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Day 1 – The High Line, Washington Square Park, Greenwich Village
The High Line always opens at 7:00AM. It takes about 30mins-1hr to walk to the whole thing, depending on how often you stop to admire the views and parks. I recommend going in the morning when it’s not very crowded, and I also recommend going from top to bottom so that you end up at the Whitney Museum afterwards. After the Whitney, either walk or take the subway to the Washington Square area. There are loads of options for lunch because you’ll be on the NYU campus, as well as Greenwich Village. My favorite cheap place to eat is Saignon Shack: Vietnamese food at its best! After lunch, enjoy Washington Square Park. It’s a great people watching spot, and there are always people showing tricks and playing games. Walk up Bleecker Street, the prime area of Greenwich Village. There are numerous boutiques, record stores, book shops, and cafes to explore.
Day 2 – Financial District, Staten Island, South Street Seaport, Brooklyn
Start out at the 9/11 Memorial and walk southwards toward Battery Park, winding your way through Wall Street as you do so. Visit Battery Park and then head to the Staten Island Ferry. It’s a free ride and takes about an hour round trip. Afterwards, continue walking along the water to South Street Seaport. For lunch, grab something nearby that catches your eye! After a relaxing lunch, it’s time to walk across the Brooklyn Bridge. I like walking in this direction because there are less people. You can get plenty of pictures of Manhattan on your way, just stop and turn around! Once crossing the bridge, find your way to DUMBO and go to the little park there. Probably the most famous pizza place in NYC, I recommend Grimaldi’s for dinner. Williamsburg is considered the hippest place in Brooklyn, so I put down a few popular bars. The Music Hall is also here, so if there’s a concert you’re interested in, go for it. This venue is legendary.
Day 3 – The Met, Central Park, Roosevelt Island, Upper East Side
Start out the day going to the Met. It can take days to go through everything, so I would stick to 2-3 hours here. From the Met walk through Central Park. Be sure to stop by the Bethesda Fountain. The Upper East Side has plenty of super expensive restaurants, but there are good deals throughout. I recommend Up Thai. After lunch, head south to Bloomingdale’s then check out out Dylan’s Candy Bar. Take the tram over the river to Roosevelt Island. It’s a unique experience, and only costs the same as a metro ride! Head back to the corner of Central Park and walk up 5th Avenue. Once you start getting hungry, head back into the Upper East Side and try dinner at Uva. Walk around the area and see what this area of Manhattan has to offer. There are numerous bars along 2nd Avenue.
Day 4 – The MoMA, Midtown, Times Square, Broadway
Start about halfway up Central Park and walk down 5th Avenue. The MoMA can take quite a long time. If you’re running late, you must at least visit the 5th floor. Midtown has all sorts of things to offer. If it’s a nice day, I suggest grabbing lunch from The Picnic Basket and eating in Bryant Park. After lunch, head next door to the New York Public Library, and then to the Morgan Library. Backtracking a little bit, head up Madison Avenue and check out St. Patrick’s Cathedral. The Rockefeller Center is just a block away. You can either go to the Top of the Rock to get a nice view of the city. It’s pricey at $32 for an adult ticket. Roam around Times Square and enter a couple of the stores. While it’s always crowded, it’s fun to see! This night might be a good night to see a show. Broadway is just a few blocks up from Times Square. There’s a theater for every budget, whether it be on Broadway, Off-Broadway, or Off-Off Broadway.
Day 5 – Guggenheim, Upper West Side, The Cloisters
Your last day should be reserved for all the things you missed out on! If you managed to get to everything, then here’s some other stuff to see. The Guggenheim Museum is extremely interesting to see. Afterwards, cross through Central Park to the Upper West Side area. You can pop into the American Museum of Natural History and have a quick look around. Walk over to Zabar’s, a really neat market, and maybe grab some lunch to go sit in Riverside Park. You can admire the docks as well. Or, for lunch, you can go to Good Enough to Eat which a super popular brunch spot (still check out the market). You can either go to the Cathedral of St. John the Divine or keep going on the metro to the Cloisters. The Cloisters are always missed out on because they are so far north, but they area really worth seeing.