Voted By Pros

The Best Scheduling Apps in 2021

September 20, 2021

For professionals, freelancers and entrepreneurs, staying productive and effective scheduling go hand-in-hand. With so many scheduling apps available, deciding where to start can be overwhelming. We’ve found our 5 favorite scheduling apps in 2021, and we break them down in this guide.

As a working professional or entrepreneur, nothing can make or break your day like your schedule. The satisfaction you feel when everything falls into place and your tasks fit together seamlessly can’t be matched. But when you’re in reactive mode and rushing from task to task with no plan whatsoever, that sort of chaotic energy can drag your business down and even creep into your outside-of-work life.

That’s why having a reliable scheduling and calendar app is so important. With the right app, when a new task or appointment falls into your lap, you don’t have to scramble or rewrite your entire schedule. You just plug it into your digital calendar and go about your busy day.

In this list, we’ll cover 5 of our favorite scheduling apps and share some of our own productivity and scheduling tips.

(And if you lean strongly towards one of these apps, be sure to vote on your favorite at the end!)

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Google CalendarGoogle Calendar

The old adage “if it ain’t broke, don’t fix it” is one you could readily apply here. Google Calendar has been a staple for appointment setting, scheduling and productivity for years and there’s a reason for it. It’s simple interface, intuitive scheduling and Gmail integration make it an easy choice for anyone seeking a free productivity tool.

Google Calendar screenshot

It may not have all the bells and whistles of paid apps, but Google Calendar provides immediate utility for anyone who needs to organize their time, whether throughout the day or far into the future. If you’re already a Gmail user, Google Calendar has the functionality to give you everything you need for scheduling and productivity.


  • Easily toggle between daily, weekly and monthly calendar views
  • Create tasks, events and reminders with a few taps
  • Automatically imports event dates (like flights or concerts) from Gmail
  • Share calendars with other Gmail users.


  • Full functionality won’t be appreciated by non-G Suite users
  • Ironically limited search function

Price: Free

App Store Rating: 4.6

Calendly Calendly

Calendly promises to save you time so you can be more productive and focused. It’s an appointment booking app that lets you eliminate the back-and-forth that happens when two parties are trying to narrow down a meeting or appointment time. Users set availability parameters before sending out an invitation link. Invitees can then select which appointment works best for them out of what’s available.

If you work alone, the free version of Calendly probably has enough functionality for you, but if you work with a team, you’ll likely end up moving up to the paid version. The mobile app is known for being less user-friendly than its desktop counterpart. It’s not as comprehensive as Google Calendar, but could make a great complimentary piece for your productivity app arsenal.


  • Great for appointment-setting
  • Integrates with Google Calendar to avoid double-booking
  • Allows users to set team availability
  • Clients can select appointment times based on your availability


  • Not as user-friendly as the desktop version
  • Not as comprehensive as Google Calendar

Price: Free, $10/month (Premium), $15/month (Pro)

App Store Rating: 4.0

Square AppointmentsSquare Appointments

Square Appointments is an all-in-one app for small businesses that lets you book appointments, send reminders and process payments, all from the same place. You can set up a customer booking website through the app and even charge cancellation fees for no-shows.

If you’re looking for an app that not only lets you manage your schedule, but run virtually your entire business, it’s well worth it to give Square a closer look.


  • Automatic reminders and confirmations
  • Allows clients to book their own appointments and select from multiple service options
  • Works well with Google Calendar


  • Per-transaction fees can be prohibitive to some business models
  • Some users complain about long loading times

Price: Free for 1 staff calendar, $50/mo or more for multiple

App Store Rating: 4.9


The Appointy app boasts an online appointment scheduling system, with loads of customization options. It will connect to your Facebook business page, adding a tab that allows customers to book their own appointments. If you have employees, you can make sure they don’t get overbooked by setting their hours and availability within the app. It also has built-in Google Calendar sync and is compatible with Square.

The mobile app does suffer from not being as user-friendly and streamlined as the desktop version. With that in mind, it can still be a powerful app when used in combination with other tools like Square or Google Calendar.


