How to plan a vacation like a project manager in 2021?

Updated: Mar 8

How to use your Project Management skills and tools to ensure your holiday runs smoothly (for the time we all can travel again).


Even when things are normal, most of us spend a big part of the year looking forward to that big summer or winter break, or even to a short weekend getaway. And while these days we can only dream about it, why not use this time and try to become better at planning your next vacation?


Maybe in 2021...

Some people plan their vacations months in advance, while others prefer spontaneity, choosing a last-minute holiday trip. When you are single, winging a vacation is simple – you can change plans on the fly to suit your mood and explore someplace new with no set agenda. Things get more complicated when it comes to a family or a group holiday.


Planning a vacation for the entire family is all about prioritizing and preparing ahead of time. The more family members you have, the more logistics there are to figure out. As the holiday approaches, the panic sets with questions like: "Are the passports valid? Will the suitcases fit the dreaded airline weight limit? Are all the transfers and hotels booked?" And even when you finally reach your destination, you're faced with new dilemmas: "Where to eat? Beach or pool? How early do you have to get up to get to the bus tour on time?" etc.


For some people, vacation planning may seem like a daunting task. Others may find it exciting. We know one thing for sure – if you are a Project Manager, you probably find the pre-vacation process almost as exciting as the vacation itself. Why? Because project managers tend to do it in the right way.


Project management methodology can help you avoid that pre-vacation chaos and stress. If you are the kind of person who struggles with the trip planning process, you should try to approach your next vacation like a project to make it all a little more exciting, delivering your vacation successfully, in time, and within the budget.


Let's start with the vacation planning structure:


The key aspects of your vacation planning are demonstrated in the diagram below as blocks: "Activities", "Reservations", "Paperwork". How you will get to your destination, where you will sleep, and what you will do are the primary things to consider regarding your vacation. "Home" is also there, because you have to think about keeping things in order for the time you are away.

You can prepare this plan with a pen and paper, but we highly recommend doing this in a project management tool (you are planning a real project after all!). You can choose any tool that you're comfortable with. We are going to show how you can organize your vacation in Infolio.

Planning your vacation on a Kanban board is weird only if haven't tried it

As you have prepared a high-level plan, the real fun begins! You're not obliged to stick to this classification. This is just a basic example. You can create any lists and statuses you wish; the main idea is that you are now in control of everything.

Group your vacation planning tasks by categories

Keep everything organized and readily accessible, especially all the budget and booking details. This way you will always know where to look if you forget something. Make Infolio your Single Source of Truth.


Follow our seven tips to organize your holiday and make it stress-free:

1/ Hold an initial meeting with the stakeholders


We mean, of course, your family or friends you plan to share the vacation with. As the vacation project manager, you should gather everyone together for a brainstorming session and lay the groundwork for your vacation project. This meeting will help you to identify your vacation goals and distribute the responsibilities of each participant. It's a good idea to start planning about 3-6 months before the vacation (it depends on the destination and the type of the trip, of course), so this meeting should be arranged in advance. There are many to consider, like work, school, etc. Agree on the vacation start date, and the duration. Make sure it suits everyone. Then, decide on the type of vacation. Focus on personal preferences: what will bring joy to everyone? A big-city adventure? A tropical getaway? Or maybe a theme park fun?


Brainstorm all the different suggestions and try to find a common ground. After you define your vacation concept, you can begin narrowing down the list of the proposed destination options to pick the best one. Ideally, by the end of your stakeholder meeting, you will define the destination, holiday type, and date.

Brainstorm your next destination on a visual board together

2/ Define your project objectives, scope, and budget


After you have figured out your vacation goals, it's time to define your project scope and budget. We all know that vacation costs can quickly spiral out of control if you are not careful. Account for all the possible expenses on accommodation, transportation, food, and activities, but stay flexible enough to adapt to the situation in case of unexpected. Don't forget that summer is the most popular time for family vacations, and consider a different season, if you would like your holiday to be more affordable and less crowded.


Decide how much you are ready to spend. Depending on your budget, you can play with your vacation duration. Count your fixed costs, such as flights and hotel rooms, and then you can allocate the rest of your budget for food and other activities.


