Around the middle of the summer we hadn’t figured out what our plans for Christmas vacation were. Last year we had gone to NYC to visit my wife’s family which had gathered there for the holiday. We were looking to do something else this year.
Looking at the school calendar we had 11 days off for the school break and were trying to fit something in that space. We wanted to include time in NYC to visit family if possible, but it wouldn’t have to be on Christmas Day.
The Possibilities
We first started by looking at taking a cruise somewhere in the Caribbean. We had never done a cruise so we were curious. Not to mention the appeal to being someplace tropical for Christmas. The tricky part is that most cruises leave from Florida. Getting to Florida (or most places) right before Christmas can be stressful and expensive with dollars or miles. Throw in the potential for weather delays and any planned trip could easily fall apart since the cruise ship isn’t going to wait for you if you’re late. Still, it was in the “maybe” column.
We also considered going to San Francisco. I travel there for work and we had spent a few hours exploring the city with the kids during a long layover on a previous trip and the kids were excited to go back. We looked at a few days and it looked promising, though still expensive.
We then pulled up Google Flights and started searching for destinations. It has a great feature where you can put in a departure city and dates and it’ll show a map of the cheapest rates to cities in the US and all over the world. We adjusted the days to go through some different scenarios departing from both Boston and NYC. We looked at Dubai (going to a place that doesn’t celebrate Christmas seemed interesting, and it would definitely be warm). We saw a really cheap fare to Paris which we had visited a few years ago and really enjoyed.
The Choice
There were a lot of good options, but none that really got us super excited. We started doing some initial planning to get a better idea of the costs of each destination.
In the end, as we were researching cruises, we found one that left from NYC so we could avoid flying to southern Florida entirely. It would also allow us some time to spend with family there. While not completely fixed, there are a lot fewer cost variables than with the other options.
With that, we had a decision. It would be a Caribbean Christmas for us!
Tomatico Travels 
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