Now that it’s officially gotten cold, if not actually snowed, in the northern part of non-Latin America, it’s time to start thinking about a winter sunshine holiday. The sooner you start sorting this out the cheaper you are likely to get your airfare so there’s no time like the present.
When not to go (if you are a cheapskate)
It doesn’t take a great deal of experience to figure out that flights right around Christmas and New Years are the most expensive of the year to sunshine destinations. While most people are staying with or visiting family, many are taking that exact time to fly down to the Caribbean for some nice weather instead.
If you can go before December 15 or after January 8 you’ll be saving a lot of money. Another interesting tip is that if you fly actually ON Christmas Eve or Christmas Day you some sometimes get some cheap fares. Almost everyone prefers to leave at least a few days early and they pay hundreds of dollars extra for those flights. If you don’t mind traveling on the holiday you can get fares as cheap as those going a month earlier.
Cheapest Caribbean destinations
Most flights to the Caribbean originate from south Florida, but since if you are living in south Florida you probably don’t care too much about flying to the Caribbean we’ll gauge our prices for those leaving from the huge New York market. Prices from Boston or Washington DC are a bit more expensive, but the rank of destinations is the same.
The cheapest destination is San Juan, Puerto Rico, with flights from New York starting at $260 round trip. From there you can reach many resorts just outside the city, or take another flight within Puerto Rico to reach some of the more exclusive areas.
Next cheapest is Nassau in the Bahamas with round-trips starting at $290, which is interesting because it’s a much shorter distance. After that you have Kingston, Jamaica at $300 round trip, though most people prefer to fly into Montego Bay, which costs $350 round trip. You can get to St. Thomas in the Virgin Islands for $300 as well.
You can actually fly to Port Au Prince in Haiti for only $320, but this year it’s still too early to even consider that so instead you might go to Santo Domingo in the Dominican Republic with round-trip flights for only $330 from New York City and only a bit more from other cities in the northeast.
If you are looking for something a bit more exclusive and exotic then you only need spend $380 to get to Turks and Caicos or $400 to get to St. Croix. Especially in the latter you are going to end up spending a lot more on a resort once you get there, but at least it’s good to know that the flights themselves are available at a good price if you book soon.