Keep all your budget expenses in the Budget task card, attach payment receipts, and update information as needed. You can leave comments, assign people, set due dates, create checklists and tags to make the task card complete and detailed.

Keep all the budget related information in one place

3/ Plan an itinerary/create a schedule


Having an idea of what you will be doing during your vacation is essential, but it doesn't mean that you have to follow your plan religiously. However, with advance planning, you will be aware of the possibilities, offers, and prices so that you won't get unpleasant surprises during your vacation. For example, if you are not planning to spend the whole week on the beach, make sure other entertainment options are worth your attention and satisfy your needs. But don't overplan.

Remember, the most crucial goal is to rest and change your focus, no matter what your secondary goals are. Create a schedule with all the necessary tasks (sightseeing, entertainment, other activities), if you can, add prices, essential notes, comments, and each visit's planned date. Let your friends or family discuss together what you will do. You can add an assignee for each activity and research the places together. Update the task's status as it changes (e.g., In discussion, Discussed, Needs approval, Booked).

Be prepared and always know what to do next

4/ Set milestones


To keep everything moving forward, you have to set the milestones. These can include purchasing tickets for attractions, getting the vacation shopping done, or securing accommodations. Each milestone can be made up of multiple tasks and should have a specific date for completion. Later you can schedule additional meetings in case any adjustments are needed.

Always set milestones for all your vacation planning tasks

5/ Teamwork and delegation


Managing a project doesn't mean that you have to do all the work by yourself. As a good project manager, empower yourself with the art of delegation. Of course, you can save the most complicated task for yourself (if you love challenging yourself). As a good project manager, you should know the strengths and weaknesses of each team member and understand who is capable of what. For example, let your kids research the information on entertainment and sightseeing tours, at the very least. By making some input to your project, all the team members will feel more excited about the upcoming event (if they aren't already).

You're going on vacation together, so everybody has to participate. And you're a team, so communication is critical. If communication isn't clear, your family might end up sharing a youth hostel room and a shared bathroom with ten other people instead of two double rooms you had dreamed about (and of course, nothing's wrong with a youth hostel, but it might not be ideal for a big family). Working together as a team is always a better choice.

Communicate and delegate!

6/ Monitor your team's and project's progress


Taking a project management approach can be just as fun as doing things informally, but it will definitely be more organized and productive. Make sure to check in with your team members regularly to see whether they have fulfilled their tasks. You wouldn't want to stand at the airport all set and ready only to find out that the person who was supposed to book the flight didn't do it. Okay, that is the absolute worst scenario, but not monitoring the project status can lead to stress. Remember that any last-minute bookings or changes are a direct threat to the project budget, so it is better to avoid such expenses.


7/ Assess the possible risks


According to Murphy's Law, "Anything that can go wrong, will go wrong".


Perhaps that doesn't sound very optimistic, but you have to be prepared that your trip might not go as smoothly as planned. Unpredictable things will happen, so you should be ready for the worst-case scenario as well. Having the right insurance package will significantly reduce the amount of stress.


Read about your rights as a traveler. Find out in which circumstances you can reclaim your money from the airline if your flight was delayed or canceled; download all the necessary apps. Knowing what to do in these extreme cases will reduce your stress levels significantly. Of course, it will still be annoying, but at least you'll have a little bit of control over the situation.

Always have a plan B and C when it comes to vacation planning

And finally, here are the main takeaways before you start your vacation planning project:

  • Plan ahead like you would plan your work project;

  • Planning is also teamwork unless you are not going alone;

  • Gather enough information before you leave;

  • Pack smart and travel light;

  • Try to book your stay and transfer in advance, unless you are in it for spontaneity;

  • Set realistic expectations;

  • Enjoy the process, no matter what.

Closing your project: Evaluation


After you've enjoyed your vacation, there's a step that has to be present in every project — evaluation. Answer the following questions and try to be honest: Have you followed the plan? Have you enjoyed your time? What went wrong? What could be done better? Make notes for the future. Learn from your mistakes and go somewhere else next time. The evaluation will make you better at planning after every project you complete.


We hope you can plan and enjoy a great holiday real soon. In the meantime, you can educate yourself more about the Project Management approach to… well, anything, really.


You can get started and use Infolio now, entirely for free. Our educational templates will help you plan your first vacation (and a lot more!) right away.



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