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.