On a whirlwind trip of the sites along the Yamanote Line, you could comfortably give Meguro, Gotanda and Osaki the slip. This is also true of Shinagawa, which strikes me as place very grudgingly built around a major station and a waterfront.
With a little bit of money and time however, especially the right time, it’s worth a look.
If both are present, you can get some joy out of a trip to the bottom and the top of the Shinagawa Prince Hotel, to the north of the station. Below is an aquarium, the Epson Aqua Stadium. Just because it is at the bottom of a hotel doesn’t mean it’s a roided up restaurant fish tank. The big ticket items are all here: dolphin shows, seals etc. The price of entry (1800 yen) is the same as a cinema ticket and it’s probably a safer bet than most movie theaters for 90 minutes or so. (although my judgement might be skewed after shelling out for Taken2 the other day).
If you’re there after 5 you would do well to have a drink at the North Bar on the 39th floor of the Prince Hotel, which offers a view well worth the 2000 or so yen (including table charge), especially if you are up there around dusk. The city’s equivalents of the dolphin and seal shows are laid out in front of you: the Shinjuku skyscrapers to the north-west, Tokyo Tower, the Roppongi skyscrapers and the still very new Skytree, to the north-east. And if you duck around to the far right of the bar (as you walk in), you can watch the planes take off in your general direction from the runway at Haneda Airport to the south.
If you’re there prior to 5, you’ll have to make do with the “Top of Shinagawa” cafe, which is on the same floor but faces mostly east to west. With a series of mid level buildings blocking the bay view in the most functionally, restaurant fish tank depressing way, all you are left with is a glimpse of Shinjuku or the Skytree, if you care to do some extreme rubbernecking. All of which frustrates in a way similar to trying to watch your favorite footy team on a streaming coverage that keeps freezing.
Which brings me to the Strings Hotel on the southern side of the station. Head upstairs and you have the lobby bar, just showing a bit of skirt if you stand up and look through the China Shadow restaurant which has seized more or less the whole view. Such a restaurant is not cheap of course, however, if you do have some change about, you’ll have a nice view of the Bay.