Best Times of the Year to Visit Key West

Mallory Square on a sunny day
Truth be told, with its year-round sunshine, crystal blue seas, eclectic array of land and water attractions and the world-famous sunset celebration, anytime is the best time to visit the Southernmost city. But, if you’re looking for a certain kind of vacation, whether it’s fishing, water sports, pub crawls, museums and history, this guide will help you plan out your trip during the ideal season to make the most of every moment. Take a look:

Winter – December through February

Museums, shopping, bar-hopping, land attractions

visitors at touch tank in key west aquarium
While the word “winter” doesn’t really apply in Key West (the average high is in the mid-70s), when it’s cold everywhere else, it’s a perfect time to grab your flip-flops and head south. The months of December through February are a great time to explore all of the island’s historic treasures, shops, famous watering holes and restaurants. Because it’s cooler out, roaming on Duval Street (the main drag in Old Town) and visiting popular spots is easy because the weather is so mild. And, the holidays are magical in Key West! There are special events going on and if you stick around for New Year’s Eve, you can be a part of the famous dropping of the conch shell at midnight at Sloppy Joe’s. For those who enjoy history and museums, land attractions, live music and entertainment, here are the top events, things to do and places to visit during winter:

  • Mallory Square (sunset celebration, shopping, dining)
  • Key West Aquarium
  • Key West Butterfly and Nature Conservatory
  • Harry S. Truman Little White House
  • Ernest Hemingway Home and Museum
  • Key West Shipwreck Treasure Museum
  • Mel Fisher Maritime Museum
  • Audubon House and Tropical Gardens
  • Key West Lighthouse and Keeper’s Quarters Museum
  • Martello Gallery Key West Art and Historical Museum
  • Custom House
  • Florida Keys Eco Discovery Center
  • Pub Crawl
  • Sunset Sail
  • Glass Bottom Boat Tour
  • Southernmost Point
  • Key West Cemetery
  • Key West Holiday Parade (December)
  • Key West Lighted Bike Parade (December)

Spring – March through May

Watersports, fishing, bike tours, boat tours & more

yankee freedom ferry at the dry tortugas
For many folks, spring is the ideal time to visit Key West, and that’s because it’s less crowded and the weather is still heavenly (average temperatures range from mid 70s to mid 80s). Springtime is perfect for exploring the water and participating in an array of water-related activities. It likely comes as no surprise that in Key West you have endless options for getting in, on, under and even above the water. Here are some of the top activities for an action-packed spring vacation including local events you may be interested in:

  • Yankee Freedom III – Dry Tortugas and Fort Jefferson National Park
  • Parasailing
  • Snorkeling
  • Fishing tours
  • Paddleboard rentals or tours
  • Fort Zachary Taylor State Park
  • Smathers Beach
  • Dolphin Watch Tour
  • Jet Ski Tour
  • Key West bike tour or rentals
  • Kayak tours or rentals
  • Boat tours or rentals
  • Sunset celebration at Mallory Square

Keep in mind that after spending a day in the sun or on the water, Key West is well-known for its many live music venues. Spring (and all year-long) is a great time to kick back and enjoy performances by both local and nationally-known musicians. Check out:

  • Sloppy Joe’s
  • Hog’s Breath Saloon
  • Green Parrot Bar
  • El Meson de Pepe’s Restaurant & Bar
  • Smokin’ Tuna
  • Captain Tony’s
  • Virgilio’s
  • Island Dogs Bar
  • Margaritaville
  • Schooner Wharf Bar
  • Irish Kevin’s Bar
  • Rick’s Bar
  • Blue Heaven

Summer – June through August

Watersports, fishing, snorkeling, festivals & more

What’s your favorite sunset color combo? ?: ❤️ ? ? ? ??

