Here's the detailed aspects of the trip. Should aid those looking at relaxed pace as we planned ours with elderly in mind.
Day 1: Singapore/Tokyo/Sapporo
SIN-NRT Delta Airlines DL280
NRT-CTS SkyMark Airlines
Arrival at Sapporo 5pm.
Day 2: Sapporo;
Morning: Nijo Market
Afternoon : Sapporo Beer Garden (Museum only), Ishiya Chocolate Factory
Evening/Night: Otaru, Odori Park
Day 3: Noboribetsu;
Shikotsu Toya National Park/Hell Valley
Day 4: Hakodate
Explore City
Night: Mt Hakodate
Day 5: Niseko
Slack day due to late arrival in Niseko
Day 6: Niseko
Morning/Afternoon: Niseko Mt. Resort Grand Hirafu
4 hour ski lessons by Ski school, british instructor
Evening: Niseko-Sapporo
Day 7: Sapporo/Tokyo
Afternoon: Sapporo-Chitose; CTS – NRT Skymark Airlines
Night: Kabukicho
Day 8: Tokyo
Morning: Taito City/Asakusa
Afternoon: Akihabara, Akiba Square(Anime Centre), Ueno(Ameyayokocho)
Night: Ginza (short walk only)
Day 9: Tokyo
Morning: Tokyo Metropolitan No. 1 Building Observatory
Afternoon: Palette Town(Odaiba)
Night: Ginza(Apple Store/Uniqlo/Gucci)
Day 10: Tokyo/Kawagoe
Morning: Harajuku(Omotesandō, Takesh!ta Street, Meiji Shrine)
Afternoon: Kawagoe/Little Edo, Candy Street
Night: Shibuya (Shibuya Crossing)
Day 11: Tokyo/Singapore
Morning: Tsujiki Market
Afternoon: NRT-SIN Delta Airlines DL281
Day 12: Singapore
Morning: Arrival 1am.
Transportation in Hokkaido: 5 day Hokkaido Rail Pass/Local train/buses/taxis
Transportation in Tokyo: NEX/Suica pass/taxi
Photos here