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Day One: Manhattan (Midtown and Central Park)

Manhattan may only be about 13 square miles, but this island has a lot to offer. Start your morning with breakfast and a walk in Central Park. Pick up coffee and a classic, hand-rolled New York-style bagel at Ess-a-Bagel, a favorite in Midtown East. Breakfast-in-hand, grab a cab or walk on famous Fifth Avenue, window-shopping at stores like Harry Winston and Bergdorf Goodman along the way. When you reach the 59th street entrance, find a bench and people-watch while eating your bagel and admiring The Pond. Then, hit up popular areas of the park like the merry-go-round, Strawberry Fields, and Bethesda Fountain.

Many of NYC’s best museums are located near Central Park, including The Metropolitan Museum of Art (whose terrace has gorgeous views over the park) and Guggenheim to the east, and the American Folk Art Museum and American Museum of Natural History to the west. Pick a museum or two to explore before grabbing lunch from one of the vendors at Turnstyle Underground Market, a food hall that’s connected to the 59th Street-Columbus Circle subway station. Grand Central Oyster Bar beneath Grand Central Terminal is another great option.

If you need a break, return to your hotel for a quick recharge. Then, head for the bright lights of Broadway and Times Square. On the way, pop into the New York Public Library to admire the stunning design (it’s free!) and/or take a peek at the celestial ceiling in Grand Central Terminal (also free!). In Times Square, snap selfies with your favorite cosplay characters and marvel at the brightly lit signs. Next, make your way to the Theater District for a pre-show dinner at The View, a rotating restaurant at the New York Marriott Marquis. The food is good, but not cheap, and the views are priceless.

Close out your first day with a nightcap at one of the nearby local bars. Depending on your vibe, there’s Rudy’s, a dive bar;  McCoy’s, an Irish pub; Mad46, the seasonal rooftop lounge at The Roosevelt Hotel; and Bar SixtyFive, a cocktail bar with sweeping views, located on the 65th floor of 30 Rock.

Day Two: Lower Manhattan

Packed with bars, restaurants, and hidden gems, Lower Manhattan holds a lot of the city’s history. It’s a great place to get a feel for the gritty side of NYC, which is often documented in films and TV shows.

Start your morning in the Lower East Side at Clinton St. Baking Co., famous for its pancakes and brunch menu. Then, head down to the 9/11 Memorial and Museum. (Tickets should be booked in advance.) After paying your respects, walk over to the Oculus, a design-forward transportation hub filled with shops and eateries. There’s a fantastic photo op on the second floor, where the ribbed white walls make it seem like you’re inside the rib cage of a whale. From here, continue your self-guided walking tour and move on to St. Paul’s Chapel of Trinity Church, which served as a refuge for people on 9/11. Dating back to the mid-1700s, it’s also the city’s only remaining colonial-era church, and once counted George Washington as part of its congregation.

Next, visit Chinatown for lunch at Jing Fong, a 700-person dim sum restaurant where you order off traditional dim sum carts and share communal tables with strangers. Walk off the dumplings on Canal Street, stopping at any number souvenir shops, fruit stands, and temples along the way. Work your way up a few blocks into Little Italy, and eventually over to the Tenement Museum, which focuses on the city’s immigrant history, particularly Chinese, Italian, Jewish, and German. The museum hosts neighborhood walking tours, but we especially like the apartment tours, which give visitors a glimpse into various immigrant living situations through meticulously restored apartments as they would have been in several different decades.

Head back into modern times with a visit to the trendy SoHo neighborhood, where you can shop boutiques, department stores, and international brand flagships. Go back up to Houston and hit up Katz’s Deli, one of the country’s most famous Jewish delis (and where the sandwiches are stacked high enough to split). End the night with drinks at a Lower East Side bar. We suggest The Ten Bells for wine, Pianos or Arlene’s Grocery for live music, and Attaboy for cocktails.

Day Three: Manhattan (East Village, West Village, and Chelsea)

Start the day at Chelsea Market and find your perfect breakfast spot. After fueling up, walk a few blocks to 14th street and hit up the High Line, an old elevated train track-turned-park. Take in views of the city, glimpses of the Hudson River, and the well-designed pockets and sitting areas until you exit around 34th Street in Hudson Yards (a new design-forward mega-mall full of designer shops and celebrity-chef restaurants). Grab your obligatory shot of the Vessel before moving on down to Greenwich Village, a neighborhood that was once a hub for creativity.

