Apparently time moves fast when you’re trying to precisely plan out every day of the next month of your life. All my hotels are booked and I have something like 6 photo shoots planned and a dozen emails to respond to confirming everything. As the reigning queen of half-assed following through, I’m glad I started booking things early enough that I couldn’t get to the end of my trip planning and then decide not to go. Locked in.
What I’m most excited for? I’m hitting a combination of places I went when I was much younger, and much too young to really appreciate (my mother reminded me this weekend that I’d once referred to the Grand Canyon as a big hole in the ground, prior to demanding that we go to the gift shop), and places that I’ve never been. The scariest/best thing is that none of it is familiar to me. These are all new experiences.
I haven’t been to New Orleans before and everyone I mention it to gets this wide-eyed look and stage-whispers, “I LOVE NEW ORLEANS” so I’m pretty sure it’s going to be fun. Food and music and warmth and different feelings. I desperately hope someone says, “bless your heart” to me at some point.
I’m going camping in the Grand Canyon (aka the big hole in the ground). I was having a hard time deciding between whether to stay in Williams or Flagstaff, so I did the only reasonable thing and reserved a campsite instead. I’ll be calling on my Girl Scout training from 15 years ago, so I’m pretty excited to build a campfire with no one watching in case I fail miserably.
All of California. I’m excited for all of it. LA, San Francisco, the drive up the coast. Call me a hippie*, but I can’t wait for the hot springs retreat I’m staying at for a night north of Napa. Yoga classes, pools, quiet. It might seem a little counter-intuitive going somewhere they ban phones, computers, and cameras when I’m trying to document constantly with at least one of those three things, but I think it’s going to be a much-need reminder of presence.
*Don’t call me a hippie.
Portland, always. All my memories of Portland involve another person, so I’m looking forward to experiencing it a little more independently. Bookstores and restaurants and doughnuts and gardens and coffee. All mine.
Things I’m not excited for: Sitting in a car for repeated 8-hour stretches. Being away from Boston when it’ll actually be nice weather. Not seeing my boyfriend or cat for a month.
Feeling pretty lucky, all in all.
Sorry, Trouble.
You Have Died Of Dysentery. 
It sounds like you probably know some good stuff about Portland already but I wanted to make sure to mention Pix Patisserie on E. Burnside – excellent French macarons. I cannot recommend the salted caramel one more highly. They recently moved to this location (incredibly, 4 blocks from my home!) and serve tapas, pastries and dark chocolate candies – excellent. Also, Alma Chocolates on NE 28th, just a few blocks away from Pix, has truly wonderful chocolates. And where else can you get a chocolate Buddha covered in edible gold?
The Classical Chinese Garden is beautiful and, I think, enhanced by it’s being right in the middle of an industrial urban area. I also love the walkways on both East and West sides of the Willamette.
Restaurants to consider: Ava Gene’s (SE) – one of the best Italian meals ever – my daughter had no problem as a vegetarian there; The Fireside (NW) – GREAT veggie burger, wonderful drinks, sweet ambiance; Pambiche (NE) – excellent Cuban food served by the nicest wait staff ever; The Screen Door (E Burnside) – Southern food – try the Screen Door Plate and a Porch Swing Lemonade and you’ll be happy you did.
I’m looking forward to reading about your trip. Good luck (and be safe).