New York City — May 22

Day One

Friday, May 22

Arrival · West Village · Flatiron · Hudson River

10:00 AM

Dream Midtown

NJ Transit from Newark Penn takes about 25 minutes and drops at Penn Station; a short cab from there to the hotel. Alternatively a car service runs $60–80 with luggage. Check in, drop bags, and you're five minutes from Central Park.

12:00 PM

Gramercy Tavern · Lunch

42 E 20th St, Flatiron. One of New York's most beloved institutions, Danny Meyer's Gramercy Tavern has defined gracious American hospitality since opening in 1994. Chef Michael Anthony's seasonal menu draws from the Union Square Greenmarket, and the warmth here is genuine — none of the stiff formality of many fine dining rooms.

History & lore — Zagat named Gramercy Tavern the most popular restaurant in New York for over a decade running. The Tavern Room up front is walk-in only and equally as good as the main dining room. The craft cocktail and beverage program is one of the best in the city. Danny Meyer went on to launch Shake Shack in 2001 — beginning as a humble hot dog cart in Madison Square Park to support an art installation, it became one of the most successful fast casual chains in the world.

1:30 PM

66 Perry Street · Carrie's original house

West Village. The iconic brownstone used as Carrie Bradshaw's apartment exterior for all six seasons of Sex and the City and both feature films. One of the most photographed stoops in New York — get the photo, then head west along the Hudson to Little Island.

History & lore — Despite being established as Carrie's home for over a decade of television, the actual apartment interiors were never filmed here — they were shot on a soundstage in Silvercup Studios in Queens. The building is a private residence. The West Village has seen some of the steepest real estate appreciation in Manhattan in the years since Sex and the City first popularized it in 1998, with the show credited for transforming the neighborhood's cultural cachet.

2:45 PM

Little Island

Pier 55 at Hudson River Park, West Village. One of New York's most remarkable recent additions — a floating park built on 132 concrete tulip piles rising from the Hudson River. Free to enter, with meandering paths, lawns, a performance amphitheater, and views back toward the Manhattan skyline. Quick 30-minute stroll on the way to the West Village for the evening.

History & lore — Designed by Heatherwick Studio and opened in 2021, the project cost $260 million, largely funded by Barry Diller and Diane von Furstenberg. The distinctive petal-shaped columns that give it its mushroom-like silhouette are load-bearing structural concrete forms. The amphitheater hosts free performances through the summer.

3:45 PM

Katana Kitten · Happy Hour

531 Hudson St, West Village. Get in line at 3:45 for the 4PM opening — first come first serve, and this place fills up fast. Happy hour runs 4–6PM Monday through Friday with $12 cocktails. Japanese-American bar blending the precision of Tokyo cocktail culture with the casual energy of an American dive bar. Order the highballs, the Meguroni, or whatever the bartender recommends. The nori fries and mortadella katsu sando are the bar bites to get.

History & lore — Helmed by award-winning bartender Masahiro Urushido, Katana Kitten landed at #27 on the World's 50 Best Bars list in 2023 — one of the highest-ranked bars in New York. Urushido trained in Tokyo before moving to New York, and the bar's philosophy draws heavily on the Japanese highball tradition: precise dilution, crystal-clear ice, and balance above everything. The subterranean space feels like it could be in Shibuya or the West Village simultaneously.

7:00 PM

Leitao · Dinner

547 Hudson St — literally 16 steps from Katana Kitten. An authentic Portuguese cervejaria modeled on the convivial beer bars of Porto, helmed by Chef Nuno Sousa. Exclusively Portuguese wines, shareable plates, and a warmth that makes every guest feel like family. Don't miss the Chicken Piri Piri, the Polvo (octopus), the Francesinha — Portugal's legendary sandwich — and finish with Pasteis de Nata and a 20-year tawny port.

History & lore — A cervejaria (literally "brewery") is a Portuguese institution — a relaxed, convivial restaurant built around beer, wine, and sharing plates rather than formal dining. Porto's cervejarias are legendary gathering places, serving food late into the night. The Francesinha is Porto's great contribution to sandwich culture: layered meats, melted cheese, and a rich tomato-beer sauce poured over the top. The Pasteis de Nata — the custard tart — has been made in Lisbon since the 18th century by Jerónimos Monastery monks, who sold the recipe to a local sugar refinery in 1837.

10:00 PM

Dante West Village · Nightcap

551 Hudson St — four doors from Leitao. Consistently ranked among the top five cocktail bars in the world by the 50 Best Bars list. The Negroni variations are the signature move — the Negroni Bianco and the Sbagliato are both exceptional. Warm room, beautiful service, the kind of place that makes you want to stay until last call.

