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Day 5 - Get to Bellingham, Washington (est. 1400 miles from SD) by 6pm, get on ferry
Day 8 - Arrive in Haines around Noon
Day 8/9 - begin the 3300 mile ride home, stopping wherever the hell we want
At 300 miles per day average - 11 days of riding home
8 days to Alaska, 11 days home = 19 days, leaving 4 days of "free" time
Ferry cost per person - about $800

OR

Day 8 - Get to Prince Rupert (est 2400 miles from SD) by 6pm, get on ferry
Day 9 - on Ferry
Day 10 - 6am arrival in Haines (or Skagway at 8am)
Day 10/11 - Begin the 3300 mile ride home, stopping wherever we want
10 days to Alaska, 11 days home = 21 days, leaving 2 days of "free" time
Ferry cost per person - about $400

OR

Day 8 - Get to Prince Rupert by 6pm, get on ferry
Day 9 - On ferry
Day 10 - 6am arrival in Haines
Day 10, 11, 12, 13 - Ride Alaska/Yukon
Day 14 - Arrive in Skagway by 11am, get on ferry
Day 15 - On ferry
Day 16 - Arrive in Prince Rupert at 5am
Day 16 - Ride home (8 days puts us at day 23)
10 days to Alaska, 10 days home = 20 days, leaving us about 3 days "free" time in Alaska/Yukon
Ferry cost per person - about $800 ($400 each way)

ALL of this is using Google maps for estimates on distances (I found both longer and shorter distances by using back roads), at 300 miles per day average.

Thoughts/suggestions/concerns?

Or

3000 miles to Skagway from SD (10 days)
3300 miles from Haines to SD (11 days)
Ferry from Skagway to Haines (about an hour)
Costs under $100 for ferry
about 2 days free time