IMHO

Great question, Cass . . . and opportunity to clarify.

Yes, there is "immigration/customs" between Tradewind arrival at SJU and one's departure gate. However, at the risk of evoking elitism in describing it, this process has been -- in my experience -- limited to the 8 or so (at most) passengers on my Tradewind flight, without any other competing in-transit passengers. Explaining, in part, the premium cost of Tradewind service. I don't know the in's-&-out's of the system, but that's the way it is.

Then, as one leaves "immigration," a Tradewind representative is present to escort each passenger to his / her airline check-in counter (or, if not needed, to the appropriate TSA check-in line). The Tradewind rep, thus, has never taken me to my ultimate departure gate, but has facilitated my transit to the farthest point that Tradewind can do so (barring, perhaps, the situation where a passenger needs wheelchair or other extra assistance).

just arrived at SJU from SBH and it is exactly as it has been in the past and exactly as you described. We have a few hours until our Jet Blue flight and went thru the entire customs/immigration area and were in the Tradewind lounge within 10 minutes of getting off the plane.

was funny to see two of the passengers stressing out over where their global entry line was (go right with global entry and left without) when it couldn’t have saved them more time than they lost looking for it. Plus if you go to global entry and have bags I think you have to go left and grab the bags first and then go back the other way?
 
So, coming down, we think carry-on only is prudent, as we arrive SJU late, after TA agents gone for the evening, then spend the nite at the airport hotel, then catch a 09h55 TA flight to SBH.
Coming back, will checked bags be a nuisance thru the customs/immigration/check-in process, or will TA agents smooth the way ?
So keep in mind our experience was much different than Eve’s as we went right into the little Tradewind only customs/security area. For us as we walked to the customs/immigration agent our bags (along with those of only the 7 people on our flight) were already waiting for us on the 2 minute walk from the entrance to customs/immigration. It only took an extra 5 seconds to lift the bag off the belt. So no issue at all. Hopefully it was just a short term issue at the airport due to staffing or construction or something else that Eve had to unfortunately deal with as it appears to be back to normal.
 
This past May, I entered everything at the Global Entry kiosk, but went in the wrong line (both were devoid of passengers) and got asked about everything I was declaring, etc.... When I handed them my Global Entry slip, they got rather annoyed. A bit stressful as I was over the allowed wine/rhum allowance. All of it was declared, but didn't need them poking around, just because. Not making that mistake again.
 
Jim A - based on your experience returning through SJU, what is the minimum amount of time you would be comfortable with between scheduled arrival on Tradewind to departure on American? We'll probably have carry-on only, we are both Global Entry, and I'm top tier status on AA and flying Business class. I'm trying to choose between two TW flights that are 3 hours apart, and I sure do like to max out the time on the island vs sitting in SJU.
 
Sorry, but I’m usually pretty conservative with flight times and don’t know the entire airport that well so not the best source. I can tell you that we could have been off the plane, through immigration, checked our bags and got boarding passes for our jet blue flight (did all this right away) and probably made it through JetBlue security and to the gate (we didn’t do this yet because we are waiting in the TW lounge) all within 30 minutes or so. But as an example of what could go wrong there is Eve’s post above and also the JetBlue security line for some reason closed for about 30 minutes or a while after we got here (just reopened). Also, I don’t know how far to the AA terminal or what the lines are like there. I know when we arrived on Delta one time it seemed a much longer walk than JB. For me I had a similar decision and went with the later flight (a little over 3 hour layover) just in case there was a delay somewhere. But again I’m pretty risk averse when it comes to flight schedules.

perhaps there is a premium IV type service that could get you through quickly
 
My recollection is that the small Immigration and Customs area used by Tradewind is also used by JetBlue.
 
So, coming down, we think carry-on only is prudent, as we arrive SJU late, after TA agents gone for the evening, then spend the nite at the airport hotel, then catch a 09h55 TA flight to SBH.
Coming back, will checked bags be a nuisance thru the customs/immigration/check-in process, or will TA agents smooth the way ?

Reminder...if you are staying at airport hotel you get a discount if you are flying Tradewind...just give them your flight information.
We are staying there tomorrow night.
 
This will be the first two-day trip down for us in 34 years. First time an unavoidable overnight in Saint-Martin.

One-day itineraries these days subject us to ungodly early wake-ups, narrow connections, and stressful late afternoon arrivals at SBH.

We have found that 3 am wake-up calls, to quote Mr. Bridger, upset our natural rythm (for a few days). So, we’re trying a noon departure, late night SJU arrival, sleepover at airport hotel, 10h00 departure, and 11h00 arrival on SBH, in time to dump baggage at villa while le ménage is being done, enjoy a nice déjeuner, nous approvisionner au marché, then nous installer à la villa.
 
This will be the first two-day trip down for us in 34 years. First time an unavoidable overnight in Saint-Martin.

One-day itineraries these days subject us to ungodly early wake-ups, narrow connections, and stressful late afternoon arrivals at SBH.

We have found that 3 am wake-up calls, to quote Mr. Bridger, upset our natural rythm (for a few days). So, we’re trying a noon departure, late night SJU arrival, sleepover at airport hotel, 10h00 departure, and 11h00 arrival on SBH, in time to dump baggage at villa while le ménage is being done, enjoy a nice déjeuner, nous approvisionner au marché, then nous installer à la villa.

One tip, Cass . . . be sure to insist at the SJU hotel that you get a renovated room. Generally, they’re upper floor rooms. The principal difference is that rooms that aren’t renovated have the dregs of beds — horrible,
 
Sorry, but I’m usually pretty conservative with flight times and don’t know the entire airport that well so not the best source. I can tell you that we could have been off the plane, through immigration, checked our bags and got boarding passes for our jet blue flight (did all this right away) and probably made it through JetBlue security and to the gate (we didn’t do this yet because we are waiting in the TW lounge) all within 30 minutes or so. But as an example of what could go wrong there is Eve’s post above and also the JetBlue security line for some reason closed for about 30 minutes or a while after we got here (just reopened). Also, I don’t know how far to the AA terminal or what the lines are like there. I know when we arrived on Delta one time it seemed a much longer walk than JB. For me I had a similar decision and went with the later flight (a little over 3 hour layover) just in case there was a delay somewhere. But again I’m pretty risk averse when it comes to flight schedules.

perhaps there is a premium IV type service that could get you through quickly

3 hrs
 
Pre-COVID, I looked for a 2-hour minimum connect time when transiting home through SJU. I wouldn't plan on any less today.

I often overnighted in SJU on both my arrival and return trips. It's an extra day in the islands, and when it was open pre-Irma, the Ritz Carlton's BLT Steak restaurant was a good spot for popovers. (Yes, I overnighted in SJU for popovers.)
 
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