We're planning a trip to Seattle/Area May 22-31. Here's our tentative itinerary:
Arrive late Thurs. Check into downtown Seattle hotel.
Fri. Check out Pike Market, waterfront, Space Needle, Pioneer Square and Underground Tour
Sat. Drive to Woodinville area for wine tasting. Stay in area that night.
Sun. Attend wine and food tasting event 12-5 at Chateau St Michelle. Stay in same accommodations.
Mon. Drive to Anacortes and take ferry to San Juan Island. Explore island with car.
Tues. Take a whale watching tour and take ferry back in early evening. Stay in Anacortes or Mt. Vernon area.
Wed. Tour Boeing plant and head back to downtown Seattle. Baseball game that night.
Thursday. Drive to Paradise in Mount Ranier Nat Park.
Friday. Leisurely drive along Rt 101 around Olympic Mountains and/or catch anything we missed in city.
Sat. depart early

Does this sound feasible or is it too much? We don't want to spend all our time in the car.

Any recommendations on accommodations in the $75-$130 range?

Should we take the car on the ferry to San Juan Island? We've read that the wait can be 3 hours, but we've also read that in order to get the most out of the island, we'll need transportion.

Do you recommend the dinner train?

This all sounds fine, except that your Friday "leisurely drive" around the Olympics won't be too leisurely...the peninsula is far too large to circumnavigate in one day. Assuming you're spending the previous night in Seattle, you could take the ferry to either Bainbridge or Kingston, then visit Port Townsend or the Lake Crescent/Hurricane Ridge area of ONP. Either one would make a pretty full day trip.

Thanks. Does anyone have any hotel recommendations for the areas we're staying in?

In downtown Seattle a hotel in that price range is going to be difficult unless you bid Priceline or Hotwire, or choose one of the motels like Days Inn or 6th Avenue Inn.

I agree. The trip around the olympics is a full two day drive.

Also, weather is a real problem around mt rainier that early in the year. I would have backup plans, just in case.

The museum of flight in seattle is well worth the time.