New York City. So many of us spend our lives experiencing it through our favorite TV shows (Friends, Gossip Girl, Sex & The City), movies, pop culture, news and more. It’s a magical city and a place that you feel you know, love and are connected to before you’ve even stepped off the plane for the first time. Almost a year into living here, the magical feeling and energy hasn’t gone away or gotten old. In fact, it’s only grown and makes me so excited to share the tips I’ve learned with all of you!!

Like any major city, planning a trip can bring up so many logistical questions which we’ll answer here. If you’re looking for restaurant, bar and activity recs, head over to our Instagram - @hellohenrys - or check out our exact itinerary from Lauren’s 30th birthday weekend in NYC HERE. For this purpose of today’s post, we’re answering the most frequently asked questions around just planning the trip - when to go, where to fly into, how to get around, etc.

A NOTE: New York City refers to the 5 boroughs of Brooklyn, Queens, The Bronx, Staten Island and Manhattan. For the purposes of this guide, I’m discussing Manhattan as this is the most visited of the boroughs and is, likely, where you’ll spend most of your first time trip. New York City is much more than the island of Manhattan and I would be remiss not to call this out in the guide.

which airport should i fly into?

New York City is serviced by 3 major airports - JFK, LaGuardia and Newark. This will be one of the first decisions that you make when planning your trip. How to decide?

Airline Loyalty - If you’re loyal to a specific airline, this will likely help to make the decision for you. For example, United diehards will probably fly into Newark and Delta fans will opt for JFK or LaGuardia. Each airport is a hub for just a few carriers, so your airline of choice will help to narrow down your decision if this is a priority for you!
Where You’re Staying - Newark Airport (technically in New Jersey) is west of New York City and would make sense for anyone staying in New Jersey or on the West Side of Manhattan. Both JFK and LGA are in Queens and make more sense for anyone staying on the East Side of Manhattan, Brooklyn or Queens.
Where You’re Flying From - LaGuardia airport operates under a perimeter rule meaning that it’s restricted from operating flights further than 1500 miles away. If you’re flying to New York from the West Coast, this airport simply won’t be an option for you, unless you have a layover.

In my opinion, JFK is the best of the 3 airports. It has the most daily flights and time options and it’s connected to the subway, making it super easy to get into the city.

how do i get into the city from the airport?

Regardless of where you fly into, none of the 3 airports are close to the city. Getting into Manhattan takes about an hour. I usually plan to arrive home 2 hours after my plane lands - taking into account de-boarding, picking up bags and the transit time.

Your options for getting into the city will really be between a taxi or public transportation.

From JFK

If flying into JFK, taxis charge a flat fare of $52 ($56.50 in peak hours) from the airport. If you’re landing late at night or with a few people to split the cost, this is the route that I would go.

In all other cases, I would recommend taking the subway. From JFK, you’ll pay $8 for an AirTrain ticket (literally you get charged just to leave the airport, welcome to New York). Your options for subway lines will then be the E,J,Z or A lines. Which one you take will depend on where you’re staying in the city. Super easy to figure out from a quick Apple Maps search. We’re also happy to help if you shoot us a DM!

From LaGuardia

If flying into LaGuardia, I would honestly just recommend taking a taxi. It’s closer to the city than JFK, so will likely run you about $40 and could be as quick as 20 minutes depending on where you’re staying in the city.

If you want to save a little money and take public transportation, you can, but it’s not as straightforward as from JFK. You’ll need to do some walking and stair-climbing with luggage and take both a bus and a subway. It could take up to 2 hours. Not ideal if you have limited time in the city.

From Newark

Distance wise, Newark is about as close to Manhattan as JFK, but is certainly not as easy or convenient. First, because it’s in New Jersey, it’s not serviced by the MTA (subway). You’ll need to take NJ Transit or an Amtrak train from the airport into Penn Station and then hop on a subway there. Alternatively, you could take a bus to Penn Station. About a 30 minute ride with either option. A ticket for the train or the bus will run you about $16.

If you’re traveling with a couple of people, taking a taxi will almost certainly be more cost-effective and quicker, once you add up the cost of the train/bus tickets and subway.

how to get around in the city?

A combo of walking, subways and taxis depending on the scenario.

Since moving here, I easily exceed 10,000 steps every day without even trying. If I have friends or family in town and we’re exploring, surpassing 20,000 steps is not surprising. The city is relatively flat and, due to the traffic, walking is often faster than catching a cab. It’s crazy what becomes normal. Last weekend, Zach and I went on a dinner date. The restaurant was 26 blocks away and we didn’t even consult with each other on how to get there. We just started walking - a no brainer.

