Advice and suggestions for someone taking their first flight to the USA

Here are some general comments about your situation. I will NOT comment on the COVID situation and leave that for other answerers, as I don't feel I know enough to be able to comment accurately there.

As a general terminology thing, there are three separate stages: "security" which is checking the contents of your bags for weapons etc., "passport control" or "immigration" which is checking you into (or out of) a country with your passport, and "customs" which is checking what you're bringing into the country (usually you can just walk straight through the "nothing to declare" entrance as a tourist but once in a blue moon you'll be stopped and have your bags checked).

Printing everything shouldn't be necessary but also shouldn't hurt. I'd do it just in case.

Most important thing is to arrive in plenty of time at the airport. Since you're a new traveller it's probably best to aim to arrive the full 3 hours before at Heathrow (though myself I'd probably only leave 1.5-2 hours for a long-haul flight these days); certainly best to have bags of time to hang around in the shops/restaurants than to be rushing at the last minute. Also make sure you go to the right terminal; Heathrow's terminals are more awkward than those at most airports to transfer between, and so you don't want to have to do that. Your Heathrow terminal should be advertised in your booking confirmation. If you're driving/being driven just follow the road signs for the correct terminal number; if you're on public transport, there are separate tube, railway, and bus stations for Terminals 2-3, Terminal 4, and Terminal 5, so go to the correct one.

Usually these days you can check in online or through a mobile app, but with non-budget airlines you can usually check in at a desk or at machines alternatively, if you would rather have a physical paper boarding pass. You may be required to check in in person due to COVID restrictions; I'm not sure. Either way your boarding pass (digital or physical) will tell you what time your gate is expected to close. It might have a gate number listed on it but this could change so don't take it as gospel; check departure boards at the airport. Try not to lose your boarding pass, but if you do, it's not a massive deal as they should be able to re-print one for you at the gate upon boarding. Definitely don't lose your passport though! This is also the time you would drop off any checked luggage, if you had any, at the staffed check-in or dedicated bag drop counters. They may ask you questions like if you packed the bag yourself or if anyone asked you to take anything with you; they're really trying to ask if someone has perhaps tried to get you to smuggle something in for them (perhaps unknowingly). Sometimes there will be a step on a checkin machine instead which will then print out a baggage tag you can attach and then take the whole thing to the bag drop station; just follow the instructions. You will also often get a small self-adhesive counterfoil which is usually stuck to the back of your passport; you'll want to have this in the unlikely event that your bags get lost in the system.

After checkin is security. For security, Heathrow tends to be pretty efficient though it does have its bad days. Have your bag prepared so you can easily remove your laptop, tablet, and liquids from your hand luggage; liquids should be transferred into the provided plastic bags (or if you already have one, you should put them in there at home and just pull that out to save time). You'll also need to remove coins/keys from your pockets, watches, phones, etc. to go into the tray. Everything, including bags, ultimately goes into trays at Heathrow; other airports differ in this aspect where you put your bags directly onto the belt. Remember that you cannot take liquids in containers over 100ml in your hand luggage. Since you're not taking hold luggage this means you can't take anything above this. There are no passport or customs controls when leaving the UK.

Once you're through security, especially if you decide to spend your time in a pub/restaurant, keep an eye on the time and keep glancing at the destination boards every now and again; I've known people to miss flights because they got too relaxed at the airport and lost track of time! Keep the "gate closes" time that will be listed on your boarding pass in mind; you don't want to be away from the gate when that time comes unless you're informed of a delay on the departure boards. There will be plenty of time once the board changes to "go to gate" so don't get yourself into a panic, but certainly you should be on your way to the gate by the time it says "boarding" else you might run into difficulty. Most large airports these days no longer have announcements that flights are about to close etc., because there are just so many flights this is no longer really possible without annoying everyone. Some flights from Terminals 2 and 5 leave from satellite terminals ("B gates" or "C gates", gates will be prefixed by one of these letters). There are trains to reach these which leave very regularly, or you can walk if you have loads of time, but do bear in mind it takes a few more minutes to get down to these terminals. But there aren't usually too many amenities in these so you might wish to stay in the main terminal until it's closer to your boarding time.

I'm assuming you're in economy class since you haven't specified otherwise. For those who can easily sleep in seats, the seats should be reasonably comfortable though you might need to bring a pillow or whatever. You can recline the seat but try to be mindful of the person behind you, especially if they have their tray down/are eating. It depends on the airline but you can usually expect a hot (microwaved) main meal plus an additional small meal (usually just cold snacks) in economy. Personally my strategy for dealing with jetlag is not to sleep on a westbound flight and just count it as an extremely long day. If you can force yourself to stay awake, by the time you get to bedtime you should be so tired that you'll sleep until the morning. But YMMV, jetlag tips vary wildly depending on who you're talking to, so if you do want to sleep on the flight it shouldn't be the end of the world.

