I travel pretty surprisingly minimalist given my enjoyment of gadgets. My kit, regardless of trip length consists of:

- Microsoft Surface Pro + Charger (usually charger is in rolling bag)
- Microsoft Arc Mouse (old folding style)
- Mini 3-Port USB Hub (for times I need to connect mouse and thumb-drive or phone)
- 2A USB AC Charger
- 3.1A Dual USB 12v Car Charger
- Retractable Micro-USB Cable
- 8" x 6" Grid Notebook
- 2-3 Pens (usually a Space Pen, Pilot V5, and random hotel pen)
- Business Cards
- Band-aids
- eGo-T Personal Vaporizer (Tank Atomizer and juice usually go in 3-1-1 bag)

For shorter trips I add:

- Microsoft Surface Touch Cover
- Koss KSC75 Clip-On Headphones

For longer trips I add:

- Microsoft Surface Power Cover
- Audio Technica ANC27 Noise Canceling Headphones

I can always fit either above configuration in the small AmazonBasics 11.6" Laptop Bag. It's surprisingly well built for the price and the perfect size for the Surface Pro. If Tumi, B&R, TravelPro, or Eagle Creek made something as small (that wasn't vertical/cross-body) I'd consider it, but it would be a hard sell at likely 10x - 20x the price. If I try to add much in terms of files/brochures/magazines it can get tight, especially if I have the larger noise canceling headphones in the front pocket. I've thought about getting the 14" version of the AmazonBasics bag for when I need more file/brochure storage, but I also have a Cocoon Grid-It 13" (thick, heavy) if I really need the extra storage or if I need to travel with a larger laptop (never since getting the Surface Pro).