Best HTML5 markup for sidebar

First of all ASIDE is to be used only to denote related content to main content, not for a generic sidebar. Second, one aside for each sidebar only

You will have only one aside for each sidebar. Elements of a sidebar are divs or sections inside a aside.

I would go with Option 1: Aside with sections

<aside id="sidebar">
    <section id="widget_1"></section>
    <section id="widget_2"></section>
    <section id="widget_3"></section>
</aside>

Here is the spec https://developer.mozilla.org/en-US/docs/Web/HTML/Element/aside

Again use section only if they have a header or footer in them, otherwise use a plain div.


Update 17/07/27: As this is the most-voted answer, I should update this to include current information locally (with links to the references).

From the spec [1]:

The aside element represents a section of a page that consists of content that is tangentially related to the content of the parenting sectioning content, and which could be considered separate from that content. Such sections are often represented as sidebars in printed typography.

Great! Exactly what we're looking for. In addition, it is best to check on <section> as well.

The section element represents a generic section of a document or application. A section, in this context, is a thematic grouping of content. Each section should be identified, typically by including a heading (h1-h6 element) as a child of the section element.

...

A general rule is that the section element is appropriate only if the element’s contents would be listed explicitly in the document’s outline.

Excellent. Just what we're looking for. As opposed to <article> [2] which is for "self-contained" content, <section> allows for related content that isn't stand-alone, or generic enough for a <div> element.

As such, the spec seems to suggest that using Option 1, <aside> with <section> children is best practice.

References

  1. https://www.w3.org/TR/html51/sections.html#the-aside-element
  2. https://www.w3.org/TR/html51/sections.html#elementdef-article
  3. http://html5doctor.com/aside-revisited/