DAY 1 - Flatiron and Chelsea
First of all, if I was planning a trip to New York, this would be the area I would pick for a hotel. There's lots of good ones around Union Square, like the W, Hyatt, Jade, or Verite. There's also many near Madison Square including a Hampton Inn, the Lex, Giraffe, and Gramercy. Chelsea has one of my favorites, the High Line Hotel, as well as the Gem, Maritime, and Dream Downtown. The reason I like these areas so much is that they have a little bit of everything. They are centrally located right between Midtown's famous landmarks and trendy downtown spots. There's lots of major brand shopping in the Flatiron District, local food markets in Madison and Union Squares, eateries running from blue-collar diners to the most prestigious restaurants in the city. There is historic architecture in Flatiron's beautiful old lofts and department stores, as well as Chelsea's historic rowhouses. And the boldest new design in the city is in West Chelsea's galleries, parks, and new condos.
Most of all, I think this area makes a great introduction to New York because of how vibrant the streets are. Most visitors head straight for Times Square or 5th Ave when they arrive. After all, you don't come to New York for quiet charm, you want to feel the energy of the streets! And Times Square sure does have energy. The problem is, the whole enormous crowd is made up entirely of tourists and office workers. The tourists stand around gawking and the office workers hustle to leave the area. Plus there's the endless annoyance of touts, tour operators, ticket sellers, and costumed characters bombarding visitors with requests for money. So while those are iconic sights, it's not the best vibe in the city. Flatiron and Chelsea are filled with shoppers, workers, residents, and tourists doing all kinds of different things. It's the true heart of the city. So let's start the day!
Morning: Head to Union Square, preferably on a Monday, Wednesday, Friday, or Saturday to see the farmers unloading their goods for the city's largest farmer's market. Local, independent farmers bring the bounty of New York, New Jersey, Connecticut, and Pennsylvania here four days a week. Fruits and veggies top the offerings, but there's eggs, fresh milk, breads, cakes, wines, ciders, herbs, honey, and even a stand devoted to duck products. I also think of Union Square as the local's version of Times Square. It's a transit and shopping hub, a green space, student hub, protest stage, and just an awesome spot to hang around.
After checking out Union Square, head north on Broadway to 20th Street. There's some awesome shops along here to explore like Paragon Sports (for gearing up to climb Everest), ABC Carpet & Home (perfect for furnishing your $10million loft), and Fishes Eddy (for quirky home goods). Take a right on 20th. Down the block is the Theodore Roosevelt Birthplace National Historic Site. TR is the only American president from New York City, and his life story is one of adventure, the outdoors, exploration, war, peace and rough and tumble politics. Unfortunately, the original home was torn down nearly a century ago, and the museum is housed in a replica. But still, it's a great museum dedicated to America's most exciting President.
Lunch: At the end of the block, on the corner with Broadway, is Beecher's handmade cheese. You can watch the cheese-making right in the shop. You can get sandwiches or their amazing mac n' cheese in the shop, or go downstairs to The Cellar for a more formal lunch. One block up on 21st is Harding's, a slightly more upscale restaurant/bar with a menu and decor that focuses on classic American cuisine. It's a cool but comfortable space. Up on 23rd Street and 5th Ave is the massive Italian food emporium Eataly, with everything from formal meals to gelato and paninis inside. And on 5th between 22nd and 23rd is Eisenberg's. One of New York's most timeless lunch spots. It's over 80 years old and wallet-friendly, featuring timeless tuna melts, egg creams, burgers, and BLTs. And on the off-chance there's a short wait at Shake Shack in Madison Square Park, you can always grab a burger.
Afternoon: Start at Madison Square Park. This is another of the city's great meeting spaces. In fact, at the end of the 19th Century's Guilded Age, this was the preferred destination of America's elite for shopping, dining, and entertainment. The square is always lively with residents at the dog park, office workers (especially publishing and tech workers) out to eat, and anyone checking out the rotating public art displays. And if modern art isn't your thing. The buildings around Madison Square are breathtaking. The East Side features the opulent towers of Met Life and New York Life insurance. But the gem is the Flatiron (pronounced FLAT-aye-urn). Built in 1902, this is one of the world's great buildings. Its namesake triangular shape is seen dramatically from the large open space where Broadway and 5th Ave intersect. While it may not have been the first or tallest of New York's skyscrapers. It's one of the most famed and beloved.
Next it's time to check out some of the shops along 5th and 6th Avenues. These streets were New York's primary shopping destination at the end of the 19th Century. Rich shoppers headed to the fine stores of Broadway and middle-class shoppers took the elevated train to 6th Avenues department stores, an area formerly called the 'Ladies' Mile'. Happily, most of the beautiful department store buildings are intact along 6th, though today they house more pedestrian brands like The Container Store and Trader Joe's. The whole area is a nice one for major brand shopping. It has many of the same stores as 5th Ave or Soho but less of the crowds. But now, it's time to head to Chelsea.
Head west on 23rd to check out the Hotel Chelsea on 7th Ave. It's one of the most famous artistic haunts in New York and has been a stopover for Patti Smith, Sid Vicious, Arthur Miller, Arthur C. Clarke, Leonard Cohen, Janis Joplin, Allen Ginsburg, Gregory Corso, Dylan Thomas and many more. Going south on 8th Ave, take a right on 21st or 20th. These are some of the prettiest historic streets in Manhattan and are dominated by the beautiful General Theological Seminary on the block between 9th and 10th Aves. This was once the estate of Clement Clarke Moore, who famously wrote 'Twas the Night Before Christmas.' You can enter the Seminary grounds if you want some quiet green space.
Turning left on 10th Ave will bring you to Chelsea Market on 16th Street. This is another of New York's best food destinations. The market was once a massive factory for Nabisco. In fact, they developed the Oreo cookie in this very building. Since the late 90s it has been a massive hub for food vendors, restaurants, markets, food makers, and just about everything food related imaginable. Stop at the Lobster Place fish market for one of the best seafood markets anywhere. But mostly take your time and check out all the side rooms where lots of small vendors are located.
Dinner: There's a lot of great options inside Chelsea Market. For sit-down meals there is Green Table with excellent farm-to-table menus. Corkbuzz is a just opened wine bar. And Cull & Pistol is the restaurant side of Lobster Place's fish market. There's some more expensive options like Colicchio & Sons, and Del Posto on 10th Ave. Also on 10th Ave is the less expensive Park, in a skylit, garden-like former parking garage. La Bottega on 9th Ave, in the Maritime Hotel also puts out moderately priced Italian.
Evening: There's nothing like seeing Manhattan from the water, so let's head to Chelsea Piers on 23rd Street and 11th Ave for an evening cruise. There are harbor cruises from Bateaux New York that feature dinner and music aboard a glass enclosed vessel. But if the weather's nice, I would opt for the more casual offerings of Classic Harbor Lines. They not only have a 1920s style yacht for harbor cruises, but also offer sunset and evening cruises aboard their two sailing schooners. I love the feeling of being under sail, gliding past the Statue of Liberty, especially since they offer complimentary wine and beer. The view of the skyline lit up on your first night on the town should be plenty of inspiration for the 29 days ahead!