Best Things to Do in Key West in May (2023)

It’s May on the Island and there is no shortage of warm weather, delicious cocktails, and fun things to see and do. Key West is, well the best place to visit, no matter the time of year. So what can you expect in Key West in May?

Key West Weather

Let’s begin with the first question… weather. May isn’t the hottest month, that’s August. And, it’s not the coldest month of the year, that’s January. But, you can expect average temperatures in the mid-80s. The average high temperature may be at 85, but the lows will only drop into the upper 70s. Yep, pleasant weather is usually expected for the month.

Humidity hasn’t crept in yet. But, it will start to increase over the month. By the end of the month, the humidity will begin to feel like the rest of the summer months. Not too many rainy days usually in May. The average is at 5 a month. The Atlantic Hurricane Season will begin officially in June, but in the meantime, you may see some tropical storms.

Getting to Key West

Heading down to Key West from Key Largo? There is a lot to see, so plan to take your time and explore.

Epic Road Trip to Key West

Flying into Key West International Airport? Don’t worry about a car. Grab a ride to your hotel and then plan to explore the Island on foot. You are on vacation. No need to stress yourself over finding a parking spot.

Hotel Rooms

I know, hotels can be pretty spendy, especially in Key West. Do a bit of research. Decide where you want to be located – Old Town, New Town, etc. What amenities can you not live without? What’s your price range? That usually helps me find a great place to stay.

11 Best Tips on Choosing a Hotel Room

One of my favorite ways to price compare is with Kayak. In one quick search, I can see what’s available and hotel prices.

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Hotel room prices vary, depending on demand. So, during peak season, the prices will be higher. Think late December through March. May is a great time to explore the Island before the humidity and rainy season hit.

Things to Do

There is always something to do in Key West. Head over to Mallory Square for the sunset celebration and watch the street performers. It’s a must-do no matter how many times you have visited Key West.

Grab a slice of Key Lime pie.

Explore Fort Zachary Taylor Park. Be sure to stay for sunset. One of the best views of sunset can be seen from the park.

Walk down Duval Street and window shop. Or actually shop in one of the art galleries. Or pop into Sloppy Joe’s or Irish Kevin’s for a cold drink and enjoy some live music. A good time for sure!

Book a trip to the Dry Tortugas National Park. These trips book up far in advance so book before you arrive to make sure you get a seat.

Yankee Freedom Ferry to Dry Tortugas

Or head out to explore the waters around Key West. The average water temperature for May is a very comfortable 82 degrees. Perfect for water sports.

Water Activities to Book

Can’t make it in May? Then check out what’s happening the rest of the year

April – Annual Conch Republic Independence Celebration

July – Hemingway Days

What is happening in May? Let’s see…

Key West Art & Historical Society: Bahana Village – Relics of a Fading Community – until May 21, 2023

Bahama Village, in the westernmost portion of the city, was a neighborhood comprised of Black Bahamians and Black Cubans, Chinese, and other groups of color. In this exhibition, their history and stories are woven together through various events that shaped the Black and Indigenous cultures of Key West. “Bahama Village: Relics of a Fading Community” contains never-before-on-view objects that tell the inspiring history, culture and contributions of the island’s Black residents. The exhibition is an excellent activity to honor the island’s Black residents during Black History Month. 281 Front Street, Key West. The exhibition has been extended through May 21.

Monday & Tuesday Evening GLOW Hours at Hugh’s Rooftop – until October 24, 2023

The Studios of Key West’s Hugh’s Rooftop offers the best views in town and an ideal spot to catch the sunset and a drink on Monday and Tuesday evenings from 6 to 8 p.m. The bar is open, admission is free. Capacity is limited, so come early. 533 Eaton Street.

27th Annual Key West Songwriters Festival – May 3-7, 2023

The Key West Songwriters Festival is the largest festival of its kind in the world. It revolves around five days and nights where live music bliss introduces crowds to the faces, voices and stories behind the songs. Performances take place at numerous theaters, bars and event spaces around Key West. Find the full schedule of performances on the festival website,

Keys Concerts by Candlelight: May the 4th Be with You – May 4

Keys Concerts by Candlelight presents “May the Fourth Be With You.” The unique concert experience features the music of Star Wars composer John Williams played by string quartet, and is led by the Southernmost Chamber Music Society member and violinist, Irie Monte. Hosted by comedian Steve Crane, the evening also features special guest appearances by the Sunshine State Stormtroopers. Doors open at 7, concert at 8 p.m. Tennessee Williams Theatre Cabaret, 5901 College Rd.

Connections Project: Mural on Display in Key West – until May 5, 2023

The Florida Keys Council of the Arts’ Connections Project mural road show is underway, and this location is its final stop. This year’s mosaic of 300 small paintings by Keys artists celebrates the Keys’ unique history and bicentennial with the theme “Pirates to Pineapples in Paradise – 200 Years in Monroe County.” The mural will be on display at the Florida Keys Council of the Arts headquarters at the historic Gato Building in Key West through May 5. 1100 Simonton Street.

Shakedown on the Green – Key West Island Market – May 6

All are welcome the first Saturday of every month for the new Shakedown on the Green Key –West Island Market, located on the Sunset Green Lawn at 24 North Hotel, 3820 N. Roosevelt. This family-friendly, Key West Island Market features local goods, artists, food trucks and more. Free admission and free parking. $5 mimosas available.

