Islamorada Calendar Events

  • 11/21/2019 Morada Way Arts & Cultural District presents: Third Thursday Art Walk
    on January 1, 1970 at 12:00 am

    Showcasing the fine arts, music and culinary nuances of the Purple Isles, the Morada Way Arts & Cultural District features national and local artisans who are showcased in galleries at Morada Way between mile marker 81 and 82, as well as "culinary art" and live music from 6-9 p.m. A great pre-holiday celebration. Free admission. Art Walk is held the third Thursday of each month.

  • 11/30/2019 Free Outdoor Pops-in-the-Park Band Concert: Leftover Turkey Tunes
    on January 1, 1970 at 12:00 am

    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.

  • 12/5/2019 - 12/8/2019 Islamorada Sailfish Tournament
    on January 1, 1970 at 12:00 am

    The first leg of the triple-crown Florida Keys Gold Cup Championship series is the only tournament in the series to offer a junior division for anglers age 16 and younger. Unlimited anglers are allowed per vessel.

  • 12/6/2019 Islamorada Chamber of Commerce Florida Keys Holiday Festival
    on January 1, 1970 at 12:00 am

    Kids can frolic in a magical 30-ton snow mountain during the event at Founders Park, mile marker 87, and watch the lighting of a 35-foot-tall community tree. Parents can bid on one-of-a-kind Keys-designed ornaments during a silent auction and explore a gift bazaar. Other activities include caroling and a holiday parade.

  • 12/8/2019 Fifth Annual Islamorada Half Marathon and 10K
    on January 1, 1970 at 12:00 am

    Winter distance runners in the Florida Keys can welcome warmer climes and the return of Islamorada's annual Half Marathon, 10k and the run-for-fun Beach N' Beer Mile. The subtropical road race is open to bucket list runners or newbies of all ages and skill levels. Registration is open for the half-marathon and 10k events Saturday, Dec. 7. At noon the fun-while-you-run Beach N' Beer Mile kicks off from the iconic Robbie's Marina, mile marker 77.5 bayside. The main half-marathon and 10k events Su

  • 12/13/2019 - 12/14/2019 Islamorada Junior Sailfish Tournament
    on January 1, 1970 at 12:00 am

    Recreation for teens in the Florida Keys can mean learning from experienced local captains and mates to tie a bimini or rig ballyhoo. One weekend each year anglers aged 16 and younger can apply such lessons in this competition. A maximum of six anglers is allowed per boat. Proceeds aid Florida Keys charities. This tournament has been held since 1964, one of the oldest sailfish events in the Keys.

  • 12/14/2019 Free Outdoor Pops-in-the-Park Band Concert: Suite Dreams
    on January 1, 1970 at 12:00 am

    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.

  • 12/19/2019 Morada Way Arts & Cultural District presents: Third Thursday Art Walk
    on January 1, 1970 at 12:00 am

    Showcasing the fine arts, music and culinary nuances of the Purple Isles, the Morada Way Arts & Cultural District features national and local artisans who are showcased in galleries at Morada Way between mile marker 81 and 82 - formerly named Industrial Road - as well as "culinary art" and live music from 6-9 p.m. Free admission. Art Walk is held the third Thursday of each month.

  • 12/31/2019 - 1/1/2020 New Year's Eve at Cheeca Lodge & Spa
    on January 1, 1970 at 12:00 am

    For a casually elegant celebration, Cheeca Lodge & Spa, located at MM 82 oceanside, is planning live music and a midnight fireworks display over the Atlantic Ocean. Known for its renowned cuisine and beachside location, Cheeca is an ideal spot for revelers and romantics to ring in 2020. Call for more information about dining and reservations.

  • 12/31/2019 - 1/1/2020 New Year's Eve Celebrations in Islamorada
    on January 1, 1970 at 12:00 am

    Revelers in the Upper Keys' Islamorada can ring in the new year with midnight fireworks on the beach at Morada Bay Beach Café at MM 81.6 bayside, who is to host a colorful large beach party with live music, beach barbecue, signature cocktails, performers and fireworks.

  • 1/3/2020 - 1/4/2020 Fish for Holly Sailfish Tournament
    on January 1, 1970 at 12:00 am

    Created to raise money for Florida Keys scholarships and domestic violence initiatives, this memorial tournament honors the late Holly Given, a Keys resident and avid angler. Participants are to gather at Whale Harbor Marina to compete for top male, female and junior angler awards as well as top offshore, bay boat and fun fish categories.