  • Very customizable
  • Allows customers to book their own appointments
  • Set employee hours and availability within the app
  • Google and Square compatible


  • Some users complain about the mobile experience, especially on iOS
  • Limited functionality with free version

Price: Free, with $19.99, $49.99 and $79.99 premium versions

App Store Rating: 2.5



Genbook is a premium appointment scheduling and business management tool geared toward self-employed professionals and appointment-based small businesses like photographers, hair stylists and massage therapists. You can book and manage appointments directly from the app and filter your appointment calendar by staff member. The app also has customer contact information and review management capabilities. Prices start at $25 per month for one user.


  • Easy to use for businesses and clients
  • Customer reviews are linked to Google
  • Automated email followups to prompt reviews and testimonials


  • Can be difficult for clients to cancel appointments
  • Importing client data can be frustrating
  • Some users report issues with GenBook’s mobile app

Price: Starts at $25/mo

App Store Rating: 4.9



Honeybook is a multi-functional business management platform that handles scheduling, appointment setting, invoices, contracts, emails and payments. Geared toward small business owners, entrepreneurs and freelance professionals, Honeybook offers a premium solution to many business challenges.


  • Robust set of tools that go beyond just scheduling
  • Easy for clients to book appointments
  • Integrates with other calendar and email software
  • Incredible support staff


  • New users often find the software overwhelming
  • Mobile app lacks some desktop features

Price: $9/mo (Starter Plan), $39/mo (Unlimited Plan)

App Store Rating: 4.5



TeamUp is a calendar app that focuses on scheduling between teams or groups rather than businesses and clients. Each team or group member can create a color-coded calendar, and all calendars are overlaid so teams can easily spot scheduling conflicts and availability. More of a desktop application, the mobile app works by accessing the URL of a previously created TeamUp calendar.


  • Great for small teams
  • Free version has plenty of useful features
  • Can sync with Google calendar


  • Mobile app is very limited compared to desktop version
  • Becomes unwieldy with larger teams
  • Users report syncing issues between mobile and desktop

Price: Free (Basic), $8/mo (Plus), $20/mo (Premium)

App Store Rating: 3.7



Another team-focused calendar app, Trello, takes a “whiteboard” style approach to organization. Team members have access to a board, which is broken down into different lists. Team members add “cards” to each list as needed. Any team member can access the board and quickly see what everyone is working on, the status of projects and upcoming deadlines.


  • Useful for teams looking for something more dynamic than a simple calendar
  • The focus on collaboration makes Trello a top choice for creative teams
  • Simple and easy to use


  • Not always the best option for larger, more complex projects
  • In-app messaging functionality is lacking
  • Big picture focused, smaller details can fall by the wayside

Price: Free option, Premium plans start at $12.50/mo

App Store Rating: 4.5

Plan your entire week in advance.

“One day at a time” is not the philosophy to follow when it comes to your schedule. Block off some time Sunday evening or early Monday morning to plan out your week. Fill in important meetings, block out the times you know you’ll be unavailable, and you’ll have a great foundation that will enable you to adapt to any developments that arise throughout the week.

Knock out your most important task first.

We humans have a tendency to rush toward the easier, nonconsequential things and put off what really matters. When it comes to your work, taking care of that big scary to-do list item as soon as you can will free up valuable mental energy and let you sail though the rest of your schedule on auto-pilot.

“Batch” similar tasks.

When we’re constantly switching gears, it can take a while for our brains to catch up and get “in the zone.” With that in mind, working with your schedule so that similar tasks are all batched together can help you stay productive and get more done. Why interrupt your workflow with a meeting when you can get all your meetings done back-to-back in a single day?

Schedule time for non-work activities.

Even if you’re the most productive person you know, you still need time to step away from your work and recharge your batteries. But for the super-productive, workaholic types, finding time to just enjoy the moment can be almost impossible. So treat your free time like you would any other important task and schedule it!

Use last week’s schedule as a template for this week.

This isn’t just to make the often arduous task of scheduling easier for you. It also helps to build routine into your week-to-week work life. When you perform the same tasks at the same time, you’ll start building habits that make busy work easier to start and quicker to finish.

Google Calendar may have won in our battle of the best scheduling apps, but we’d still love to hear your opinions! Which app is your personal favorite?

  1. What is your favorite scheduling app?

    • Google Calendar
    • Calendly
    • Square Appointments
    • Appointy
    • GenBook
    • Other
    • Vote

Written on August 19, 2021 | Last updated: September 20, 2021

Our editorial content is intended for informational purposes only and is not written by a licensed insurance agent. Terms and conditions for rate and coverage may vary by class of business and state.

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