Tokyo - Sapporo travel

During my upcoming trip to Japan (24 Nov-5 Dec 2019); I am also planning to include 2-3 days of Sapporo. For my visit to Sapporo; I am planning to take the following approach:-
1. 29th Nov - Tokyo - Shin-Hakodate-Hokuto (Shinkanset Hayabusa 33)- 17:20 - 21:44; Shin Hakodate Hokuto - Hakodate (JR Hakodate line) - 22:11 - 22:37
2. Overnight stay at Hakodate (Hotel La'gent Plaza Hakodate Hokuto) on 29th Nov; check out 30th Nov.
3. 30th Nov - Hakodate- Sapporo (LTD. EXP SUPER HOKUTO 1 - Hakodate-Sapporo (JR)) - 06:02 - 09:48
4. Stay in Grids Sapporo Hotel&Hostel (check in 30th Nov - check out 2 Dec)
5 On 2nd Dec - SAPPORO(JR) - SHIN-HAKODATE-HOKUTO (LTD. EXP SUPER HOKUTO 2; 06:00 - 09:13); SHIN-HAKODATE-HOKUTO - TOKYO (SHINKANSEN HAYABUSA 16; 09:35 - 14:04); TOKYO - SHIN-OSAKA (SHINKANSEN NOZOMI 367; 14:20-16:50).
Please let me know how feasible is this plan looking like? And I also wanted to know if there is any provision of sending luggage beforehand and travel bag-free from Tokyo-Sapporo & Sapporo-Osaka.

It's a lot of time sitting on the train you have planned, over a fairly short time.

We flew to Sapporo (New Chitose) from Tokyo, picked up a car at the airport and had a drive around for a couple of days, caught the train from Sapporo to Hakodate and had a couple of days there before carrying on to Tokyo. There are a lot of nice things to see near Sapporo and on the way back, it's a shame to race through.

To my taste the whole trip is rushed-too much getting from A to B, and not enough enjoying the destinations.

I agree, that�fs an awful lot of travel time just to check out Sapporo for a couple of days. You stay over night in Hakodate just to sleep (late check in, early checkout). That seems like an awful waste to me.

Tokyo to Sapporo is one of the busiest air corridors in the world. There are plenty of flights every day. It would save you time and money to just fly there and back to Osaka. There is nothing to see on your northbound trip as you will be doing it in total darkness. On the return, you may fly over Fujisan, which should peek over the clouds if it were cloudy that day.

It takes 2 days for luggage from Hokkaido to Kansai, so I would suggest sending your luggage from Tokyo to Osaka and take an overnight (or two) bag to Sapporo as a carry-on.

Agree with PPs that this is TOO much time on train and not enough time IN destination (at least for my liking).

Also the night in Hakodate doesnt make sense to me. You arrive at your hotel in the city shortly before midnight and need to take a train next day in the morning at 6 am from Shin-Hokuto again. If you stick with that plan, I would at least get a hotel right at Shin-Hokuto station. I remember there was one right outside of the station (there isn't really anything else there though).

I would also fly. Look into discounted tickets by ANA or JAL that they offer for foreign tourists. E.g.
https://www.nl.jal.co.jp/nll/en/flight_planning/

Enjoy your trip to Japan!

I'm going to the 4th the flying. If you fly, I can see spending 3 or so days in Hokkaido, because the travel times are just much lower. I flew from Chubu to Hokkaido years ago and it was a really lovely flight. I went right over Towadako. Seeing Mt. Fuji from the air is a true treat and I like it better than from the shinkansen.

Since you're already looking at paying for a Nozomi, paying for the airline tickets instead shouldn't be an issue.

Good luck!

I understand the stop at Hakodate, and will also assume you are doing this on a rail pass (7-day) as a budget trip/saving money. There is a big "however" - given everything else Japan has to offer, wasting two days travelling to/from Sapporo for a single full day is not a good use of time. Unless there is something really really really you must do above everything else in Japan, don't do it just for the sake of it.

In any case, fly Sapporo-Osaka.

Thank you all for your worthy replies; I have reorganized my plan based on your suggestions and dropped the idea of Sapporo for this time.