Late spring · Weather & things to do
Winter Park in May
Winter Park's warmest month brings highs averaging 89°F (31°C), lows of 68°F (20°C) and about 3.9 in (100 mm) of rain.
Our comfort score puts it mid-table at 71/100, 8th of 12.
- Avg high
- 89°F (31°C)
- Avg low
- 68°F (20°C)
- Rain
- 3.9 in (100 mm)
- Humidity
- 67%
- Cloud cover
- 43%
- Daylight
- ~13 h 25 min
- Comfort score
- 71/100 · Good
What May feels like
Afternoons run hot at about 89°F (31°C), which leaves mornings and evenings as the time for walking.
Lows average 68°F (20°C).
Showers are part of the month, adding up to about 3.9 in (100 mm).
Plan around May
May sits mid-table; the best months are November – April.
- Comfort slips from 86/100 in April to 71/100.
- Our Orlando New Year's Eve route is planned for Dec 30 – Jan 1, a window set by the holiday season rather than the weather — May falls outside it.
What to pack for May
- Light, breathable clothes89°F afternoons
- Sunscreen, sunglasses and a hathigh UV on clear days
- Refillable water bottleeasy to dehydrate in the heat
- Packable rain jacket or umbrellaabout 3.9 in of rain
- Comfortable walking shoesmost picks involve some walking
What to do in Winter Park in May
Afternoons run hot (89°F), so these picks mix early-start outdoor spots with cool indoor breaks.
Kraft Azalea Garden
A free lakefront garden of cypress trees and azaleas on Lake Maitland, with a columned exedra at the water.
Why now May scores 71/100 for comfort, good conditions for being outside.
Knowles Memorial Chapel
A Spanish Revival chapel on the Rollins College campus, near the shore of Lake Virginia.
Why now Highs near 89°F and 3.9 in of monthly rain make this an easy outdoor pick.
Park Avenue
Winter Park's brick main street of shops, cafes and sidewalk tables, lined along Central Park and the train station.
Why now One to do outside while the weather is on your side.
Winter Park Scenic Boat Tour
An hour-long pontoon tour, running since 1938, through Winter Park's chain of lakes and the canals between them.
Why now Go early — afternoons average 89°F.
Nearby in May
- Walt Disney World in May~19 mi · highs 89°F, 3.5 in rain · similar daytime temperatures, about as wet
- Downtown Tampa & the Riverwalk in May~81 mi · highs 87°F, 3.5 in rain · 1°C (2°F) cooler by day, about as wet
- St. Augustine in May~90 mi · highs 81°F, 4.2 in rain · 4°C (8°F) cooler by day, about as wet
- Downtown St. Petersburg in May~96 mi · highs 87°F, 3.5 in rain · 1°C (2°F) cooler by day, about as wet
NASA POWER 2001–2025 monthly averages on a ~50 km grid. Comfort scores weigh temperature, rain, humidity and cloud: see how we score each month. Check a forecast before you go.
Winter Park in May: quick answers
Is May a good time to visit Winter Park?
It's middling, scoring 71/100. The best months are November – April, at up to 92. Expect highs of 89°F (31°C) and 3.9 in (100 mm) of rain.
How hot is Winter Park in May?
Average highs are 89°F (31°C) and average lows 68°F (20°C), making it the warmest month by daytime highs.
Does it rain a lot in Winter Park in May?
Some: about 3.9 in (100 mm) of rain falls across May on average, the 5th-wettest month of the year. The annual total is about 51.2 in (1301 mm).
What should I pack for Winter Park in May?
Bring light, breathable clothes (89°F afternoons), sunscreen, sunglasses and a hat (high UV on clear days), refillable water bottle (easy to dehydrate in the heat), packable rain jacket or umbrella (about 3.9 in of rain) and comfortable walking shoes (most picks involve some walking).
More on Winter Park
Planning Winter Park in May?
Bring the crew into one shared trip: vote on dates, build the day-by-day plan, split costs and share one packing list.