Our cruise departed from Tokyo in October, 2018, from the Harumi Port. If you're a fanatic about avoiding cab rides, we took the subway from our independent Shinjuku-area Hilton's Tochomae Station (E28, Oeda line), a 30 minute ride to Kachidoki Station (E17.) Crossing the street (depending on which exit you use), you have to determine (say, with Google Maps) the correct direction for the 03 or 05-1 bus to the nearby end of its line, Harumizen. This is, literally, the Cruise Terminal, so don't get off at any of the nearby hotels just before the end of the line. It looks like a transportation terminal! Another guest told us there was a convenient city bus from the Tokyo rail station, which is much closer to Harumi Port than Shinjuku. There were all-afternoon lunch hours upon boarding, so you did get a round three-meals for every day of the cruise.
Shimizu, Japan, our first stop was a short run. This is not much of a town, although they did give our small ship a warm welcome, with a ceremonial fireboat, and a sweet send-off, with local musicians and a small display of daytime fireworks! The reason to come here is to, maybe, view Mt. Fuji in the distance. Although they told us that the last two Windstar visits revealed no trace of the mountain, we were luckier! Happening to have a starboard cabin, when we threw back the curtains during the 7 AM pilotage, we found Mt. Fuji magnificently in front of our window. In addition, our ship-tour to a mountain shrine (Kunozan Toshogu), accessed by a five-minute cable car ("ropeway") ride just happened to coincide with a seasonal costumed procession and devotional ceremony by local civic groups and supporting businessmen in suits. No one had to tell us to step back respectfully and stand quietly. But the locals warmly gestured for us to join them in paying their respects. You may know that this is called by some travel-book readers a "Rick Steves moment." Many steps had to be climbed, despite the cable-car ride. It is theoretically possible to do this outing independently, with a local bus. I don't know the details. Our ship excursion included a second stop at a 2-story tower for viewing Mt. Fuji. It was starting to cloud over by then, and was invisible when we got back to the ship.
Osaka, Japan The second cruise stop was not far away, an overnight stay. Our Tempozan port was just three blocks, in a straight line, from elevated rail station C11, (Chuo line). This gives you prompt, full access to the city. (There is a very nearby free city ferry to the next peninsula, but it looks like the other ferry stop could be a mile from Universal Studios and Harry Potter.) But I will suggest that (especially since the overnight stay eliminates any danger of missing the ship's departure) that you skip Osaka and go on your own to Kyoto. If you have been to Kyoto, you could go to Nara for the day instead. Both trips are quite inexpensive. Osaka, Kyoto, and Nara use the same RFID public transit card. Even the differently-named RFID card popular in Tokyo works in these three cities too. You can even use the card to pay for single JR tickets. However, I never found any way to put money onto the card other than (obviously, Japanese) CASH. And I didn't have time to get my 500 Yen deposit back by turning in the card.
Cabin 315 Deck 6 “Balcony Suite”. We received an email about a month before our departure offering us an upgrade from the lowest deck (fixed windows) to a choice of six other cabins. This was a single charge of $400, covering both passengers. We accepted it. Star Legend has only single sinks, but we were very happy with our huge tub with hosed shower head. The motor yacht cabins are much larger than on the sailing vessels, and that helps us to prefer the MV cruises. Our pair of stewards took good care of our room, which did not show much wear and tear since the last renovation of this older ship. Some guests might want more than one 120 Volt outlet, but we always carry lots of Shuco prong adaptors for our electronics (which don't care about the voltage.) The “Balcony” is a worthwhile splurge. It's almost floor to ceiling glass, opens 100%, and has a balcony with a glass front, about 17” deep. There seem to be some slight drafts around the outside, but the opaque drapes muffle it. The doors can apparently be locked remotely during a storm. We never used the DVD player. Sattelite TV channels are very limited, and Standard Definition at best. Because we went to the Yacht Club so often (particularly for early breakfast) this cabin turned out to be very well located to run up the stairs to Deck 8. Very happy with this cabin. The only “noise” was a thoughtless directly-adjacent guest who slammed his door every single time he exited or entered. That's not Windstar's fault.
Port was actually Tokyo Harumi Terminal, not Yokahama.