Long US road trip - where do I start?

[Barak]

Hi, I'm planning a 100-day (or less) hiking/sightseeing itinerary to the US west and east coasts. I need some help.

What's the problem?
Currently it is too long (107 days) and it's hard to pick the days to skip.

Why is it hard?
I have some constraints, such as:
- Starting after 1-Jun
- Ending before 20-Sep
- Prepare to solar eclipse at 20-Aug at Yellowstone NP
- Travel in Grand Canyon and Las Vegas area in June (otherwise too hot)
- Travel in Rockies in July-August (otherwise too cold)
- [not a must] try to be at 4-Jul in a big city
- try to have chilled days in the city after a long hike

In addition, I've never been to the US before so have no idea what's beautiful and what's amazing... I prefer amazing! :-P

What help do I need?
I need both:
- your general recommendations concerning tips for getting my schedule better
- most importantly suggestions on which days would you skip to get from current 107 days down to under 100 days.

Thanks a lot in advance!! :)

My itinerary:

#d start date what?
1......03-Jun Arrive to USA
2......04-Jun New York - overcome jet lag, get hiking gear @REI
4......06-Jun Washington D.C. - museums, white house, capitol etc.
1......10-Jun Baltimore
1......11-Jun Philadelphia
1......12-Jun FLY New York to SLC, rent car, drive to Arches NP
2......13-Jun Arches canyon - hiking
1......15-Jun Drive to Bryce Canyon, Fishlake forest
2......16-Jun Bryce Canyon - hiking
2......18-Jun Zion Canyon - hiking
1......20-Jun Zion to Grand Canyon NP
6......21-Jun Grand Canyon NP - long hike
1......27-Jun Drive to Las Vegas (via Rd89) , Sedona, Kaibab NF
2......28-Jun Las Vegas, Hoover Dam
3......30-Jun Death Vally NP - three 1d hikes
1.......03-Jul Drive to LA
4.......04-Jul Los Angeles
2.......08-Jul Sequoia national park
1.......10-Jul Way to Yosemite
7.......11-Jul Yosemite - long week hike
4.......18-Jul San Francisco
3.......22-Jul Travel along west coast up to Portland (medford, beach)
1.......25-Jul Portland
2.......26-Jul Seattle & Ferry to Victoria & Vancouver
11.....28-Jul Canadian Rockies
3.....08-Aug Glacier national park
2.....11-Aug way to Yellostone
7.....13-Aug Yellowstone NP
2.....20-Aug Solar Eclipse near Yellowstone + prep day, drive to salt lake city - Fixed dates (can't change those)
2.....22-Aug Salt lake city, return car & fly to New York
3.....24-Aug New York to Boston
3.....27-Aug Boston
3.....30-Aug Boston to Montreal
2.....02-Sep Montreal - visit family ( a must )
2.....04-Sep Montreal to Toronto
1.....06-Sep Niagra Falls / Toronto
1.....07-Sep Niagara Falls to New York
10....08-Sep New York, Long Island
.......18-Sep Fly home

Moderator Note: Please keep all questions about the same trip in the same thread.