Rishiri-Rebun itinerary

Hello,
I intend to make a visit to the Rishiri-Rebun islands but since I have already been to Hokkaido several times I thought of flying there from Tokyo.

There is one direct flight each day from Tokyo to Wakkanai airport, as well as several flights from Tokyo to Sapporo, and from Sapporo (Okadama airport) to Rishiri airport there are apparently two daily flights. Not sure which approach would be best, it only seem to differ a few thousand yen depending on whether you travel by Sapporo or Wakkanai.

I made a rough plan to the visit.

Day 1: Tokyo - Wakkanai, Wakkanai - Rebun island
Day 2: Rebun island sightseeing, hiking or cycling
Day 3: Rebun island sightseeing, ferry Rebun - Rishiri, possibly some sightseeing
Day 4: Rishiri island sightseeing, hiking or cycling, (possibly hiking mt Rishiri).
Day 5: Sightseeing, ferry to Wakkanai or flight to Sapporo, flight back to Tokyo.

Is this doable?

Intend to stay near the harbour closer to the ferries as I will only rely on bike and foot to transport (as the bus does not run very frequent).

Depends what time you'd make it to Wakkanai as to whether or not it would work according to your itinerary. Have you seen the ferry timetable?
http://www.heartlandferry.jp/english/

Also Wakkanai airport isn�ft close to the harbor. There might be an occasional bus or taxi.

So while it might be nice to go to an island by ship it may take longer then flying there. However getting from Chitose to the Sapporo city airport also takes its time.

There's an airport limousine bus that takes 35 min to the ferry terminal, three times a day https://www.uu-hokkaido.com/air/timetable/bus.shtml#wkj
I haven't used it as we drove there. As you'd be aware, Hokkaido takes a while to travel in and you have to plan well because of limited services. I'm sure your itinerary will work.

Thank you for your comments and ideas.

I do expect about a full day of travel back and forth to Rishiri/Rebun. Taking into consideration that sightseeing on the arrival/departure day may or may not be possible.

I read on Wikipedia on Rishiri airport that there apparently are seasonal flights from Chitose airport with ANA, could find no source to confirm this though...

https://en.wikipedia.org/wiki/Rishiri_Airport

I opt out for the Sapporo - Wakkanai train though :)

I know travel in Hokkaido is slower, and I rented a car when I went to Shiretoko last year.

Anyone been to Rishiri/Rebun maybe know if cycling is a good option?

I'd say cycling on Rishiri would be totally an option and I think I've read there's rental cycles available. Rebun is more of a hiking area, which we very much enjoyed even with small children in tow.

When is this trip?

In late June it is planned to.

Regarding cycling, I haven't cycled on Rishiri and Rebun (I wasn't even there). But this web page here has some suggestions:

https://hokkaidowilds.org/cycle-touring/japan-far-north-rishiri-rebun

I cycled down from Wakkanai to Rumoi, which was a very pleasant experience:

https://bicycletraveljapan.blogspot.com/2017/09/week-1-summary.html

I learned from the guy at Hokkaido Wilds that there is a very nice cycling lane from Sapporo to Kita Hiroshima. Which was a great experience. If you bring a bicycle and have a day time in Sapporo, it would be a great ride e.g. from Sapporo out to New Chitose Airport.
https://bicycletraveljapan.blogspot.com/2017/09/day-6-sapporo-to-kitah...

Enjoy your trip to Northern Hokkaido!

Not sure if this is repeated in the responses above but I will mention my experience. I cannot talk about the cycling component of the question.

There is indeed a direct flight from Tokyo to Wakkanai once a day on ANA. I took that flight in November 2019 and it is a very pleasant flight. You arrive at Wakkanai Airport around 12:40pm. I recommend the direct flight straight from Tokyo.

Day 1: Completely doable, but refer to the Heartland Ferry Schedule. http://www.heartlandferry.jp/. Depending on your visit, ferry service is very limited especially in winter. Also, the ferry departures do not correspond to the airline arrivals at the airport. My advice is to take the bus to Wakkanai and get off either at or before Wakkanai Station (http://www.soyabus.co.jp/airport). Then walk to the ferry terminal. The walk is through an industrial area but there are sidewalks. The ferry ride is about 1.5 hours. At the terminal, you can purchase tickets at the vending machine.

Day 2: Not sure where you are going within Rebun, but stay at a hotel near the ferry terminal (there are two or three hotels). There is a bus stop in front of the ferry terminal that takes you to various locations on the island. http://www.soyabus.co.jp/routebus/rebun. Cycling in Rebun might not be recommended because of the terrain. Also, if you are going to the base of Momoiwa, you have to go through a tunnel where cycling might not be permitted.

