Cheap flights to the Caribbean make it a perfect destination for May
One of the interesting patterns in travel is that popular destinations often have their high seasons based on the weather people are escaping, rather than weather in the destination itself. For this reason, most tropical destinations are at the most crowded during December and January, even though they have perfect weather all the way through June.
Destination: Caribbean
No one can blame you for wanting to get out of the snowy northeast during December or January, but chances are your flight is going to be expensive and the hotel you’ll be staying in will have doubled its prices compared to a few months before.
However, if you really want to get the most value for your vacation, you should think about going to the Caribbean in May, and you’ll be able to likely stay for 11 or 12 days for the same price you’d pay for just 6 or 7 if you go when everyone else goes.
The Bahamas
Let’s use the Bahamas as an example, since it’s known as the cheapest Caribbean-area island to reach and among the cheapest once you arrive. Currently you can get flights from New York City to Nassau for just over $300 in late April and May, which is at least $100 cheaper than in January, even if you buy well in advance. Better still, resorts that were charging $100 per night for a room in January will usually be charging around $60 per night in May.
Even from Los Angeles, where few people go to the Bahamas, you can get a round-trip flight to Nassau for $394 on most dates, with one quick plane-change in Ft. Lauderdale. Sure, it takes longer to reach than it does to reach Mexico, but it’s actually just about as cheap as getting to Mexico, and you’ll have zero worries of violence or unrest like some people do to many cities in Mexico as well. Not only that, the Bahamas is a very “exotic” destination for people from the West Coast, so the novelty value alone should be worth something compared to the herds who go to Mexico every year.
Dominican Republic
Even though it shares Hispaniola Island with the troubled country of Haiti, the Dominican Republic is safe and prospering, plus it’s known as the cheapest country in the Caribbean for tourists. From New York City you can fly there in May for $362 on almost any date, which is slightly more than to the Bahamas, but the money you’ll save once you arrive should easily make up for it as long as you are staying more than two days.
From Los Angeles you can reach Santo Domingo, which is the capital and main airport in the DR, as it’s usually called, for only $442 on almost any dates you choose. Again, this is a bit more than for the Bahamas, but the resorts and cultural experiences are very cheap once you arrive. With the main language being Spanish, most people from Southern California should feel right at home, although English is also widely spoken in tourist areas.