History & lore — The original Caffè Dante opened in Greenwich Village in 1915 and became a haunt for artists, writers, and Italian immigrants for nearly a century. The Negroni was born in Florence around 1919, when Count Camillo Negroni reportedly asked his bartender to strengthen his Americano by replacing soda water with gin. Dante was named the world's #1 cocktail bar by the 50 Best Bars list in 2019 — the first American bar to claim the top spot.

Day Two

Saturday, May 23

Midtown · Chinatown · Lower East Side

8:15 AM

Morning run · Central Park

Out the hotel door and into the park in under five minutes. The Reservoir loop runs 1.58 miles of flat, legendary running with the Midtown skyline visible through the trees. The full outer loop stretches 6.1 miles. Back by 9:15.

History & lore — Central Park's 843 acres make it the most visited urban park in the United States, drawing over 42 million visitors a year. The Jacqueline Kennedy Onassis Reservoir — the running route — was completed in 1862 and holds over a billion gallons of water. Frederick Law Olmsted and Calvert Vaux won the design commission in 1858 with a plan they called "Greensward." On a Saturday morning the loop fills with some of the fastest amateur runners in America.

9:30 AM

Birch Coffee

884 9th Ave at W 57th St — a few minutes walk from the hotel. One of New York's well-regarded independent roasters, known for thoughtfully prepared espresso drinks and a neighborhood café atmosphere. Quick stop before heading downtown to Summit.

11:00 AM

Summit One Vanderbilt

One Vanderbilt Ave, Midtown. An immersive observation experience unlike any other viewpoint in the city — not just a deck, but an art installation 1,000+ feet above 42nd Street. Glass floors, suspended glass rooms cantilevering off the building, infinity mirror corridors, and views stretching clear to the horizon on a clear day. Book timed tickets at summitov.com. Allow 1.5 to 2 hours.

History & lore — Opened October 2021, Summit was designed in collaboration with artist Kenzo Digital. One Vanderbilt itself stands 1,401 feet — the fourth-tallest building in New York. The suspended glass rooms called "Après" project over the building's edge with nothing but air and the city below. At the right time of day you can see the curve of the earth over the Atlantic.

1:00 PM

Upside Pizza · Lunch

20 E 40th St — two blocks from One Vanderbilt. A 90s-themed no-frills Midtown slice institution: no chairs, no restrooms, no pretense — just excellent pizza made with homemade mozzarella and high-quality ingredients. Get a regular slice and a Sicilian square. The pepperoni Sicilian and the Upside Don (breadcrumbs, Parmigiano-Reggiano, EVOO) are the signatures. Grab it and eat on the sidewalk like a New Yorker.

History & lore — Founded by brothers Eli and Oren Halali, who built the concept in consultation with Anthony Falco of Roberta's fame — stepping far up from their earlier dollar-slice shops. The hot pink 90s logo and the stripped-down counter format are deliberate: every square foot goes to the gas ovens and premium ingredients rather than décor. Slices run $3–5 and the quality punches well above that price point. Now with multiple Manhattan locations, the original 8th Ave spot remains the flagship.

5:00 PM

Chinese Tuxedo · Dinner

5 Doyers St, Chinatown. The most elevated dining room in Chinatown — a former Chinese opera house that opened in 1893, now transformed into a stunning two-level restaurant with a dramatic bar, exposed brick, and candlelight. The menu is modern Cantonese: Peking duck, exceptional pan-fried noodles, salt and pepper squid, and a standout wine program. One of the most unique and beautiful dining rooms in New York.

History & lore — The building at 5 Doyers St housed the Chinatown Music Hall from 1893, one of the first Chinese-language opera venues in America. Doyers Street — the infamous "Bloody Angle" — was the site of gang warfare between the Hip Sing and On Leong tongs in the early 1900s, with the sharp curve blocking sightlines for ambushes. Today it's one of Chinatown's most atmospheric lanes, and Chinese Tuxedo has made it a destination dining address.

7:00 PM

Apotheke · Cocktails

9 Doyers St — literally steps from Chinese Tuxedo on the same street. An apothecary-themed speakeasy — mixologists in pharmacy coats, cocktails organized by "painkillers," "aphrodisiacs," and "stimulants." Opens 6:30PM Saturdays, so arrive right at 7 to get a good seat before it fills up.

History & lore — Doyers Street earned the nickname "Bloody Angle" in the early 1900s — the sharp curve blocked sightlines and made it the preferred location for gang ambushes. It was said to have the highest murder-per-square-foot rate in New York City history. Apotheke was named one of the best speakeasies in the United States by Architectural Digest.

9:30 PM

Double Chicken Please · Late night

115 Allen St, Lower East Side — short cab from Chinatown. Free Range up front with seasonal draft cocktails, The Coop in the back — dark plush lounge with culinary cocktails inspired by dishes. French Toast (vodka, roasted barley brioche, maple syrup), Custard Bun (sake, salted egg yolk), Japanese Cold Soba. Order the fried chicken sandwich. Open until 1:30AM on Saturdays.

