If you are looking for a hotel with commanding views of the ocean and the sweeping, rocky coastline, the Shimoda Tokyu Hotel may well fit the bill. However, it is not perfect and the room rate may be the determining factor. The hotel is perched high on a hill and certainly boasts impressive views. The staff were consistently friendly, welcoming and helpful, though one or two didn't always get things right. For example, we were told the taxi fare to town would cost 3,000yen but it only cost around 900yen. A pleasant surprise but we may not have even bothered to catch a cab had we believed it to be 3,000yen. Still, all staff meant well and made us feel very welcome.
There is a free shuttle bus service from/to Shimoda Station. Buffet breakfast is good. Onsen very comfortable. The hotel is secluded - no traffic noises - so is very quiet and calming. The seclusion may be a negative for some. Having said that it's only a 10-15min walk to the town/village. It's a bit trickier walking back because of the hill. Take it easy if walking up the hill!
The hotel needs an overhaul. Carpets are tired and pretty grubby looking in places. They are cleaned but there are many stains ingrained into the carpet. Much of the furniture is as other reviewers have said, tired looking. We were there in Spring so we didn't need to rely on air conditioning so I can't really comment on that. We enjoyed opening the window to feel fresh air and listen to the rain. The window slides open only about 10cm which is a good thing - keeps you secure but allows some breeze in. Having accepted that the decor was a bit daggy (but kept as clean as possible as it is) we were comfortable and had a great time. There is no bar in the hotel so stock up in town and put some bottles in the fridge in your room.
For me, the rating here would be 3.5 but would be 5/5 if a lot of money was spent sprucing up the place.
Good things to do as a tourist in the area:
Walk - there a lots of great walks which are flat and are on solid, secure pathways which hug the coastline. There are some walks which are hilly too eg to lighthouse at the point.
Talk the #4 bus to the lighthouse. From the end of the line it's about a 15-20min walk uphill (not too taxing) to the lighthouse. Great views. You need coins for the bus ride. There's a change machine on the bus but you can also get change at the information counter at Shimoda Station itself (the other main Tourist Information Office is just down the road from the station). When you hop on the bus, take a ticket from the machine and sit down. The panel above and to the left of the driver shows what fare is owed relative to the number on your ticket. It's not complicated. It's a good system.
Take a boat ride. There's a replica 'black ship'. Can't remember its name but its iconic in the area and you'll see photos of it everywhere. There are other boat rides too.
The aquarium is very good and well worth a visit.
There's a cosy little jazz bar/cafe called Cheshire Cat. It's very small and quaint and the man who runs it, a trumpet player, is very obliging. I'm not sure if much live music is played there but very good recorded jazz is played and some jazz memorabilia and instruments adorn the place.
Gorisaya is a good isakaya in town.
Go to the sashimi/sushi cafe at the building where the Game Fishing and Shimoda Museum is located. It's about 100 metres from where the black ship departs and can easily be seen from the pier when you get off the boat. The fish and other seafood is very fresh and reasonably priced.
If you're an angler you could take a fishing rod and try to catch a fish. Not sure if you can hire fishing gear but you probably can. Or just watch the anglers on the groin wall that juts out into the bay. It's between the aquarium and the town, near where some Japan Coast Guard vessels are moored.
The weather was pretty ordinary when we stayed recently, but if it was fine we'd hire bicycles and go for a ride. As mentioned, it's mostly flat.
Tips:
You can catch the shuttle bus to/from the hotel to save walking up the steep hill the hotel sits on. Download the shuttle timetable from the hotel's website and keep it handy.
It seems the only place to withdraw cash for a non-Japanese person is from the post office. Ask for directions from the Tourist Information centre - the post office is nearby.
There's a laundromat on the road along the waterfront in the main part of Shimoda (not too far from the station). You need to take coins, or buy something from one of the nearby vending machines to get some 100yen coins for the washing machine and dryer.