Key West in May: Weather, Events, and What to Expect

There is a week in May when you notice that the island has changed gear. The snowbirds’ cars have gone from the side streets, the waiters have time to chat, the sea off Fort Zachary Taylor is warm enough that nobody gasps getting in, and the first puffy afternoon clouds start building over the Gulf around three o’clock. The heat has a little more weight to it, but the evenings are long and golden and the sunsets come after eight. Key West in May is the island exhaling after the winter rush — warmer, quieter, cheaper, and for a lot of repeat visitors, the best month of the year to be here.

This guide covers May weather and water temperatures, the Songwriters Festival and the month’s other dates, how crowds and prices change, why May is one of the best months for snorkeling, diving and fishing, what to watch out for (humidity, the first summer storms and sargassum), what to pack and how May compares with April and June. Weather figures are NOAA 1991–2020 averages for Key West International Airport. Event dates and price patterns were checked in September 2026; confirm 2027 dates before you book.

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Key West in May at a glance

§ 02

May weather

May is the hinge between Key West’s dry season and its wet one. The average high is about 86°F and the average low about 76°F, so even nights are warm. It is the sunniest month of the year on average, with more hours of sunshine than any other, and for the first half of the month it often feels like a warmer April.

As the month goes on, summer arrives. Humidity rises, the sea breeze softens, and by late May the pattern of the wet season begins to appear: a sunny, hot morning, clouds building in the afternoon, and a short, heavy shower or thunderstorm that clears within an hour. May averages about three inches of rain on seven or eight days — more than April, much less than June through October. Rarely does it rain all day.

See our Key West month by month guide for the full year, and Key West in April for the month before.

The water in May

At about 81°F, the sea in May is warm enough to stay in for as long as you like, and it is often calm and clear. The winter winds are a memory, the summer storms are only just beginning, and the reef is at its most inviting. May is one of the best months of the year for snorkeling, scuba diving and the ferry to Dry Tortugas.

The caveat, as through spring and summer, is sargassum. In heavy bloom years, drifting seaweed can pile up on Atlantic-facing beaches such as Smathers, and 2026 was forecast to be one of the heavier seasons. The next week’s conditions can be completely different from last week’s. If a particular beach matters to you, check recent local reports shortly before you go, and remember that sheltered beaches like Fort Zachary Taylor are usually less affected.

§ 03

May events

Key West Songwriters Festival (April 28–May 2, 2027)

Billed as the largest festival of its kind in the world, the Songwriters Festival fills the island with songwriters — many of them the people behind country and pop hits you know — playing their own songs and telling the stories behind them in bars, restaurants, hotel courtyards and small theaters. It runs over five days and nights, with a mix of free shows and ticketed headline events, and it has a warm, intimate atmosphere that is completely unlike a big-stage music festival. The 2027 festival is announced for April 28 to May 2. Book accommodation early; the first weekend of May fills up. See our Key West Songwriters Festival guide.

Mother’s Day (May 9, 2027)

A popular weekend for brunch reservations and sunset sails. Book restaurant tables ahead.

Memorial Day weekend (May 29–31, 2027)

The unofficial start of summer brings a busy long weekend, with boaters, families and Florida residents driving down. Expect higher hotel rates, heavy traffic on the Overseas Highway on Friday and Monday, and a full sandbar and harbor. If you want a quiet May trip, avoid this weekend; if you want a lively one, it is fun.

The rest of the month

Between these, May is one of the quieter months on the Key West events calendar, which is part of its appeal. Live music is still everywhere every night, sunset at Mallory Square still happens every evening, and fishing tournaments begin to appear on the calendar as the offshore season heats up. For the full year, see our Key West events guide.

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Crowds and prices in May

May is shoulder season, and for value it is one of the best months of the year.

Room rates in May are usually well below their February and March peaks. The middle weeks of the month, midweek, often bring the best deals of the whole spring — for weather that many people consider better than winter’s. Restaurants are easier to book, attractions less crowded, and the island feels more relaxed.

For budget tips, see our Key West on a budget and cheapest time to visit Key West guides.

§ 05

What to do in Key West in May

Snorkel and dive

With warm, clear water and generally calm seas, May is one of the best months to get out on the reef. Snorkel trips to Sand Key and the Sambos are excellent, and certified divers can explore the reef and the wreck of the Vandenberg in good conditions. Go in the morning, when the water is usually calmest and before any afternoon storms. See our Key West snorkeling and Key West scuba diving guides.

Visit Dry Tortugas National Park

May is one of the best months for the trip out to Fort Jefferson: calm seas for the crossing, warm, clear water for snorkeling around the moat walls, and long days. It is also bird migration season, when the islands of Dry Tortugas are a major stopover for migrating birds and the sooty terns nest on Bush Key. Book the ferry or seaplane well ahead. See our Dry Tortugas day trip guide.

Go fishing

May is one of the best fishing months of the year. Tarpon season is at its peak, with huge fish rolling in the channels and on the flats. Offshore, mahi-mahi (dolphin fish) arrive in numbers, and reef and wreck fishing are good. Guides book up early for tarpon dates. See our Key West tarpon fishing and Key West deep sea fishing guides.

Sail at sunset

With sunset after 8 p.m. and warm evenings, May is a lovely month for a sunset sail. A classic schooner or a relaxed catamaran trip with a drink in hand is a Key West ritual. Our Key West sunset cruise guide says which trips are worth it — and which are warm white wine in a plastic cup.

Try water sports

Warm water and lighter winds make May a good month for parasailing, jet skiing, paddleboarding and kayaking. Early morning paddles through the mangroves are especially good, before the heat builds. See our Key West water sports guide.

