I take it you haven’t been here before? I’ll tell you my top five highlights for the Bend area: The High Desert Museum, the Cascade Lakes Scenic Byway, The Deschutes River Trail, Downtown Bend and Mirror Pond, and The Old Mill District on the Deschutes River. I would devote a day to driving the mountains (Cascade Lakes) and a couple of days to exploring town. Maybe catch a concert at the Les Schwab Amphitheater? Maybe head north 45 minutes and spend a day at Smith Rock State Park – it’s spectacular. If you want tidepools and the coast, you’ll need to drive four hours west. Well worth it, but your call if you want to take the time. Enjoy!