I avoid red eyes like the plague but scheduling forces me to do one soon. I need to attend late afternoon functions in Boston the day of arrival. My options are:

-- Non-stop in UA domestic first to Boston, check in to hotel on arrival guaranteed, sleep for 3 hours or so and get out of the hotel around lunch time.

-- Flat bed flight to JFK, stop in the new Delta JFK lounge for a shower and breakfast before heading on to Boston on Delta in first, arriving a little after noon. (I'll be using my Platinum Amex to get into the lounge, and it appears I would have access to all the facilities there.)

I'm leaning toward the flat bed with connection because otherwise I won't get much real sleep en route at all, but even if all goes well I won't be able to sleep more than 4 1/2 hours or so on the plane.

Any advice?

I'd go for the latter. Four hours sleep on the plane is better than none, and what if your first option is late? Then you'd be a mess!

The latter for sure.

Of the two I'd take the non-stop but personally I'd try to get an earlier flight if possible so I could get some more sleep at the hotel once there.

ouch

if you fly to JFK you could also train/car to boston, looks like acela first class seating is only 1-2

ex-SFO >
UA 444 to BOS leaves at 4:42pm
UA 806 to ORD leaves at 7:19pm but max sleep (at hotel) is probably not much longer

Can you sleep in the first class UA seat?

When I take red eyes, even the brutal ones from the west coast to DFW or ORD, I can sleep just fine in the first seats. If you're like me, I'd opt for the nonstop with the guaranteed hotel room and a real bed at the end. Even delta flat bed is still on a plane and 4.5 hours isn't enough sleep no matter how comfy the bed is.

It depends if it is a business or leisure trip. Also how valuable is time vs. comfort for you?

If you are on a leisure trip and value comfort, then definitely the second option. You may be on a leisure trip, but value time, then the first option.

If you are traveling on business and have time to relax, then second option, so you can get a good sleep on lie flat seats and take a shower at the DL lounge at JFK and take your time in connecting to Boston.

If you are on business, but have a pile of work to do on the date of arrival before the event later in the afternoon, take the non-stop flight to save time.

Paid first should get you Delta lounge access. Although you should check whether your Boston flight is mainline or connection since a connection will have you leaving out of the connection gates in Terminal 2 which is further from the brand spanking new lounge. If it's on the client's dime why don't you fly in on the late afternoon flight out of SFO which means a latish night in Boston but a full day's rest before your functions.

I'd take the non-stop.

I'd do non-stop here. Take a nap in the hotel if needed and you will feel great. Extra connections and lounge showers only add stress to your life.

That being said, I'd sleep like a baby on a domestic first red-eye. I end up flying overnight in coach so often that even domestic first would be wonderful.

If you had asked which was the more thrilling route to take, I'd choose the bed to JFK just for the experience and the chance at exploring the lounge.

However, if the only criteria is getting some sleep before a business meeting, I'd go for the nonstop. You reduce the stress of a connection and get to the hotel faster to have a last chance to settle in and take a quality nap. On this short a flight, a lie flat bed is not going to do much to enhance the sleep you get. I haven't had any trouble sleeping on UA redeye flights. Bring some eye shades and ,most importantly, noise cancelling earphones.

I'd say the nonstop. The flight is too short for the lie flat to make enough difference in sleep to outweigh the stress of going through JFK and flying on to Boston.

Agree.

That lounge isn't worth a stop in my opinion - go with the non-stop.