Greece

SANTORINI
Accommodation:
We stayed at the Galaxy Suites in Imerovigli, which I can’t recommend enough for a quiet romantic getaway (less so for a party weekend- stay in Fira). Their modern suites are perfect, each with private (well, not completely private) jacuzzi, room 17 is the best.
Food:
For walking distance of Imerovigli, we had great meals at Skyros Taverna (ask for table on lower level), and Blue Note. Kapellino’s has great pizza.
Activities:
Santorini is a perfectly managable size to rent a car, scooter, or 4-wheel bike & just cruise around the island. There are zillions of tavernas, villages, wineries, beaches, and churches to keep anyone occupied. We loved Red Beach for its amazing colour & clear water, and of course Oia is famous for its sunsets. Skoros Winery has a great caldera view.

St Petersburg

Accommodation:
The Pushka Inn is a great hotel with a fantastic location near the Hermitage. Its singles are around 4,000 RUB in high season.
Food & Nightlife:
Restaurant Restoran (traditional Russian), as is Aquarel (fusion, on a floating location). For bars on the off nights (Sun-Wed), the strip near Church on Spilled Blood (Depeche Mode, Bubble Bar, etc) are usually lively and friendly, but the crowd can be very young.

Moscow's Golden Ring

Transport:
A car and driver is an extremely good way to explore this region, which may cost around $200/day, inc. car, plus fuel. Else car rental, train, or tours are an option.
Accommodation & Restaurants:
The Hotel Sokol in Suzdal is a clean, new, and extremely well-located place for approx $90/night. The eatery inside the Kremlin has good food, and “Salmon & Coffee” has great ice-cream.

Kazakhstan

ALMATY
Nightlife:
Gas/Petroleum have a good party on Wed nights. Da Freak, Crystal, Most, Fashion, Grand Opera are great clubs on weekend.

Kyrgyzstan

BISHKEK
Accommodation:
Silk Road Lodge is well-appointed, but location isn’t great.
Nightlife:
Apparently Retro Metro has a good retro foam party on Monday nights. I’ll leave it to you to verify.

Uzbekistan

TASHKENT
Accommodation:
Recommend the Grand Mir (~$150) for location & amenities.
Food & Nightlife:
Al Dakhan does great Middle Eastern food, but we weren’t able to unearth anything resembling nightlife.

SAMARKAND
Accommodation:
Highly recommend the brand new Hotel Malika Prime (not to be confused with the old Malika) for excellent location.
Food:
Venezia does great pizza.

Ukraine

ODESSA
Food:
Restaurants tend to be much better quality in the centre of town, rather than in Arcadia.
Accommodation:
Keep in mind Arcadia (where the beach and partying action is in the summer) is about 20mins from the centre of town, so depending on your interests, you’ll need to stay accordingly. My favourite in Arkadia is the Morskoy (~$100), but be warned, it’s RIGHT next to some of the biggest nightclubs, so unless you’re out partying, you won’t get much sleep.
Nightlife:
In Summer, all the action is at Arkadia. There are a strip of nightclubs along the beachfront. My pick is Ibiza, followed by Itaka, but you can find anything to suit your tastes.

KIEV
Accommodation:
As it’s difficult in Kiev to find reasonably-priced hotels, it is common to rent apartments. We had terrible experiences with Partner Guesthouse, who are an apartment firm, so do NOT recommend them.
Restaurants and Nightlife:
We had great meals at Shinook and Tsarskoe Tselo (both Ukranian), and Avalon is always a good bet for a decent meal and some drinks on an off-night.
Kiev has rocking nightlife, Buddha Bar has just opened for high-end cocktails (Safe is also good), Tsar and Barsky are top high-end clubs, and Patiba is still going strong for nightclubbing in a not quite so pasfusny environment.

LVIV
Accommodation:
We had good accommodation at Hotel Opera, a high-end pick.
Restaurants & Nightlife:
Partisan (“Kryvka”) bar is a must-do (but you’ll need a password at the door, and don’t try speaking Russian in there!)

POPOVKA
You’re kidding, right? ;-)

YALTA
Accommodation:
Highly recommend Hotel Bristol ($160) for amenities and location (& it’s duck-free (we checked)).