Sunset Celebration at Mallory Square
2026-03-05 17:00 - 21:00 (America/New_York) | Mallory Square, 1 Whitehead Street, Key West, Florida, 33040, United States
The Sunset Celebration at Mallory Square in Key West is a must-see event. Renowned street performers captivate audiences with their vibrant talents, creating an unforgettable atmosphere. This historic waterfront location transforms with lively acts, local artisans, and delicious food vendors, all set against stunning sunset views, providing an enchanting experience for all ages.

Bria Ansara at Berlin's Cocktail Bar
2026-03-05 18:00 - 21:00 | Berlin’s Cocktail Bar & Lounge, 700 Front Street, Key West, Florida, 33040, United States
Immerse yourself in an unforgettable evening with Bria Ansara at Berlin’s Cocktail Bar. Nestled in Key West’s A&B Lobster House, this hidden gem offers a captivating blend of live jazz by the talented Bria Ansara and vintage ambiance. Indulge in classic cocktails and savor exquisite dishes while soaking in views of the Gulf of Mexico.

Filming Sit with Kit Podcast Episodes
2026-03-05 18:00 - 21:00 | Angelina’s Pizzeria, 208 Duval Street, Key West, Florida, 33040, United States
Join charismatic host Kit in filming Sit with Kit podcast episodes at Angelina’s Pizzeria in Key West. Known for its vibrant energy and engaging conversations, the podcast captures Kit’s unique style and wit. Enjoy a behind-the-scenes experience while savoring delicious NY-style pizza in the heart of Old Town.

Catch The Mania Trivia at Brady's Pub
2026-03-05 19:00 - 21:00 | Brady’s Pub Key West, 1900 Flagler Ave, Key West, Florida, 33040, United States
Join us at Brady’s Pub for Catch The Mania Trivia, hosted by an enigmatic entertainer who promises a night of fun and excitement. Dive into a lively atmosphere filled with challenging questions, laughter, and camaraderie. Enjoy traditional Irish fare and happy hour specials while testing your knowledge in a captivating setting.

Andy's Cabana Open Mic No Mic Night
2026-03-05 19:00 - 22:00 | Andy’s Cabana, 308 Petronia Street, Key West, Florida, 33040, United States
At Andy’s Cabana Open Mic No Mic Night, the real star is the performer who captivates the audience with raw, acoustic talent. In the heart of Key West’s Bahama Village, entertainers deliver authentic, unamplified performances that resonate through the cozy venue, creating an intimate and unforgettable musical experience.

iWITNESS True Crime Walking Tour
2026-03-05 20:00 - 21:30 | iWitness Crime Tour – Meeting Place, 308 Front St - 2nd Floor, Key West, FL, 33040, United States
Join the iWITNESS True Crime Walking Tour and embark on a thrilling journey through Key West’s most notorious crime scenes. Led by an engaging expert witness, the tour brings scandalous stories to life with a perfect blend of intrigue and humor. This unforgettable experience offers unique insights into the island’s murky past.

Karaoke with Foss at RockHouse Live
2026-03-05 21:00 - 2026-03-06 02:00 | RockHouse Live Key West, 404 Southard Street, Key West, Florida, 33040, United States
Experience an unforgettable night of entertainment with Foss at RockHouse Live in Key West. Known for electrifying performances, Foss brings charisma and energy to the karaoke stage, ensuring a lively and engaging atmosphere. Join us for an evening of music, drinks, and fun at this iconic venue.

Karaoke at Bobby's Monkey Bar
2026-03-05 21:30 - 2026-03-06 03:00 | Bobby’s Monkey Bar, 900 Simonton Street, Key West, Florida, 33040, United States
Join the vibrant scene at Bobby’s Monkey Bar in Old Town Key West for an unforgettable karaoke night. The spirited entertainer keeps the energy high, ensuring everyone has a blast. Dive into the lively atmosphere as you sing your heart out amidst a fun-loving crowd. Don’t miss the daily happy hour!

