How to Spend a Long Weekend in New York

Got a few days to explore the Big Apple? Here's our guide to ensuring your fleeting visit is also a fabulous one.


Flat Iron Building, New York

For your long weekend in the Big Apple, you’ll find yourself with more on your bucket list than rest in your remarkable Plum Guide home will allow. Its nickname the 'City That Never Sleeps' will soon come to make a lot of sense. You'll want to see it all and do it all but with only a few days worth of exploring, we're afraid that simply is not possible. Worry not, though, because we here at Plum Guide have curated a guide to the ultimate long weekend in New York for you. Whether you fancy catching the latest Broadway show, dining at the hottest new restaurant or soaring up all the skyscrapers you possibly can, here’s the only itinerary you need for your few days in the city.


Prometheus Fountain, Rockefeller Center, Manhattan

Prometheus Fountain, Rockefeller Center, Manhattan

It’s said that anything can happen in a New York minute. While you may want to hit the concrete jungle at full speed, on your first day we suggest you take it a little easy and pace yourself. Drop off your bags, freshen up, put on comfortable walking shoes, and hit the town for some serious city exploration.

If you need a spot of caffeine to pep you up, please avoid Starbucks and try these coffee shops instead: Cafe Grumpy, Ground Central, Birch Coffee, or La Colombe. Each of these roasters has several locations dotted around Manhattan so you shouldn’t find yourself too far from any of them at any given time. The flat white at Cafe Grumpy is our personal favourite brew in the city. Give it a try. You may just find yourself a convert too. If you’re a true coffee aficionado, try The Coffee Project in the East Village. Sign up for a coffee tasting class or just order up a deconstructed latte and educate yourself.

New York is known for many things – shopping in the city being one of them. When you’re ready for the retail therapy, hop on the subway and make your way to SoHo, the metropolis’ retail hub. Here you’ll find a concentration of internationally recognised labels, flagship shops of every major luxury brand, small boutiques run by local designers, and street vendors hawking their handmade arts and crafts along the sidewalk.

If you’re feeling hungry from all the shopping, you'll be spoilt for choice amongst New York's food scene. Balthazar is the legendary French brasserie and bakery that with refuel and revive you before you burn through more cash. Their buttery, flaky croissant is a can’t miss treat. If you’re ready to leave the bag-toting crowds behind for lunch, follow Prince Street eastward into NoLita (short for North of Little Italy). It’s less touristy (though not by much) but you’ll find more unique New York-based fashions and a myriad of delicious lunch options. If you’re craving a mouth-watering Cubano sandwich, Cafe Habana on the corner of Prince and Elizabeth Streets has you covered. Their grilled corn on the cob smothered in cotija cheese is a messy delight you should definitely get your hands on. If the wait at Cafe Habana is too long, head next door to the take out counter. There are a few tables and a counter where you can eat. It’s the same great menu for you to enjoy, though you will miss out on the fun vibe of the restaurant.

Cafe Gitane on Mott Street is another local hotspot and serves up hearty French-Moroccan dishes. America’s first pizzeria, Lombardi’s isn’t far from here and still serves the same incredible New York-style pizza since it first opened in 1905. If you’re seeking something a little more out there, cross over the Bowery and keep your eyes peeled for a tiny alleyway riddled with graffiti and street art. Tucked away at the back is Freemans, a New American restaurant and cocktail bar housed in a Colonial tavern with a hunting lodge vibe. The restaurant may be hidden, but the locals in the neighbourhood keep it packed and lively. Morgenstern’s Finest Ice Cream, a few doors down is the best way to finish off your afternoon, even if you have to queue for longer than you would expect for a scoop. Yes, it really is that good.

If you’re weighed down with your shopping, drop off your haul at your Plum Guide NYC apartment and then head to Midtown. Start at the Empire State Building. As tempting as it might be, hold off from shelling over the entrance fee to visit the Observation Deck. Wait until you get to Rockefeller Center, a short walk away, and make your way up to the Top of the Rock, the 70th floor observation deck that offers the best aerial view of the city. We prefer this view as it includes sweeping views of Central Park and the Empire State Building. If you can time it right, the soft light of dusk will give you incredible photos to post on Instagram straight away look back on in years to come. In the area, you can also catch a glimpse of other famous landmarks like Radio City Music Hall and St. Patrick’s Cathedral.

