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Shoreline Of Key West Fl
Key West. Photo: Tristan Dietz, CC BY 3.0, Wikimedia Commons

Key West

Windsurf spot · United States

Is it worth the trip?

34Poor out of 100 for your dates

Usually stay home

Every day scores the same, usually

Each day of your trip, out of 100

Mon 2 · 34 out of 100

From the usual week for these dates, not the forecast.

Tue 3 · 34 out of 100

From the usual week for these dates, not the forecast.

Wed 4 · 34 out of 100

From the usual week for these dates, not the forecast.

Thu 5 · 34 out of 100

From the usual week for these dates, not the forecast.

Fri 6 · 34 out of 100

From the usual week for these dates, not the forecast.

Sat 7 · 34 out of 100

From the usual week for these dates, not the forecast.

Sun 8 · 34 out of 100

From the usual week for these dates, not the forecast.

No forecast for this spot on these dates. Usual weather for your dates

The spot in six facts

  • Faces Nopen to the N
  • Best wind: E or Walong the shore
  • Avoid: Sblows out to sea
  • Shelteredto the swell
  • Water 26 °Cno wetsuit
  • Best Jan, Oct–Nov2 good days in 7

Usual weather for your dates

not a forecast
Usual windsurf conditions at Key West, each day of your trip
DayWindAir
Mon 2to 8usuallyE 12 kn26°C

No forecast for this spot on these dates. These are the usual readings for that week.

Best time to go

best Jan, Oct–Nov

Good windsurf days in a typical week, each month, from 2016 on (ERA5 history scored the same way).

  1. Jan2of 7: a trip from Sat 2 Jan
  2. Feb1of 7: a trip from Sat 6 Feb
  3. Mar1of 7: a trip from Sat 6 Mar
  4. Apr1of 7: a trip from Sat 3 Apr
  5. May1of 7: a trip from Sat 1 May
  6. Jun0of 7: a trip from Sat 5 Jun
  7. Jul0of 7: a trip from Sat 3 Jul
  8. Aug0of 7: a trip from Sat 7 Aug
  9. Sep0of 7: a trip from Sat 4 Sept
  10. Oct2of 7: a trip from Sat 2 Oct
  11. Nov2of 7: a trip from Mon 2 Nov
  12. Dec1of 7: a trip from Sat 5 Dec

Tap a month to see this spot for a trip then.

Typical, not a forecast. Reanalysis wind misses some local thermal winds, so a spot known for an afternoon breeze may do better than this.

Map

the spot and its town

Each place wears how it usually is on these dates, from past years' weather: green good, amber fair, pale red poor, as the key says.

The map needs JavaScript. Every place on it is listed on this page, and each place's page links to Google Maps.

One finger scrolls the page; two fingers move the map. Pins are our own positions. Map OpenFreeMap, © OpenMapTiles, data © OpenStreetMap contributors.

More windsurf near here

1 place

About

the place in full, sources, credits

About Key West

Known for kitesurfing and windsurfing, by the OpenStreetMap map of the area. The shore faces N, so wind from the S blows out to sea (our estimate from the coastline).

Water about 26°C: no wetsuit. Typical sea temperature for the time of year, not a forecast.

A spot for kitesurfing and windsurfing, as OpenStreetMap maps it, on a shore facing N. Wind from the N blows onshore, wind from the S blows out to sea, and wind from the E or W runs along the shore. It is sheltered to the open sea. The sea is about 23°C in January, its coldest month (2 mm shorty), and 30°C in July, its warmest (no wetsuit). For windsurfing at expert level the best months are usually January, October and November, with about 2 good days in 7. From the weather of past years. The town to stay in is Key West. Within 5 km we also list 2 wind sports spots and 3 dive sites.

The score is the conditions only: the journey, the price and the partners never change it (how we score, how we earn).

Rough cost (estimate): about US$871–US$1,600 each

about US$871–US$1,600 each · 6 nights, 2 sharing: flights, taxi, stay, food.

Our estimate from typical public prices, not a quote: check the real prices before you book (where they come from). Prices are about, in US Dollar (USD): our pound figures at the European Central Bank's rate of 30 October 2026.

How we worked it out 
Rough cost per person for this trip
WhatHow we worked it outEach
Flightsreturn ORD to EYW, estimated from distance and season, 3 airlines on the route, with a hold bagabout US$208–US$429
Taxiairport and back, sharedabout US$20–US$33
Stay6 nights, a mid-range double, sharedabout US$301–US$502
Food7 days eating outabout US$342–US$636
Totalabout US$871–US$1,600

Kit hire is not priced yet: we have no sourced price, so it is not in it. Prices from public sources, checked in 2026.

Where to stay: Key West

Closest

Key West

4 min by car · 248 places to stay

about US$114/nightcountry average

See 248 places to stay in Key West · Booking.com

About Key West its beds, food and every spot near it

About US$114 a night is our estimate of the country's average 2-star double room that month: not each town's price, and not a quote. Drives are estimates. Prices are about, in US Dollar (USD): our pound figures at the European Central Bank's rate of 30 October 2026.

Getting there: about 5h 35m

About 5h 35m door to door from Chicago

Fly ORD → EYW, direct, then 20 min by road

An estimate, one way; the journey never changes the score.