Round two.
As I needed to be in Baltimore Monday night and back for Shabbos, I decided to take my first vacation with our 2 month old. We wanted to go somewhere short and direct. As I've been to Florida many times I wanted something more exotic. I checked Southwest website and found direct flights from BWI to SJU.
The cost of the ticket was about 14,000 Southwest miles per a person and since PR is part of the US, a lap child is free. Also, Southwest allows you 2 free suitcases, but we only ended up taking one each.
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As far as the hotel was concerned, I looked around and it seemed that most people stay the Ritz. The Ritz is right near the airport and Chabad. Since we were travelling with our baby, I wanted to stay some where real nice. As we weren't really going to leave the hotel that much. So even though the Ritz was a better location and was only $200 a night plus taxes, I still wanted to stay at the St Regis as the grounds were a lot nice, it would be more relaxing and a lot better chance of getting upgraded. I don't remember the exact cost, but with the AAA rate, double take promo, 500 points booking with SPG app and all the SPG points I would be earning during my stay (including valet parking and $60 resort fee) the total price came out to around $350 a night which is a bargain compared to the 30k they charge a night not including parking and resort fee. Trust me, it was worth every penny. I'm sure there a lot nicer hotel out there, but for only traveling 4 hours away, I don't think you can beat it (CMIAAW). I will try to give more detail about the hotel later.
We had a 8:00am flight, departing from BWI, so we decided to stay at the Aloft near BWI for 2,000 Starwood points plus $40. I decided since I wouldn't have to pay for parking and I would get stay credit etc. it was worth it. We didn't end up checking into the hotel till 1am and needed to get up at 5am, to daven etc. Since it was our first time flying with our daughter, I wanted to be at the airport extra early. The airport shuttle comes around the hotel every minutes and I believe we ended up leaving the hotel 6am with the hotel shuttle.
The night before I freaked out, as I thought we left our daughters birth certificate at home, till my wife realized it was buried in her wallet. I called up Southwest and they told me all I need is some type of document with her birth day and I will be fine. I ended up giving them the copy of her birth certificate (which they asked for), but not sure if I needed it. On the way back, I gave them her insurance card with her birthday on it, which they told me they need the birth certificate. So I'm not completely sure (CMIAAW), but when going to PR I would suggest taking your kids birth certificate.
Check in and security went as smooth as possible, as the UBV is breeze to take apart and put through the X-ray machine. With plenty of time to kill we sat around by the gate, as the lounge is in a different terminal, we has no patience to start schlepping around. We bought some Bagels from Goldbergs New York Bagel shop the day before (my favorite bagel store), which were amazing (as usual).
Southwest doesn't work like most airlines, where each person is assigned a seat. They divide everyone into 3 groups "A", "B", and "C". You are able to check-in online 24 hours before your flight and they start putting you in group "A" and once "A" is full then "B" etc. So Even though we were in group "C", meaning the last group that boards. Since we have a child under the age of 4 we got to board right after group "A". Since it was a full flight they made us gate check our car seat, which we brought up till the plane. Surprising, the first 2 seats (bulkhead) were empty, which the extra leg room helped having a lap child. All in all the flight was a lot better than I and my wife thought it would be. Our daughter only cried for a minute or two during the whole flight (that's what happen when you hold her the whole time).
To be continued...