Just a little note about when you're on the plane. Above your head will be seatbelt signs, when these are lit you're supposed to return to your seat and fasten your seatbelt securely. In my experience, most European airlines will only use these if there is a genuine safety reason (particularly strong turbulence, takeoff, and landing), so they should be obeyed strictly. But if you're on an American airline, they tend to use them pretty often for long periods of time, basically whenever they'd rather you not be wandering around the cabin. So when flying with an American airline they usually tolerate people ignoring them to get up to use the toilet, for example.

Upon arrival at JFK, be prepared because the airport is pretty grim by European standards, though ultimately it's not that bad. It's just not a particularly pleasant environment even for an airport. You'll firstly go through immigration, I believe this entails answering some questions on a touchscreen terminal, which then prints a ticket for you to go through the staffed booths with. This system may or may not be back in use; reportedly it was out of use during the height of COVID. You might be feeling stressed after the flight, just take your time and read the questions carefully, and you should be fine. Once you speak to a human they'll possibly ask you a couple of questions about the nature/duration/etc. of your trip, just take your time and answer these honestly and you'll almost certainly be fine. Honestly I've never felt threatened or intimidated at US immigration. This is the point where any COVID restrictions will come into play as well, which I am not qualified to comment on.

Since you're connecting onto a domestic flight if you had hold luggage you'd need to collect it to take it through customs (customs doesn't exist for domestic flights which is why it needs to be done then). But since you don't, you can just head straight through customs out into arrivals. The next step at JFK is to find the terminal for your departing flight, and head on the AirTrain free shuttle if you need to change terminals. You'll then need to find your way back into departures, pick up a physical boarding pass if you need/want one, and go back through security. This is just how US airports are I'm afraid, very few of them supply a shortcut for connecting passengers. Security in the US will likely be slightly stricter than at Heathrow; you'll likely be asked to take your shoes off as well. But other than that it'll be similar. Probably worse-organised and a larger queue than at Heathrow, though perhaps not.

You should have plenty of time left for your connecting flight. If a delay or cancellation on your incoming flight leads you to have insufficient time to make your connection, though, you can talk with your airline at their checkin desk for them to book you onto the next available flight at no charge. This is because you have booked it all on one ticket, the connection is essentially "guaranteed" by the airline.

At Pittsburgh you'll just go straight out of the airport, no immigration, no customs, nothing, since it's a domestic flight. So don't expect that to take too long. I've never been to Pittsburgh but there's a very short, frequent train ride you'll need to take from the airside terminal to the landside terminal.

Generally at airports, signage is pretty good so I don't think you'll need to ask for directions. But if you do I'm sure you can find someone to ask.

On your return trip, at Pittsburgh, you'll have to go through security but not any immigration or customs, again because it's a domestic flight.

At JFK you'll have to do all the same stuff in reverse (though note that if you have hold luggage, this may be able to be checked through to your destination since there will be no need for a customs check, so you might not have to collect it; ask the staff on checkin at Pittsburgh); leave into the arrivals area, check your departure terminal, catch the AirTrain if you need to, pick up a boarding pass if you need to, go through security, and finally hang around until your flight. The US also does not have exit customs/immigration checks.

Assuming it's an overnight "redeye" flight, my personal jetlag recommendation (again YMMV) is to get what little sleep on the plane you are able to, which will probably be not very much, then once you arrive, whatever you do do not sleep until the evening. Force yourself to do something if you have to, personally I often work a full day in the office to stop myself being tempted to sleep. By the evening you'll be so tired you'll hopefully fall asleep at the correct time. Eastbound jetlag is MUCH worse for most people, as you'll find yourself lying awake at night until a ridiculous time in the morning wondering why you can't sleep, and it's very unpleasant.

Upon arrival at Heathrow you'll have passport control; you will be directed through automatic passport gates which are reasonably easy to use. You likely won't talk to a human at Heathrow assuming you have a UK passport; though thinking about it this might have changed because of COVID. From there you'll pass through baggage reclaim and straight through the "nothing to declare" aisle at customs - almost certainly (unless you've bought a bunch of stuff beyond the personal allowance). And that's it, you're out!

