Islamorada Calendar Events

  • 2/22/2020 - 2/23/2020 Upper Keys Gigantic Nautical Flea Market
    on February 22, 2020 at 4:29 pm

    Find hundreds of marine- and watersports-related vendors offering wares to thousands of buyers seeking deals on new and used boats, marine equipment, electronics, fishing tackle, dive gear, nautical arts and crafts, and more. Located at Founders Park, MM 87 bayside, on Plantation Key. Saturday hours 8AM - 5PM, Sunday 9AM - 3PM. Free Parking at Coral Shores High School. Admission donation $5 for 18 and above.

  • 2/22/2020 'Trolley Through Time' with Matecumbe Historical Trust
    on February 22, 2020 at 4:29 pm

    Join us for a colorful and much acclaimed historical tour on the islands of Islamorada.  Enjoy an enlightening trolley ride through time. First tour starts at 10 a.m. from the Whale Harbor Restaurant, 83413 Overseas Highway.  A monitor is located at the front of the trolley showing over 90 photos of the past as you see them today. Tours take approximately one hour.  Call for reservations, seating is limited. Adults are $20, children six and under are free. 

  • 2/25/2020 Florida Keys Concert Association presents: Lincoln Trio
    on February 22, 2020 at 4:29 pm

    Grammy-nominated Chicago-based Lincoln Trio is made up of Desiree Ruhstrat, violin, David Cunliffe, cello, and Marta Aznavoorian, piano, and was chosen to celebrate the Abraham Lincoln Bicentennial celebration with President Barack Obama. They will delight sophisticated music lovers, young admirers of contemporary programs and students discovering chamber music for the first time. Performance at Island Community Church. Performance 7:30 p.m. Tickets online.

  • 2/28/2020 - 2/29/2020 Costa Backcountry Fly Championship Series
    on February 22, 2020 at 4:29 pm

    Tournament anglers are to compete to catch the most inches of snook and redfish on fly in a challenge where 1 inch equals one point. Awards are to be given to the grand champion and runner-up, and to the anglers who catch the largest snook and redfish. The field is limited to 30 boats.

  • 2/29/2020 Free Outdoor Pops-in-the-Park Band Concert: Wild Kingdom
    on February 22, 2020 at 4:29 pm

    Florida Keys Community Concert Band Presents its 2019-2020 season at Islamorada Founders Park, Bayside, MM 87, Plantation Key. Performances are outdoors; no chairs provided. Starts at 4:00 p.m. Admission free for all concerts.

  • 2/29/2020 'Trolley Through Time' with Matecumbe Historical Trust
    on February 22, 2020 at 4:29 pm

    Join us for a colorful and much acclaimed historical tour on the islands of Islamorada.  Enjoy an enlightening trolley ride through time. First tour starts at 10 a.m. from the Whale Harbor Restaurant, 83413 Overseas Highway.  A monitor is located at the front of the trolley showing over 90 photos of the past as you see them today. Tours take approximately one hour.  Call for reservations, seating is limited. Adults are $20, children six and under are free. A pop-up shop will provide information,

  • 3/3/2020 Florida Keys Concert Association presents: An Evening of Opera Highlights
    on February 22, 2020 at 4:29 pm

    A cast of great singers with piano accompanist, will delight your ears and heart with wonderful arias and duets from your favorite operas.  FLKCA's opera highlights evenings are among the most highly anticipated events of the season. Performance at Island Community Church. Performance 7:30 p.m. Tickets online.

  • 3/4/2020 Keys History & Discovery Center presents: Winter Lecture Series
    on February 22, 2020 at 4:29 pm

    This week's topic, Above & Beyond: JFK and the Florida Pilots During the Cuban Missile Crisis, is to be presented by Author Michael Tougias. Doors open at 5:30 p.m., with cash bar and snacks. Lecture is 6-7 p.m., including time for questions. Lecture series runs October through May.

  • 3/6/2020 'Buckles and Boots' Annual Cocktail Party, Habitat for Humanity of the Upper Keys
    on February 22, 2020 at 4:29 pm

    "Buckles and Boots" means a casual flair for the evening, from 6:30 p.m. until 10 p.m. at the Islander Resort Conference Center, Islamorada, mile marker 82. Tickets for the cocktail party are $250 per couple or $150 per person. This year, the special guest speaker is Grammy-award-winning singer, songwriter and actor Huey Lewis. A long-time supporter of Habitat for Humanity, he hopes this cocktail party will exceed previous years' revenues for the fundraiser and make a significant contribution

  • 3/19/2020 Morada Way Arts & Cultural District's Third Thursday Art Walk
    on February 22, 2020 at 4:29 pm