Yoga on the Beach - Smather's Beach
2026-03-06 08:00 - 09:00 | Smathers Beach, S Roosevelt Blvd, Key West, Florida, 33040, United States

Glass Bottom Boat Cruise - Key West's Window to the Sea
2026-03-06 11:30 - 14:00, 2026-03-07 11:30 - 14:00, 2026-03-08 11:30 - 14:00, 2026-03-09 11:30 - 14:00 | Fury Key West- Departure Point 2, 0 Duval St, Key West, FL, 33040, United States
Experience the captivating Glass Bottom Boat tour in Key West, where our knowledgeable captain and crew offer an engaging eco-tour. Enjoy unparalleled views of North America’s only living coral reef and vibrant marine life through special glass windows to the reef. An unforgettable journey exploring Key West’s underwater wonders awaits.

Glass Bottom Boat Cruise - Key West's Window to the Sea
2026-03-06 13:30 - 16:00, 2026-03-07 13:30 - 16:00, 2026-03-08 13:30 - 16:00, 2026-03-09 13:30 - 16:00 | Fury Key West- Departure Point 2, 0 Duval St, Key West, FL, 33040, United States
Experience the magic of Key West’s marine life aboard the Glass Bottom Boat. While our knowledgeable captain and crew guide you on an informative eco-tour, the true star is the vibrant underwater world. Discover the majestic elkhorn coral and over 300 fish species through special windows to the reef, a breathtaking journey usually reserved for divers.

Glass Bottom Boat Cruise - Key West's Window to the Sea
2026-03-06 16:00 - 19:30, 2026-03-07 16:00 - 19:30, 2026-03-08 16:00 - 19:30 | Fury Key West- Departure Point 2, 0 Duval St, Key West, FL, 33040, United States
Experience an unforgettable journey with Glass Bottom Boat – Key West’s Window to the Sea. With an engaging and knowledgeable captain and crew, embark on a captivating eco-tour showcasing Key West’s vibrant marine life through special glass windows. Witness North America’s only living coral reef with over 300 species of colorful fish.

Karaoke at Two Friends Patio
2026-03-07 20:00 - 23:00 | Two Friends Patio Restaurant, 512 Front Street, Key West, Florida, 33040, United States
Experience unforgettable evenings at Two Friends Patio with lively karaoke sessions hosted by charismatic entertainers. Sing your heart out on the open-air patio, soaking in the vibrant atmosphere and engaging with the talented hosts who bring the event to life. It’s a must-visit for music lovers in historic Key West.

Fishmonster Max- Daily Party Boat Fishing
2026-03-08 08:00 - 13:00, 2026-03-09 08:00 - 13:00 | A & B Marina, 700 Front St # 105, Key West, Florida, 33040, United States
Fishmonster Max offers a thrilling daily party boat fishing experience in Key West, perfect for families and groups. With its stable twin hulls, the boat ensures a smooth, comfortable ride. Dive into the fun-filled fishing adventure where every trip feels like a celebration at sea, creating unforgettable memories.

Distillery Tour - Key West Legal Rum Distillery
2026-03-08 11:00 - 17:00, 2026-03-09 11:00 - 17:00 | Key West First Legal Rum Distillery, 107 Simonton Street, Key West, Florida, 33040, United States
Experience an engaging distillery tour at Key West Legal Rum Distillery, featuring a skillful entertainer who brings the history and craft of rum making to life. Enjoy free tastings of unique, vegan-friendly spirits made on this historic site, as well as lessons in mojito making, all amidst the charming Key West seaport. Free tours every 30 minutes and tours last about 15 minutes.

Mojito Class by Key West Legal Rum Distillery - Min 4 people
2026-03-08 11:00 - 17:00, 2026-03-09 11:00 - 17:00 | Key West First Legal Rum Distillery, 107 Simonton Street, Key West, Florida, 33040, United States
There is a minimum of 4 people. Please contact mojitoclass@gmail.com to schedule. Please put how many people and date in the subject line. Join Key West Legal Rum Distillery’s Mojito Class led by Crystal Menta. Having sailed to Cuba and back, Crystal shares the secrets of crafting the perfect mojito. Enjoy mixing and muddling in this interactive session, complete with a mojito tumbler, muddler, and bar spoon. A must-do Key West experience!

Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise
2026-03-08 15:00 - 18:30 | Sunset Watersports – 201 Williams St, 201 William Street, Key West, Florida, 33040, United States
Join us for a vibrant aquatic adventure in Key West with our Reef Snorkeling, Dolphin Watch Eco Tour, and Sunset Cruise. Our passionate and friendly staff are the heart of the experience, guiding you through mesmerizing dolphin encounters and breathtaking snorkeling. As the sun sets, unwind with a refreshing drink on our luxurious vessel.
