Special Events

Check out our Special Events!

Southernmost Trivia "Literally". 

You are invited to play the most fun trivia EVER! We guarantee it!

When you play trivia with us… you are physically playing Trivia as far South in the continental USA as you can get.  If you love trivia… this is one to brag about to your friends.  Teams of 6 or less battle it out to earn the title, “Smartest on the Island”. All categories, not just island trivia.  This is a fun and silly trivia hand designed for guests 12 and over.  FREE TO play! Everyone Welcome to play- you just need to reserve a table!  Awesome prizes and the opportunity to meet, drink, and eat with the “crazy” locals.

PLEASE email [email protected] for reservations.

What: The BEST trivia in the world, at least the best view for trivia.

   Who: Created and hosted by Amy Andrade

When: Every Wednesday night, 6pm sharp

   Where: Southernmost Beach Café, end of Duval Street


Fantasy Fest!

Fantasy Fest is an annual 10-day party in paradise for grown-ups. Started in 1979 by a small group of Key West locals, the party was created to bring visitors to the island in what was a typically quiet, but beautiful season. It worked. Fantasy Fest has grown every year since its inception and is now the wildest extravaganza around! Fun-loving revelers from around the globe bring their creativity and imaginations as they descend upon Key West each year in October for 10 days filled with costuming, parades, libations, and excitement!

Southernmost Beach Resort Events

Tuesday, Oct 24


A sunset beach concert not to be missed! New England based, Rob Benton has spent the last decade as both a solo artis, a member of the duo “key West Kings”, and lead guitarist performing alongside artists as diverse as Nelly, Lee Brice, Lansdowne, Skidrow, Everlast, LFO, New Kids On The Block, J. Geils Band, and many more! Rob also made an appearance on NBC’s “America’s Got Talent” television show, which earned him a contract with MGM Grand headlining a yearlong residency at Circus Circus Casino on the Las Vegas strip! A dynamic performer, Rob’s style is extremely unique. By combining percussion, looping, beat boxing, electrified rock, and hip-hop elements to his solo acoustic playing; he fills out his sound like a four-piece band. Whether playing original tracks from his own albums, “Dawn Meet Day” and KWK’s “Caroline Street” or covering one of the multitude of artists who have influenced him over the years, Rob makes every song his own. 6:30-9:30 FREE! Reserve your space HERE

Thursday, Oct 26


Bring all you favorite guys and ghouls for a one-of-a-kind TRIVIA experience.

This spooky Fantasy Fest trivia features all the fun decorations of a proper Halloween Party, 6 great rounds of Trivia, Creepy drink specials, and the BEST part of all… all players in costume receive 5 bonus points! Reservations are a must; tables will fill fast! 6pm Sharp! FREE! Reserve your space HERE

Sunday, Oct 29

We’ll have plenty of food and drink specials, and a live DJ spinning all your favorites, along with free Booze Bandages for the first 50 guests, to bring you back to life! Deep Eddy’s Bloody Mary specials. Sunday, 10/30, 1-4pm Southernmost Beach Resort’s Pineapple Pool. FREE! Reserve your space HERE