After four trips to New York City, you’re in a great position to explore it like a local would. Wander through trendy Tribeca, the ultra-hip Meatpacking District, the charming West Village, and the funky East and Greenwich Villages.

These spots are particularly great for uncovering new secrets each time you visit them. I’ll name some highlights in these areas and any others that you’re interested in seeing and then I’ll leave the rest of the exploring up to you. You’ll also spend one of your free days in Brooklyn, getting there by way of its famous bridge and then exploring its unique parks and atmospheric streets. Sports fan? Why not see a Yankees game while in town? And if you’re looking to do some shopping in the city, I can work with you to figure out which neighborhoods offer the best matches for your style and budget. In all of these neighborhoods, I’ll tell you about the best places to eat. If you liked Chelsea Market, you’ll love my favorite food hall. And having a drink in Grand Central’s hidden, turn-of-the-century bar is great for a time warp. I’ll tell you how you can eat at some of New York’s most popular restaurants without a reservation, and where the city’s best food trucks will be parked on the days of your visit. Uncover secret speakeasies and hole-in-the-wall ethnic restaurants. I’m a firm believer that New York is best discovered through its eateries!

Booming Brooklyn

Spend a day exploring Brooklyn, New York’s most booming borough. First-time visitors will want to arrive by way of the promenade of the iconic Brooklyn Bridge, accessible from City Hall Park in the Financial District.

Once in Brooklyn, you can take in some of the best views of the Manhattan skyline from the Brooklyn Heights Promenade, a walkway running between the East River and the charming row homes of the Brooklyn Heights neighborhood.

You can also find impressive vistas at Brooklyn Bridge Park, a dynamic green space with diverse recreation offerings in Dumbo (Down Under the Manhattan Bridge Overpass). Here, you can explore its Greenway with a bicycle rental from Citi Bike, or you can walk the gardens of the Greenway Terrace on foot. Bring some friends, and play bocce and shuffleboard on Pier 2. Or grab a cone from the Brooklyn Ice Cream Factory, and just sit and watch the world go by.

Brooklyn Bridge Park is a great place to visit on a Sunday, when the Smorgasburg Festival is held on Pier 5 between 11 a.m. and 6 p.m. This “food flea market” hosts between 75 and 100 vendors each week, offering a great “taste” of New York City. The market offers a great lunch option, but if you find yourself in this neighborhood on any other day, the brick oven pizza at the famous Grimaldi’s is your best meal bet… and yes, it’s 100% worth the wait.

Once you’ve had your fill of Brooklyn Heights and Dumbo, take the subway to Williamsburg, Brooklyn’s trendiest neighborhood. With its eclectic galleries and offbeat bars, this hipster haven is the new Greenwich Village.

This neighborhood is a great place for dinner and drinks. Among the best restaurants are Bozu for Japanese small plates, Fette Sau for the hands-down-best BBQ you’ve ever tasted, and Traif for nouveau-American cuisine. For after-dinner drinks and entertainment, your best bets are Barcade, where you can play vintage video games, the divey Pete’s Candy Store, which has great live music, the festive Radegast Hall and Beer Garden, and Gutter, with its vintage bowling lanes.

The Villages

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Some of Manhattan’s most interesting neighborhoods are its “Villages” – East and West. Bordering one another in the city’s Lower Manhattan area, you can explore them both, and some bordering districts, in a day.

The West Village is all about charm charm charm. This is the place to go if you want to enjoy a relaxing morning with a cup of coffee at a tucked-away cafe or an evening at an atmospheric wine bar. Culinary highlights in this neighborhood include French-inspired brunch at Buvette, cupcakes from Magnolia Bakery, contemporary Chinese at RedFarm, and burgers at the famous gastro pub, The Spotted Pig. Wine bar hop between The Other Room, nearby Aria, and Vin Sur Vingt, and go to Employees Only for creative cocktails.

Since you’ve already explored Greenwich Village and its famous Washington Square Park, head just north of this neighborhood to the Flatiron District. Here you’ll find exciting Union Square, which hosts an array of street market vendors, the area’s namesake Flatiron Building, and Eataly, an Italian market on steroids. Central to the market experience is La Piazza, where you can saddle up to one of the mini bars for a glass of wine and a delicious charcuterie board.

Continue on to the East Village, a mecca for fusion food, secret speakeasies, and vintage-clothing boutiques. Spend some time window shopping along the neighborhood’s shady lanes before choosing a dinner spot. Many of the culinary highlights in this neighborhood come courtesy of celebrity chef David Chang. His Asian-fusion Momofuku Ssam Bar is a first-come-first-serve standout; you might have to stand in line, but this place is worth the wait. Can’t get enough Chang? Go across the street for dessert at Momofuku Milk Bar where the pastries and baked goods are to-die-for.

The East Village is also home to the lion’s share of the city’s creative cocktail joints. Death + Co. is a sleek speakeasy with low lighting, serious bartenders. Other neighborhood favorites mixing great drinks include Pouring Ribbons and The Wayland.

Downtown (and Midtown) Chic

Gone are the days when the Upper East and West sides were the most sought-after addresses in New York City. Today, the elite areas are downtown, in trendy Tribeca and super-chic Soho. Both neighborhoods are known for their upscale shops, galleries, and restaurants, but Tribeca will give you a more intimate experience than its more popular neighbor to the north. If you find yourself in this general area around meal time, consider trying at lively Balthazar, which embodies a Parisian brasserie, or Distilled, a popular upscale pub.

While Brooklyn, the Villages, and Downtown are great areas to explore on free days, you might also be looking for some activities closer to your Midtown hotel. A good find is the hidden Campbell Apartment in Grand Central Terminal. This secret bar was once the private saloon of a 1920s finance tycoon. Relaxing with a cocktail in this secret spot is a special experience. If you’ve never explored Grand Central, you should also take some time to appreciate the soaring atriums and vintage details of one of the world’s most beautiful train stations.

Also in Midtown is one of the best dining spots in the city, Gramercy Tavern. The restaurant’s dining room is very expensive and requires reservations. However, you can sample the chef’s fare from an a la carte menu in the adjoining Tavern. Here, the setting is more casual, the food more affordable, and it’s walk-in only!

Other great splurge spots in Midtown include Colicchio & Sons and The Modern, both of which have relatively casual bar areas where you can enjoy the restaurant’s delicious food at a discounted rate.


The Campbell Apartment… has a dress code – no t-shirts or athletic shoes allowed!

The Modern… is the restaurant attached to the city’s Museum of Modern Art, where you can view famous paintings like Van Gogh’s Starry Night.

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