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Sailing with my oldest son on a 7 night Freedom out of San Juan on September 29th. Wife and I are doing Alaska this month and the same Freedom sailing in December so we are trying to keep cost down. Flying non stop both ways would have been $500 each. We are flying in the day before the cruise, but staying a day after is not an option for my son. We got a great deal on the return flight ($118 each on SouthWest) and have two options for our outbound. What would you do?

Both are AA flights since SW was too high and we will not fly Spirit.

#1 Depart DFW at 6:30am with a stop and plane change in Miami having us in SJ at 2:30pm.

Pros: Give us time to explore SJ. There would be no cost using 12.5k AA miles each.

Cons: Plane change with risk of missing connecting flight or luggage not making the switch. Possibility that Miami could have closures or delays because of hurricane season.

#2 Depart DFW at 12:30pm and fly nonstop to SJ and arrive at 6:30pm.

Pros: Non-stop and don't have to get up at 4am. Much better odds that luggage will make it. 

Cons: Use 27.5k AA miles for one ticket and $250 for the other. Little or no time to explore SJ after checking into hotel.

Our flight home does not leave until 4:30pm so we could possibly explore town before leaving if we can find a place to secure luggage. I was leaning towards the non-stop since we got a great deal on the cruise and hotel. $313 each for a balcony cabin and $85 at the Embassy Suites. I have left the decision up to my son but interested in your thoughts.

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What time does the ship depart the following day?  Could you explore a bit prior to embarkation?

I would likely do the non-stop as well.  Too many "what-ifs" with the other option, especially during hurricane season.  But my opinion is also biased because I always choose non-stop unless there is no other option.

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NON STOP  Too many issues crop up now a days.   D.F.W.   has been a thorn in our side for years.   Then again so are some of the others as well. When we went to Barcelona 2 years a go we were on United and we were supposed to fly from Knoxville to Chicago to Frankfurt to Barcelona.  Chicago was closed due to weather so we were routed thru Atlanta on Delta to Barcelona.   Only problem was we lost our business class seats on the long flight and we were in separate rows.  Got to Barcelona fine and got reimbursed for the business seats.  The main thing was we got to Barcelona a day early and earlier than the original flights.  That was actually a godsend as I had a crown come off on the flight over seas  and I was able to get it re cemented on the  day that we got in to Barcelona at 11 a.m. and not 3:30 p.m.  

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our last cruise, (November) we left out of SJ and the area still was in bad shape from the hurricane.   There was not really anything to see.  Now, our cruise was the 3rd one after SJ reopened to cruises. Our next cruise will stop in SJ and there are not a lot of excursion choices.   The airport was still in pretty bad shape at that time.  Not enough seats for people and the AC did not work well.   Also, when you are going home, plan on it taking longer to get through security.  Your luggage goes through a scan before getting into the airport, looking for agriculture items. (make sure you do that first because otherwise, they will send you back out at the desk, slowing getting through regular TSA.  The waiting for that line is outside.  TSA pre does not apply 

Make sure you confirm the day of travel that the hotel has your reservation.  We had people at our table who came in the day before the cruise (came from Europe) and the hotel had no record of their reservation, even with their reservation number.   They were able to find a room at another hotel, but it was stressful.

Non stop flight gets the vote here.

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