    Third Thursday ArtWalks are held every month throughout the year, offering attendees live music, food and, of course, original art and hand-crafted jewelry, as well as pottery, sculptures and more! This monthly event, from 6-9 p.m., is a focal point of artistic expression, culinary and cultural awareness to the Upper Keys. Stroll through the Art District, sip some craft beers, eat local food, along a quarter-mile span of the Old Highway between the historical 1935 Hurricane Monument and the ico

  • 3/21/2020 Windley Key Day
    on February 22, 2020 at 4:29 pm

    Celebrate the 85th anniversary of the Florida Park Service with fun activities all day. Free Entry into the park and activities all day include breakfast and lunch by Craig's Food Truck, raising money for the Friends of the Islamorada Area State Parks, native plant giveaways, trail game, ranger hikes, fishing activities, live animal presentations and more. From 9 a.m. to 3 p.m. at Windley Key Fossil Reef Geological State Park.

  • 3/22/2020 5th Annual Islamorada Moose Lodge Seafood Fest & Art Show
    on February 22, 2020 at 4:29 pm

    Featuring delicious fresh seafood samplings from top restaurants, libations, local craft beers, local fine artist, family fun activities and continuous music. A family and dog friendly event. Proceeds benefit Moose charities. Event is held from 11 a.m. to 5 p.m. at the Islamorada Moose Lodge, 81573 Old Highway.

  • 3/28/2020 - 3/29/2020 29th Annual Florida Keys Island Fest
    on February 22, 2020 at 4:29 pm

    Music, art, food and fun complement this annual art show with nearly 100 artists and crafters, live music and a "Taste of the Islands" foodie competition. Free admission, festival hours are 10 a.m. to 5 p.m. at Founder's Park, mile marker 87 bayside on Plantation Key. On-site parking for a $5 donation. Sponsored by the Islamorada Chamber of Commerce.

  • 4/5/2020 BayJam 26
    on February 22, 2020 at 4:29 pm

    This music and art festival features local and guest artists performing on the shores of Florida Bay at the ICE Amphitheater at Founders Park, mile marker 87 on U.S. 1. Attendees can savor the sounds from 11 a.m. to 8 p.m. from the hammock-like performance center set against the aqua waters of Florida Bay. Admission is $10 donation, $5 for students with ID. Proceeds go to Keys' student art and music scholarships. Seniors and kids under 17 admitted free.

  • 4/24/2020 - 4/26/2020 Redbone @ Large Sunrise/Sunset Tarpon Tournament
    on February 22, 2020 at 4:29 pm

    The Upper Keys competition is one of dozens of fishing events held each year whose proceeds benefit the Cystic Fibrosis Foundation.

  • 4/25/2020 Free Outdoor Pops-in-the-Park Band: Young Musicians Concert
    on February 22, 2020 at 4:29 pm

    Florida Keys Community Concert Band Presents its 2019-2020 season finale at Islamorada Founders Park, Bayside, MM 87, Plantation Key. Performances are outdoors; no chairs provided. Starts at 4:00 p.m. Admission free for all concerts.

  • 4/26/2020 - 4/29/2020 Herman Lucerne Memorial Tarpon Cup
    on February 22, 2020 at 4:29 pm

    For those who have always wanted to fish one of the classics, but couldn't wrangle an invitation, this is an old-school, 'downtown Islamorada' kind of tournament. True to the Herman Lucerne spirit of inclusiveness, the Tarpon Cup includes both a Guided and Unguided division. Limited to 20 teams, registration will open in October 2019. Organizers hope the HLM Tarpon Cup will soon be regarded as one of the classic parts of the Spring Florida Keys fishing tournament schedule.

  • 5/1/2020 - 5/3/2020 Nick Sheahan Dolphin Rodeo
    on February 22, 2020 at 4:29 pm

    A tournament honoring the memory of Nick Sheahan, a Florida Keys student, funds from this event benefit a namesake community scholarship fund. Hosted at Tavernier Creek Marina, cash prizes and $25,000 to the angler with the dolphin that beats the state record. Hosted at Tavernier Creek Marina, entry fee for adults is $185, $50 for juniors.

  • 5/18/2020 - 5/20/2020 Golden Fly Invitational Tarpon Tournament
    on February 22, 2020 at 4:29 pm

    Special flies, skillful, accurate casts and a bit of luck are the recipe to win this prestigious challenge limited to 25 anglers. Competitors use a tournament-furnished tippet not greater than 16-pound test. Eligible tarpon must weigh at least 70 pounds to score weight points.