If you’re going between neighborhoods or visiting different tourist sites, I would recommend using the subway. It’s super easy. Will share a few tips below.

If it’s past 10PM, I would recommend taking a cab. Plenty of people do take the subway at all hours of the night, but I’d rather be safe than sorry. If I’ve been drinking and/or it’s late, I would rather pay for a taxi. If you’re with a group of people or a guy, your threshold for time cutoff may be different. For example, when I’m with Zach, I’d feel okay taking a subway up to midnight.

I haven’t used Uber or Lyft once since moving. Getting a taxi is so easy. You just walk out onto the street, raise your hand and hop in. I’ve never waited longer than a minute. Just be sure the taxi roof light is on. If it’s off, that means the cab is occupied or out of service. Lastly, be sure to give the driver your cross streets - example: 67th and Madison - vs reading off a full address.

subway tips?

The subway may seem overwhelming, but you’ll get the hang of it much more quickly than you would expect! A few tips…

Subways and buses are $2.75 per trip regardless of how far you’re going. This is part of the reason why people walk so much. If you just need to go one stop, paying $5.50 round trip might not be worth it and you’ll just walk.
Set up Apple Pay on your phone or watch. You can tap at the turnstile and this is much easier than purchasing a metro card and you won’t run the risk of having money leftover at the end of your trip that you haven’t used.
As a bonus, as of this month, MTA just rolled out a feature that after 12 trips in a week, any additional trip is free. By using Apple Pay, it will track the number of trips for you. Previously, you had to purchase a weekly unlimited pass in advance and it was always annoying if you didn’t end up taking enough trips to make it worth it. Or alternatively, if you took way more and hadn’t purchased one. It’s so nice that it does it all automatically now!
Use Apple Maps and select the transit directions. It’s SO easy and helpful. It tells you exactly which subway to take, how to get there, which exit to leave from and how frequently to expect the train. We like to connect it to our Apple Watch so that we aren’t staring at our phone and maintain awareness.

3960250F-0001-4D6E-9745-318C925340D2 (1).JPG

where to stay?

One of the more overwhelming decisions of planning your trip. As with any vacation, we recommend planning your itinerary first and then selecting accommodations that are centrally located to a majority of what you plan to do.

The island of Manhattan is essentially divided up into three sections. There are technically a couple others, like Lower or Upper Manhattan, but for the ease of this guide we’ll keep it to these three.

Uptown - This is where you’ll find most of the museums, Central Park and a more residential feel - think Gossip Girl. I would consider anywhere north of 59th Street to be Uptown.
Midtown - This is where you’ll find many offices and business centers, the theaters, Times Square and many tourist attractions.
Downtown - Below 14th Street. This is the heart of nightlife, culture, restaurants, etc. Think Sex and The City.

Uptown is certainly worth visiting during your NYC weekend, but you could get a taste for it in a day and it likely won’t encompass the bulk of your plans, so I wouldn’t recommend staying there. In addition, this is where many of the bougiest hotels are - The Mark, The Carlyle, etc. - so not the most affordable option.

Midtown and Times Square area are extremely convenient in terms of access to all subway lines, making it easy to get to all of the spots on your list, and it has a plethora of hotel options, many of them more affordable. It does feel extremely touristy and overwhelming though. It also serves many business travelers, so lacks some character in my opinion. Stay here if you’re on more of a budget or have plans to visit a vast number of neighborhoods and want to get to each quickly.

If you plan to focus primarily on eating, shopping and nightlife, staying Downtown would be my top recommendation. You’ll distinctly feel the culture and energy of New York City and be able to walk to a majority of places on your list. You can still easily jump on a subway to check out Central Park or The Met if you choose to do that for one afternoon. Hotels feel boutique and trendy here. If you want to stay here, look for spots in Soho, Noho, Bowery, Greenwich or similar.

Lastly, a note on hotels vs. Airbnbs. Airbnbs are technically illegal in New York City if the stay is for an entire home/unit and the stay is for less than 30 days. There are, however, plenty of Airbnbs listed and I know many friends who have successfully stayed in great ones. However, I’ve also heard many stories of friends arriving only to have their reservation cancelled last minute or the listing removed. If you’re booking one, just be prepared that this could be a possibility.

When booking a hotel, we’ve had success in the past using Hotels Tonight in New York City to score a great deal on a nicer hotel than we would typically be able to afford. This option may not be for everyone, especially if you’re tied to a specific neighborhood, but, if you’re open to it, it can be a great way to score a deal!

when to visit?

New York City is an incredible place to be on any day, but, for a first time visitor, spring and fall would be our top recommendations.

