When To Come

The short answer on when to come to Islamorada on a small budget is almost anytime. Almost. The Keys have become a popular year-round destination for sure and there is plenty to do all the time. The weather is almost guaranteed to be warm everyday. Even in the middle of summer with the scorching humidity, people love to come down and enjoy the water-sports. One of my favorite activities is to dive over 100' without the need of a wetsuit. However, for the purpose of this article, I am going narrow it down on the best time to come, when not to come, and a few suggestions on coming at other times.

  • The best and cheapest time to visit Islamorada is November and December (until Christmas, not after). September and October also have great deals and may be considered "offseason," however, I prefer the middle of November through the middle of December primarily because the weather is getting colder in northern parts of the U.S (like where I live in New England). Also, the Keys are starting to cool off from their summer heat and "hurricane" season is pretty much over. Overall, this timeframe is the best because its the lowest prices you will find at any of the hotels, the lowest prices on airfare (even if you have limited flexibility) and car rentals are dirt cheap. But Islamorada remains as awesome as it is all year.
  • It's simple on when not to come to Islamorada on a tight budget: when its busy. Although, locals will say that it's always busy nowadays. But to generalize actual peak season I can simply say from December 26th through the end of March. It's going to be busy plain and simple and price points for hotels, airfare and cars are typically at "peak" rates. That said, I'm not saying deals can't be found during this timeframe and you'll see what I'm talking about below with tips on traveling during this time. But overall, this is peak season, especially middle February through March as school breaks happen during this time. Other times to avoid spending a ton to get down here (outside of the Christmas through March period) are a few major holidays. This includes Memorial Day, Independence Day, Mini Season (last Wednesday and Thursday in July) and Labor Day.
  • As I've mentioned, I visit Islamorada frequently. Sometimes more than once a month. Since I come throughout the year, I have mastered ways to find great deals even during peak season. So here are a few tips on keeping your spending to a minimum.


By now, you probably know that the more flexible you are with your travels the better deals you will find. So if you are traveling for a weekend away and can take off from work a Friday or a Monday (or both), you can find airline tickets at dramatically lower costs. Or if you are taking a week and your job permits you to fly from a mid week day to mid week day, again you can find super cheap airfare all year long.

  • Short Stay or Mid week vacation
    A short stay and/or mid-week vacation means you spend less money. Better prices on airlines, hotels and cars. In addition, its worth coming to Islamorada even if you have only a couple days. I do it quite often and that includes flying from Boston. Let's say you can take two days off from work and have very little money to spend. If you take off a Tuesday/Wednesday, you can fly out Monday after work and come back Wednesday night or early Thursday. Anyone traveling from the east coast such as New England, NYC or D.C. areas have so many airline options that are cheap and are quick non-stop flights. I'm not saying you should take off Tuesday/Wednesday over a Friday/Monday. I get that you could have more time by stretching out your weekend. This is strictly about saving money as well as telling you its still worth it.

Check out our next blog, Locals Guide Part Two: Cheap Islamorada Vacation / Where And How To Fly, to find out more ways to save.

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