History & lore — Founded by GN Chan and Faye Chen, Double Chicken Please began as a touring pop-up before opening its LES location in 2020. It debuted at #6 on the World's 50 Best Bars in 2022 and climbed to #2 in 2023 — the highest-ranked bar in New York. The concept is built around "hacking" classic dishes and rebuilding them as cocktails. Over 70% of seating in The Coop is first come first serve, with limited Resy reservations six days in advance.

Day Three

Sunday, May 24

Tribeca · Coney Island · NoMad · SoHo

8:15 AM

Morning run · Central Park

Push north past the reservoir to the Harlem Meer for a different route and more mileage. Back by 9:15.

9:30 AM

Zibetto

1385 6th Ave near W 56th St. An Italian-style espresso bar near the hotel — quick, precise, no-nonsense. The kind of stand-up bar you'd find in Milan: excellent espresso, light pastries, zero pretense. Perfect post-run fuel before heading downtown to the West Village.

History & lore — The Italian espresso bar tradition — standing at the counter, drinking in two minutes — produces a fundamentally different coffee ritual than the American café model. In Italy, sitting at a table costs significantly more than standing at the bar; the quick espresso is a working person's punctuation between tasks. The beans are typically roasted darker and pulled shorter, producing a more concentrated, syrupy shot.

10:15 AM

Teleferico · Roosevelt Island Tramway

59th St & 2nd Ave, Upper East Side — a short cab from Zibetto. A single MetroCard tap ($2.90) sends you gliding 250 feet above the East River with unobstructed views of the Midtown skyline, the Queensboro Bridge, and the city stretching in both directions. Ride over and back — the whole experience takes about 45 minutes, then head downtown to the West Village for lunch.

History & lore — One of only two commuter aerial tramways in the United States, running since 1976. It was originally built as a temporary measure while Roosevelt Island's subway connection was completed — and then simply never removed. It appeared prominently in Spider-Man (2002), where it carries a cable car full of passengers over the river. At 250 feet, the view of Midtown Manhattan from the cabin is genuinely extraordinary — you're level with the upper floors of the skyscrapers as you cross.

12:00 PM

Artesano · Lunch

90 Chambers St, Tribeca. Elevated Peruvian cuisine from Chef Rodrigo Fernandini, drawing on Michelin kitchen experience. The ceviche mixto is the standout — elevated tiger's milk, fresh catch, chulpi corn. A vibrant, sun-drenched atmosphere that feels transportive in the middle of lower Manhattan. Short cab from the tramway stop, then head to the West Village after.

History & lore — Peruvian cuisine has been called one of the world's great undiscovered food cultures — heavily influenced by Japanese, Chinese, Spanish, and indigenous Andean traditions. Tiger's milk (leche de tigre), the citrus-cured liquid that "cooks" fish in ceviche, is so beloved in Peru it's sometimes drunk straight as a hangover remedy. The Japanese-Peruvian fusion tradition, called Nikkei, dates to the wave of Japanese immigration to Peru in the early 20th century.

1:30 PM

Coney Island

Take the D, Q, or N train from W 4th St — about 45 minutes direct to the end of the line. Nathan's Famous hot dog is mandatory the moment you exit the subway. Walk the Riegelmann Boardwalk, ride the Wonder Wheel, and sit on the Atlantic beach. Memorial Day weekend will be buzzing with New Yorkers — lean into it.

History & lore — Nathan's Famous has been selling hot dogs from this corner since 1916, when Nathan Handwerker opened with a recipe from his wife Ida and a price of five cents — undercutting his former employer by half. The Wonder Wheel, built in 1920, is a New York City landmark. At its peak in the early 1900s, Coney Island attracted over a million visitors on a single summer day, making it the most visited amusement destination on earth. The original Luna Park opened here in 1903 and burned to the ground in 1944.

4:00 PM

Head back to Manhattan — freshen up

Subway back uptown — budget 50 minutes. Get changed and dressed for Le Coucou — smart casual at minimum, the room rewards dressing up.

5:45 PM

Le Coucou · Dinner

138 Lafayette St, SoHo. Chef Daniel Rose's French brasserie is one of the most beautiful dining rooms in New York — cream walls, antique mirrors, candlelight, and flowers that make you feel as though you've stepped into a Parisian institution that's been here for a century. The duck, the sole meunière, and the cheese cart are non-negotiable. Plan 2.5 hours for the full experience — out by ~8:15.

History & lore — Le Coucou won the James Beard Award for Best New Restaurant just one year after opening in 2016 — one of the most coveted awards in American dining. Chef Daniel Rose is an American who trained in France and opened the celebrated Spring restaurant in Paris before bringing this vision to New York. The room was designed by Roman and Williams, the studio behind some of the most celebrated interiors in the city.

