When to Go

Deciding when to go to Key West can be influenced by several different things. Among these things are the weather, the available activities at different times of the year, and the kinds of special events that might be going on. In relation to weather, Key West and the Florida Keys in general, basically enjoy a tropical climate that promises warm temperatures throughout the year. Sure, it gets a little cooler in the winter, but you can still expect temperatures to reach into the 70s and maybe even the 80s. In fact, winter is the peak Key West travel season, as many northerners come down to bask in the warm sunshine.

Things to do in January

If you like a good party, early January is worth considering when trying to decide when to go to Key West. The city throws an excellent New Year’s Eve shindig that includes three different spin-offs of the famous midnight ball drop in New York City’s Times Square. Another noteworthy Key West festival that is held in January is the Key West Literary Seminar. In relation to outdoor activities, you can pretty much enjoy the full gamut in January. That includes fishing, sunbathing, relaxing on the beach, and bicycling. The average high temperature for Key West in January is around 74 degrees Fahrenheit. The average low is just 10 degrees cooler.

Things to do in February

February in Key West offers average high temperatures in the mid-70s and the lowest average amount of rain for any given month. Thanks to the comfortable temperatures and relatively low amount of rain, February can be especially ideal for such pursuits as biking, jogging, or golfing. This is also a great month for walking tours around the Historic Old Town district and for other sightseeing endeavors. Among the more popular Key West events that takes place in February is the Kelly McGillis Classic Flag Football Tournament.

Things to do in March

By March, the average high temperature in Key West rises to around 78 degrees. Couple this with the relatively low amount of average rainfall, and this can be a prime month for all kinds of outdoor activities, such as fishing and boating. No specific events stand out in March, though there’s always something going on in Key West, so you should have little trouble adding some kind of event to your March agenda. As a side note, some consider March to May to the best time to visit Key West. Reasons include the clear skies, the highly agreeable temperatures, and the fact that the winter crowds are tapering off. Reasonable hotel rates are just one more thing to find favor with during this period.

Things to do in April

In addition to taking advantage of great weather and enticing lodging rates, April visitors to Key West can revel in the island’s beaches and perhaps take part in the Conch Republic Independence Celebration. This week-long celebration honors the unofficial secession of Key West from the United States, which was declared in tongue-in-cheek fashion on April 23, 1982. April is at the tail end of the peak Key West travel season, so the crowds should definitely be tapering off. This means you won’t likely have to share the beaches, scuba diving spots, and other attractions with as many people as you would in the prior months.

Things to do in May

Key West is only some 90 miles from Cuba and definitely has a sufficient amount of Cuban-related heritage to celebrate. Hence the Cuban American Heritage Festival, which is held in Key West every May. Another reason to consider May as your month to visit Key West is the prime fishing. In fact, this might just be the best month overall for Key West fishing. It is definitely one of the best times to fish for sailfish. Also, May is widely regarded to be the best time to fish for tarpon in Key West Harbor. Daytime temperatures in May often climb into the mid-80s, so relaxing by a pool or on the beach are other tempting activities.

Things to do in June

As the summer heat and humidity really start to get oppressive throughout the Florida Keys, spending time at the beach or at a swimming pool start figuring among the most popular things to do. May through October is normally the wet season, so months like June can have increased rain showers. The summer showers often come in the morning and are followed by intense sunshine. While the increased heat, humidity, and rain dissuade many people from visiting Key West in the summer, this is the best season to get lodging discounts. Rates do go up in June when the PrideFest Key West Festival is in full swing. This festival for LGBT community is held over the course of several days and features various events, including the Pride Parade.

Things to do in July

One of the best Key West festivals takes place in July. This festival is the Hemingway Days Festival. It honors one of the island’s most famous former residents – the famous writer, Ernest Hemingway. In relation to activities, July might not be the most ideal month for such on land activities as biking and golfing. The heat and humidity tend to be too oppressive for these kinds of endeavors. Instead, July visitors often take to the water. Diving can be especially rewarding in summer months like July, as the water clarity can be great. Overall, this is a great month for hotel deals and a less crowded environment.

Things to do in August

June through August is a fantastic time to go scuba diving and snorkeling in Key West. As noted in the July section, the water clarity can be great during these months. Also worth noting for the month of August in particular is the Key West Lobsterfest. This August event celebrates the lobster season and is without question one of the biggest parties of the summer in Key West. Lobsterfest events include a lobster boil, a pub crawl along famous Duval Street, a free concert and street fair, and a Sunday brunch that leans towards the decadent side.

Things to do in September

September through November is when hurricanes are most probable in the Florida Keys. That’s not to say that these intense storms are extremely common, and as long as you know the weather forecast, you will have a good idea as what to expect overall. September is one of the most affordable times to visit Key West. This might have something to do with the fact it averages the most rainfall of any month. Basically, it is more common that you will be interrupted when trying to golf, fish, or enjoy any other number of outdoor activities. Among the special events that take place in Key West in September is Bike Week.

Things to do in October

Mid-October is when the peak tourism season in Key West begins to start up. This coincides in part with the Goombay Festival and Fantasy Fest. Two of the best Key West festivals, these celebrations feature parades, live entertainment, plenty of food and beverages, and more. The Goombay Festival is family friendly, while Fantasy Fest is a more hedonistic celebration that caters to the adult crowd. The slightly cooling, yet still warm temperatures are just one more reason to consider an October trip to Key West, as they allow for the enjoyment of a wide array of activities.

Things to do in November

In November, the average high temperature for Key West is around 80 degrees and the chance of rain decreases. In fact, from November to April, Key West is normally sunny and quite dry on the whole. In other words, this is a great time to enjoy any number of outdoor activities, including walking tours and kayaking excursions. It helps to explain why November through April is the peak Key West travel season.

Things to do in December

The Holiday Season is a great time to visit Key West. From Thanksgiving to New Year’s Eve, the island city is in full holiday mode and offers a variety of festivities that can add extra depth to a visit. There’s even a holiday parade with floats that features an appearance by Santa Claus. Add in the usually comfortable temperatures and relative lack of rain, and it only becomes more clear that December can make for a fantastic month for Key West vacations. Virtually all possible activities can be enjoyed, so getting bored shouldn’t be an issue.  

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