  • 1/7/2020 - 1/9/2020 Florida Keys Outfitters SailFly Tournament
    on January 1, 1970 at 12:00 am

    This time of year the weather is ideal for a hot Atlantic sailfish bite. Enter for a chance to compete in one of the toughest and most exciting angling events of the year. For info visit floridakeysoutfitters.com and search "Sailfly entry" or visit the facebook.com/floridakeysoutfitters events tab.

  • 1/9/2020 - 1/19/2020 ‘Uncorked,’ the Key Largo Food and Wine Festival
    on January 1, 1970 at 12:00 am

    Experience the fabulous restaurants of Islamorada, and don't miss the festival highlight at Postcard Inn Beach Resort & Marina scheduled for Saturday January 18, 2020. The Grand Tasting is a multi-sensory experience not to be missed. Area restaurants and wine experts will come together to present samples of their finest cuisine and world-class wines. Live music, celebrity chef appearances and cooking demos combine to serve up the recipe for a spectacular afternoon of tasting in the fabulous Flor

  • 1/17/2020 - 1/19/2020 8th Annual Baygrass Bluegrass & Craft Beer Festival
    on January 1, 1970 at 12:00 am

    Flavorful traditional bluegrass, old-time, "soulgrass" and Americana singing bands are to attract thousands of music lovers The three-day jam features satellite events at local spots and culminates in an all-day main event in a waterfront setting. Friday includes a weekend warmup with performing musicians, barbecue and a craft beer; Saturday features live music popups; Sunday at Founders Park, MM 87 bayside on Plantation Key, the weekend's main event is as much a craft beer festival as a musical

  • 1/18/2020 Free Outdoor Pops-in-the-Park Band Concert: What a Wonderful World
    on January 1, 1970 at 12:00 am

    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.

  • 1/20/2020 - 1/21/2020 31st Annual Al Flutie Over the Hill Rip-Off Sailfish Tournament
    on January 1, 1970 at 12:00 am

    Dubbed "almost too much fun for old guys to handle," the tournament is locally referred to as the Flutie, welcomes anglers age 50 and over. Proceeds benefit "Catch the Cure" for Cystic Fibrosis and the Monroe Association for ReMARCable Citizens, providing life services to Monroe County's adult intellectually disabled residents.

  • 1/24/2020 - 1/26/2020 Cheeca Lodge Presidential Sailfish Tournament
    on January 1, 1970 at 12:00 am

    Second in the Gold Cup series. Anglers put 20-pound line and light-tackle skills to the test during the two-day challenge against the high-flying acrobatic fish, known for tail-walking the waves. Only circle hooks can be used. "The Presidential" typically awards sophisticated sculpture trophies to top anglers who release the most sailfish.

  • 1/29/2020 - 1/30/2020 IFC Sailfish Tournament
    on January 1, 1970 at 12:00 am

    Presented by the Islamorada Fishing Club, the event is the last leg this year of the three-pronged Florida Keys Gold Cup Championship series and typically draws a field of up to 30 boat teams of elite sport fishermen. Kickoff is 1/29 and fishing day is 1/30. A total cash payout for a full field at the IFC Sailfish Tournament could reach $30,000.

  • 1/31/2020 - 2/1/2020 Swamp Guides Ball
    on January 1, 1970 at 12:00 am

    Sponsored by the Florida Keys Fishing Guides Association, this all-release event offers team and individual awards to anglers for bonefish, redfish and snook. Anglers fish the shallows of the Florida Keys and the saltwater fringes of the Everglades. Social events are to be headquartered at the Lorelei Restaurant & Cabana Bar.

  • 2/4/2020 - 2/5/2020 Poor Girls Sailfish Tournament
    on January 1, 1970 at 12:00 am

    This regional charity competition raises monies to spay and neuter feral cats in the Upper Keys. Trophies are awarded to first-, second- and third-place teams, grand champion and runner-up grand champion anglers as well as for the largest dolphin fish, kingfish and tuna, among others.

  • 2/7/2020 - 2/9/2020 Islamorada Women's Sailfish Tournament
    on January 1, 1970 at 12:00 am

    In this light-tackle challenge, awards await the grand champion team (boat), first runner-up and second runner-up team, captain and mate. Other awards are presented for the high-point angler; outstanding catch; largest tuna, dolphin fish; kingfish; and hard luck. Proceeds benefit Keys charities.

  • 2/9/2020 - 2/10/2020 Islamorada Bartenders Sailfish Open
    on January 1, 1970 at 12:00 am

    Headquartered at the Lorelei Restaurant & Cabana Bar, this fun fishing event is only for actively employed bartenders and restaurant employees. Trophies are awarded to individual anglers as well as the bar a team represents, with the huge perpetual trophy going to the winners along with bragging rights for the year.