The Village attracted artistic, progressive types and was a favorite hangout for famous writers, musicians, and artists like Jack Kerouac, Bob Dylan, Mark Twain, and Andy Warhol. Grab a drink or just snap photos at legendary spots, like Stonewall Inn, a tiny bar that was the epicenter of the 1969 Stonewall riots for gay rights; Kettle of Fish, a bar frequented by beat poets and Bob Dylan; and legendary jazz bar, the Village Vanguard. It’s also a great spot for people-watching, record shopping, and checking out boutiques.

Give your legs a rest at Washington Square Park where you can grab a delicious dosa from the NY Dosas food cart (the line moves quick!) and find a spot on the grass or by the fountain. While you’re taking a breather, decide if you feel like watching some stand-up comedy at the legendary Comedy Cellar or checking out some live music at the iconic Blue Note Jazz Club. (You’ll need to buy advance tickets for either.)

Next, belly up to the bar at the closest oyster happy hour (we like Mermaid Oyster Bar). Taking advantage of the drink specials and dollar-something oysters nudge you one step closer to being a true New Yorker. If you’re catching a performance in the West Village, grab an award-winning Napoli-style pizza from Keste beforehand. If you’re catching a comedy show in the East Village, fill up on delicious Filipino food and cocktails at Jeepney first. After the show, take a stroll through the East Village, popping into any bar that suits your style.

Day Four: Brooklyn (Williamsburg and Greenpoint)

If you’ve timed this right, you’ll end up in Brooklyn on a Saturday, so you can take advantage of the Brooklyn Flea, the ultimate antique and artisan goods market in town, as well as Smorgasburg, a massive gathering of food trucks. Locations vary by season, so always check before heading out. After stuffing yourself, head back to your hotel to drop off any purchased goodies, so you don’t have to lug them around all day. Instead of slipping into a food coma, walk it off by cruising Williamsburg’s main strips: Bedford Avenue, Wythe Avenue, and Berry Street. After a few laps, get off the main drag and head toward Domino Park, a six-acre park along Williamsburg’s westernmost side. Otherwise, take in the views from the elevated walkway, play a game of bocce, or just chill out by the fountain and people-watch.

If you need a break, take one back at your hotel — you’ve earned it. If not, head to The Williamsburg Hotel’s rooftop bar for sunset sips. Alternatively, go inside The Water Tower bar, an actual water tower repurposed as a bar. As soon as the sun sets, head to Greenpoint for dinner. This old Polish neighborhood is slowly gentrifying, but still has some incredible, authentic Polish food. Dig into sausages, potatoes, borscht, and more at Karczma, then head for drinks at Ramona, a slick, dual-level cocktail bar decked out in all white. Bar hop your way back to your hotel, or make a pit stop for retro bowling at Greenpoint’s divey Gutter Bar.

Day Five: Brooklyn (Prospect Heights, Prospect Park, and Park Slope)

Start your day early and grab a coffee and pastry at one of the many cafes in Williamsburg before heading south toward the Prospect Park, Park Slope, and South Slope neighborhoods. If it’s nice out, stroll through the Brooklyn Botanic Garden (check their site if you want to see what’s blooming and where), then head next door to the Brooklyn Museum, New York’s third-largest museum (and one of our personal faves).

Work up an appetite while admiring the museum’s excellent permanent collection, well-curated traveling exhibitions, and intricate period-style rooms. For lunch, walk over to Cheryl’s Global Soul for home-cooked brunch and a positive vibe. Spend the rest of the afternoon either bar hopping or boutique shopping off Park Slope’s Fifth Avenue and Seventh Avenue. Skylark, Commonwealth, Parish Cocktail Bar, and The Owl Farm are some of our favorite bars, while Bird Brooklyn, Housing Works thrift store, and Homebody Boutique are some of our top spots to shop.

If your legs will take you, walk all 25-plus blocks down to the Green-Wood Cemetery, a National Historic Landmark in South Slope (or just call a car). Cross through the impressive Gothic Revival-style entrance into 478 acres of graves, tombs, mausoleums, and green space. Or, walk on over to Prospect Park, Brooklyn’s own wilder, younger sister park to Central Park (both designed by the same team). Here, you can relax in the shade or watch dogs chase frisbees.

When you feel your belly rumbling, choose between upscale seafood at Littleneck or savory barbecue at Dinosaur BBQ, both in Gowanus. After dinner, mosey around the corner to The Royal Palms Shuffleboard Club for a bit of friendly competition, flamingo wallpaper, and retro-hip vibe.

