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Get Organized: Vacation Planning

 & Jill Duffy Contributor

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    Buying Guide: Get Organized: Vacation Planning

    Get Organized: Vacation Planning

    Contents

    Nothing makes me happier than a well-planned vacation. When you organize and plan your vacation in advance of your time off, you can make the most of every minute while you're gone.

    The lead up to your holiday should be as stress-free as the vacation itself. The more organized you are during the planning phase, the more likely things will fall into place. When you have the information you need at your fingertips—at the airport or car rental kiosk, in the taxi, at the hotel check-in desk—you stop worrying about what might happen next and actually enjoy being in the moment. Here's how to do it.

    Get Organized3 to 6 Months Out: Planning
    Budget. At least three months before your vacation, you should know roughly where you'll go and with whom. Wanderlust can lure you to far-flung destinations, but your budget may keep you closer to home. Three months out, you should have a realistic grasp of your vacation budget, both in total and per day. Ask people you know who have been to the destination before what's a good price for flights and accommodations to get a baseline figure against which you can judge results from travel search websites, like Expedia and Travelocity.

    Flights and accommodations. Typically, the largest expense of a vacation is airfare, and when you're not traveling by plane, it's accommodations. For inexpensive alternative forms of accommodations, such as apartment rentals rather than hotels, see Travel for Less: Tips for Booking Vacation Rentals.

    Start tracking prices for airfare and looking for deals on hotels at least three months before your trip. Free travel search websites, such as Orbitz (4 stars, Editors' Choice) and Kayak (3 stars), have price tracking features that let you sign up for email alerts, letting you see when the cost of a flight goes up or down.


    Bing Travel has a price indicator that tells you when you search whether a price is expected to go up or down, how soon, and at what confidence level, although the features has some limitations. (Find more recommended apps at the end of this article.)

    Time off. Before you book anything, make sure you can take the specific dates off of work and arrange for child or pet care. You might even use social media—a general Facebook message, for example—to offer friends and family the use of your home while you're gone. Sometimes, the opportunity to live in someone else's house for a week is a vacation in itself (and they can water the plants and bring in the mail while they're at it).

    About Our Expert

    Jill Duffy

    Jill Duffy

    Contributor

    My Experience

    I'm an expert in software and work-related issues, and I have been contributing to PCMag since 2011. I launched the column Get Organized in 2012 and ran it through 2024, offering advice on how to manage all the devices, apps, digital photos, email, and other technology that can make you feel overwhelmed. That column turned into the book Get Organized: How to Clean Up Your Messy Digital Life. I was also the first product reviewer at PCMag to test fitness gadgets, including everything from early Fitbits to smart bras.

    Currently, I'm passionate about the meaning of work and work culture, and I enjoy writing about how managers and employees can communicate better, with or without software. My most recent book is The Everything Guide to Remote Work. I also love a good workplace drama. 

    In addition to writing about work, I cover online education, focusing on learning for personal enrichment and skills development. I have a soft spot for really good language-learning software. Although I grew up speaking only English, some twists and turns in life led me to learn Spanish, Romanian, and a bit of American Sign Language. I've studied at the university level, as well as at the Foreign Service Institute, where US diplomats and ambassadors learn languages.

    My writing has also appeared in WIRED, the BBC, Gloria, Refinery29, and Popular Science, among other publications.

    Follow me on Mastodon.

    The Technology I Use

    Squeezing every last bit of usage out of the devices I already own is the only way I can tolerate my personal consumption. In other words, I do not own the latest cutting-edge technology. I buy things that will last and try to take care of them.

    My life is organized by Todoist, and my notes live in Joplin. Where would I be without Dashlane as my password manager? Probably locked out of all my many online accounts—I have more than 1,000 of them.

    When I share my contact information, it's an excruciatingly long list of phone numbers, messaging apps, and email addresses, because it's essential to stay flexible while also remaining somewhat mysterious.

    Read full bio