Go to File>Open and select the jpg map image you wish to annotate.

If you want to draw a circle around a particular area on your map, you will need to select the Ellipse Tool. It can be accessed either by hitting "L" on your keyboard, or from the main toolbar. On the main toolbar, the Rectangle Tool is generally the default shape tool. If you click and hold your mouse button down on the Rectangle Tool, a small submenu will pop out and you will see the option to select the Ellipse Tool.

Fill Color is the color that your shape will be filled with, while Stroke Color is the color that your shape will be outlined with.

When editing either the Fill Color or Stroke Color, make sure the one you are editing is "active" on the toolbar. Which ever square icon appears in front on the toolbar will be "active." In this case the Fill Color icon is in front of the Stroke Color icon, so Fill Color is "active." You can edit the active color by clicking on it. Clicking on the non-active color will bring it forward on the toolbar and make it the active color.

Since you’re going to be using the circles that you draw to highlight a particular area on your map, you probably don’t want them to be filled with any color at all. To set your Fill Color to none (or transparent), with the Fill Color active (up front on the Toolbar), click on the small white square with the red line through it, just under the Fill/Stroke Color icons on the toolbar.

Click on the Stroke Color icon on the toolbar to bring it in front of the Fill Color and make it "active."

Double-click the Stroke Color icon to edit your Stroke Color. The Color Picker should be fairly intuitive. You can change the hue with the slider bar, and select your color by clicking on the large square on the left, then click OK, once you’ve got your desired color.

With the Ellipse Tool still selected (if it’s not at this point, just click on it) move your mouse over your map image and click-and-drag to draw your ellipse. To make sure you draw a proportional circle, hold down the Shift key while you click-and-drag. To have your circle radiate out from the initial point you started at, hold down the Alt key (in addition to the Shift key), while you click-and-drag.

Illustrator defaults to a stroke weight of 1pt. If you want to change the weight of the stroke (outline) you can do so by selecting your desired stroke weight from the Stroke drop-down box at the top of the page. Note: In order to modify the stroke of a shape, make sure that it is selected.

By default, your circle should remain selected after you first create. However, instances may arise, where you want to come back and edit it later. In order to edit any object in Illustrator, it must be selected. To select an object, click on the Selection Tool (black arrow) in the upper-left corner of the main toolbar. This will activate the Selection Tool and allow you to select an object simply by clicking it.

Select the Type Tool from the toolbar (it is the "T" icon). Next, click the area where you want to add your text and start typing.

With your text selected, you can edit the Font settings (typeface, style, size) at the top of the screen with the drop-down menus.

Text behaves just like any other object in Illustrator when it comes to Fill Color and Stroke Color. Typically, you will not have a Stroke Color associated with text (Illustrator defaults text to a Stroke Color of none and a Fill Color of black), so to change the color of your text you want to edit the Fill Color, by making sure Fill Color is active on the toolbar (Fill Color icon should be in front of the Stroke Color icon on the toolbard) and double-clicking the Fill Color icon to bring up the Color Picker.

Just like shape object, you can move your text by selecting it with the Selection Tool and doing a simple drag-and-drop.

Once you’ve got everything finished and ready to save as jpg, go to File>Export (see next step).

After you select Export from the File menu, the Export dialog box will pop up. Select JPEG(*JPG) from the Save as type drop-down menu, give your file a name and click "Save."

After you click "Save" on the Export dialog box, the JPEG Options box will pop up. You should not need to edit any of these settings, so you can just click "OK," and you should be all set with your annotated JPG map file!