Westwinds Inn

A Classical Key West Inn

Toll  Free:  800-788-4150 / Front Desk:  305-296-4440

Events 2015

Westwinds Front Pool

Contact for Performance


  • Armory, The Studios of  Key West (TSKW)
  • FKCC/Tennessee Williams Theatre
  • Red Barn Theatre
  • San Carlos
  • Waterfront
  • 296-0568
  • 296-1520
  • 296-9911
  • 849-1927
  • 294-5015

Please Note: Local area code 305 & <www> of Internet address are omitted.

NOTE: 24 Hr. Clock is used so 8:00 PM = 2000 hrs.

September 2015 Events

2rd - Annual Key West Brewfast; Labor Day weekend; ENJOY tasting award-winning microbrews, pool parties...
Sept. 2nd: 1700 hrs; kick-off party; Waterfront Brewery (201 William Street). Key West Brewfest <Event Schedule>. Westwinds Inn wishes you a Happy & Safe Labor Day weekend!

17th9th Annual Bike Week Bar Stroll & Upper Duval Crawl; 1800 hrs; Southernmost Beach Café (end of Duval Street on the Atlantic); Cost: $25 (You will receive a T-Shirt & a map of participating bars where you can get a free drink.)

17th - 20th43rd Annual Phil Peterson's Key West Poker Run; thousands of motorcycle riders from all over the country participate in;
this fun event which begins in Miami and ends in Key West. The lucky winner gets a brand new Harley-Davidson® 500 Street; wave to the riders as they make their journey down US 1 to the Florida Keys.   <Schedule of Events>

October 2015 Events

23rd - 24th35th Annual Goombay Festval; 1000 hrs – 2300 hrs; Petronia Street festival (begins at Duval Street); good food, drinks, live music; fun for the whole family. FREE

23rd - 1st November: 36th Annual Key West Fantasy Fest; Don't miss the celebration! Our theme this year is “All Hallows Intergalactic Freak Show”.  Go to Fantasy Fest's <Schedule> to see what's happening. Have fun!

26thHeroes or Villians 5 Mile Run/Walk; 1800 hrs; Southernmost on the Beach; win a prize for most creative, best group, scariest or funniest costume. Awards Ceremony after the race. See who won! ENJOY the beach party at sunset! If you are interested in entering the contest, please <REGISTER Online>.