Start your first morning with a classic New York breakfast at Keen's Steakhouse & Bar (lobby café) or nearby Culture Espresso for strong coffee and pastries, then take a relaxed stroll to admire the art deco façade of the Empire State Building from the sidewalk and snap photos without committing to a long visit. Continue north a few blocks to explore the serene Bryant Park - grab a newspaper, sit at a park table, and watch street performers while planning the day; finish with a quick browse through the architectural wonder of the New York Public Library (Stephen A. Schwarzman Building) before lunch.
Wander south-east toward Grand Central Terminal to admire the celestial ceiling and grab a quick bite at the bustling Grand Central Market, then sip a classic New York cocktail at the hidden-speakeasy vibe of The Campbell inside the terminal. From there, stroll down to the neon spectacle of Times Square as dusk falls-linger for the street performers, flagship stores, and rooftop bars like St. Cloud at the Knickerbocker for skyline views before an early dinner nearby.
As the city lights come alive, wander west to the atmospheric Hell's Kitchen dining strip and sample small plates at 5 Napkin Burger or inventive tapas at Toloache for a lively neighborhood meal. After dinner, take a leisurely rooftop cocktail at 230 Fifth Rooftop Bar for unobstructed views of the Empire State Building lit up, then end the night with a classic New York jazz set at intimate Birdland Jazz Club or a nightcap on the bustling pedestrian plaza at Herald Square to soak up Midtown's nighttime energy.
Begin with a hearty brunch at Dominique Ansel Kitchen in the West Village for inventive pastries and strong coffee, then wander south through the cobblestones of Stone Street to soak up old-New York charm and grab a quick craft beer. Cross over the iconic Brooklyn Bridge on foot for skyline views, arrive in DUMBO to stroll the waterfront at Brooklyn Bridge Park and pose beneath the Manhattan Bridge at the famed Washington Street photo spot before grabbing a light mid-morning coffee at A/Café.
Cross back into Manhattan and explore the lively streets of South Street Seaport, where you can browse maritime shops, pop into the historic Pier 17 for waterfront views and seasonal rooftop events, and sample fresh oysters or seafood at The Fulton. From there, head to nearby Battery Park to catch the harbor breeze and ride the Staten Island Ferry (free) for classic Statue of Liberty views, then return and wander up to the atmospheric Stone Street Historic District for late-afternoon craft beers and small plates in its cobbled, lamp-lit setting.
As twilight falls, head to Brooklyn Heights Promenade for golden-hour skyline views, then wander the tree-lined streets to discover cozy neighborhood bars like The Heights Casino Bar or the intimate wine list at Vineapple Bar (try a local craft pour). Finish with a riverside dinner at Juliana's Pizza in DUMBO or seasonal small plates at The River Café for a memorable meal under the Brooklyn Bridge lights, followed by a relaxed nightcap at Pebble Bar to soak in the night views before returning to Manhattan.
Start the day with a stroll into Central Park from the southeast corner, renting a rowboat at the Loeb Boathouse for a peaceful on-water hour, then wander north past the romantic Bow Bridge and leafy paths toward the quieter North Meadow for birdwatching and people-watching. Exit the park on the west side to explore the architecturally intriguing Lincoln Center plaza-grab a coffee at the nearby Joe Coffee Company and enjoy the open-air sculpture and rehearsal halls before heading south to the High Line for the next phase of your day.
After your High Line visit, head down to the vibrant Chelsea Market for a leisurely lunch sampling lobster rolls at The Lobster Place or tacos at Los Tacos No. 1, then stroll the nearby cobblestones of the Chelsea Market Passage and pop into independent galleries along West 20th Street. From there walk west to the Hudson River Greenway and rent Citi Bikes at the Hudson River Park Pavilion for a scenic ride north to the sleek waterfront Pier 84-pause at the lawn for skyline views, then return to the hotel to collect bags and freshen up before your 20:00 transfer to JFK.
As dusk falls, head south along the Hudson to the lively waterfront at Intrepid Sea, Air & Space Museum for a quick exterior stroll and dramatic skyline photo ops, then continue to the nearby Pier 57 Rooftop Garden to relax with a craft cocktail or seasonal vendor snack while watching ferries glide by. Finish the night with a cozy pre-flight dinner at House of Small Wonder (for warm, comforting fusion dishes) or the nearby Japanese izakaya Sake Bar Hagi-both are close to Midtown and make it easy to return to your hotel to collect bags before your 20:00 transfer to JFK.