Although Key West is famous for its party-going crowd, it has taken enormous strides to make the area family-friendly.

Parents and kids alike will have a blast fishing off the shore, snorkeling above the reefs, playing on splash pads, or even visiting Dry Tortugas National Park.

For older and more adventurous kids, parasailing, jet skiing, jeep adventures up the Keys, and Banana Boat rides offer hooting and hollering fun.

There are also many great ways to combine learning and entertainment, such as dolphin-watching tours or visits to the Key West Aquarium or the Turtle Hospital.

You and your kids will love the Mallory Square Sunset Celebrations, complete with jugglers, musicians, magicians, clowns, and psychics.

Did you know that Key West averages 260 sunny days per year? It’s true!

And with winter temperatures rarely falling below 70ºF, there are few better places to spend a fall or winter getaway.

Unlike the sweltering summer months, Key West is much more comfortable during the other seasons.

The water is still warm enough for swimming and snorkeling, and your toes will love digging into the white sand at Smathers Beach.

It’s no wonder one of the top reasons to head to Key West is the deliciously warm South Florida weather.

Doesn’t swapping your winter boots for flip-flops sound like a dream come true?

Although I’ve touched on this already, another great reason to travel to Key West is that you won’t need your passport.

At a time of year when international travel can get more expensive than ever, traveling within the U.S.A.  could be a great choice.

Plus, you won’t have to worry about the hassle of ensuring your passport is up to date, checking whether or not you need a visa, or meticulously combing through your destination’s Covid-19 regulations.

There’s plenty to love in Key West, no matter whether you’re traveling solo, with your significant other, or as a group of friends.

Take selfies at the Southernmost Point Buoy, go on an Old Town Literary Walking Tour, book a Sunset Tiki Boat Tour, go on a Key West Ghosts and Gravestones Tour, and grab dessert at the Better Than Sex Dessert Restaurant.

Don’t forget to eat Key Lime Pie, then go dancing at Rick’s Key West.

Shed your heavy winter gear and let your skin breathe free for a while on Key West’s amazing beaches.

Smathers Beach features two miles of perfect Bahamas sand, while Fort Zachary Taylor offers a place to swim and explore a Civil War fort.

Higgs Beach and Simonton Street Beach are smaller beaches perfect for relaxation and gorgeous ocean vistas.

Sunset strolls on the beach, luscious swims, scuba diving, and snorkeling will be a fun addition to your fall or winter, don’t you think?

Without winter’s bluster to keep everyone holed indoors with nothing to do but watch movie marathons, Duval Street keeps things popping all through the fall and winter.

Rent bicycles and pedal from the Southernmost Point to Mallory Square, stopping in at shops, cafes, restaurants, and museums along the way.

Alternatively, take a trolley tour, wander on foot, and enjoy perusing the island-inspired works of art at various galleries.

Fancy a drink? If so, it’s time for a “Duval Crawl.”

Stop in for drinks and live music at any of the dozens of speakeasies, saloons, and watering holes along Key West’s main drag.

Captain Tony’s and Sloppy Joe’s are two famous stops.

Be sure to visit Hemingway House, the former residence of Ernest Hemingway and his six-toed cat.

If you want to save on prices, September, October, and March through May are quieter times to visit Key West.

The weather can still be hot and humid in September and October, though, so keep that in mind.

November through January is considered peak season, with visitors flocking to the area to enjoy holiday festivities, parades, events, and fabulous weather.

How Is The Weather In Fall And Winter In Key West?

The weather in October and November in Key West ranges between the high seventies and mid-eighties, while December weather is in the seventies.

January is the coldest month, with lows down to 65º and highs of 75º.

What Are The Best Ways To Get To Key West?

One of the easiest ways to get to Key West is to fly into Key West International Airport (EYW) on the island.

From there, you can take an island shuttle to your hotel or lodging. Taxis, Ubers, and car rentals are also available.

You can also travel along the Keys and throughout the city using public buses on the Key West Transit System.

As you can see, this Florida destination is a perfect fall and winter getaway!

For more tropical places to visit to keep summer alive, check out this post!