Day 3-4: I would take the ferry to Oshidomari (the main town) of Rishiri Island rather than the smaller town. In my experience, driving is almost essential given local landmarks and places of interest are so remote. I know in your message, you will only walk or cycle. If you can cycle your way around the island, there are pretty good trail and path systems. http://www.soyabus.co.jp/routebus/rishiri.

You did not mention when you are going. I did the research for hotels and all hotels do not operate between October to April/May. However, I am assuming you are going in the summer since you will be cycling.

I have attached links to the Soya bus network which provides private transportation throughout the Cape Soya area. Any questions let us know. I have traveled extensively in Wakkanai, Rishiri, and Rebun in November 2019 and I know you will have an amazing time.

@Villagemayor

I expect to be going around mid-late June. Still in the early planning stage as I wanted to make sure it would not be too much of a hassle to go there. :)

I might consider going to or from Rishiri airport if it is possible to connect through Shin Chitose as there are more flights to Sapporo from/to Tokyo. But still I am quite curious about Wakkanai as well, hence going to Rebun first and leaving from Rishiri (or the other way around).

I read on Wikipedia on Rishiri airport that there apparently are seasonal flights from Chitose airport with ANA, could find no source to confirm this though...

Start with Skyscanner.

https://www.skyscanner.jp/transport/flights/spka/ris/?adults=1&childre...

You can see flights from Sapporo (Chitose-ANA or Okadama-JAL). You can book from the link provided.

Note that Tokyo-Sapporo-Rishiri can be more expensive than Tokyo-Wakkanai-(bus and ferry)-Rishiri or Rebun. I think ANA (and probably JAL also) have not released the promotional airfare for June yet, so you must wait (probably until the end of March, I am not sure) to book the cheap flight. Tokyo to Sapporo and Tokyo to Wakkanai should be the same (around 100 USD). If you take Sapporo to Rishiri flight you must add around 100 USD (maybe, I am not sure) while the bus and ferry will cost less than 50 USD.

Anyone been to Rishiri/Rebun maybe know if cycling is a good option?

I visited the islands twice, first end of May 2016, lovely weather, and was blown away by the beauty of the islands, decided to return in the middle of July 2017 and stay 3 nights. Alas, what a big disappointment, those last visit was foggy, visibility was so bad and lasted till the day we departed.
I do not know much about cycling in the  islands. Frankly, I did not see anyone cycling during my visits. I would highly recommend the soya bus half day tours to soak-up the islands' beauty, and decide what to do with the rest of your stay. 
http://www.soyabus.co.jp/en/teikan/course ;   
I also highly recommend flying from Sapporo to Rishiri island. The fares could be too good to refuse. Check the following links in the month of May:
https://www.ana.co.jp/en/us/promotions/share/experience_jp/ ;

Wakkanai itself isn't too interesting other than a few landmarks and parks. If you want to expand your stay, Cape Soya is a great alternative and there are daily bus tours so you don't need to drive.

The ANA Sapporo routes within Hokkaido are 5500 yen each, including to Wakkanai.
http://ana.ms/20Xtf8t

Same for JAL, and they also have a SPK-RIS flight for 5500 yen.
https://bit.ly/2RewiJX

The ANA Sapporo routes within Hokkaido are 5500 yen each, including to Wakkanai.

I checked this site. The fare is 53.06 USD for Sapporo to Wakkanai on 16th Mar, but on 16th June it is 123.46USD. I think ANA has not released the promotional fare on June yet. As for Sapporo to Rishiri, no flight on 16th March, and on 16th June is 133.46 USD. I am not sure whether this goes down to around 50 USD on, say late March.

It's true they have not renewed the fare yet. But the Experience Japan Fare is over 6 years old; they've renewed it every time. There are no guarantees, but zero reason to think they won't renew it this time as well.

I checked JAL's website for their promotional fare. On 16th Jun, it is about 50 USD from Okadama (Sapporo) to Rishiri. So ANA will change the fare for June, maybe on March.

I really appreciate your help in this :)

If there are flight connections from Shin Chitose, I would prefer to fly through there, or possibly have a stopover in Sapporo (or Wakkanai). Seems like the fastest option however.

Things have changed due to Covid19, but it is said the domestic travel within Japan will be allowed after 19th June. At this time or anytime before the travel around Japan has not prohibited and many of the domestic flights were still available until now though.

Anyway, Covid19 is going to settled down in many prefectures in Japan, so the government changed the status of emergency. At this time international travel to Japan is not allowed (with some exceptions), but domestic travel will begin gradually. I am a Japanese and booked accommodations and flights to Rishiri and Rebun for late August.