Ocean Key Resort & Spa by helicopter

Calendar of Events

Key West calendar of upcoming events - there's never a dull moment in Key West!

38th Annual Key West Fantasy Fest
October 20 – 29
This outrageous 10-day costuming and masking celebration features flamboyant masquerade competitions including one for pets, a headdress ball, exuberant promenades, street fairs and a grand parade that stars marching groups, island-style bands and lavish floats. The 2017 festival theme is “Time Travel Unravels.”

Sunset Pier Tiki Bar
Oct 31st
Tsunami Wave Riders / Donny Brewer - 4pm
Facebook Event Page
It's "Tuesday on the Island" and not much going on? That's what Buffett says, but we think it's the perfect day to party!
Join us from 4:00p -7:30p on Tuesday, Oct. 31st at Sunset Pier for drink specials, the best sunset views and fabulous Trop Rock music!
The Tsunami Wave Riders open the party, performing from 4p-5:15p. Followed by our fav Texas Trop Rocker, Donny Brewer!
As always, we'll have free giveaways for everyone! Just our way of saying Thanks to YOU to our "Paradise Crew" for supporting us and Trop Rock music.
If you're getting to the island early, come hang out with us.
We can't wait to see you!

Sunset Pier Tiki Bar
Nov 1st & 2nd
Trop Rock Junkies - 6pm
Join the Trop Rock Junkies Wednesday Nov. 1st and Thursday Nov. 2nd, 6-9PM out on the Sunset Pier at the Ocean Key House, 0 Duval St. for Key West's most celebrated event, the sunset. Join all your parrot head friends from around the country for a fun night of food, drinks, dancing and of course a fabulous sunset.

Sunset Pier Tiki Bar
Nov 3rd
The Sauce Boss - 5:30pm
Over a million miles on the road, over 200,000 bowls of gumbo served for free, thousands of gigs, tons of hot sauce, scores of free concerts at homeless shelters..Bill “Sauce Boss” Wharton brings his high energy, gumbo stirring, swamp funk to the gig. For those who don’t know about the Sauce Boss, he brings his own hot sauce to the gig, and he cooks gumbo while smoking his slide guitar. At the en...d of the Show, everyone gets a bowl. Now he's added some new flavors to the “stew”. Sauce Boss not only plays slide, sings his tamales off, makes gumbo, and feeds everybody… he will also be playing a drum kit with his feet. “You take that 53 Telecaster, pump it through that 48 Fender amp, add a bass rig, mix in some drums, all simmered down over some funky swamp blues, and smothered with gumbo, and you got a recipe for the largest one-man band on the planet.”

36th Annual Key West World Championship Races
November 5 – 12
Super Boat International returns with teams from all around the world who compete April through October in the National Series Points races and conclude in November for the famous Key West World Championships. High-speed offshore powerboats race in Key West Harbor and surrounding waters to continue Key West’s longstanding tradition in this annual challenge, known internationally as the Indianapolis 500 of powerboat racing. A portion of the 6.5-mile course runs through Key West Harbor, meaning smooth water where racers can achieve speeds above 140 mph and provide fans breathtaking displays of skill and power.

Key West Holiday Fest
Featuring a series of enchanting holiday-themed events this November. It kicks-off with the Lighting of the Harbor Walk of Lights at the Historic Key West Bight on Wednesday, November 25th at 6:00 pm. Gather at Green and Elizabeth Streets for the best viewing, and visit Seaport restaurants and shops. The Harbor Walk of Lights stretches the entire length from Green Street to the Ferry Terminal. In December, tour festive decorated inns during this year's annual Holiday Historic Inn Tour and taste fine wine and light appetizers. The Annual Lighted Boat Parade is Key West's magical nautical display of lights and creativity, and takes place on December 5th at the Historic Seaport. Key West Holiday Fest's full schedule, available at keywestholidayfest.com, includes these events and others including holiday jazz concerts, snorkeling trips, pet photos with Santas and much more.

Key West Lighted Bike Ride
December 6
The Lighted Bike Ride helps to gather the needed toys for the struggling, working families of Key West for the holidays. At the Holiday Helpers Store, eligible parents walk through the store, empowered by the ability to pick free, new toys their children will want instead of just allocating non-specific toys to parents. The ride is a family event beginning with a registration/checkin at 6 p.m. with the Lighted Bike Ride beginning at 7:00 p.m. Families and individuals with lighted and decorated bikes ride through the streets for the community to see. Registration for the ride is one unwrapped toy for the Key West Holiday Store. Register online.