Name: Fantasy Fest Spooky Trivia - Southernmost Beach Resort
Start: 2026-10-21T18:00:00-04:00
Location: Southernmost Beach Resort & Guesthouses

Southernmost Beach Resort & Guesthouses

Bring all your 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! $25, including your first spooky drink! Reserve your space and get your tickets <a href="https://keystix.com/fantasyfest" target="_blank" rel="nofollow noopener">HERE</a>

Local Event: Fantasy Fest Spooky Trivia - Southernmost Beach Resort

Monroe County

Monroe

Key West

Florida

Fantasy Fest Spooky Trivia - Southernmost Beach...

Bring all your favorite guys and ghouls for a one-of-a-kind TRIVIA experience. This spooky Fantasy Fest trivia features all the...

Fantasy Fest Spooky Trivia - Southernmost Beach Resort

Southernmost Beach Café

In honor of Tutu Tuesday, join us at the Southernmost Beach Café for $22 bottomless mimosas (2hr max) throughout the day. Then join us for a fun evening of Salsa dancing while wearing your tutus, lessons by Salsa John, sponsored by Dulce Vida Organic Tequila and Bogle Family Vineyards. Enjoy margarita and sangria specials while you dance your tutus off - 7pm, Southernmost Beach Resort – FREE!

Local Event: Tutu Salsa Sessions

Tutu Salsa Sessions

In honor of Tutu Tuesday, join us at the Southernmost Beach Café for $22 bottomless mimosas (2hr max) throughout the day. Then...

The Marker Key West Harbor Resort 200 William St. Key West, FL 33040

<a href="https://www.themarkerkeywest.com/specials?gclsrc=aw.ds&amp;gad_source=1&amp;gad_campaignid=24099178968&amp;gbraid=0AAAABCN8GszL_QDofRqfTLbb8r1a9wdq3&amp;gclid=Cj0KCQjwt9jVBhDXARIsAFSP-6evafZyNgB7aZO_ZD2rYgKOPNBsDwqfhj_COkCxFy_xz1Sor4Fi_pAaAlo7EALw_wcB" rel="nofollow noopener" target="_blank">The Marker Key West</a> keeps the <a href="https://fantasyfest.com/" rel="nofollow noopener" target="_blank">Fantasy Fest</a> celebrations going with <a href="https://iamlesgreene.com/" rel="nofollow noopener" target="_blank">Les Greene &amp; The Swayzees</a> on Thursday, October 22, beginning at 2 p.m. Guests can enjoy live music, poolside fun, and food and drink specials featuring Dulce Vida Tequila and Deep Eddy Vodka, all set against The Marker’s lush tropical grounds and open air waterfront dining.

Local Event: Fantasy Fest Les Greene & the Swazees The Marker Key West Harbor Resort on October 22

Fantasy Fest Les Greene & the Swazees The...

The Marker Key West keeps the Fantasy Fest celebrations going with Les Greene & The Swayzees on Thursday, October 22, beginning...

Fantasy Fest Les Greene & the Swazees The Marker Key West Harbor Resort on October 22

Southernmost House Key West

Join us at The Southernmost House from 10:30AM to 5PM for the hottest, most glamorous oceanfront, adults-only Playboy Bunny Pool Party! Enjoy an all-day pool pass, live DJ beats, drink specials, and plenty of sunshine. And yes—topless sunbathing is welcome, as long as you're sporting your bunny ears. Includes access to the Southernmost Pool area and bar, where you can soak up the Bunny Pool Party atmosphere, enjoy music and entertainment, grab your favorite drinks, and take in the oceanfront setting throughout the event. . Admission: $40.00 |1400 Duval Street | 305-296-3141 | 10:30AM-5PM Purchase Tickets - <a href="https://www.southernmosthouse.com/southernmost-house-events" target="_blank" rel="nofollow noopener">HERE</a>

Local Event: Southernmost Playboy House - Beach Bunny Pool Party Bash

Southernmost Playboy House - Beach Bunny Pool...

Join us at The Southernmost House from 10:30AM to 5PM for the hottest, most glamorous oceanfront, adults-only Playboy Bunny...

Southernmost Playboy House - Beach Bunny Pool Party Bash

The Oldest House

Experience an exclusive evening with a front-row view of the parade from the porch of The Oldest House. Indulge in small bites by award-winning Chef Juan Cuadra of Salty Chef, complemented by fine wines and a top-shelf bar in a private, intimate setting strictly limited to 20 guests.

Local Event: Front Row To The Icons at The Oldest House

Front Row To The Icons at The Oldest House

Experience an exclusive evening with a front-row view of the parade from the porch of The Oldest House. Indulge in small bites...

