We’re going to WDW in May with kids and MIL. We’ll have one day, just us, at Hollywood Studios, on our anniversary.
I’d like a really nice dinner together, and as far as i know, none of the restaurants in HS qualify as “really nice” so i’m interested in what excellent dining there is at nearby resorts. Or, within HS if anyone disagrees with my previous assessment.
Flying Fish, Bluezoo, take the skyliner over to Riviera for Topolino. Hollywood Brown Derby is in the studios but I’d pick somewhere else.
In HS, one of my favorites, and very nice, Hollywood Brown Derby.
The only placed that I have eaten at Disney Springs are Wolfgang Puck Express, QS, and Homecomin’ which we enjoyed, but nothing fancy.
I would jump on the boat and you have several options at the resorts:
Ale & Compass (Yacht Club)
Shula’s Steakhouse (Dolphin)
Kimono’s (Swan)
Il Molino (Swan)
Flying Fish (BW)
Trattoria al Forno (BW)
I can’t speak personally for most of these but based on reviews and menus/photos, all seem like decent choices.
Also, Boardwalk is of course nice to walk around in and maybe grab a drink etc.
IF you have parkhopper tickets, then of course Epcot opens plenty of other options for dining. You could grab the skyliner there with Monsieur Paul (France) and Teppan Edo (Japan pavilion) being very close to the WS entrance.
I really like Hollywood Brown Derby. I also enjoyed Il Mulino at the swan. I hear great things about Bluezoo and Flying Fish but haven’t experienced first hand.
Lyft Ofer to Gran Destino. Start off at Dahlia and then have dinner at Toledo. It’s lovely up there.
We ate at Kimonos earlier this month. The sushi was truly excellent and the karaoke was highly entertaining. We really didn’t want to leave but RD…
If sushi and karaoke sounds like a great date, I’d recommend it. If you’re looking for quiet and romantic or aren’t into karaoke, there are probably better choices. (I think the karaoke starts at 9pm nightly.)
I did a date night with my husband many yrs ago and we just went to the 50s primetime cafe, but we weren’t looking for “really nice.” It’s really fun…
We had a fantastic date night meal at the Yachtsman at the Yacht Club.
Can anyone give an educated guess as to how much time i should plan on to go from HS to Yacht Club for dinner and then back?
Walk is about 20-25 minutes (1.25mi). Probably the same with a boat depending on how long you need to wait for one.
we can walk there?! that’s awesome!
Yes, we stayed next door at Beach Club and walk time to HS was about 25 min. We could never get the timing right on the boats. Skyliner will also get you there, but we found it to take slightly longer, even with zero wait. I’d allow 40-45 min for Skyliner, assuming there isn’t a queue.
fantastic. thank you
is there a clearly marked walking path? i dont want to get lost 
Just use google maps. It’s mostly along the waterway so pretty straightforward. Make sure to get walking directions, not driving!
From the gates, you walk past the skyliner and there is a walkway right next to the lake. You walk past/behind Boardwalk (on the right) and after it you’ll have a bridge and you can already see the YC.
If you want to save your feet a bit, you can take the boat in one or both directions
Edit: @amvanhoose_701479 beat me to it 
You can also check the satellite version of Google Maps for a very clear view of the route
