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Yes, but that would deprive you of spending $1200 for a flight from one Caribbean island to another! What fun is that?!?!?

For some real fun, we have been known to work a full day, then take the night flight from Boston to San Juan that gets in around 3AM. Then sleep briefly in Tradewind's comfy chairs waiting for their 6am flight (often as cheap as $299 at that hour) and then head for a beach at 8am to sleep in the shade to recover. It's a cheaper Jetblue flight because no one sane is taking that flight AND it saves a night of St Barth hotel/villa prices, so overall at least $1000 per person cheaper plus you get the full (but sleepy) first day. It makes a 4 day weekend on the island crazy but do-able.
 
Thanks Happy! I'd definitely do that too if it was available from the DC area. Is it?!?!? You have some amazing travel tips/flight info that you've been dropping in this thread!

But how do you leave after just four days?!?! Seems like cruel and unusual punishment!

Anyhow, welcome to the forum and keep the travel tips coming!!
 
Hi Bart, according to 'google flights' there are no red-eye non-stops from DC, but there are a few one-stops, which doesn't sound so fun. Spirit flies from DCA at 8:40PM to Orlando then on to San Juan, arriving at around 4am in good time for the 6:30am Tradewind. The price of $146 round trip is unbeatable, but the pain level is pretty high as well. Combine that with a $299 one way Tradewind flight and it's almost cheaper than staying home, but you don't want to be so cranky from that overnight flight that you spoil your whole trip.
 
There is an option of a late day flight and a stay at the no-tell-motel inside security at SJU.
 
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