Be warned - this is quite a rushed itinerary.
Day 1
Arrival in Tokyo at 9am. Activate 14-day rail pass. Travel to Kamakura, dump luggages at the JR rail station and pending the day exploring Kamakura. Overnight in Tokyo.
Day 2
Day trip to Nikko, one of Japan’s UNESCO World Heritage Sites. Overnite in Tokyo/Sendai/Hiraizumi.
Day 3
Early morning, take train to Hiraizumi (depending on where you are staying - we stayed in Tokyo to minimize movement) and explore Chuson-ji. Back to Sendai to and spend late afternoon and evening, then overnight.
Day 4
Take train to Matsushima Bay for bay cruise and explore Matsushima, then spend afternoon and evening exploring Sendai again. Overnite train to Hakodate.
Day 5
Quick 3-hr visit to Hakodate’s morning market (superb super-fresh seafood!!) and then train to Shikotsu-Toya NP. Visit Mt Usu and Mt Usu-Shinzan, the volcano museum, the biggest onsen in Japan, then evening train to Asahikawa via Sapporo. Overnight in Asahikawa in the city’s oldest ryokan.
Day 6
Day trip to Daisetsuzan NP. We climbed Hokkaido’s highest peak, Mt Asahi, or Asahi-dake. Overnite in Asahikawa. Try the Asahikawa ramen! there’s a ramen village and a famous ramen shop, Ichikura, is open till 4am.
Day 7
Morning trip to Furano. There’s a cheese factory, farm tomita is a must to try the super nice melons, lavender ice cream and see the rainbow-colored fields of flowers. In the late afternoon, take the train to Wakkanai and overnight here.
Day 8 & 9
Take the first ferry to Rebun-to, the lower of the 2 northernmost islands. You have to catch the first ferry at about 6:30am coz the tour buses on the island are timed exactly to match the first ferry and the end right before the afternoon ferry. There is only one hike worth doing here, and its a 10hour ascend and return to rebun-dake, or mt rebun. So i took the tour instead coz i wasnt feeling up to it. Hop onto an island tour a and finish by noon, then take the ferry to Reshiri-to.
Spend the afternoon doing small hikes around the ferry terminal, then camp overnight and do a 4-hour hike at the northern tip of the island to see some gorgeous scenery. Grab the afternoon ferry back to Wakkanai, spend some time here if you want, and take the train back to Otaru via Sapporo. Overnight in Otaru.
Day 10
Explore Otaru, the “Venice of Japan”. Many music boxes, glassware and craft stores. Try the street side melon slices, freshly-grilled seafood, and steamed / grilled corn! Heavenly.
Overnight in Otaru / Sapporo.
Day 11
Explore Sapporo - the beer brewery, the park, tv tower, and Sapporo’s version of ramen. The bata-kon (butter + corn) ramen is worth trying. Evening train and overnight in Kushiro.
Day 12
Breakfast at the Kushiro morning market, superb seafood. Get a seafood donburi and choose your own toppings from many many selections of the freshest wriggling seafood.
Grab a rental car and drive to the various observation points of Kushiro Shitsugen NP. Short hikes are available.
In the evening, drive down to Akan Kohan, an Ainu village beside Akan Lake in Akan NP and set up camp, see the village crafts and traditional Ainu dances and music. There is a small museum but if you are going to the Northern People’s museum in Abashiri later, then give it a miss. There are many free foot onsens around so try them! This is an onsen town so many good onsens abound if you don’t want to camp.
Day 13
Drive up to Kawayu Onsen, you can be based here. I chose to camp at Kussharo lake. Grab info from tourist centre, visit the nearby Mt Iowa where you can see many sulphuric discharges and mini-hot springs bubbling on the ground. You can also try a onsen-cooked tamago.
Drive to Mashu lake - don’t miss this out whatever you do. Then drive to Kussharo lake for sunset and that’s where i camped over.
Day 14 & 15
Sunrise at Mashu lake again. Drive up to Shari for lunch and to get NFL on Shiretoko NP. Over the next 1.5 days, drive around Shiretoko NP, Rausu and various sights and hikes in the area. Don’t miss the Shiretoko pass and kamuiwakka hot spring falls, which is only accessible by bus - bring a bathing suit!
Day 16
Drive to Abashiri, see the Northern Peoples Museum and the Abashiri Prison Museum. Fly back to Tokyo in the evening.
Day 17
Morning flight back to SG
What i would have done differently - take a flight to Sapporo direct from SG and rent the car for a longer period. Hokkaido is very drivable.