On the subject of travelling with a checked bag, well, it's up to you. I wouldn't say it adds a huge amount of difficulty, but it likely adds a lot of irritating waiting around. This is why personally I like to travel without one wherever possible. But others clearly have very different opinions to me! Just think of it more as a decision whether you want to add a bit of extra faff at each airport but then not have to carry a bag around versus carrying a bag around everywhere but having less time waiting around by the baggage reclaim belt/in bag drop queues/etc.. I'm sure you can make that decision for yourself which you'd prefer. My point is I doubt it'll make or break your trip which one you choose, and it shouldn't cause you any problems.

Tl,dr: Don't worry you'll be fine

Some of your points in detail:

I depart from Heathrow and arrive at JFK, and then depart from JFK to PIT (Pittsburgh) with a stopover of 5 hours. I'm hoping 5 hours is enough time to get through customs/immigration

5 hours is plenty. This will work in 99% of all cases. If doesn't (e.g. because of massive delays. cancelled flights, lost bags, etc.) the airline will rebook you for free on the next available flight and might provide hotel and food vouchers

I have no intention of leaving the airport at JFK.

You can, but there is no need. On arrival in JFK you will be first herded to immigration. Make sure you pick the correct line for ESTA. After that you will herded to the baggage claim. Pick your bags and head to the exit. There will be customs officer at the exit and they may or may not want to see your docs or ask you questions. Most often you can walk just through. Go through the door and CONGRATS you are in the US now. You are free to leave the airport and go wherever you want to.

After customs there will be big signs for "recheck baggage". You can drop your bags there and they will be transferred to Pittsburgh. Your bags will already have a tag that says "PIT" on it.

Look at your boarding pass or the monitors to determine which terminal and gate your next flight is leaving from. Follow the signs. You will have to go through security again to get to the gate. Chances are you will take the Air-Train: https://www.jfkairport.com/to-from-airport/air-train . Follow signs to the Air Train. Hop on the train, get off at your departure terminal, go through security and head to your gate.

After 2 weeks, I will then be taking a return flight back to London, which I've already booked in advanced.

No problem here

I also have a PCR test booked within 3 calendar days before my flight as per the entry requirement to the US for UK citizens.

Keep checking entry requirements. Covid rules do change frequently so make sure you stay up to date.

I'm looking for advice/suggestions on what I should do to be best prepared for this.

1. Familiarize yourself with the JFK layout and Terminals. Determine what terminal you will be departing from and what's the best way to get there
2. Download apps for airlines, ESTA, etc. on your phone. Make sure you have vital documents "available offline" in case you have trouble with connectivity
3. Make sure you have vital documents (Covid, Esta) as paper copies. Technically you don't need them but it can speed up things and is a nice backup.
4. Every time you leave an area (plane, security, customs) do a quick pat down check: wallet, passport, phone.
5. Relax and enjoy

that people will naturally be less approachable or friendly.

Untrue. Most people will be more than happy to help you. And if you happen to run into a grump, just ignore them go to the next person. You also speak the language which helps a lot.

As part of this, I've arranged to only take hand luggage on board with me to almost try limit me being a "burdeon" or causing trouble.

Given a 5 hour layover, there is no problem with checking bags. Actually in your case, I would recommend that. Travelling with just a backpack as carry on is more comfortable than wheeling a small suitcase around. Domestic flights in the US are often packed, so you may have to fight for overhead space and they may force you to check anyway. And on the way back, you can drop off your bags in PIT and don't have to think about them until you pick them up in London.

Also, I've heard a lot of rumours that US border agents are particuarly "brutal".

Unfortunately this is hit or miss. Some agents are professional and courteous, many are bored, but there are also some that can be outright abusive. Just answer the questions as asked. You are doing everything correctly and you have nothing to worry about. Since you come from a "nice" country, chances are this will be quick and easy.

and whether that changes on the 2nd time when I land in PIT.

Landing in PIT is easy. There is no customs or immigration. You can just walk off the plane, follow the signs to exit and walk out the secure area. That's where you can meet with your girlfriend. You can go together down to baggage claim (which is landside) and collect your bags.

. I have also ensured the ticket is flexible

Flex tickets are in most cases a bad deal. They just waive the change fee, but you are still responsible for any fare difference. If you actually have to change it, it's still a good idea to shop around for alternatives. If you are interested in details, ask a separate question.

The actual mechanics of navigating the airport and being at the right place at the right time are simple enough if you read all the information that is sent to you and the signs at the airport. Being fluent in English will help you, but many airports rely on symbols you may not know.