Key Largo Triathlon – May 7

This event will feature an Olympic and Sprint distance Triathlon and Duathlon, as well as an Olympic distance Aquabike race. Swim, bike and run in paradise! The swim takes place in the beautiful clear waters at John Pennekamp Coral Reef State Park, mile marker 102.5; the bike will be out and back on Overseas Highway/Card Sound Road. The 10k/5k run takes you through a lovely, laid-back Florida Keys neighborhood. This is the first of two 2023 Key Largo Triathlons in 2023.

Waterfront Playhouse – Arsenic and Old Lace – May 9 – 27, 2023

Meet Abby and Martha. Two delightful ladies. Their nephew Teddy and a host of “acceptable” gentlemen who populate the basement. An uproarious farce involving murder, mayhem and a little arsenic!

USS Higbee Community Concert with Howard Livingston – May 10

Join Navy League Key West Chapter as they host a Community Concert at Coffee Butler Amphitheater to welcome the crew of the USS Lenah Sutcliffe HIGBEE DDG123 to Key West. The concert features a lineup of acclaimed musicians including country artist Cliff Cody, American Idol singer-songwriter Kristen McNamara, and headliner Howard Livingston and the Mile Marker 24 Band. This is your opportunity to meet the HIGBEE crew before the ship is commissioned on May 13. Tickets $10 available online. Active military free, as are children under 12. Food and drinks available for purchase – no outside coolers. Doors open at 4 p.m. 21 Quay Road.

Florida Keys History & Discovery Center Lecture: Dr. Corey Malcom – Monroe 200, the Bicentennial – May 10

Dr. Corey Malcolm is the Lead Historian for the Florida Keys History Center. Dr. Malcom specialized in researching the maritime past of the Florida Keys and the Bahamas. For many years, he served as Mel Fisher Maritime Museum’s Director of Archaeology, where he participated in shipwreck research projects, including the 1622 galleon Nuestra Señora de Atocha, the 1700 English slaver Henrietta Marie, and the 1827 pirate-slaver Guerrero. He was also instrumental in bringing the Key West African Cemetery on Higgs Beach and its story to light. Please register in advance. Tickets $10 in-person, $5 virtual. Mile Marker 82 Islamorada at the Islander Resort.

Marathon Community Theatre: Scapino! – until May 13, 2023

An Italian menu – think minestrone, macaroni, ravioli – sung to a snappy tune opens SCAPINO!, a fun-filled adaptation of Moliere’s ”Les Fourberies de Scapin.” Set in contemporary Naples, Italy, the leading character, Scapino, devises a complex plot to help two pairs of lovers against parental opposition that, it turns out, does not even exist. Scapino, a fast-talking, quick-thinking scamp cleverly manipulates and cajoles everyone around him into doing what he intends them to do. Slap-stick, over-the-top hilarity ensues in this uniquely musical farce. Shows at 8 p.m. except for a Sunday matinee on May 7 at 3 p.m. Tickets $28, available online. 5101 Overseas Highway, oceanside.

Afro Roots Fest – Islamorada – May 19 – 21, 2023

Three days of music and fun with an all-star lineup of Afro Roots artists takes place on the stage at Florida Keys Brewing Company, 81611 Old Highway. On Friday at 6 p.m., the Miami-based power quartet Electric Kif opens the three-day event. Saturday at 6 p.m., enjoy the Cuban stylings of Cortadito and the Afro-Brazilian rhythms of Miamibloco. On Sunday, jam to the Nag Champions, Johnny Dread and Group Barrio Abajo beginning at 2 p.m. All three shows take place in the beer garden and admission is free.

Key West Business Guild: Pride Follies – May 20

The Key West Business Guild presents Pride Follies, a fun evening of the best and worst of local Key West entertainment, hosted by the former Queen of Fantasy Fest, Destiny Montgomery. Doors open at 7 p.m. and show starts at 8 p.m. at Key West Theater, 512 Eaton Street. Tickets $15 to $35.

The Studios of Key West: Tangos to Tarantellas – May 21

The Music Room presents Tangos to Tarantellas, an annual children’s welfare fundraiser showcasing the best classical musicians in the Keys. The twist? They’re all under 18 years old. Join musical director Robin Kaplan and her students for “a happy hour soiree” of classical dance music while enjoying refreshments and delectable bites. Helmerich Theater, tickets free at the door. Show starts at 5 p.m. 533 Eaton St., Key West.

Key West Art & Historical Society: Out of the Box – The Art of the Cigar Label – until October 22, 2023

The Key West Art & Historical Society presents “Out of the Box: The Art of the Cigar Label.” The exhibition offers a compelling sampling and interpretation of 19th and early 20th century inner and outer cigar labels, showcasing more than 40 lithographs related to the Key West and Cuba cigar manufacturers. From the 1880s into the early 20th century, cigar manufacturers desired an avenue to market their particular cigars to consumers. Mass production of cigars in Cuba and Florida contributed to the successes of lithographic arts. Layering up to 10 colors in a stone-lithography process, and even adding gold leaf embellishments and embossing, vibrant images sold cigars through romantic landscapes, patriotic figures, Grecian representations of women, and lush tobacco fields. Included with museum general admission. 281 Front Street, 10 a.m. to 5 p.m. daily.

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