Calendar of Events
Current Islamorada Events
- Sponsored Event
- Mar 29, 2025 - Mar 30, 2025 Key West
- NAS Key West Southernmost Air Spectacular
- Website Boca Chica Field, Key West
- Naval Air Station Key West FL 33040
- NAS Key West E-mail
- View video
- The Blue Angels & other military & civilian acts will fill the skies of the Florida Keys March 29-30th, at the NAS Key West Southernmost Air Spectacular air show at Boca Chica Field.
- Buy tickets!
- Sponsored Event
- Nov 18, 2024 - Dec 30, 2024 Key West
- Waterfront Winter Wonderland
- Website
- 21 Quay Rd Key West FL 33040
- Liz Love E-mail
- Enjoy Visits with Santa, live music performances, and festive celebrations throughout the season! Home to Key Wests only ice rink, we will also have thrilling carnival rides and fun for the whole family at Waterfront Winter Wonderland!
- Buy tickets!
- Sponsored Event
- Jan 18, 2025 - Jan 19, 2025 Key West
- Key West Half Marathon & Runfest
- Website Key West Historical Seaport
- 231 Margaret Street Key West FL 33040
- 305-240-0727 E-mail
- View video
- The 27th Anniversary of the Key West Half Marathon & 5k will take place during the week-end of January 18-19, 2025. On top of previous years race day events, this years race will include the Papa’s Pilar Rum Stroll and Key West Beach N’ Beer Mile!
- Buy tickets! Call now!
- Sponsored Event
- Jan 25, 2025 - Jan 26, 2025 The Lower Keys
- Big Pine & Lower Keys Nautical Expo
- Website Lower Keys Chamber Grounds MM31
- 31020 Overseas Hwy Big Pine Key FL 33043
- View video
- The LKCC welcome you Saturday Jan 25 8am-4pm and Sunday Jan 26 8am-2pm to one of our biggest events with over 100 vendors. This event is fun for the whole family and includes an array of nautical pieces and much more that makes Florida Keys living great
- Sponsored Event
- Dec 01, 2024 - Dec 23, 2024 Key West
- Key West Holiday Fest 2024
- Website Key West
- The Key West Lodging Association 305-296-4959 E-mail
- Key West Holiday Fest 2024 offers a month of festive tropical fun! Enjoy lighted parades, inn tours, concerts, holiday shows, and the Waterfront Winter Wonderland with ice skating, rides, and more. Events run Nov. 27–Dec. 31.
- Buy tickets! Call now!
- May 17, 2024 - Dec 31, 2024 Islamorada Arts & Culture
- History of Diving Museum: Salvaging the Deep
- Website
- Learn about some of the world's deepest wrecks and how salvage divers got there in the museum's featured exhibit, on display through Dec. 31. Mile marker 82.9.
- Dec 1, 2024 - Jan 5, 2025 Islamorada Arts & Culture
- The Protect Center: Sea of Trees
- Website
- Over 100 uniquely decorated and sponsored trees light your way nightly from 10 a.m. to 6 p.m. daily from Nov. 29 through Jan. 5. In addition to the beautiful lights and trees, you'll find photo opportunities and shopping. On these select nights - Nov. 29, 30; Dec. 1, 6, 7, 13, 14, 20, 21, 22 from 6 to 9 p.m. - enjoy Santa's Village with holiday-themed cocktails and snacks, workshops for kids and visits with Santa. Admission of $10 adults; $5 kids supports the Dolphin ICU at The Protect Center. MM 82 bayside.
- Dec 14, 2024 Islamorada Arts & Culture
- Florida Keys Community Concert Band: Pops in the Park Holiday Harmony
- Website
- The Florida Keys Community Concert Band's free holiday concert is to include the Burton Handbell Ringers as special musical guests. Enjoy holiday favorites, sing alongs, snow ball games and a visit from Santa. From 5 to 7 p.m. at the amphitheater in Founders Park, MM 87 bayside.
- Dec 14, 2024 - Dec 15, 2024 Islamorada
- Islamorada Half Marathon & 10K; Rumrunner 10K & 5K; and Beach N' Beer Mile
- Website
- Participants of all ages and skill levels participate in these popular annual subtropical footraces to be hosted at the newly renovated and rebranded Three Waters Resort (formerly Postcard Inn). Saturday's Rumrunner 5k and 10k races start at 8 a.m., followed by the Beach 'n Beer Mile "fun run" at noon. The Islamorada Half Marathon and 10k races start at 7 a.m. Sunday as the sun rises.
- Dec 18, 2024 Islamorada Arts & Culture
- History of Diving Museum: Merry Divemas
- Website
- Dive into some holiday fun at the museum from 5:30 to 7 p.m. Bring the family for cookie decorating, ornament making, festive snacks and photos with Santa Claus! The event is free but donations are appreciated. The event is to be followed by an Immerse Yourself presentation at 7 p.m. about the Journey of the Christ of the Deep statue.
- Dec 19, 2024 Islamorada Arts & Culture
- Morada Way Third Thursday Art Walk
- Website
- The Morada Way Arts & Cultural District’s Third Thursday Art Walk in Islamorada is the organization’s landmark, monthly event. This Thursday, enjoy a holiday-flavored edition of the art walk with Keys-inspired fine artists, vendors, residents, and visitors congregating on Morada Way in Islamorada. Enjoy a relaxing evening from 6-9 p.m. perusing local fine art, imbibing local craft beer and wine and listening to music, in the area between mile markers 81 and 82.
- Dec 19, 2024 Islamorada Fishing
- Papa Joe's: Premier of George Poveromo's Episode with Past Pantaleo
- Website
- Catch a special airing of George Poveromo’s World of Saltwater Fishing at Papa Joe’s Waterfront on December 19 at 6:30 p.m. The premier episode, from his upcoming 2025 season on Discovery, features Poveromo and Islamorada artist Pasta Pantaleo chasing and catching mahi-mahi offshore of Islamorada. George Poveromo and Pasta will both be on hand to emcee the airing and socialize with the audience along with other angling personalities. 79786 Overseas Hwy. bayside.