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I always make an outline of our travel schedule, beginning with our flights from Seattle, to, in this case, Bangkok. It gives me a visual aid for planning the itinerary. I note where we are staying each night (initially, this is just the city) and transport from one place to the next. Noting the transport is a good reminder than any day that is a transition from one place to the next will be mostly taken up with transport.

My first draft for this trip looked like this

Day 1 leave SEA
Day 2 arrive BKK
Day 3 fly BKK-CCU-IXB, ground to Gangtok
Day 4 Gangtok
Day 5 Gangtok
Day 6 Gangtok to Pelling
Day 7 Pelling
Day 8 Pelling to Darjeeling (ground)
Day 9 Darjeeling
Day 10 Darjeeling
Day 11 Darjeeling
Day 12 Darjeeling
Day 13 Darjeeling, ground to Bagdogra, fly to CCU
Day 14 Kolkata
Day 15 Kolkata
Day 16 Kolkata
Day 17 fly to BKK
Day 18 Bangkok
Day 19 Bangkok
Day 20 Bangkok
Day 21 Bangkok
Day 22 Fly SEA

I like this arrangement, though the beginning of the trip will be a killer. Fly from Seattle to Bangkok, a brief overnight at the airport hotel, then fly on through Kolkata to Bagdogra followed by a five hour drive to Gangtok.

The friend who recommended Glenburn also told us that they could arrange all of our Sikkim reservations. So I drew out an itinerary and emailed them with our request.