<a href="https://fantasyfest.com/" rel="nofollow noopener" target="_blank">Fantasy Fest</a> continues at <a href="https://www.themarkerkeywest.com/specials?gclsrc=aw.ds&amp;gad_source=1&amp;gad_campaignid=24099178968&amp;gbraid=0AAAABCN8GszL_QDofRqfTLbb8r1a9wdq3&amp;gclid=Cj0KCQjwt9jVBhDXARIsAFSP-6evafZyNgB7aZO_ZD2rYgKOPNBsDwqfhj_COkCxFy_xz1Sor4Fi_pAaAlo7EALw_wcB" rel="nofollow noopener" target="_blank">The Marker</a> with the Channel 3 Reggae Rehab Pool Party on Sunday, October 25, from noon to 5 p.m. Guests can spend the afternoon poolside with live music from Channel 3 and enjoy <a href="https://www.dirtymonkeywhiskey.com/" rel="nofollow noopener" target="_blank">Dirty Monkey Banana Peanut Butter Whiskey</a>, bringing reggae rhythms and laid-back island energy to the resort for a lively Sunday celebration.

Local Event: Fantasy Fest Channel 3 Reggae Rehab The Marker Key West Harbor Resort on October 25

Fantasy Fest Channel 3 Reggae Rehab The Marker...

Fantasy Fest continues at The Marker with the Channel 3 Reggae Rehab Pool Party on Sunday, October 25, from noon to 5 p.m....

Fantasy Fest Channel 3 Reggae Rehab The Marker Key West Harbor Resort on October 25

You bring your inner Mr. Chow, Alan, Stu, or anyone else from the Hangover gang, and we'll bring plenty of food, drink specials and swag by Dirty Monkey Banana Peanut Butter Whiskey, and a live DJ spinning all your favorites including “Allentown” We’ll also have $10 Deep Eddy’s Bloody Mary specials, of course. Sunday, 10/25, 1-4pm Southernmost Beach Resort’s Pineapple Pool. FREE!

Local Event: The Hangover "But Did You Die?" Pool Party at Somo's Pineapple Pool

The Hangover "But Did You Die?" Pool Party at...

You bring your inner Mr. Chow, Alan, Stu, or anyone else from the Hangover gang, and we'll bring plenty of food, drink specials...

The Hangover "But Did You Die?" Pool Party at Somo's Pineapple Pool

La Concha Key West, Autograph Collection 430 Duval Street Key West, FL 33040

Celebrate Halloween at the best bars across Duval Street with welcome shots/treats, drink specials and more.
Key West's Halloween Bar Crawl is taking over Duval Street on Halloween eve.
Dress up, grab your crew and join one of Key West’s biggest Halloween nightlife events, featuring 5+ of the city’s best bars in one of its most popular neighborhoods. Costumes make the perfect icebreaker, so come ready to mix and mingle for an even more memorable Halloween experience.
🎃 One Ticket. One District. One Huge Halloween Night. Your wristband gives you access to participating venues across the district, up to 5 complimentary welcome shots and other perks. Choose your own route, bounce from bar to bar and see where the night takes you.
🧡 Bring your friends and save 20% on group tickets of four or more! Tickets are limited and prices go up as we sell out, so get yours early before they're gone.

MANDATORY CHECK-IN BETWEEN 5PM–8PM: 📍 La Concha Key West, Autograph Collection — 430 Duval St, Key West, FL 33040

WHAT'S INCLUDED 🔶 Up to 5 Complimentary Welcome Shots/Treats – Redeem at the bars of your choice (limit 1 per venue) 🔶 Signature Halloween Drink Specials – Curated for the occasion 🔶 Free Cover – At all participating venues (no re-entry at some locations) 🔶 Professional Event Photography – You bring the look, we’ll capture the moment 🔶 Instagram Costume Contest – Post your look, tag us, and win

HOW IT WORKS 1. Check in between 5–8PM at La Concha Key West, Autograph Collection. 2. Collect your wristband, bar map and event perks. 3. Choose your route and crawl in your own time, there is no set schedule. 4. Sip, dance, mingle, repeat. It’s your Halloween, your way.
 For updated participating bars &amp; restaurants please click on link below <a href="https://www.eventbrite.com/cc/halloween-bar-crawls-2026-key-west-fl-4868829" rel="nofollow noopener" target="_blank">eventbrite.com/cc/halloween-bar-crawls-2026-key-west-fl-4868829</a>
 COSTUME CULTURE 👻 You don’t need to go full theatrical, but this night is about the look. Make it iconic, creative, stylish - or simply bold. 📸 Post your best shot on Instagram and tag @downtowncrawlers to enter the contest. Winners will be announced the week after the crawl.Happens on the following Dates: Oct 30, 2026, 5:00pm to Oct 31, 2026, 12:00am Timezone: Eastern Time (US &amp; Canada) Oct 31, 2026, 4:00pm to 11:30pm Timezone: Eastern Time (US &amp; Canada)<a href="https://eventvesta.com/events/166426/t/tickets" target="_blank" rel="nofollow noopener">View Tickets &amp; More Info</a>

Local Event: Halloween Bar Crawls 2026 - Key West, FL

Halloween Bar Crawls 2026 - Key West, FL

Celebrate Halloween at the best bars across Duval Street with welcome shots/treats, drink specials and more.
Key West's...

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Fantasy Fest Spooky Trivia - Southernmost Beach Resort

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