DAY 3 - Midtown South
Morning: After we've gotten to see the skyline from the water and from Brooklyn, it's time for the all-time classic view. Head over to 5th Ave and 34th Street. It's time to go up to the 86th floor of the Empire State Building. This is, of course, one of the most popular visits in New York, which means the lines can often be massive, especially at peak times of year and on weekends. So first thing in the morning is the best time to check it out. It opens at 8 AM, and on busy days is packed by 10. So either head over early, or visit at off-peak times. Nevertheless, the view is a classic, especially the south view looking over Downtown and the Financial District. And one piece of warning, there are lots of vendors selling a variety of passes to the top, but they are often shilling crappy package deals so just avoid them and head inside.
From there, head west on 34th to the flagship store of Macy's department store, the largest store in the U.S. It's a top choice for a lot of visitors to the city, though often too huge and crowded for my tastes. But the nine floors of shops to have some great quirks. In particular, the still operating original wooden escalators from when the store opened in 1902. They have replaced a lot of the wooden stairs with metal, but there are at least a few of the wooden ones left.
Lunch: There's not a whole lot for great lunch options in the area. Mostly, the lunch spots are geared toward office workers grabbing a quick bit on their lunch break. There are a few better than average spots. Lena Latin Grill on 35th between 6th and 5th is nice South American fare. And Picnic Basket on 37th, just east of 6th Avenue does very good sandwiches. But generally, it's an eat and run type of area for lunch. Nothing wrong with grabbing a turkey and swiss from any ol' deli.
Afternoon: Walk north on 6th Ave to 40th Street and head into Bryant Park. This small green space serves as the only proper park among Midtown's office towers, so not surprisingly it's the most crowded park in the U.S. Depending on the season there's lots going on here. There's a great ice skating rink in winter, as well as shops at Christmastime. Summer brings back the wide sunny lawn to lay out on. The park also features an award-winning public bathroom! Mostly it's just a nice spot to take a break and watch everyone enjoying their lunch in the sunshine. And on the eastern end of the park, is the New York Public Library.
Head into the Library through the main 5th Ave entrance. This is one of the architectural gems of the city, as well as one of the greatest research facilities in the world. There's more than 40 million items in the collection, but all are kept in the library for on-site research. The lobby is almost entirely marble, and the ceiling of the main reading room is stunning.
From there, head east to 1st Avenue. You can walk, but it's about a mile. So you can also use your Metrocard to ride the M42 bus (catch it on 42nd Street, naturally). At 1st Avenue, along the East River is a place unique from the rest of New York. In fact, it's not even part of the United States. It's the United Nations, and the 18 acres it sits on belong to every country on Earth. And you don't even need a passport to visit! Tours are available weekdays during business hours. The tour itinerary varies based on what rooms are in use and the ongoing renovations at the UN. But assuming everything is open, tours see the Assembly building, including the Security Council meeting hall, and the General Assembly Hall. Also, be aware that the General Assembly meets in late September, so you won't even be able to get close to the UN during the Assembly.
For the day's finale, walk west on 42nd Street. You will pass the Ford Foundation's landmarked garden courtyard on 42nd between 1st and 2nd Aves. You can head in and take in the tropical feeling interior garden. You'll also pass the magical Chrysler Building on Lexington Ave. The Chrysler usually takes the crown for New Yorker's favorite building. There's something about the soaring steel and whimsical art deco gargoyles and spires that makes the building special. It's an unmistakable icon, and you can enter the building to see the fantastic lobby during business hours.
The last stop for the afternoon is the one and only Grand Central Terminal (technically, it's not called Grand Central Station). The 102 year old station still serves as a daily commute for tens of thousands of Manhattan office workers. The terminal survived railroad business losses, threatened demolition, and terrible renovations. It was restored in the 90s to its original glory and is one of the unmissable sights of New York. There's so much history, architecture, and great little stories to the terminal that it's worth getting the $9 audio tour from the tour window, or downloading it to your phone. After all, you want to know where the secret tennis courts and the hidden cocktail bars are don't you?
Dinner: There's no need to leave Grand Central, when one of the great eateries of the city is right there in the terminal! The Grand Central Oyster Bar was a part of the station the day it opened and still slings about 25 different kinds of oysters every day. Not to mention to oyster pan roast soup and dozens of other mollusk and crustacean classics. There's actually three different dining areas, but all with the same menu. You can have a more formal setting at the table section, have a less formal meal at the counters and oyster bars, or even head into the wood-paneled, nautical themed saloon. Though if you eat in the saloon, you miss out on one of the grandest dining rooms in the world.
But let's say raw oysters aren't your thing, but raw fish is. You could always head over to Sushi Yasuda on 43rd between 3rd and 2nd Aves for a real taste of tradition Japanese sushi.
Evening: It's time to take it easy and get a view and some drinks. Rooftop bars have been sprouting up like wildfires all over the city, in particular around Midtown South, where the Empire State Building rises above the old garment district roofs. There's some great high-end options, like Top of the Strand (37th between 6th and 5th) and Mad 46 (Madison and 45th). There's also some more casual and inexpensive options on top of the Metro Hotel (35th between 5th and 6th) and the roof of the La Quinta Inn (32nd between 5th and 6th). They're all pretty relaxed, but if you really want to party the night away with a view of the Empire State Building head to the massive three-level nightclub 230 5th (at 27th Street).