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Hidden Gems around the Florida Keys in October

October 2023

Discover the Hidden Gems and Upcoming Events in the Florida Keys This Fall

Whether you live in town or are just here visiting, it’s always fun to explore the unique blend of natural beauty and local culture that the Florida Keys have to offer. From snorkeling in the crystal-clear waters to enjoying a slice of key lime pie at a waterfront café, there’s no shortage of memorable moments waiting to be made. Why not dive into the community events and enjoy the islands a bit more!

Colorful fish swim in tropical coral reef generated by artificial intelligence

REEF FEST | October 19 – October 22 2023

A Celebration of Marine Conservation

“Calling all ocean lovers! Join us for diving, snorkeling, kayaking, educational ocean presentations, and more. Explore the marine life of the Florida Keys, learn from ocean experts, and celebrate marine conservation.”

Website – Click Here for More Information

Fantasy Fest

October 20 – October 29

If you have never been to this event, be prepared to be engulfed with free spirits. This 10 day costuming and masking celebration allow individuals to show off their most eccentric attire. With over 30 cleverly themed parties and performances this is a Halloween for the adults. This years theme is Uniforms and Unicorns.

WEBSITE – Click Here for more information

Key West Museum of Arts & History : Pon Pinder – Eyes on the Island

July, 14 – November 5
Located at 281 Front Street, Key West

This is the inaugural showcase focusing solely on the life’s work of Don Pinder, a renowned photographer for the Key West Citizen from 1925-2003. The exhibit, running until November 5th, features over 50 captivating photographs—both in black-and-white and color—that span Pinder’s 35-year journey capturing the essence of Key West’s history and vibrant culture. Open daily from 10 a.m. to 5 p.m.

Richard O’Brian’s Rocky Horror Show

October 5, 2023 – October 21, 2023
Marathon Community Theatre | 5501 Overseas Highway, Marathon

Tickets are $33 Dollars

Website | More Information

Islamorada All Tackle Bonefish and Permit Championship

October 9, 2023 – October 11, 2023

Fall-All-Tackle | This 3-day challenge attracts all levels to this 2-day fishing tournament. This tournament has been in place since 1970. There is one angler per boat. Trophies for the three longest bonefish and three of the longest permit.


Stock Island Animal Farm Open House @ the Sheriff’s Office

October 8, 2023
Located at 5525 College Road, Stock Island

Come visit the animals at the farm for a day of fun! They have miniature horses, pigs, goats, bunnies, alligators, lemur, alpaca, and more. This event is FREE of charge.

Facebook –

24 North Hotel | Paint & Sip Night with Local Artist Lance Berry

October 10, 2023
24 North Hotel – 3820 N. .Roosevelt Boulevard, Key West

$40 per ticker includes your first drink, plus all of the art supplies and instructions youll need to create your own masterpiece.

Ladies Let’s Go Fishing! Keys Salt Water Weekend Seminar & Fishing Fever Inshore/Offshore Tournament

October 13, 2023 – October 15, 2023
Contact Bettey Bauman 954- 475-9068

More Information

Men and women helped to collect garbage in a black bag.

Stock Island Cleanup and Community Day

October 14, 2023
6751 5th Street, Stock Island | 10:00 AM – 2:00 PM

Music, Crafts, Food, Silent Auction, and Booths showcasing environmentally- minded organizations. Group cleanup teams are invited to register in advance to spend the morning cleaning up locations around Stock Island. | WEBSITE

Pirates of the Conch Republic

October 23, 2023
512 Eaton Street, Key West

Starts @ 8:00 PM The search for the Bodacious Booty – a burlesque parody

Tickets & More Information

407 Wallstreet, Key West, FL

Waterfront Playhouse : Richard Rocky Horror

October 18 – October 27, 2023
407 Wall Street at Mallory Square – Key West

More Information | Buy Tickets

Underwater Pumpkin Carving

October 28, 2023
Amoray Dive Resort 800-426-6729

Carving theme is Mermaids and Sailors. Entry Fee is $115 per certified diver for the 1:00 pm dive trip. | WEBSITE

Presented by the Florida Keys Home Team

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Taylor Engel

Florida Native, living in the Florida Keys for over 20 years! Realtor, Property Manager, Animal Lover, & Consultant for Rodan + Fields Skincare!

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