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Milestones vs Things 3

A milestone-driven project planner vs the most polished GTD task manager on Apple platforms. Both are native, both respect you — they're just for different jobs.

Download on the App Store Free · Works on iPhone, iPad, and Mac.

Things 3 is, by most measures, the best task manager ever made for Apple platforms. It's been refining the GTD model — Inbox → Today → Upcoming → Areas → Projects — for over a decade. The interaction design is famously good.

Milestones is a project planner first and a task manager second. The headline structure is Project → Milestone → Task: every project is broken into milestones with their own deadlines, and tasks live underneath them. The active-milestone concept tells you exactly what's blocking you next.

If your work is a stream of small, mostly independent to-dos, Things 3 is hard to beat. If your work is a handful of bigger projects each with phases, Milestones gives you more structure where you actually need it.

Feature comparison

Milestones vs Things 3

  • Built for

    Milestones

    Project planning with milestones and phases

    Things 3

    Personal task management (GTD)

  • Platforms

    Milestones

    iOS, iPadOS, macOS — native SwiftUI

    Things 3

    iOS, iPadOS, macOS, watchOS, visionOS — native

  • Project structure

    Milestones

    Project → Milestone → Task (3-level)

    Things 3

    Area → Project → Heading → To-Do (4-level)

  • Milestones with deadlines

    Milestones

    First-class concept

    Things 3

    Headings have no dates

  • Active milestone view

    Milestones

    Yes — focus on what's next per project

    Things 3

    No equivalent

  • Today / Upcoming / Inbox

    Milestones

    Yes

    Things 3

    Yes

  • Sync

    Milestones

    Private iCloud sync

    Things 3

    Things Cloud (proprietary, free)

  • Apple Watch app

    Milestones

    Not yet

    Things 3

    Yes

  • Quick Entry / global capture

    Milestones

    Quick capture sheet

    Things 3

    Quick Entry with Autofill

  • Tags

    Milestones

    Custom color tags, cross-project filtering

    Things 3

    Custom tags, nested tags, filtering

  • Account required

    Milestones

    No account

    Things 3

    Things Cloud account (free)

  • Pricing

    Milestones

    Free; optional Pro upgrade

    Things 3

    Paid one-time per platform (~$10 iPhone, $20 iPad, $50 Mac)

Pick Milestones if

  • Your work is project-shaped, not task-shaped. You think in phases and deadlines.
  • You want to know which milestone is the bottleneck right now — not just what's due today.
  • You'd rather not pay separately for iPhone, iPad, and Mac.
  • You don't want your tasks routed through Cultured Code's servers, even encrypted.
  • You're planning bigger commitments — a launch, a thesis, a renovation — not next week's chores.

Pick Things 3 if

  • Your work is mostly small, independent to-dos: errands, follow-ups, household.
  • You're a long-time GTD practitioner and Things' Areas/Projects/Headings model fits your brain.
  • You want an Apple Watch app, polished Quick Entry from anywhere, and a 10+-year track record of stability.
  • You don't need milestone-level planning — flat projects with checklist-style headings are enough.
  • You're happy paying once for unmatched interaction design (and Things 3 absolutely earns it).

Bottom line

Things 3 is the best small-tasks app on Apple platforms, full stop. Milestones isn't trying to beat it on that ground — it's trying to be the planner *above* it. If your projects are bigger than 'a list of headings under a project', Milestones is the better home. For everything else, Things 3 still wins.

FAQ

Frequently asked questions

Can I use both Things 3 and Milestones?

Plenty of people do. Things for next-action GTD-style task management, Milestones for higher-level project planning ('what's the active milestone', 'when do I want this shipped'). The two don't sync, but they don't really need to — they sit at different altitudes.

Does Milestones support repeating tasks like Things 3?

Yes. Tasks support recurrence (daily, weekly, monthly, custom). Things 3 has more options for natural-language repeats and the polish of a decade of refinement, but the core scheduling is there.

I love Things' Quick Entry. Does Milestones have something like it?

There's a quick capture sheet that gets you a task in seconds, but Things 3's Quick Entry with Autofill is genuinely best-in-class. If global capture from any Mac app is the linchpin of your workflow, Things wins that round.

Privacy: Things Cloud vs iCloud — does it matter?

Things Cloud is encrypted and Cultured Code is a trustworthy company. But your data still sits on their servers. Milestones uses your own iCloud account directly — no third-party server in the path.

Is Milestones a Things 3 replacement on the watch?

Not yet. There's no watchOS app today. If you triage tasks from your wrist, Things 3 is still the better fit there.

When the project is bigger than a list of headings.

Free, native, private. Pair it with Things 3 if you want.

Download on the App Store

Free · No account required · Private iCloud sync