Most people choosing between the Financial District and Times Square are really choosing between two different kinds of trip. Times Square is the entertainment core: theatres, the big attractions, the crowds, the lights that don't go off. The Financial District is the bottom of the island: office towers on weekdays, harbor air, cobblestone side streets, and evenings that go genuinely quiet once the workday ends.
The distance between them is smaller than most visitors assume. From Fulton Street, the 2/3 express runs up the west side to Times Square-42nd Street in about 15 minutes. That's the number that decides this question for a lot of people: you can stay down here and still make an 8pm curtain without rushing.
The short version
Pick Times Square if you're in town for two or three nights, you've got show tickets, and walking distance to a theatre is worth more to you than square footage or sleep. Pick the Financial District if you're here for four nights or longer, if you're travelling with kids or a group, if you'd rather cook a few meals than eat out three times a day, or if you want to be able to open a window at 10pm and hear nothing.
What you get for the money
This is where the Financial District tends to win. Space in Times Square is expensive because you're paying for the address, and a lot of what's available is a standard room. Down here the same budget generally buys more room, and in our case a different kind of stay: our suites have a full kitchen, a separate living room, and space to actually spread out. There's a laundry room in the building, a fitness center and guest lounge on the lower level, a conference room if you need to sit down with people, a restaurant, and a rooftop terrace that's a nice place to end an evening.
That matters most on longer trips. Three nights, you can live out of a hotel room. Ten nights with a family, you want somewhere to put the groceries and somewhere for one person to work while another one sleeps.
Noise, nights, and weekends
Times Square is loud at all hours, which is honest rather than a complaint. It's designed to be. The Financial District runs the opposite pattern: busy from 8am to 6pm on weekdays with people going to work, then quiet, and quiet again all weekend. Some visitors find weekend FiDi too still for their taste. Most find it a relief. If your idea of a good evening is being able to hear the harbor from a rooftop instead of a crowd, this is the better end of the island.
Food
Times Square has volume and convenience but you have to be selective. The Financial District has a real dining scene now, and it's concentrated: Stone Street is a closed cobblestone lane lined with restaurants and bars about eight minutes south of us, the Seaport is five minutes east for waterfront tables, and Tribeca is a fifteen-minute walk north for some of the best cooking in the city. Bagel counters and cafes for breakfast are all within a couple of blocks.
Getting around
Both are well connected, but the Financial District is unusually good for it: the 2/3, 4/5, A/C, J/Z and R/W all run through Fulton Street and Wall Street, the ferry terminals are a short walk for Staten Island, Governors Island and the Statue of Liberty boats, and you're walking distance from the Brooklyn Bridge, Battery Park, One World Trade and the 9/11 Memorial. Times Square is a hub too, and it's better for reaching Midtown and the Upper West Side quickly.
What we'd tell a first-time visitor
If it's your first trip and it's short and show-heavy, Times Square is a defensible choice. If it's your first trip and you want to actually see New York rather than one intersection of it, stay down here and use the subway. You'll see more of the city, sleep better, and the walk out your door in the morning goes past 18th-century streets rather than a ticket booth.