlook sync.
You use iCloud: AllMyMeetings, CalendarBridge, OneCal, or SyncGene.
You need a HIPAA BAA: CalendarBridge.
You prefer multi-way sync groups: OneCal.
You want an AI assistant to manage your calendars: AllMyMeetings, OneCal, and CalendarBridge all offer MCP servers. AllMyMeetings' works on the free plan.
You also need contact sync: SyncGene / CiraHub.
The bottom line
Most calendar sync tools now cover Google, Outlook and iCloud, and several include booking links and AI connectors. The differences are in pricing model, privacy options and whether you can stay free. Start with a free plan or trial, connect your accounts, create one test sync, and see whether it behaves the way you expect.
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