Photo
The feel of the place
The short answers
The essentials before the detail
When to come
Oct to Apr
Every spot here is in season then
Number = how many of the 2 spots are in season that month.
Windiest modelled month
April · 63% of days · Whale Harbor Marina
The month the wind model rates highest; the season above is when riders and schools go.
modelled
days with three hours in a row at 12 kt or more, between 06:00 and 19:00 local, in April at Whale Harbor Marina, the strongest month any spot here models
A weather model's cell over this place, not a station on it. Good for comparing places, weaker for one beach.
What it costs
mid to high
Resort double ~$69-$296+ depending on season
Schools
3
in the directory
Permits & rules
2 spots
with rules of their own for permits, zoning or the bathing season, on the spot cards
Good to know before you go 2
- No real public transit - budget for a rental car and gas for a lot of highway driving
- Mile Marker addressing takes a minute to get used to - everything is 'MM__' not a street address
The spots
Anne's Beach
Anne's Beach sits oceanside at MM 73.5 on Lower Matecumbe Key, and the reason riders stop here is the flats: warm knee-deep water over sand and grass, with a deeper channel just south of the launch for foiling or winging.
Whale Harbor Marina
Whale Harbor Marina is a marina launch in Islamorada, not a public beach, and that shapes everything about riding here.
Schools
3 in the directory
Otherside Boardsports
IKOPASA
Doeslessons · rental · foil · wing · shop · camp
RidesAnne's Beach · Whale Harbor Marina · Veterans Memorial Park (Vets Beach) · Bahia Honda State Park · Coco Plum Beach · Curry Hammock · Grassy Flats Resort
othersideboardsports.com
Florida Keys Waterman Company / Grassy Flats
Doeslessons · rental · accommodation · downwinders · foil · wing
RidesWhale Harbor Marina · Anne's Beach · Veterans Memorial Park (Vets Beach) · Bahia Honda State Park · Coco Plum Beach · Curry Hammock · Grassy Flats Resort
floridakeyswatermancompany.com
Florida Keys Kiteboarding
PASA
Doeslessons · rental · downwinders · shop
RidesWhale Harbor Marina · Veterans Memorial Park (Vets Beach) · Bahia Honda State Park · Coco Plum Beach · Curry Hammock · Grassy Flats Resort
kiteboardingfloridakeys.com
Getting there & around
Nearest airports
- Miami International (MIA) is the main gateway, ~1.5-2hr drive down US-1
- Fort Lauderdale (FLL) as an alternative
Car
Transfers
Kite bag rules for your airline
Type the carrier you are flying: what it charges for a kite bag, and the year of the policy that says so.
Checked so far for USA:Southwest AirlinesDelta / American / United
Every carrier, with limits and what riders report at the counter →
Practical
Cash & cards
Internet & working
What riders say
5 recurring claims
The tag says how far the riders who mention it agree; the figure is how many mention it.
Anne's Beach is one of the easier Upper Keys places to keep progressing after lessons: flat, shallow, warm water, but with awkward launch space.
consensus5 riders
The tide can make Anne's feel like two different launches: high tide leaves little beach, while low tide opens room but can get almost too shallow near shore.
consensus4 riders
Whale Harbor is more of a self-sufficient locals' launch than a casual beach stop; the launch is small, there may be a launch fee, and south wind leaves no room for error.
majority3 riders
The bridge-current warning is real, not theoretical; riders mention dropped kites getting pulled toward the bridge when the current runs that way.
majority2 riders
Crowding at Anne's is unresolved: some riders and guides call it calm and small, while another spot report says weekends and peak season can get packed.
contested3 riders
The trade-off
- Rare natural sand beach in the Keys
- Shallow, warm, forgiving water for beginners and freestyle/big-air landings
- Small size keeps it from ever feeling overwhelmingly crowded
- Minimal or no launch space at high tide
- Sharp objects on the bottom - booties recommended
- Deep channel with strong current just downwind - risk of being swept under the nearby bridge in light wind if you go down in deep water
- Gets very crowded on weekends/peak season per another source (directly conflicting with the 'never too crowded' claim)
- North wind is gusty/difficult
Wind micro-knowledge
3 facts · Wind shadows · Tide and wind
Tips from riders
- Wear booties even though 'not necessary', recommended especially for beginners
- Launch from the sand area at the second entrance, left of the parking lot
- Avoid the deep channel downwind, especially in light wind, due to current and the risk of being swept toward the bridge
Scene & life
- Fresh-caught fish (some restaurants will cook your own catch)
- Key Lime Pie
- Green Turtle (breakfast/lunch)
- Islamorada Fish Company (waterfront, tarpon feeding at sunset)
- Lazy Days
- Alabama Jack's (biker hangout on Card Sound Road, just before the Keys proper)
- Sport fishing charters
- Scuba/snorkeling at Alligator Reef and wrecks like The Eagle
- Theater of the Sea (dolphin swims, snorkel cruises)
- Key West (further south)
- Everglades (north via US-1/Card Sound Road)
- Hog Heaven Sports Bar (pool, darts, marina views)
- Holiday Isle tiki bar with live entertainment
Events
The Wind Games (formerly Kite Games)
The Wind Games (formerly Kite Games)
competitionFeballrecurring
The 2023 edition ran Feb 10-12 at Islamorada: kite races, wing races, freestyle, poker runs, floaty flails, team relays. It was rebranded from the long-running annual 'Kite Games' to 'The Wind Games', so it has a multi-year history, though 2023 is the only edition on record.
Itinerary idea
FAQ
When is the best time to visit?
Winter (December-April) is high season with the most reliable weather and wind; hurricane season runs June through November.
Is Islamorada suitable for beginners?
Anne's Beach has shallow, often knee-deep flats good for learning and twin-tip riding, with a deeper channel further south; Whale Harbor Marina, by contrast, is an experienced-rider marina launch, not a beginner spot.
What is the wind like?
East and northeast are the main steady wind directions at the Islamorada spots.
Do you need a car?
Yes. US-1 is the only road through the Keys and Islamorada's islands are spread out, so a rental car is essential.
Where should you base yourself?
Islamorada village, across keys like Plantation, Windley and Upper/Lower Matecumbe, is the central base for Anne's Beach and the area's fishing and dining scene.
How this place scores
Scores out of 10, compared with other places. The data figure under each label is how much of this record that score had to work from, so a high score on thin data is a thin score.
- Flat waterdata 100%10.0
- Wavesdata 100%8.2
- Safetydata 88%6.8
- Beginner friendlydata 88%5.9
- Room on the waterdata 62%5.4
- Off the waterdata 87%5.4
- Wind reliabilitydata 10%4.8
- Familydata 100%4.6
- Kite communitydata 87%4.3
- Ease of accessdata 27%4.0
- Affordabilitydata 0%not scored
- Long staydata 0%not scored
A paler bar was scored from less than half of the record.
Scores by trip type
- Freestyle and flat waterdata 90%7.0
- Learning to ridedata 90%6.6
- Wavesdata 100%6.6
- Family tripdata 100%5.5
- Kite and workdata 45%4.6
Nothing here carries a figure for a long stay and affordability, so every line above is built without them.
Still open
Things we could not verify. If you have ridden here, you can help.
Show the 2 open questions
- The crowding contradiction between sources is unresolved - no rider account to settle it
- Is there a named rider group for the Islamorada kiters?
When to go and nearby places
Last updated: 4 September 2026