ORGANIZING YOUR DIGITAL VACATION PHOTOS SERIES–STEP 4: The Best Kept Secret to Organized Photos Revealed

Welcome back again for what is the final step in this series. It’s the one I’ve been most excited to share with you. It’s the step that brings everything together. It’s the step that creates the results you’ve hung in here for: To find what you want when you want it; to have an organized vacation folder, not chaos.

I want to apologize for the delay in getting this step out to you. I wanted to try a new, more visual way to convey the information to you. As it turns out, I’m not able to do it on this platform at the moment. So I’ll have to take you through the steps using screenshots instead.

Going back in time a bit, you created a folder structure in Step 1 for your vacation pictures. We’re going to build on that now with filenames. And if you thought you’d have to rename each file one by one or else keep them as they are, a meaningless set of letters and numbers, you’re in for a pleasant surprise. You’ll have your photos renamed faster than you ever thought possible. Dare I say, it will be a mind-blowing experience!

Renaming your files means you can:

  • Have your files super organized in short order
  • Find any file you want in a matter of seconds
  • Share photos with meaningful filenames for which your friends and family will love you
  • Create photo books, photo gifts and collages, as well as select your best photos for getting prints made quickly so you don’t miss a fantastic 2-day sale
  • Create and share online photo albums and slide shows with ease
  • And so much more

So let’s get started. We’ll begin with some necessary but good practices to follow before we get into renaming your files.

Filename Length Restrictions

To ensure cross-platform compatibility (makes sharing your files with others easier) file names should be less than 244 characters. The allowed amount for both Windows and Mac is 260 characters. However, the actual file name needs to be less because the folder name path is included in that too, as well as drive location (c:\). If the location for a file is deeply nested in subfolders, the actual file name would need to be very short. But the 244-character limit is long enough for your purposes because the key to exceptional organizing is less in the folder structure than in the filenaming.

IMPORTANT: Never use a symbol in the file name. This can cause issues saving and transferring the file to another drive, platform, cloud service, etc.

Folder and Filenaming Conventions


You have your folder system already set up. I’m using a chronological structure as follows:

2016 Photos > 2016-03 Viking River Cruise

All my files will be under this folder. I haven’t created subfolders at this point. But as I start renaming the files of my friends’ pictures with whom I traveled, additional folders might be necessary. I could create folders by location (e.g., I could do Switzerland, France, Germany and Amsterdam) to break up the photos for easier management. You can do whatever works best for you.


File naming is the SECRET to great search results and easy organizing. The file naming convention most professional organizers use is as follows:

XXXX-XX-XX_WHO_WHAT_WHERE (or some combination of this)


You want to use underscores or dashes, NOT spaces between words. Spaces in filenames cause files to become corrupt and unreadable by different applications and systems. It’s difficult to do this all the time with every file you create, but by following my renaming system for photos it will be super easy. Spaces in folder names are usually okay and are much easier to read with them.

Example 1: 2016-03-28_Basel_Switzerland_Downtown

Example 2: 2016-03-28-Basel-Switzerland-Downtown-Church-Sharon

Just a reminder: Always include the full date in the file name, as shown above, even though the date or partial date is in the folder name. Keep in mind that the image file might be separated from the folder one day, such as when you share it with others. It’s always good to have enough information in the filename to identify its content apart from the folder name and contains the words you would use to search for it.

For example, if you excluded the date in the filename, as shown in the example below, you’d know that the photo was taken in January 2016 when looking at in the folder structure, but if you moved or shared the file, no one would know what date it was taken.

Example: 2016 > 2016 01 04 > Mary_Birthday (Not ideal. No indication in the filename of the year or even month the picture was taken.)

What if you have no idea when the picture was taken? Always include the XXXX-XX-XX date format, even when you don’t have a date. Doing so keeps your files uniform and sorting consistent. You also might eventually come across the date or get it from someone else so you can quickly add it later.

Examples: 2016-03-2x or 2016-03-xx

When creating descriptions for your filenames, think of the words you would use to search for a specific photo and add those to your filename. They can be people, places, objects, events or anything else you come up with. For example, flowers, mountains, ocean, beaches, food, sunsets, colors such as blue, red, green.