Airports generally have websites with helpful maps, and lots of pictures so you can see what it looks like and what signs to look for. You need to be sure to arrive at the airport in plenty of time to reach the gate by boarding time. (Emails from the airline tell you these times; so does the airport website.) This could include time to check your bag. You mention traveling carry on only. I don't recommend this for first time travelers. You're not burdening anyone when you check in a bag; dragging a big rolly bag everywhere you go (including into the bathroom at the airport, into restaurants and shops etc) can make the whole thing more stressful. Plus you can't put large liquids like a shampoo bottle into hand luggage. Checking your luggage and carrying just a small backpack with the things you need at the airport and during the flight will make your airport experience easier. Yes, you will need time at Heathrow to check your bag, and you will have to claim that bag at JFK to clear customs, then re-check it to PIT, but a 5 hour connection should make that very feasible.

Bag or no bag, check the websites of all 3 airports to start to feel familiar with them. JFK has a whole section on making connecting flights. You can also search you tube for videos from people departing from Heathrow, connecting at JFK, and landing at PIT. This will make it all feel more familiar and comfortable.

Be 100% sure about your covid rules. Are you allowed in? Do you need a test and when? Is the vaccine you got on their list (AZ is not, for example)?

Print everything - your ESTA, your covid stuff, contact info for your girlfriend, everything. Know things like the date you're flying back without having to look it up on your printouts. Be prepared for an agent to question you if you are actually planning to marry your girlfriend during the visit and stay in the US. Be prepared to show all the things that will take you back (besides your pre-booked flight) - your job, studies, family, etc etc in the UK. It should all go smoothly but don't panic if you get asked a few personal questions.

Also, you won't go through customs again at PIT. Once admitted at JFK, that's it. The JFK-PIT leg is a domestic flight.

Just a few more notes to add to the excellent answers already posted.

As a native New Yorker, I’d say that your British accent will be a definite plus when asking strangers for directions or for seeking help from a random person. You’ll find the average New Yorker to be friendly and helpful to polite strangers with British accents.

The average social distance for talking with an American stranger is about 1 meter, about the same as in England. You may encounter members of other cultures at JFK who prefer to stand much closer or farther away than you are accustomed to.

Be advised that your phone, tablet and laptop are theoretically subject to search by border agents, and if you fail to cooperate by entering a PIN or password to unlock it, you can be refused entry to the USA. The chance of an actual search is quite small, but if there is anything that you wouldn’t want an official to see or copy, you can save it to the cloud before you leave home and retrieve it after you clear Customs. Once through Customs, your electronics won't be disturbed.

If you drive a car, for goodness sake, keep to the right!

If you bring prescription medications, keep them in their original containers, which should be labeled with your name and the name of the medication. Random pills in an envelope are a bad idea, and may be illegal to carry that way even if legally possessed.

For police, fire or health emergency anywhere in the USA, call 9-1-1.

Take the phone number of the British Consulate in New York: (+1) 212 745 0200. They would be the ones to call if you find yourself in a pickle and need help from your government. The consulate in Pittsburgh is temporarily closed.

In case you're wondering, there are no formalities of any kind in crossing the borders between U.S. states. You may see a sign that says "Welcome To (state)" and the state motto.

So relax and enjoy your trip!

I've been through many an airport where I didn't even speak the local language. Airports are designed to be easy to navigate, there's always a million signs up above the crowds that you can compare with your ticket and boarding pass. The key things are your flight number and your gate number. Note that it is not unusual to find multiple flight numbers (on different airlines) listed for one flight. If the screens are switching back and forth between your flight and some other flight heading to the same place that's what's going on and it doesn't mean you've done something wrong.

A few points:

• You need to know the precise address of your first night to fill it in a form. US border control is usually strict(er) (than other countries) about this
• Be able to show funding if asked. Like one or two credit cards, a small wad of cash maybe have (possible) access to online banking. They might ask on what money you will live
• Just answer any question honestly and to the point without starting to tell long winded stories
• Is it also your first flight? Dont forget to think/read about what goes into hand luggage and check in luggage

I have never really exited the EU, well, I went to the UK a couple of times when it was part of it but that cannot count as the process was easier.

But I have taken flights to 3 or 4 countries before, and I regularily take national flights so I will try and give you a little bit of advice as I'm sure bigger questions can serve you better as a guide.

I am also more or less of your age so, you may find identified.

Try to always have printed versions of every documentation

Yes, I usually use my phone for the check-in and I do not usually have to use the printed version of anything (appart from the passport and that type of things), but still, you should always have one on reach. Your phone can suffer for whatever and leave you alone, so, always paper with you.

Also, be carefull with the internet when flying abroad. Do not rely on it 100%. I once took a flight to Amsterdam and my phone couldn't automatically change the company to the one mine has a contract with there, so I had to regret a lot not having a map, value the option of taking a printed map with you. I managed to manually change the company but something like this could make your way to your final destination trickier, specially in enormous cities like New York. At least you have the language wild-card. I only knew that people in the netherlands say straat instead of street.