If you’re not done treating yourself, Fifth Avenue offers the iconic Saks Fifth Avenue department store and expansive outposts of top international brands. Otherwise, we suggest dining in one of New York City’s top-rated restaurants. Seafood lovers can dive into a stellar meal at the jacket-required Le Bernadin, the long-standing upscale 3-Michelin starred restaurant in midtown. If you prefer something just as elegant and refined but a little more low-key, Gabriel Kruether near Bryant Park, is an excellent 1-Michelin starred alternative. If the jetlag hasn’t set in, try the Campbell Bar in Grand Central Station for classic cocktails in an opulent setting or the bustling Refinery Rooftop bar that is every bit a looker as the views of the city it offers.


New Yorkers love a good brunch on the weekends so there really is no other way to start off the Saturday of your long weekend in New York. Head to the artsy, student-filled East Village, which is perfect for people watching. Veselka has been featured in many a New York movie, but the celebrity hasn’t gone to this Ukranian cafe’s head. Their pierogies are as good as they ever were. The Caribbean-inspired takes on breakfast staples at Miss Lily’s 7A Cafe will transport you to the islands with its tropical vibe. The coconut pancakes are to die for and will definitely leave you craving for another taste long after you’ve paid the check. Maharlika serves a fairly more adventurous menu of Filipino breakfast staples for the uninitiated, but this upscale Filipino restaurant is where to go to get acquainted with the taste of aromatic garlic rice, sweet pork sausage, and ube, the tasty Asian purple yam. For more traditional American breakfast fare, Clinton Street Baking Company’s fluffy pancake stacks are worth every minute of your wait in the queue for a table.

Next up, marvel at the unique architecture of the East Village and stop in a few quirky shops as you meander your way south towards the Lower West Side's Tenement Museum. Enter the fascinating time-capsule of a building and you’ll be transported to the early 1900s where the cramped area was home to the largest concentration of immigrants. It’s a fantastic way to learn about the history of the neighbourhood, as well as how New York City came to be the melting pot it is today. The Lower East Side is also home to many street artists and the walls, storefronts, and even trash bins are their canvas. Colourful and eye-catching, sometimes political, but always interesting, these are the perfect backdrop to elevate your selfie game and garner Instagram likes.

If you need a refreshment or a respite for your tired legs, explore the newly opened Essex Market on the corner of Essex and Delancey Streets. There’s often live entertainment in the mezzanine level that showcases New York City’s local talent. If you’ve got a sweet tooth you need to pacify, Sugar Sweet Sunshine’s cupcakes and banana pudding hit all the right spots. They have a booth inside the Essex Market, as well as a stand alone shop on nearby Rivington Street.

Venture into the densely populated Chinatown neighbourhood and find yourself amazed at the frenetic life on its streets. From produce vendors shouting their prices to passers by to the urgent whispers of illicit knock-off handbag dealers, Chinatown assaults the senses. With its whole roasted chickens dangling from the windows, fresh fish and seafood sitting on dripping beds of ice, and the undeniable scent (or stench depending on which camp you fall under) of fresh-cut durian fruit, a walk in Chinatown truly is an experience to savour.

If your legs haven't fallen off yet (well done you), continue your walk into the Financial District to visit the World Trade Center complex and 9/11 Memorial. Alternatively, hail a cab and save yourself a 20 minute walk. The mood is sombre within the Memorial grounds and the 9/11 Museum offers special insight into the events that unfolded on that fateful morning in 2001. Give a moment of silence to those who lost their lives from a distance and continue along at your own pace towards the Staten Island Ferry terminal. The contrast of architectural style in this district is stark so keep your eyes pointed upwards. From the landmark Woolworth Building to the historic City Hall to the ultra modern soaring wings of the Oculus transportation hub, your eyes will be working overtime absorbing all the wonderfully intricate details.

From the Staten Island Ferry terminal, hop on the ferry to Staten Island. Don’t worry, we’re not suggesting you actually visit Staten Island when you’ve got all of Manhattan island to discover. Simply ride the free ferry to Staten Island, get off, go through the terminal, and hop back on the ferry returning to Manhattan. Why do this you ask? Because the free ferry passes the Statue of Liberty each way and offers you up close views of the Lady. If you manage to catch an evening ferry, you’ll be treated with gorgeous sunset photos on the water.

For dinner, you’ve got plenty of options around the city. You can head back to the East Village for some affordable international cuisine. We really like Oda House for their authentic Georgian cuisine. The adjaruli khachapuri, a bread boat filled with cheese and a poached egg, is positively divine. Somtum Der dishes out spicy and fragrant Northern Thai cuisine surrounded in warm bamboo furnishings. The honey buttered crisps at Oiji is a perfectly sweet way to start a meal at this modern Korean restaurant. If you want an even more affordable meal, the Japanese izakayas lining St. Marks Place offer plenty of budget options. If you’re up for exploring a new area for dinner, try the Upper East Side instead. The posh residential neighbourhood features excellent dining and benefits from fewer tourists. For something more casual, we love Heidi’s House by the Side of the Road. The name is indeed a mouthful, but with a mouth full of anything from this American hole in the wall restaurant and wine bar, you’ll be really happy you came. Italian restaurants can go either way in New York. They can be homey and churn out pasta like nonna does, or they can be crazy expensive for a forkful of spaghetti. Sfoglia hits the mark with a delicious menu of Italian specialities in a refined space that doesn’t feel too stuffy or too dingy.