So you want to find all the photos that you’re in? Add your name to the filename for those photos. Want to find all the photos of a particular object such as churches, castles, mountains, etc.? It’s easy. Add it to the filename. Have fun with it.

Bulk (Batch) Renaming Files Using the Operating System’s Renaming Tool

Renaming files in bulk is the SECRET to which most photo takers are not privy. Now that you’re in on the secret, you hold great power–if you decide to use it!

Many people don’t know that Windows and Mac have a bulk renaming tool built into the software. It’s super easy to use and it’s quick. Here’s a good article that explains the steps for a Mac.

Here’s a brief overview of the steps for Windows 8.1 (It should be similar for other versions):

  1. Highlight to select the files you want to rename with the same description.
  2. Right-click, and select Rename.
  3. In the opened file name box, type the description you want, then hit Enter.
  4. The files will all have the same filename with a consecutive number (1), (2), (3), etc., appended to the end.

This is a quick way to get the basic information such as date and person in all the filenames. To add additional information to some of the files simply do another pass by selecting those images and adding the information you want.

Let’s See It in Action

1.Select the files you want to rename exactly the same.

2. Right-click on the first image file, and from the drop-down menu select Rename. The filename is highlighted.

Files selected for renaming


3. Type the new filename where the highlighted text is. DO NOT REMOVE “.JPG” FROM THE FILE NAME. 

Remember to begin with YEAR-MONTH-DAY, followed by WHO, WHAT and/or WHERE (or any combination of these) and use dashes and/or underscores, not spaces between words.

This is my description: 2016-03-28_Basel_Switzerland

NOTE: For more useful sorting, follow the same naming pattern after the Date for all your files. For example, if you start with DATE_WHO_WHAT_WHERE, then stick with that. I usually use DATE_WHERE_WHAT_WHO and then any other miscellaneous info I want to include. (But honestly, I don’t always stick with that. The beauty of naming your files with this information is that you’ll find what you need quickly through a search even if your naming order is a little inconsistent.)

Enter new filename

Voila! All 60 of the files are renamed in the same amount of time it takes to rename one!! Pretty incredible, huh? You can do the same thing.

Notice that Windows appends a number to the end of each image file. As you know, no two files can be named the same thing so the number makes each file unique.

All files renamed at the same time

Adding Additional Info to a Renamed File

After you bulk rename some files, you might want to rename some of them again by adding more information such as names of people in certain photos or a specific place or event. For example, if I wanted to add “Church” to several of the photos I renamed in the above example, it would look like this:

Three files renamed a second time

The numbering system for these three files starts over with “1.”  At the same time, the original numbers for those files no longer exist. You can see this in the new third file (the one with “Church”), which is now appended with (3) and the original number appended (7) no longer exists. So the sequence for the files renamed the first time around would be: 3, 4, 5, 6, 8, 9, and so on. And the “Church” files are 1, 2, 3.

When this folder is sorted by “Name,” it will begin with the 2016-03-28_Basel_Switzerland (3).jpg file because the original (1) and (2) associated with that image no longer exists.

Windows renaming is limiting in that you can never get a numbering system that stays intact if any files are renamed. If you don’t care about the numbering, then Windows’ renaming tool will work fine.

If you want more flexibility and options, check out a third-party file renaming application.

Using A Third-Party Application to Bulk Rename Files

If you want more customization options, you can use a third-party application. You can do a search for a bulk or batch file renaming application. There are ones available, free and paid versions, for both Windows and Mac.

For Windows, I use a free one called File Renamer Turbo. I’ve tried quite a few and this is the easiest one for me to use that has a fair amount of options. If you’re interested in trying a third-party application, this might be a good one to try.

I’m not going to explain how to use this application step-by-step, but instead give you a taste of what an application of this type looks like and its versatility.

Overview of File Renamer Turbo

File Renamer Turbo offers basic and advanced options.

Basic options
Advanced options

To Rename Files

1.Select the files to rename, then right-click on a selected file.

