The Best Time to Visit Key West and Things You Can Do (with Friends and Family)

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Looking for an island paradise with a unique culture, history, restaurants, bars, and amazing natural beauty? Key West, Florida is the destination for you. But what is the best time to visit Key West, Florida, the southernmost city in the continual continental United States just 95 miles north of Cuba? This guide is the end all be all for your worries.

With tons of activities and events to partake in each Winter, Spring, Summer, and Fall along with a wonderful Caribbean climate, Key West never disappoints. The city’s motto is, “One Human Family,” which makes any time of the year is the best time to visit Key West, Florida.

Weather in Key West and the Best Times to Visit

Winter in Key West (December-February)

The Winter season is one of the best times of year to visit Key West, Florida. With temperatures averaging in the mid-70s, it is the perfect time of year to take in the many sites and treasures of Key West, Florida.

With the weather being much milder, the Winter season is a great time to visit Key West’s many boutique shops, museums, and restaurants. This season in Key West also sees the least amount of rain out of the entire year. This makes this time of the year the best time to visit Key West’s many dry outdoor activities.

Spring in Key West (March-May)

With average temperatures ranging from the mid-70s to mid-80s, many find springtime to be the best time to visit Key West, Florida. Spring in Key West is an amazing time to check out the waters of the Keys and participate in a multitude of water-related activities.

Be sure to check out endless opportunities for fun in the water such as parasailing, snorkeling, jet-skiing, glass-bottom boat sailing, and dolphin tours through Fury Water Adventures Key West.

Outside of water-related activities, Key West offers a plethora of dry activities perfect for your springtime visit to Key West, Florida.

Summer in Key West (June-August)

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Summer in Key West is when the weather gets hot, hot, hot! With average highs in the upper 80s, Summer is the best time to visit Key West, Florida for those ready to get their tan on.

August in Key West also experiences some of the most precipitation in the year, averaging out at 5 inches of rain per month, so be sure to be checking those weather apps!

Be sure to check out Key West’s world-famous beaches during your summertime trip! Some of the top beaches to check out include Smathers, Higgs, and South beaches (the latter being well known for families with small children).

Besides for beaches, the best time to visit Key West is summer for all the events that happen throughout the season.

Fall in Key West (September-November)

With temperatures averaging in the mid to low 80s, the fall season is arguably the best time to visit Key West, Florida. Though the fall season does see the highest amount of rain for the year, a whopping 7 inches in average per September, the calm and tranquillity of fall in Key West, Florida cannot be beaten.

Though autumn is known for its hurricanes in the Gulf of Mexico, it is still a great time to embrace the natural beauty of marine life in Key West, Florida. Key West is home to the third largest coral barrier reef in the world, so diverse marine life is abundant here!

During your visit to Key West, be on the lookout for unique marine ecology and species like parrotfish, barracuda, and loggerhead sea turtles. Check out cruises like the Yankee Freedom III for snorkel tours.

The fall season in Key West also offers a plethora of events and festivals to peruse:

Things to Do in Key West: Places to Visit and Events to Attend 

There are several amazing places that you can visit in Key West if you don’t feel like attending any events or if events are not just something you enjoy doing. Some of the nice places you can visit on the island include:

Places to Visit in Key West

Mallory Square

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Known as the place, “Where the Sun Sets and the fun Begins,” Mallory Square is the perfect spot for all things entertainment, food, drinks, and fun! Let your night begin by checking out the Key West Sunset Celebration.

Held every night throughout the year, the Sunset Celebration held right off of Mallory Square is the perfect way to embrace the natural beauty of Key West as the sun sets over a pink and orange glowing Gulf of Mexico. The Celebration is a great fusion of locals and visitors with vendors such as magicians, jugglers, psychics, musicians, artists, and food vendors lining the street.

Harry S. Truman Little White House

If a flair for American history is what you crave during your visit to Key West, Florida, be sure to check out the Harry S. Truman Little White House. This incredible building served as President Truman’s winter retreat after originally serving as the Key West Naval Station.

Outside of Truman, the building has hosted multiple presidents, a king, and now serves as Florida’s only presidential museum.

Endless Delicious Restaurant Culture

Key West is known to many restaurant connoisseurs as a haven for tastes and flavors of the deep South. The Winter Season is the best time to visit Key West, Florida to check out everything these restaurants have to offer.

Be sure to check out spots like Two Friends Patio Restaurant for mouth-watering conch fritters, Bagatelle for delicious sesame-crusted seared tuna, and Alonzo’s Oyster Bar for a casual yet sophisticated array of oyster delicacies.

Dry Tortugas National Park

This national park is located approximately 70 miles west of Key West, this remote and picturesque national park can only be accessed by boat or seaplane and is the perfect way to spend your day in Key West.

The 100 square mile park comprising seven small islands hosts an abundant array of coral and marine life as well as several rare bird species.

Once a major spot for trade vessels in the Gulf of Mexico, the Park served as the site of Fort Jefferson, the largest all-masonry fort in the United States. Be sure to check out opportunities to camp, scuba dive, and cruise throughout the islands!

The Continental Southernmost Point

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If events aren’t your cup of tea, then another site that is perfect to visit Key West, Florida especially during summer is the Southernmost point on the continental United States.

Located at 24 degrees 33 minutes north latitude and 81 degrees 44 minutes, the point is famed as the Southernmost point on the continental U.S. Though some may beg to differ, the site is still one to behold and is a great stop during your trip to Key West, Florida.

