The following is a draft. It's not bad. It's fairly close. Chris, Sean and I hashed this out over about 3 pitchers at High Street. But it's still just a draft. Please do not take it too seriously.
Assuming an Aug 1 Departure
FLY FROM PORTLAND, LAND IN LONDON
EARLY AUGUST
Cambridge, 2 days, leave 8/4
Edinburgh, 4 days, leave 8/8
Glasgow, 1 day, leave 8/9
Manchester, 1 day, leave 8/10
Liverpool, 1 day, leave 8/11
Swansea, 1 day [optional], leave 8/12
Cardiff, 3 days, leave 8/15
[option: stop in places like Bath, Bristol, etc.?]
London, 3-4 days, leave 8/18
TOTAL: 17 days, 7-8 cities
MID-AUGUST
Eurostar
VALIDATE FIRST EUROPE RAILPASS
Brussels, 3 days [option: go to another small town, say for chocolate or beer?], leave 8/21
Amsterdam, 3 days, leave 8/24
Hamburg, 1 day, leave 8/25
Copenhagen, 3 days, leave 8/28
Oslo, 3 days, leave 8/31
EARLY SEPTEMBER
Stockholm, 3 days, leave 9/3
[possibly Copenhagen (doubleback), possibly Trelleborg ferry]]
Berlin, 4 days, leave 9/9
Warsaw, 4 days, leave 9/13
Krakow, 3 days, leave 9/17
MID-SEPTEMBER
Bratislava, 3-4 days, leave 9/21
Budapest, 3 days, leave 9/25
Vienna, 3 days, leave 9/28
EARLY OCTOBER
Prague, 4 days, leave 10/3
Munich, 3 days, leave 10/7
[Innsbruck, optional], 1/2-1 day leave 10/9
Zurich, 1 day leave 10/10
Bern, 1/2 day leave 10/10
MID-OCTOBER
Lausanne [including Geneva?], leave 10/15
Milan, 3-4 days, leave 10/18
Venice, 3 days, leave 10/21
Florence, 2 days, leave 10/23
Rome, 3-4 days [maybe my dad will come along for this?] leave 10/27
overnight through Milan [going through]?
Lyon, 2 days, leave 10/29
Marseille, 2 days, leave 10/31
EARLY NOVEMBER
Barcelona, 3 days, [1 train to Bar, leaves mid-arvo], leave 11/3
[Palma de Mallorca?]
Madrid, 3-4 days, leave 11/7
Lisbon [overnight, arr. 11/8], 4 days, leave 11/12
San Sebastian, 2 days, leave 11/14
MID-NOVEMBER
Bordeaux, 2 days, leave 11/16
Paris, 4 days, [or maybe Dad come along for this part?] leave 11/20
AT PARIS, CHECK PASS – USE THE HELL OUT OF WHAT’S LEFT!
Eurostar
London, 2-3 days, Or just head home straightaway.
Fly home.
TOTAL CITIES: 40
TOTAL COUNTRIES: 17
DATES: Aug 1-Nov 20
TOTAL TIME: just shy of 4 months
Now we’re getting somewhere.