Do not be scared of weird things going on

I was once flying back to Spain from Sweden, and I was in a swedish airport. I was given a "random" check (where random may mean 'you look like a criminal under my eyes' check), so they had to rub on me this thing that looks like a TV remote that has a 'paper' which contains the extract they analyze on the fly. Then some red s*** apears on the screen, and I manage to read:

EXPLOSIVES DETECTED

I was shocked and could only express a stupid "whaaaat?" in my incredible spanglish accent, but THEY COULDN'T CARE LESS S#*&. They just repeated the process with a 100% poker face, green screen, no explosives in my socks, so I was free to go.

So yeah, some weird things happen in airports, they are constantly on the lookout for weird things happening so... Just be collaborative whenever you are required. I would say it is VERY unlikely you will lose a flight due to weird procedures in an airport. They may get your bag and send to the bin your previous night bag organization, or they may make you leave behind some liquid bottle you forgot to organize in the correct size or whatever, but those are no dramas. You have 5 hours, I don't know if JFK is some kind of a behemoth of an airport, but you should be fine with that by a long margin.

Also, remember when you arrive to your destination that they do drive on the corre... right side of the road, we do not want an UK pedestrian smashed by a V8 Ford Pick-Up! (Sorry for the bad stereotypes, no offence intended ;)) Also they use the wron... imperial system so no kilometers for you I guess.

Even during the flight, if you are not used to fly, do not panic if the plane starts moving like crazy when turbulences arrive. But you should pay attention to the safety demonstration, I would say specially if you haven't taken a flight lately, it is just a couple of minutes and it is important that everyone knows, but again, very unlikely anything happens.

In this case I guess you will have no problem with the language, but if you ever fly to another place again, keep in mind that the planes usually speak the origin and destination languages. BUT, if the crew flying is for example, native from the other place, you may NOT understand sh**, really, they speak very quickly and the sound system of the planes isn't the best, also, some of them may have very thick accents, but you shouldn't really have a problem cause the indications usually are the same always and some of them are accompanied by some icons above your seat.

Exchange at least a little bit of your coin (in this case £) to the destination's local cash (in this case, USD($)) before flying

Again, if you are that kind of modern hypster that likes to wear his phone to the airport's bathroom and take a photo of how you wash your hands without touching the tap because it has a sensor, here is an advice from an IT guy. That thing fails sometimes (and the code we developers do more than sometimes), so you should always have some good old green bills, and not to consume anything on it or to admire washington's face, but to use it in case your phone decides it is a good thing to start restarting every 2 mins after a water drop makes contact with it's screen. A credit/debit card is not very prone to fail but I would again trust more Washington, he was, at the end, a founding father.

Again, as MTA has pointed out, and some small things:

Emergency number: 911

Minimum drinking age: 21 (maybe you get a couple of gins or whatever and your girlfriend friends have 20, and you have paid some extra alcohol you may not want to consume)

If you are planning on driving, Make sure UK's driving licence has value in the USA, USA's DO NOT have value in Spain, and I think neither in the UK, check it is not the case the other way around.

Be careful with some small cultural details. Here in spain, just as an example, we all use very loosely and easily the N word, I wouldn't like to use it like here in the USA. I guess your girlfriend will give you advice on these things, and obviously she will know better than me, but just be a little careful, USA's culture is shockingly different in some little aspects and as the foreigner I think you should try to adapt.

P.S: As someone from Spain, where the average social distance before covid was 'please wash your teeth more often' or 'do not rub that against me again you assh*$^' I have to say that I find MTA's answer interesting!

I've heard a lot of rumours that US border agents are particuarly "brutal".

You will be fine.

In my experience, US border agents will try to trip you up with their questions. That's their job, that's the whole point of them asking these questions. For example, they may ask the same question twice in different forms at different times during the interview, or they may ask you to confirm an earlier answer you gave them but will give you the wrong one ("And you said you are traveling for business, correct?" when you earlier said you are traveling for pleasure).

You will be tired. You will be stressed. You will be nervous. You will make mistakes.

That is okay.

The agents are trained to observe people's reactions. They can tell the difference between you giving a wrong answer because you are nervous, and you being nervous because you are lying. They can tell the difference between you being slow to answer because you are tired and you being slow to answer because you need time to come up with a lie. They expect you to be tired from the flight and be intimidated by them, and they will use this to their advantage to coax the truth out of you, but not to screw you over.

Answer the questions truthfully, precisely, accurately, short and to the point, and politely.