Summer can get uncomfortably hot - especially in July and August. In a place where you’ll be doing a ton of walking, the heat and humidity makes the experience a little less enjoyable and can lead to some cranky travelers. If you’re fine to just hang out on a rooftop bar or get out to The Hamptons, it can still be a good time, but if you want to see a lot of sites, we’d avoid the summer.

Similarly, the winter can be miserably cold and snowy. With the exception of Christmastime, which I’d recommend everyone experience once, it won’t be fun walking around, seeing everything when you’re freezing.

April, May, September and October would be our top recommendations. Flights and accommodations might be a little more expensive, but it’s definitely worth it to ensure good weather and an enjoyable trip!

how long to stay?

While a long weekend is certainly not enough to even scratch the surface on all that New York has to offer, we’d recommend 4 days for your trip. It can be an exhausting place to visit, with all of the walking and having so many activities packed in. Additionally, it’s a very expensive place. Between your hotel cost, as well as meals, activities, etc., more than 4 days could hit your bank account hard. We’d recommend 4 days for your first-trip, being a little more narrow about what you want to see - maybe just a couple of neighborhoods - and then plan to do a few more trips over the years to see everything that’s on your list!

what to wear? tips on shoes, style, etc?

Sneakers are everything here. A combo of both the walking culture and just the cool, street style. Definitely plan to wear a sneaker during the day here. We both wear our APLs while exploring, but Jordans, Air Force 1’s, Yeezys, etc. are very common. Wear what you want of course, but if style is a priority to you, we’d leave the Brooks, Asics, athletic sneakers at home. I’ll often have a pair of heels in my purse so that I can change before heading into a restaurant or coming off the subway, but without sacrificing comfort getting around.

When it comes to style, New York is definitely casual, but people dress the part. That’s been one of the most fun parts about moving here. People care about their style and really take risks with what they wear. Anything goes here, but people definitely make an effort and own it. It’s an “it factor” that is hard to describe, but you can see it instantly. For us, personally, it’s fun and energizing to be around.

For going out, a heeled sandal, some leather pants and a simple bodysuit or crop top is totally fine. A dress isn’t necessary - but also wouldn’t be weird if you wanted to wear one. The vibes between Uptown and Downtown are different too. Downtown has more of a young, cool, casual energy, where Uptown style is a little more classic, sophisticated and refined.

Some of our favorite influencers to get a sense of style in New York City would be @laurenireland, @mariannahewitt, @retroflame or @laurenwolfe. The first two (Lauren and Marianna) actually live in LA, but visit NYC very frequently and their everyday style aligns perfectly with what we think of when it comes to downtown/NYC cool girl.

how much to budget?

As with any trip (and most things in life in general), anything worth doing in life is worth doing well. For example, there’s no point in booking a trip to Paris and spending the time in your hotel room, unable to go to the Eiffel Tower or The Louvre, if you don’t have the budget for it. This why we try to get the best deals possible on our flights and hotels, so that we can experience as much as possible when we’re there! We’d recommend building a realistic budget and saving up to be able to have the experience that you want.

Everyone is different and there is no shortage of cheap eats here, but, in general, below is what we would recommend budgeting for:

Transportation - $50-75. Between your round trip airport subway ride, a few taxis and subway trips, this should cover you for a long weekend. If you take a taxi from the airport instead and take taxis around the city vs the subway, expect this to be higher.
Accommodations - $300/night. There are certainly options much higher, as well as much lower than this, but for an average 3-star hotel, I would plan for around $300 a night if you’re traveling during a prime travel month.
Drinks - $20 each. The average cocktail will run between $18-20. After tax and tip, we would budget about $25 a drink. Of course, if you’re going to dive bars, drinking beer or splitting a bottle of wine, there are ways to reduce this cost, but this would be the standard cocktail at most places that we go to.
Food - Varies. You can get dollar slices of pizza or $1000 omakase dinners. Cost of food will depend so much on your tastes and what you want to experience, but for a typical restaurant, I’d budget about $30 for a dinner entree, $15 for an appetizer. $25 for a lunch entree and $20 for a breakfast entree, as kind of a bare minimum.

Wow! I knew there would be a lot of information to cover here, but, even I wasn’t expecting it to be this intensive. We hope this guide helps you to plan the logistics of your NYC trip easily and effectively. We are always here to answer any and all questions that arise to help you plan the best trip ever!! Again, check out our two NYC highlights, countless Reels and informative feed posts for more specific NYC recs on our Instagram - @hellohenrys.

Lastly, if you don’t play Empire State of Mind as you’re touching down and Welcome to New York as you’re crossing over the bridge into the city, who are you!?

Happy Travels!!