Karaoke at Bobby’s Monkey Bar
Enjoy a vibrant evening of karaoke at Bobby's Monkey Bar in Key West's Old Town. This lively venue features talented local entertainers who bring excitement…
21 events found.
Events for May 20, 2026
Ongoing
Simonian Wolf at Irish Kevin’s Bar
Simonian Wolf captivates audiences at Irish Kevin's Bar with their charismatic presence and multifaceted talents. Known for their passion for innovation and creative problem-solving, they…
Free
Fishmonster Max- Daily Party Boat Fishing
Join the Fishmonster Max daily party boat fishing excursion at A & B Marina in Key West's historic seaport. While the details of the entertainer…
$85.00
Yoga on the Beach – Ft Zachary Taylor
Join a rejuvenating Yoga on the Beach session at Fort Zachary Taylor State Park in Key West. While the serene setting offers historic charm and…
$20
Aqua Yoga at Southernmost Beach Resort
Aqua Yoga at Southernmost Beach Resort offers a serene experience led by an expert yoga instructor. Immerse yourself in tranquility as you practice yoga in…
$20
Oren Polak at Irish Kevin’s Bar
Oren Polak captivates audiences at Irish Kevin's Bar with his versatile music and charismatic stage presence. Known for delivering Music for Everyone, Everywhere, his performances…
Free
Mojito Class by Key West Legal Rum Distillery – Min 4 people
Join the Mojito Class at Key West First Legal Rum Distillery, where a charismatic entertainer will guide you through a lively mojito-making experience. Delight in…
$75.00
Distillery Tour – Key West Legal Rum Distillery
Explore the Key West First Legal Rum Distillery, nestled in the Historic Seaport. Delight in daily tours and rum samples while embracing vibrant nightlife vibes.…
Free
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Join the Glass Bottom Boat Cruise in Key West for an unforgettable journey beneath the sea. While soaking in vibrant marine life through crystal-clear waters,…
$69.95
Wednesday Filet Day at Mary Ellen’s
Mary Ellen's Wednesday Filet Day is a must-visit in Old Town Key West, where the lively atmosphere pairs perfectly with live music from talented local…
Free
Glass Bottom Boat Cruise – Key West’s Window to the Sea
The Glass Bottom Boat Cruise in Key West offers a unique marine adventure, enhanced by a captivating entertainer who brings the vibrant sea life into…
$69.95
Bradd Shadduck at Irish Kevin’s Bar
Experience the dynamic performance of musician Bradd Shadduck at Irish Kevin's Bar in Old Town Key West. Renowned for engaging live music and audience participation,…
Free
Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise
Experience an unforgettable adventure with Sunset Watersports' Reef Snorkeling, Dolphin Watch Eco Tour, and Sunset Cruise in Key West. Guided by knowledgeable and engaging staff,…
$79.95
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Embark on the Glass Bottom Boat Cruise in Key West for an unforgettable maritime adventure. While the vibrant marine life and crystal-clear waters captivate, it's…
$69.95
World Famous 801 Girls- 5pm Show
Experience the vibrant energy of the World Famous 801 Girls at their 5pm show in Old Town Key West's iconic 801 Bourbon Bar. These talented…
Caribe of Key West at El Meson de Pepes on Mallory Square
Experience the vibrant sounds of Caribe of Key West at El Meson de Pepes on Mallory Square. This family-owned Cuban restaurant enchants guests with live…
Sunset Celebration at Mallory Square
Experience the vibrant Sunset Celebration at Mallory Square, where entertainment takes center stage. Revel in the captivating performances of street entertainers like jugglers and the…
Free
Irish Kevin at Irish Kevin’s Bar
Irish Kevin, a charismatic and fun-loving entertainer, captivates audiences at Irish Kevin's Bar in Key West with his humor and charm. Known for his lively…
Free
Line Dancing at Kaya Island Eats
Kick up your heels at Kaya Island Eats for an unforgettable evening of line dancing. Nestled in Key West, this laid-back venue blends Caribbean culinary…
Free
Karaoke at Bobby’s Monkey Bar
Enjoy a vibrant night of music at Bobby's Monkey Bar in Key West's Old Town. Experience the lively island atmosphere as entertainers bring the karaoke…
Kari Wolf at Irish Kevin’s Bar
Experience the enchanting melodies of Kari Wolf at Irish Kevin's Bar in Key West. This dynamic musician captivates audiences with her soulful performances, creating a…
Free