8:15 PM

To be decided

Nightcap cocktails

Attaboy — 134 Eldridge St, LES. 10-min walk from Le Coucou. No-menu bar — tell the bartender what you're in the mood for and they create something bespoke. Dark, intimate, one of the best bar experiences in the city. Open until 3AM.

Employees Only — 510 Hudson St, West Village. Classic speakeasy cocktails, excellent bartenders, beautiful room. Short cab from Le Coucou. Open until 4AM.

Bar Pisellino — 52 Grove St, West Village. Beautiful Italian aperitivo bar, spritzes and natural wine, perfect post-dinner decompression. Steps from Le Coucou's neighborhood.

10:45 PM

Nubeluz · Nightcap

25 W 28th St, 50th floor, Ritz-Carlton NoMad. José Andrés's sky-high cocktail lounge — 270-degree views of Manhattan fully lit up at night. The city at this hour from 500 feet is genuinely breathtaking. Reserve on OpenTable. Dress code: cocktail-appropriate attire. Open until midnight on Sundays — arrive at 10:45 for a perfect final drink of the night.

History & lore — Nubeluz takes its name from the Spanish words for cloud (nube) and light (luz). The U-shaped onyx bar glows with warm golden light and the outdoor terraces face both east and west — Empire State Building and Flatiron on one side, Times Square and Hudson Yards on the other. At night the city below looks like a circuit board stretching to the horizon.

Day Four — Departure

Monday, May 25

Central Park · Upper East Side · SoHo · Newark EWR

8:15 AM

Morning run · Central Park

Last run of the trip. Full outer loop (6.1 miles) if you have the legs, or a relaxed reservoir loop. The park on Memorial Day morning is magical — quieter than the weekend, runners and cyclists making the most of the holiday. Back by 9:15.

9:30 AM

Cafe Aroma

1873 Broadway at Columbus Circle. Family-owned café right at Columbus Circle, freshly ground coffee and in-house baked pastries. Open from 7AM on weekends. A short walk from the hotel — the last morning coffee of the trip.

10:00 AM

Return to hotel — shower & get ready

Back to Dream Midtown to freshen up. Check out and leave bags with the concierge — collect them before heading to the airport.

11:00 AM

Carrie's new house · Upper East Side

Near E 73rd St, Upper East Side. The brownstone exterior used in And Just Like That as Carrie's apartment. Quick cab from the hotel, a photo stop, then stroll down Madison Avenue before heading to SoHo for lunch.

History & lore — And Just Like That premiered in December 2021, reviving the franchise over 17 years after Sex and the City ended. The shift from the West Village original address to the Upper East Side was a deliberate storytelling choice — reflecting the characters' changed circumstances and New York's evolving geography of aspiration. The UES has historically been associated with old money and established society in a way the bohemian West Village never was.

12:30 PM

Balthazar · Lunch

80 Spring St, SoHo. The definitive New York brasserie — steak frites, moules marinières, a legendary bread basket, and excellent Bloody Marys in a room that has hummed with the energy of the city for nearly thirty years. The perfect final meal before heading home.

History & lore — Keith McNally opened Balthazar in 1997, modeling it directly on the grand brasseries of Paris. It became one of the most coveted tables in New York almost instantly. The room — aged mirrors, red leather banquettes, zinc bar — was designed to look as though it had been there for a hundred years. McNally went on to open Pastis, Morandi, and Minetta Tavern, defining a certain era of downtown New York dining almost single-handedly.

3:00 PM

The Metropolitan Museum of Art

1000 Fifth Ave at 82nd St. Open Memorial Day, 10AM–5PM. Cab from SoHo takes about 25 minutes. You have roughly 90 minutes inside before the 5PM close — more than enough to do one wing justice. The Egyptian wing, European paintings, or the Roof Garden are the natural choices. Leave by 4:30 to stay comfortable on timing.

History & lore — The Met is the largest art museum in the United States, covering 2.2 million square feet and housing over 2 million objects spanning 5,000 years of world culture. The Temple of Dendur in the Egyptian wing — a complete ancient temple — was a gift from the Egyptian government in 1965, given in thanks for American assistance in saving monuments threatened by the Aswan High Dam flooding. The institution was founded in 1870 by a group of American businessmen and civic leaders who wanted to bring art to the American people.

4:45 PM

Return to hotel — collect bags

Cab from the Met back to Dream Midtown takes about 15 minutes. Collect bags from the concierge and arrange car service for Newark.

6:30 PM

Depart for Newark EWR

Car service is strongly recommended on Memorial Day weekend — NJ Transit can be unpredictable and EWR Monday evening is one of the busiest travel moments of the year. Budget $60–80 and leave no later than 6:30PM for a 9PM flight. Check in online the night before. You've earned a smooth exit.