Explore Old Town — early and late

May is warm enough that a midday walk in full sun can wear you out. Do your sightseeing in the morning and late afternoon: the Hemingway Home when it opens, the Key West Cemetery before the heat, a bike ride through Old Town in the golden hour. Save the middle of the day for the beach, the pool or an air-conditioned museum.

Eat well

Stone crab season ends on May 1, so plan accordingly if claws are on your list. Spiny lobster is out of season until August. Fresh local fish — mahi-mahi, snapper, grouper, hogfish — is at its best, and May’s quieter restaurants mean you can walk into places that were fully booked in March. See our best restaurants in Key West guide.

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A five-day May itinerary

The rule for May is simple: water in the morning, shade or air conditioning in the middle of the day, and the town in the evening.

• Day 1: Arrive and settle in. An evening walk down Duval Street, sunset at Mallory Square, and dinner outdoors while it is warm.
• Day 2: Morning snorkel trip to the reef. Lunch and a nap. Late-afternoon swim at Fort Zachary Taylor, then live music.
• Day 3: Dry Tortugas by ferry, leaving early and back by late afternoon. A quiet dinner.
• Day 4: Dawn tarpon or backcountry fishing trip, or a kayak through the mangroves. Afternoon at the Hemingway Home or the Mel Fisher Maritime Museum, both cool refuges. Sunset sail.
• Day 5: Bike ride through Old Town in the early morning, Cuban coffee, key lime pie, and home.

If your trip includes the first weekend of May, swap in Songwriters Festival shows for the evenings. For a longer trip, our Key West 7-day itinerary adds a day up the Keys.

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What to watch out for in May

• Heat and humidity. Late May can feel properly tropical, especially for visitors from cooler, drier climates. Plan activities for mornings and evenings, drink plenty of water and take breaks in the shade.
• Afternoon storms. From mid to late May, afternoon thunderstorms become more common. They are usually short, but lightning is dangerous on the water and at the beach. Get out of the water and off exposed boats when you hear thunder.
• Sunburn. May is the sunniest month of the year, with a very high UV index. Use high-SPF mineral sunscreen, a hat and a rash guard for snorkeling.
• Sargassum. Check beach reports if you are set on Smathers or another Atlantic beach.
• Memorial Day weekend. Busy, with higher prices and heavy traffic on the highway.
• No-see-ums and mosquitoes. Insects become more active in warmer, damper weather, particularly around mangroves and at dusk. Bring repellent.

§ 08

May for different kinds of travelers

Couples

May is quietly romantic: long evenings, warm water, late sunsets and easier reservations than in winter. It is a popular month for weddings and honeymoons, with rates below the spring peak. See our Key West romantic getaway guide.

Families

Before school vacations begin in most of the country, May is a relatively quiet month for families, which means shorter lines at the family attractions. The warm water is perfect for children, and a hotel pool becomes a daily highlight. See our Key West with kids guide.

Anglers and divers

May is prime time for both. Tarpon, mahi-mahi and clear reef water make it one of the best months of the year to be on the water. Book guides and dive boats early.

Budget travelers

The middle of May offers some of the best value of the year for good weather. Midweek stays in the middle two weeks of the month are the sweet spot. For even lower prices, late summer and early fall are cheaper, but bring hurricane risk and heavier rain.

§ 09

Beyond Key West in May

The whole island chain is at its best for water activities in May, and a day or two up the Keys is easy to fit in.

• Looe Key Reef, off Big Pine and Ramrod Key, has some of the best snorkeling in Florida, and May’s calm seas suit it perfectly. See our Looe Key Reef guide.
• Bahia Honda State Park (MM 37) for the best natural beach in the Keys.
• Islamorada, the sportfishing capital, where spring tarpon draw anglers from around the world, and where you can hand-feed tarpon at Robbie’s.

For a longer trip, our where to stay in the Florida Keys guide suggests how to split a week between Key West and the other islands.

§ 10

What to pack for May

• The lightest, most breathable clothes you own — linen, cotton, quick-dry fabrics
• Swimwear, a cover-up and a rash guard
• High-SPF mineral sunscreen, a wide-brimmed hat and polarized sunglasses
• A compact umbrella or light rain jacket for afternoon showers
• Insect repellent
• Comfortable sandals and water shoes
• A reusable water bottle
• A light layer for air-conditioned restaurants

Our Key West packing list has the complete checklist.

§ 11

May vs April vs June

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Is May a good time to visit Key West?

Yes — for many people it is one of the best. You get warm, clear water, the sunniest skies of the year, excellent snorkeling, diving and fishing, lower prices than winter and spring, and a relaxed island that has room for you. The Songwriters Festival at the start of the month is a bonus for music lovers.

May is less ideal for people who struggle in heat and humidity, who want a cool, breezy walking holiday, or who are traveling on Memorial Day weekend and hoping for peace and quiet. For those travelers, April or November may suit better. Our best time to visit Key West guide compares the options.

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Frequently asked questions

Related Key West Guides

• Key West month by month — every month compared
• Key West in April — the month before
• Key West Songwriters Festival — May’s headline event
• Best time to visit Key West — weather, crowds and prices
• Key West fishing seasons — what is biting and when
• Dry Tortugas day trip — best in the calm seas of late spring

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Photo Credits

Dive and charter boats at Key West Bight: Key West Bight Marina, Key West, Florida by Sharon Hahn Darlin, CC BY 2.0, via Wikimedia Commons.

The schooner Western Union under sail: Florida Keys Scenic Highway – The Schooner Western Union At Full Sail – NARA – 7718451 by Unknown author Unknown author or not provided, Public domain, via Wikimedia Commons.

View from Fort Jefferson, Dry Tortugas: Fort Jefferson, Dry Tortugas National Park, Florida (51135890187) by Ken Lund from Reno, Nevada, USA, CC BY-SA 2.0, via Wikimedia Commons.