We’d be remiss if we mentioned dining in the Upper East Side and didn’t include Daniel, the elegant Michelin-starred outpost of famed chef Daniel Boulud. Jackets and reservations are required at this impeccable French restaurant (and a trust fund would also be helpful to cover the bill). If you fancy a night out, party with the young, wild and free crowd in the East Village or Lower East Side. Some hotspots worth checking out include Beauty and Essex, an upscale lounge and restaurant (though we suggest going just for cocktails) hidden behind a pawn shop, Bar Goto for heavy-hitting Japanese cocktails in an intimate space, or the low-key Immigrant bar which serves its beers at one bar and all its wines at the opposite bar. It takes some getting used to, but it’s a cool, calm spot in the midst of the East Village chaos.


Central Park, New York City

Central Park, New York City

For you early birds, the Flower Market in the Chelsea neighbourhood is a Sunday morning delight. Open starting at 5 am, wholesale florists cover the sidewalks with lush and vibrant flowers that can be bought at huge discounts. Even if you resist a bouquet (or two or three), it’s a quiet and rather lovely way to spend the last morning of your long weekend in New York. Then, make your way to Chelsea Market. Grab a light breakfast to nibble on and perhaps a cup of coffee to take with you to the High Line. This picturesque elevated park and walkway was built over the old railroad tracks of the West Side Line that became decommissioned in 1980. The Spur is the newest section that recently opened at the northern edge of the High Line and features the Vessel, a remarkable honeycomb-like structure that’s become an instant sensation.

Sunday’s yet another day to enjoy a leisurely brunch and this time you should head into the West Village for a look at another side of New York. With stunning row houses and brownstone buildings, this is where the wealthy live and play. It’s a beautiful neighbourhood to walk around and explore. Whenever you’re ready for that brunch, try Buvette, an adorable French cafe with incredible croque monsieur sandwiches and mini croissants. Waverly Inn is another great brunch spot. Sitting inside the renovated townhouse, this might be the only chance you get to see what it’s like to live in a home this regal. Head north up to Central Park for an afternoon inside this massive urban park. Yet another famous New York City location for filming movies and television shows, you’ll no doubt spot easy to recognise spots like the Boat Pond, Belvedere Castle, Bethesda Terrace, and Strawberry Fields, to name a few.

If you’re in the mood to see some art, make your way to either perimeter of Central Park. Choose between the Metropolitan Museum of Art, which houses a staggering 5,000 years worth of art, the American Museum of Natural History, the Guggenheim, the Frick Collection, the Neue Galerie and many more.

For the last night of your long weekend in New York, head into the chaotic bright lights of Times Square and catch a Broadway show. If you didn’t plan in advance, TKTS offers hugely discounted same-day tickets to a number of Tony award winning plays and musicals. The busy ticketing booth also offers seats to a few offbeat shows, including cabarets and stand-up comedy. (Sorry though, Hamilton tickets are obviously not available here.)

Squeeze in a convenient pre-dinner meal in the nearby vicinity. Unfortunately, there isn’t much of an impressive selection in this area but luckily, we’ve managed to source a few solid options. (We really are good to you, aren't we?) Kashkaval Garden is an intriguing French-Turkish cafe with a cheese heavy menu that will be sure to please. I mean, who can say no to melted cheese? Gallagher’s Steakhouse is the legendary Prohibition-era speakeasy where you can devour a huge juicy prime rib if you so choose. ViceVersa serves up creative Italian pasta dishes and has an atmospheric backyard garden if the weather is nice. Bid the city a glittering farewell with a final nightcap at the St. Cloud Rooftop Bar inside the Knickerbocker hotel.

After reading this guide to a long weekend in New York, you're no doubt wanting to plan a trip to the city. Look no further than our collection of homes in New York. Our home critics handpick only the very best of them, meaning all you need to worry about during your trip is how you're going to get all of that shopping back home with you.

Written by

Connie Hum is an expert at slow travel. She loves taking her time exploring a new destination or rediscovering a place that previously captured her heart. Her international adventures and travel mishaps can be found on her blog

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