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Although the temperatures go up during the summer months, Key West is paradise for those looking to work on their tan, make a splash in the warm water, catch some fish or just get the most out of those long-summer days and nights. And because a daily shower usually cools things off a little, evenings are the perfect time to stroll down Duval or catch the sunset at Mallory Square. Here are some top things to do and see in summer:

  • Sunset celebration at Mallory Square
  • Key Lime Bike Tours
  • Snorkeling tours
  • Parasailing
  • Jet ski rentals & tours
  • Kayak tours & rentals
  • Fishing charters & tours
  • Sunset sails
  • Key West Aquarium
  • Key West Butterfly and Nature Conservatory
  • Dry Tortugas Beach
  • Kayaking in the mangroves
  • Fishing charters
  • Smathers Beach
  • Higgs Beach
  • South Beach (great for families with small children)
  • Fort Zachary Taylor Beach
  • Key West Pridefest (June)
  • Key Lime Festival (July)
  • Fireworks on the water (July 4th cruises)
  • Lobster season (mini-season late July; regular season starts August 6)
  • Key West Lobsterfest

Fall – September through November

Weekend escapes, Labor Day getaway, fall festivals & more

couple riding bike rentals in key west
Another great time to vacation in Key West is during the cooler fall months. Although still warm enough to hang out by the pool or snorkel the reefs, the island is calmer and more tranquil — perfect for couples, seniors and families who have younger children. Whether you’re looking for a weekend escape, a Labor Day getaway or a longer stay, Key West is the ideal fall destination. Some of the top things to do in fall are:

  • Bike tours
  • Snorkel the reef
  • Parasailing
  • Glass Bottom Boat Tour
  • Shopping, dining, bar hopping on Duval Street
  • Mallory Square Sunset Celebration
  • Key West Womenfest (September)
  • Key West Musicians Festival (September)
  • Fantasy Fest (late October)
  • Goombay Festival (October)
  • Live Music Sunset Cruise
  • Ghosts & Gravestones Tour (Halloween & all year!)
  • Key West Cemetery

Tours — All year long!

Anytime is a great time to explore the city via tour, and in Key West you have several options. There are tours (most run all year long) that offer a variety of experiences, from learning local history to discovering the island’s most famous ghosts.

old town trolley tour bus on sunny day in key west

Old Town Trolley Tours

Old Town Trolley Tours take place on open-air, orange and green trolleys and are fully-narrated by a local conductor who can’t wait to share his or her city with you. The tour allows you to get off and spend as much time as you’d like at each stop and because there are trolleys coming and going all day, you can just hop back on and proceed with the tour when you’re ready. The total tour is 90 minutes but they offer the option to spread your tour out over two days and with more than 100 points of interest along the route, you’ll see the best of Key West while sitting in comfort on the trolley.

conch tour train passing by southernmost house

Conch Tour Train

One of the most popular attractions on the island, the Conch Tour Train takes you on a 90-minute journey through Old Town. It makes three stops, including one 10-minute rest where you can grab ice cream, fudge or other refreshments and jump back on for the rest of the tour. You’ll see many of the city’s most popular sites along the way and when you disembark, it is just a short walk to the Key West Lighthouse, the Southernmost Point, the Key West Butterfly and Nature Conservatory, art galleries, shops and restaurants.

ghosts & gravestones key west ghost tour guides

Ghosts & Gravestones

Do ghosts really exist? If you’re even the least bit curious and you love a good spooky story, book your seat on the Ghosts & Gravestones Tour. This Key West ghost tour is a favorite and includes exclusive entry into the East Martello Fort where you’ll meet the infamous Robert the Doll and more. It’s an evening of supernatural fun, led by a Ghost Host who will enlighten you with stories of lost souls, murder, misfortune and the Lady in Blue. This tour is not suitable for children under 13-years-old.

Old Town Trolley’s Holiday Lights & Sights Tour – December only

This special tour only runs select nights in the month of December and is a special way to kick off the holiday season! The 60-minute tour starts at Mallory Square and includes delicious holiday cookies and cider, cheerful holiday tunes (feel free to sing along!) and a tour through the city to see the most beautiful lights and holiday displays. Ideal for the whole family!

Key West — the perfect vacation all-year-long!

For every season, there’s an abundance of things to see and do on the island paradise of Key West — so use this guide to help you plan the vacation you’re dreaming of. And remember, no matter what time of year you visit, Mallory Square should be on your itinerary, the sunset celebration takes place every evening, complete with food and drink vendors and street performers.