Day Six: Brooklyn (Brooklyn Heights and DUMBO)

Today is the day you’re going to walk across the Brooklyn Bridge. Start your journey from the Manhattan side, where the entrance to the pedestrian walkway is right across from City Hall (have a quick look, if you’re so inclined). Walking across the bridge will take about an hour, but don’t forget to turn around every now and then for gorgeous views of the city skyline. Once you hit the Brooklyn side, you’ll be between the DUMBO and Brooklyn Heights neighborhoods. Walk a few blocks to Gran Electrica for tacos and some dramatic views of the bridge. Next, saunter along the DUMBO waterfront, stopping for a whirl on Jane’s Carousel before heading over to the Brooklyn Bridge Promenade for some stellar views of Lower Manhattan. (Bonus: It’s free!) There are benches at the beginning of the promenade, so if you want a little rest, take it now.

While you’re walking, scope out the piers, green spaces, and possible events down below at Brooklyn Bridge Park to see if any pique your interest. After leaving the promenade, we recommend heading through the park to Ample Hills Creamery. Grab a scoop of their famous Salted Crack Caramel ice cream.

Once you’ve soaked in all the views, devoured your ice cream, and perhaps played a few games, head back to your hotel via the East River Ferry, which stops in Manhattan and Williamsburg, if you’re not staying in the area. Local tip: The ferry costs the same as a subway ride, but you’ll get the most bang for your buck if you time it right and turn it into a sunset “cruise.”

Day Seven: Queens (Astoria)

No trip to NYC would be complete without a visit to Queens. It’s the city’s largest borough and one of the most ethnically diverse urban areas in the world. Head to Astoria, which was named ‘NYC’s Best Neighborhood,” thanks to its growing cultural, culinary, and local community scene. Start your day with a true New Yorker’s breakfast: an egg sandwich from the local bodega (in this case, it’s George’s Deli, off the 30th Avenue stop). Walk around the Socrates Sculpture Park, then ponder the surreal, biomorphic sculptures and high-design furniture of Japanese-American artist Isamu Noguchi at The Noguchi Museum up the street. If you’d rather look at something less sedentary, check out what’s on offer at the Museum of the Moving Image.

Astoria is known for their Greek restaurants and taverns, so go ahead and snag a table at Bahari Estiatorio for lunch. Here, you’ll find a good range of authentic options on the menu. Next, it’s on to souvenir and gift shopping, so we hope you saved some money. Stellar local shops can be found on and around Astoria’s Ditmars Boulevard, where you can sift through vinyl records, handmade soaps, vintage clothing, and other quirky, but quality, goods. Wrap up your time in Astoria with a few goodbye beers at the Bohemian Hall & Beer Garden, a longtime favorite that has been luring New Yorkers to the borough long before Astoria was cool.

If You Have More Time

Anyone who finds themselves with a bit more time, or has already done a few things on this itinerary, can swap out or add on some other quintessential NYC experiences.

Want to see more of Brooklyn? Take the ferry from Manhattan (or the subway, if you’re already in Brooklyn) to Red Hook, an industrial neighborhood on the waterfront. The area is home to Sunny’s (Brooklyn’s oldest bar), Pioneer Works (an art studio collective that hosts open studios on most Sundays), and a few bars worth checking out, like Fort Defiance and Brooklyn Ice House. In the summer, the multi-story Brooklyn Crab has lawn games and unbeatable sunset views starring Lady Liberty. Speaking of which, we are big fans of seeing the Statue of Liberty from the comfort and perspective of a boat — not a tour. In general, checking out the city’s surrounding islands — Governors Island, Ellis Island, Roosevelt Island, and City Island (a quaint spot with vintage trinket shops, casual waterfront seafood, and a laid-back vibe) — is a great way to see a different part of the city and peep its famous city skyline from a different vantage point.

Flushing in Queens is a must-visit for anyone who wants to get a feel (and taste) of New York’s newest Chinatown. While you can find good food on every block, the New World Mall food court is hailed for having a fantastic selection of over 20 eateries from different regions of China and all around Asia. The famous Unisphere is nearby in Flushing Meadows Corona Park, and is a fun place to visit, especially on hot days or in the fall, when the park trees are painted with fall foliage.

Where to Stay in New York City

Our Top Pick for a Luxury Hotel in NYC: Mandarin Oriental, New York

Our Top Pick for a Boutique Hotel in NYC: 11 Howard

Our Top Pick for a Romantic Hotel in NYC: The Plaza

Our Top Pick for a Kid-Friendly Hotel in NYC: TRYP New York City Times Square South

Located within walking distance of Times Square, the TRYP hotel is convenient for many tourists. Spacious rooms with tons of fun details, a solid Mediterranean restaurant, and a modern fitness center make it a solid choice for families, groups of friends, and business travelers alike. Even better, there are a wide range of accommodation types, including Family Rooms that can sleep up to eight guests as well as Fitness Rooms with exercise bikes.

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