We took a 3-month trip with my gf to travel though 9 states and 8 national parks. We were maintaining a simple routine:
7 days in each place, then moving to a new place every Monday but not further than 4 hours drive.
Great idea and I like the simple design.
Have you thought about integrating with different readers/highlighters (Kindle, Pocket, etc.) so users could import their highlights to your service?