Ernest Hemingway Home and Museum

Located in the heart of Old Town Key West, the Ernest Hemingway Home and Museum is an amazing spot to check out during your trip to Key West, Florida.

This beautiful estate, once home to the famed American author, Ernest Hemingway now serves as a museum for patrons to visit the world of this fantastic author.

Events to Attend and Things to Do in Key West 

Some of the amazing events that are organized at different times in the year include:

Key West Hometown Holiday Parade

The Key West Hometown Holiday Parade alone marks the Winter Season as the best time to visit Key West, Florida. Every December, The Parade marks the beginning of the holiday season in Key West.

Enjoy watching various community members, floats, churchgoers, musicians, and colorful characters prance down the streets of Key West harolding in the Christmas season.

During the Fall Season, some of the best events, activities and places to check out in Key West include:

Key West Bike Tours

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What better way to explore Key West, Florida than by traveling the local way: by bike! Key Lime Bike Tours is the best way to check out the sights and sounds of springtime in Key West.

With personalized tours from personable guides, Key Lime Bike Tours ensures a wonderful explorative experience for you. Travel down fruit laced streets and discover the true soul of Key West, Florida.

Tune in to the Sounds of Key West

Spring in Key West, Florida is also the perfect time to check out the live music scene of the islands. Hop from bar to jazz club in the Old Town for samples of the unique music and art offered from this special place.

Check out spots like Hog’s Breath Saloon, Margaritaville, Sloppy Joe’s, and more for nights of music and fun!

The summer season in Key West has some of the best activities. Some of these activities include:

Key West Lobsterfest

Occurring every August is one of Key West’s prized annual events, Key West Lobsterfest! Each summer, Key West, Florida rings in the beginning of the lobster season with a long weekend of parties, boils, live music, and lobsters galore.

Be sure to check out events like Lobster Boil on the Roof at the Waterfront Brewery, Lobster Duval Pub Crawl, and the free Street Fair and Concert happening right in Key West’s Old Town.

Key Lime Festival

Known as America’s favorite citrus celebration, the Key West Key Lime Festival is the perfect activity for your visit to Key, West Florida during the summer.

Key West is the birthplace of key lime pie, so what better way to celebrate this tasty treat than by partaking in all the eccentrics and citrus the Key Lime Festival has to offer.

Held every July right in Old Town, Key West, this festival is a wonderful way to celebrate the flavors that make Key West, Florida so unique. Be sure to check out fan favorite events such as Key Lime Cocktail Sip and Stroll and the Key Lime Pie Hop!

Key West Pride

Every June, visitors and residents of Key West come together to celebrate Pride. With free play readings, pool parties, talent shows, and of course a parade, the Key West Pride is a great way to partake in the Key West community.

With the, “One Human Family,” philosophy which Key West prides itself on, the Key West Pride is an amazing way to embrace the unique openness this old Southern town has to offer.

Key West Musicians Festival

Held at the Smokin’ Tuna Saloon, the Key West Musicians Festival is a free festival for visitors and residents to come and enjoy local Key West musicians and artists.

With music covering the streets of Key West throughout the year, the Key West Musicians Festival is an amazing way to congregate and celebrate local musicians and songwriters. With acts like Tony Baltimore, Liz O’Connor, Alfonse, and the Marshall Morlock Band, the Key West Musicians Festival is a can’t miss.

Fantasy Fest

Beginning in 1979, the annual Key West Fantasy Fest is a 10 day adult party extravaganza. Filled with creativity, libations, parades, costuming, and excitement, Fantasy Fest is an absolute playland.

The event, held every October before Halloween, is an amazing way to embrace Key West’s unique and lively culture. Each year hosts its own theme too, so be on the lookout for fun costumes to invent for themes as creative as, “A-Conch-Alypse,” and, “Habitat for Insanity.”

Spooky Season

Key West in autumn is known for its historically spooky vibes. The 19 acre Key West Cemetery is home to over 1,000 gravestones known for their unique structures.

Be sure to book a seat on the Ghost and Gravestones Tour of various Key West cemeteries such as the African Slave Cemetery were 15 souls perished on their journey up North.

Ride the Trolley of Doom, visit Captain Tony’s Saloon, and learn about the deadly Hurricane of 1846, and more during your trip to Key West in the spooky autumnal season.

No matter when you decide to plan your trip, each season is the best time of year to visit Key West, Florida. With a multitude of fun and unique events as well as natural beauty, tasty restaurant culture, and amazing historic sites, Key West is the perfect vacation destination.

Have you been to Key West, Florida and feel you know the best time to visit? Leave a comment down below! We’d love to hear experienced opinions.

Where to Stay in Key West

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There are several options for accommodation available for people visiting Key West for either vacation, business or family trips. The biggest determinant of the kind of place where you will like to stay is most times affordability or how much you are willing to pay for it.

You will find various types of hotels available from motel rooms, bed and breakfast guest houses, standard inns to 3 – 4 stars rated hotels. Resort-style beachfront hotels and luxury beach apartment rentals are also available.

However, you can also find affordable homes on Air BnB, VRBO or on other platforms that provide temporary home rental or booking services. Another option that may cost you far less is to use your RV camper if you have one, or you can easily rent it for your trip. It may save you some money especially if you are planning for a long stay (but don’t forget to do your research before making that decision).

Key West is a great holiday or vacation destination if you are looking for a nice place to visit with weather that is almost tropical. However, taking the time to plan and figure out the best time for you to visit can make all the difference in your experience when you finally make the trip.