I'll be visiting New York City for what is basically the first time. I'll be staying in mid-town around Times Square just for the experience.

My meetings are around 1 Wall Street, and also on Long Island.

My questions are:

1. Which airport should I try to fly into? I have all three as options so could do any of them. I'll be getting in around 10:30 a.m. on a Tuesday and leaving around 5:00 on a Thursday.

2. Based on #1, how should I get from the airport to the hotel? Taxi? Car service? Train? I'll have a little luggage though not a ton.

3. How should I get from midtown to Long Island? Again, car, taxi, train?

4. This one probably sounds the worst but: will I have any problem getting a cab from my hotel in midtown to my meetings which are downtown? (I think at least??? Don't have all the terms down yet).

5. Finally, assuming that I'm leaving from downtown and my flight is around 5:00 what time do I need to leave to get to the airport?

Sorry for the ignorance...NY seems very confusing to me.

I would answer your question differently depending on where you need to go on Long Island (i.e. proximity to LIRR)

Suggestion#1: Fly in/out of LGA, take cab to mid-town/meetings. If Long Island meetings occur outside of Queens, would rent a car from midtown and drive. A convenient car rental would allow you to drop off at LGA on departure, so you might consider renting on arrival to LGA or ask about a midtown rental and LGA return option, though I suspect it will cost more than using a cab to midtown.

fly to LGA...cab to your hotel and back.
You shouldn't have any trouble cabbing downtown, but check w/ your hotel first. I stayed at the Michealangelo in midtown a couple of weeks ago and they had a free "limo" service running to Wall Street on weekdays.

Long Island is (110+ miles) and there is little public transport. So how to get there depends very much on exactly where you're going. Provide more info and I'm sure someone will advise.

As this is your first trip to NY, fly into LGA (it is the quickest and most convenient airport) and take a cab to your hotel. It will cost about $30, maybe more, maybe less, with tip. There are cab lines just outside the doors leaving the baggage areas. If you want to save money, look for the shuttle bus to Penn Station/Grand Central ($15), then get a taxi from there to your hotel ($8?).

There are trains to Long Island (LIRR) which are very reasonably priced, but you will need to find the one that gets you where you need to go. If you're in a better hotel, they might help you with this, if not then you'll have to go to Grand Central to catch the LIRR. You'll need to give Fodors more info on this Long Island leg -- what time is your meeting, where is it (city and address). If it's convenient to the train stop, that's good. This will be the most hassle-free way to go.

Your hotel can call a cab for you that will arrive at about the time you want to leave (fingers-crossed) -- but there is no telling how long it will take you to get to Wall Street what with NY traffic. If they use the westside roads then it should be a breeze, but you never know. You might want to use the subway -- it is the quickest and most reliable way to get around Manhattan. Everybody from the mayor to celebrities hop the subway to get across town. There are stops at Times Square, and there are many subway stops in lower Manhattan, one will invariably be in the vicinity where you need to go on Wall Street -- your hotel could tell you exactly what to do. It will cost $1.50 each way for a token (is that right?) and there are booths to dispense tickets and give you change, not to worry about correct change.

If your flight leaves at 5P, then you should be at the airport by 4P -- unless it is a major holiday the next day in which case you should allow yourself an extra half-hour to deal with many people leaving the city, and the security (which tends to be quick and painless at LGA, IMHO). Traffic is awful even at 4P and you should allow yourself a half-hour so leave by 3:30. Be sure to grab the NY Times before you leave because they often sell out at LaGuardia. You surely don't want to get onto your plane w/o the NYTimes!!!

More info about the Long Island leg is needed.

I travel to NYC to work frequently. My work also takes me to Wall Street!
Anyway, I prefer staying at the Regent Wall Street but occasionally I have my daughter with me and she wants to stay in Midtown.
I have found it easier just to take the subway in the mornings. I have little tolerance for the heavy traffic and it just seems such a waste of money.
In fact, the subway system is so efficient in NYC I rarely take cabs anymore. The only exception is when the traffic is not so bad and there is more than one person. I guess I weigh the costs. 3 people = 6.00... can I cab it for close to the same price?

Subways cost $2/trip (and have been at this price for sometime now). There are no tokens any longer (as 12/31/03). You can buy a Metrocard for the number of trips you expect to take during your time in NYC. There is a special 1-day Metrocard at price of $7 (I believe).

Best airport to arrive at is LGA, taxi into midtown Manhattan would be about $25 w/toll (if any) and tip, though can be as high as $30 depending on time of day and traffic.

For transport to Long Island, the railroad leaves from Penn Station at 7th Ave. & 33rd St., but we have no idea where in Long Island you are going. And once you get off the train, how far your destination is from the station, you may have to take a local taxi.

Getting downtown from your hotel shouldn't be a problem either by taxi, subway or car service.

Keep the following numbers available for car services:

Tel Aviv 212-777-7777
Carmel 212-666-6666

both have websites, have rates to/from Manhattan/Airports and hourly rates for travel around the city.

I travel to NY City frequently for business and I was very intimidated in the beginning. But, the city is great and hopefully, you will enjoy whatever free time that you have. I like staying in the Times Square area because it's fun to walk around if you have some free time. It's easy to get a cab for any trip and your hotel can help you. As far as the drive to Long Island, you need more info....what city and can you get the train to that destination. I would consider returning to LaGuardia and getting a rental car out of there rather from in the city, especially without experience driving in the city

Fly into LGA. A taxi to midtown will cost about $25 tip and toll included.
Long Island RR to get to the island. You get the LIRR at Penn Station, 32nd and 7th Ave. - not Grand Central. You don't need a rental car in NYC. Parking for 24 hours will cost in excess of $30 a day. Either taxi or subway to Wall St. Subway could be faster than the taxi considering downtown traffic.