Check out the windsurfing web cam with wind speed observations from the airport.

Water conditions (e-coli counts and beach closings) at toronto.ca

Water: Flatter upwind to choppy water on a NE-E. more chop starts on a S and rollers and larger swells on a SW as the wind builds. Water quality is generally good. Check water quality after a heavy rainfall. During the summer the lifguards fly a green flag when the water is considered safe and a red flag when the water in not. Cherry Beach has had the most safe swimming days of all beaches from Osahwa to Burlington.
blueflag.ca

Water Temperature:
The water is the coldest in Spring. Warmest, typically at the end of August. The water then becomes cooler afterwords. Be prepared with the appropriate Wetsuit, Steamer or even a Drysuit if needed cold water days. Be very careful of how cold the water may be in Spring.
Beach: Pump up and launch on a SW near the open end of the bay at the far end of the sand. The beach is about 25-40m wide and 150m long. and divided by obstacles notably: The lifeguard Station and powerlines attached to it.

If you get blown downwind past the lifeguard tower do not attempt to walk back upwind past the station and powerlines or between the trees and washrooms. This is extremely dangerous.

Kiting Level: Cherry is not recommended for beginners (Not able to kite upwind unless you are with a Certified Instructor) due to obstacle and the limited landing zones downwind including the lifeguard station, dock and below that area as well which includes a narrow beach area and trees.

Certified Lessons: Cherry Beach can be a good waist deep and deep water Location to learn to kiteboard in the right weather condition with an experienced local knowledgable Certified Instructor. As well, zodiac support can be beneficial as an option.

If you plan on kiting at Cherry on your own. You should be able to easiliy ride upwind, (intermediate). If you are uncomfortable with the area, you can take a Cherry Beach Site Intro Lesson with a Certified Instructor such as  PBKiteboarding.com who is a local kiter who knows the area very well and offer Zodiac support to follow students who can't stay upwind.
New to kiting? Contact PBK and get a trainer kite and cut your Kiteboarding learning curve while helping to keep Toronto Beaches safer and accessible in the future.

Every Kiteboarder should know how and have completed a deep water self rescue with a Certified Instructor (Deep water, without touching the bottom).
The beach is sandy, dusty when very dry, and about 30m wide, with pebbles and  generally large rounded rocks up to 12" in size. close to the shoreline and most noticably as the water is lower in the summer months. Booties are best.
There are large trees beyond the beach area. The beach is generally not too crowded but caution should be exercised when there are civilians walking on the beach.

Cherry Beach sits inside the mouth of a deep bay. The mouth of the bay faces the SW. In a SW you would reach across the bay to the other side and back (about 700 metres).

Wind: Wind is strongest in spring and fall. Summer is usually accompanied by thermal action. Best directions are ENE for flat water and S-SSW for cleaner and full wind. SW can come in clean through the mouth of the bay. W and NW is offshore and not suitable. WSW starts to become unpredictable.

Keep an eye on the weather before you head out for a possible switch in wind direction from S-SW to W-NW, which is offshore. Many days the wind can increase during a coldfront switch from Medium to very string Winds. especially in the fall.

Spring and Fall are best for stronger winds and can be 15 to 25 knots or more 2 or 3 times a week and occasionally stronger.

For a couple interesting articles about the Leslie Spit over the past few years see: Friends of the Spit  <_a20_href3d_22_http3a_2f_2f_www.atlanticcallcentres.ca2f_gta2f_localhistory2f_article2f_2370 href="">