2. From the drop-down menu, select File Renamer Turbo > Rename with File Renamer Turbo.

3. Click Add Basic Filter, then select Insert.

4. In the Insert field, type the new filename. Notice that it placed the text in front of the original filename (see the preview text in red).

New filename added

5. To remove the original file name, click the check box “Overwrite existing text on that position.” The original file name is deleted.

Overwriting original filename

To make each filename unique, I need to append a number to the end.

6. Click Add Basic Filter, then select Counter.

7. In the Prefix box, add “<filename>_”. (The “<filename>” displays by default in the Suffix field. I cut and pasted it into the Prefix box so that my filename appears before the number. I added the underscore to stay consistent with my convention.)

8. Options are set as shown below, with Leading Zeros Mode set to Custom. I set mine to denote a “one thousand” range. In the preview (red text) see how the counter is placed at the end to accommodate up to 9,999 photos.

Appending a unique number to each file

9. Click Rename. Whoo hoo! All 60 files are renamed with a customized counter.

Renamed files with unique file number

Let’s say I want to add “Church” to some of the filenames. This is where a third-party application makes the difference. I would simply go through the same process of selecting the files, opening the app, selecting “Insert” and typing the text and placing it where I want it in the filename.

The image below shows the renamed files. Notice that the numbering system remains intact! You now have a consistent and customized numbering system in place.

Additional search term added to filename

This application, unlike Windows’, offers the capability to create a new subset of vacation photos with an appended counter that starts where the previous batch left off. So if I wanted to assign a number to each photo that in the end would reflect the total number of my vacation photos, I would start the numbering for my Germany pictures with “61.” Always starting my next batch of images where the last batch left off, I should end up with the last photo reflecting somewhere in the 2000s.

If you want to get really crazy, you could write the unique filename number on the back of the photos you got printed so if you wanted to later reprint it or share the digital file with someone, you’d just search by that number in your vacation folder to find it super quick.

Search in Action!

This is what you’ve been waiting to do. To see the results of your work in action.

So here is my search results for “church.” It took about 1 second to find my photos with a church in them.

How long would it have taken to find them with the original filenames? For me, who knows? Probably forever. And I might have missed some.

Which way do you prefer? Fast? Or Forever?!

Search results for “Church”

Regardless of whether you use Windows (or Mac’s Finder Renaming tool) or a third-party application, bulk renaming your files means you can create useful filenames QUICKLY that can be used in a Search that will return exactly what you need in seconds…every time!!

A bulk renaming tool will take a little time to explore its options and figure out how to use it. But once you get the hang of it, you’ll be renaming your files with ease. You’ll even discover it’s fun to rename your files because it’s so easy and searching becomes a breeze.

As a reminder, you can only rename files in bulk using a computer. There isn’t a cloud service such as Google Photos, Flickr or Dropbox that allows for renaming in bulk.

Final Words

Let’s recap your successes as you’ve followed through this series:

  • Created clear and meaningul folder names
  • Created an organizational folder structure that makes sense to use, is simple to maintain and is easy to apply to other events
  • Eliminated picture clutter by deleting unwanted, bad and duplicate photos before renaming them, as well as starting a good habit that will serve you well going forward
  • Renamed hundreds, or even thousands, of files super fast using a bulk renaming tool (the “secret tool”) so that your filenames mean something to you
  • Created a powerful search system to find specific photos instantly so you can have fun doing what you’ve always wanted to do with them: ENJOY THEM MORE, SHARE THEM, HAVE FUN CREATING LOTS OF THINGS WITH THEM!

Alrighty, now go have fun with this! You’ll have your vacation photos renamed and organized in no time. Do some searches for words you used in your filenames and watch how quickly you get back exactly what you want. I guarantee you’ll have a big, ole grin on your face when you see the results!!

Thanks for taking this journey with me. Now I’ve got to get the rest of the vacation photos renamed. I just received a batch of photos from another person with whom I traveled. Gotta go. I have some fun to get to!!

If you need

Share your success story in the Comments.

Have ideas for future articles? Send me an email at info@shoeboxphotoscans or post your ideas on my Facebook page.

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