May in Fort Myers averages 71–90°F — the wet season is beginning, with highs hitting 90°F and the afternoon thunderstorm pattern that defines Southwest Florida's summer starting to establish itself. Light, breathable fabrics and sun protection are the priorities; a compact rain poncho or packable shell covers the frequent but brief afternoon storms along the Caloosahatchee Riverwalk and the Edison and Ford Winter Estates. About 9 rainy days fall in May, mostly as late-afternoon convective showers.
Also packing for this trip?
Full May packing list for Fort Myers →
Checklist of clothes, shoes, and gear — separate from these outfit ideas.
Compare prices across top booking sites for May 1–4.
Powered by Hotellook · prices from Booking.com, Agoda, and more
top / Tank & Cami
tank top
breathable — lets heat escape in warm weather
bottom / Shorts
denim shorts
breathable fabric for high-heat days
lightweight linen pants for more coverage
footwear / Waterproof Boots
ankle boots
rubber sole for traction — keep feet dry all day
outerwear / Rain Jacket
shell jacket
lightweight
Based on typical May conditions in Fort Myers. Weather varies year to year — check the live forecast when you're within two weeks of your trip.
Fort Myers's May marks the transition from the comfortable dry season to the wet season's arrival — the 90°F afternoon heat intensifies, the Gulf water warms to around 80°F for comfortable swimming, and the afternoon thunderstorm pattern that will dominate through October begins establishing its daily rhythm. The Edison and Ford Winter Estates' gardens are lush with late-spring tropical bloom, and the Caloosahatchee Riverwalk handles the heat better in the early morning and evening hours. About 9 rainy days bring the first serious wet-season moisture, typically as brief late-afternoon convective storms that clear before sunset. Fort Myers's Florida resort-casual style adapts fully to summer mode in May — lightweight cotton or moisture-wicking fabrics, shorts and sundresses, sandals, and sun protection are the practical and aesthetic standard. The Sanibel and Captiva barrier island beaches remain excellent in May before the summer crowds fully arrive; a compact rain poncho handles the brief but sometimes intense afternoon storms without the bulk of an umbrella.
Warm conditions with light rain highlight the Essential Black Sleeveless Crop Top as the hero item. White straight-leg jeans with Black low-top tennis sneakers sustain the relaxed casual mood.
Warm conditions with light rain highlight the Navy linen sundress as the hero item. White low-top sneakers sustain the relaxed casual mood.
Hot conditions with light rain highlight the Navy linen sundress as the hero item. The Everyday Brown Leather Sandal with Brown woven leather belt sustains the relaxed casual mood.
Warm conditions with light rain highlight the Navy linen sundress as the hero item. The Padded Leather Thong Sandal with Classic Small Gold Hoop Earrings sustains the relaxed casual mood.
Warm conditions with light rain highlight the White smocked sundress as the hero item. Tan flat slide sandals with Simple Silver Curb Chain Bracelet sustain the relaxed casual mood.
Light, breathable warm-weather clothing is essential for 90°F afternoons. Lightweight cotton or moisture-wicking shorts, sundresses, and tops handle the heat and humidity on the Riverwalk and at the Edison and Ford Winter Estates. A compact rain poncho covers the afternoon thunderstorms that arrive most days by 3–5 p.m. Sandals handle the beach and outdoor dining comfortably; reef-safe sunscreen and a wide-brim hat are the essential accessories.
May is a transitional month for Fort Myers — the snowbird crowds have departed, making Sanibel's beaches and the Edison and Ford Estates less crowded, and the Gulf water is warm enough for excellent swimming. The heat is real (90°F) and the afternoon thunderstorm pattern is establishing, but mornings are beautiful and evenings are pleasant. It's the last relatively affordable month before summer pricing peaks in some areas.
Sandals handle Sanibel's beaches and the Caloosahatchee Riverwalk's paved path comfortably. A pair of water-resistant walking sandals or waterproof trail shoes handles the afternoon storm aftermath, when puddles form on the Riverwalk and the Edison Estates' garden paths. Flip-flops work at the beach but lack support for the longer walking distances at the Estates' campus.
Afternoon highs average 90°F with morning lows near 71°F — both warm, with the Gulf humidity adding significant perceived heat above the thermometer reading. The wet season's arrival means the heat index can push toward 95–100°F on the most humid days. About 9 days bring rain, primarily as afternoon convective storms that can be intense for 30–60 minutes before clearing.
Pack lightweight warm-weather clothing, moisture-wicking fabrics, sandals, a compact rain poncho, high-SPF broad-spectrum sunscreen, a wide-brim hat, and sunglasses. Insect repellent becomes increasingly relevant in May as the wet season's mosquito population begins building. A light cardigan handles air-conditioned restaurant and shopping interiors.
Packing tools
Free calculators — city and month pre-filled when we know them. No account required. Start with how many outfits, sudoku packing, or bag fees.
Trip
Planning a trip to one city?
One city → typical weather for your month, packing counts that fit your bags, and email your plan.
Outfits
How many outfits for this trip?
Trip length, bag size, and climate → exact tops, bottoms, layers, and outfit combinations.
Jacket
Not sure about a jacket?
City + month → base / mid / shell stack and pack-or-skip verdicts for rain jacket, coat, and thermals.
Shoes
Shoes for this climate?
Climate, activities, and bag size → pair count, primary/backup types, and climate-matched picks.
Bags
Will this trip cost bag fees?
Airline + fare bucket + bags you plan to bring → fit verdicts and typical carry-on / checked fee ranges.
Capsule
Try sudoku packing for this climate?
City + month → climate-ready 3 tops / 3 bottoms / 3 layers you can edit — up to 27 mix-and-match outfits.