Islamorada events 2026 to 2027, with the organizers’ dates

Islamorada’s calendar is short: a few Village and Chamber events at Founders Park, a monthly art walk, a free museum talk and a winter run of sailfish tournaments. Every date below is the one its organizer posted when we checked on Wednesday, October 21, 2026. Where a date shows up only on someone else’s page, we say it is not confirmed. To see what falls on a given day, and which fishing seasons are open then, use the checker.

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What's open, in season or on in Islamorada on this date?

Pick a date. We check it against the published rules and schedules: FWC's recreational seasons for the fish and shellfish people come here for, the lobster and stone crab seasons, dated events from their organisers, and hurricane season.

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Dated events coming up

1. WedNov 18

   History of Diving Museum "Immerse Yourself!" talk, 3rd Wednesday 7pm · 7 pm

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2. ThuNov 19

   Morada Way Art Walk, third Thursday 6 to 9pm · 6 to 9pm

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3. WedDec 16

   History of Diving Museum "Immerse Yourself!" talk, 3rd Wednesday 7pm · 7 pm

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4. ThuDec 17

   Morada Way Art Walk, third Thursday 6 to 9pm · 6 to 9pm

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5. WedJan 20

   History of Diving Museum "Immerse Yourself!" talk, 3rd Wednesday 7pm · 7 pm

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6. ThuJan 21

   Morada Way Art Walk, third Thursday 6 to 9pm · 6 to 9pm

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The published seasons and schedules this checker uses

• Spiny lobster regular season OPEN: FWC's regular spiny lobster season runs August 6 to March 31, with a daily bag limit of 6 per person. Outside it, lobster is closed except during the two-day sport season. FWC: Spiny Lobster recreational regulations
• Spiny lobster sport season (mini season) 2027: FWC lists the 2027 sport season as Wednesday and Thursday, July 28 and 29, 2027, for residents and non-residents. FWC: Spiny Lobster recreational regulations
• Stone crab claws OPEN: FWC's state-waters season is open October 15 to May 1 and closed from May 2. Claw minimum 2 7/8 inches; 1 gallon of claws per person or 2 gallons per vessel a day, whichever is less. FWC: Stone Crab recreational regulations
• Snook harvest CLOSED, Southwest region incl. the Keys: FWC's Southwest region, which takes in the Keys, closes snook harvest December 1 to the end of February and May 1 to September 30. When open: a 28 to 33 inch slot and 1 fish per person per day. FWC: Snook recreational regulations
• Atlantic shallow-water grouper OPEN (black, red, scamp, yellowfin, yellowmouth, hinds, coney, graysby): Under FWC's Atlantic rules (black, red, scamp, yellowfin and yellowmouth grouper, hinds, coney and graysby) the season is May 1 to December 31, so these grouper are closed January 1 to April 30. FWC: Groupers recreational regulations
• Atlantic gag grouper OPEN: FWC lists the Atlantic gag grouper season as May 1 to August 1 and closed Atlantic state waters to recreational gag from August 2 by executive order. FWC: Groupers recreational regulations
• Hogfish OPEN (Atlantic rules, incl. Florida Keys): FWC's Atlantic hogfish rules include the Florida Keys: open May 1 to October 31, 16 inch fork length minimum, 1 per harvester. FWC: Hogfish recreational regulations
• Mutton snapper OPEN year-round (Atlantic): FWC lists Atlantic mutton snapper as open year-round: 18 inch total length minimum, 5 per person within the 10-snapper aggregate. FWC: Snappers recreational regulations
• Tarpon: catch-and-release only, all year: Catch and release all year. FWC says a tarpon over 40 inches must stay in the water unless the angler is pursuing a record with a tarpon tag ($51.50 a year). FWC: Tarpon recreational regulations
• Bonefish: catch-and-release only, all year (peak March to October): Catch and release only since September 1, 2013 (FWC). FWC says bonefish can be caught year-round in the Keys, with peak season generally March through October. FWC: Bonefish
• Atlantic hurricane season: June 1 to November 30 every year (NOAA National Hurricane Center). Trips, tournaments and events can be called off at short notice. NOAA National Hurricane Center: Tropical Cyclone Climatology
• Morada Way Art Walk, third Thursday 6 to 9pm: Every third Thursday of the month, 6 to 9 PM, on Morada Way (Morada Way Arts and Cultural District). Morada Way Arts & Cultural District: Art Walk Information
• History of Diving Museum "Immerse Yourself!" talk, 3rd Wednesday 7pm: "Immerse Yourself!" talks on the third Wednesday of every month at 7 PM, free, at 82990 Overseas Highway (History of Diving Museum). History of Diving Museum: home page
• 22nd Annual Islamorada Holiday Fest: Friday, December 4, 2026, 4 to 10 PM on the Great Lawn at Founders Park, with the parade at 7:30 PM (Islamorada Chamber of Commerce). Islamorada Chamber of Commerce: Holiday Fest 2026
• 63rd Islamorada Sailfish Tournament: Fishing days Saturday and Sunday, December 5 and 6, 2026; festivities begin Friday, December 4 (the tournament). Islamorada Sailfish Tournament: home page
• 9th Fish for Holly Sailfish Tournament: January 8 and 9, 2027, based at the Islander Resort (the tournament). Times were not posted when we checked. Fish for Holly Sailfish Tournament: Tournament page
• 35th Annual Island Fest: Saturday and Sunday, April 10 and 11, 2027, 10 AM to 5 PM at Founders Park (Islamorada Chamber of Commerce). Islamorada Chamber of Commerce: Island Fest
• 8th Annual Trunk or Treat: Saturday, October 24, 2026, 6 to 8:30 PM at Founders Park; the Village lists a $15 parking fee. Islamorada, Village of Islands: 8th Annual Trunk or Treat (News Flash, Oct. 1, 2026)

Worked out from rules and schedules checked October 21, 2026, on each agency's or organiser's own page. Fishing rules change, sometimes at short notice: check FWC's current regulations (and the Florida Keys National Marine Sanctuary rules on the water) before every trip. This checker is a planning aid, not a legal statement of the rules.

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Coming up: October to December 2026

Trunk or Treat: Saturday, October 24, 2026

The Village says its 8th Annual Trunk or Treat runs from 6:00 to 8:30 p.m. at Founders Park, 87000 Overseas Highway, with a $15 parking fee. Its notice lists a costume contest, an obstacle course, pumpkin decorating and a DJ. Details: the Village news flash.

• The Village says its 8th Annual Trunk or Treat is Saturday, October 24, 2026, 6:00 to 8:30pm at Founders Park, with a $15 parking fee. Islamorada, Village of Islands: 8th Annual Trunk or Treat (News Flash, Oct. 1, 2026)
• The Founders Park Rules page gives the address 87000 Overseas Highway, Islamorada FL 33036. Islamorada, Village of Islands: Founders Park Rules

Morada Way Art Walk: every third Thursday

The Morada Way Arts & Cultural District says its Art Walk happens every third Thursday of the month from 6 to 9 p.m. on Morada Way, and that it has run since 2011. That puts the next two on Thursday, November 19 and Thursday, December 17, 2026, and the Chamber calendar lists both. The district’s own upcoming-events page was still showing older dates when we looked, so go by the third-Thursday rule, not that page.

• The Morada Way Arts & Cultural District says its Art Walk is every third Thursday of the month, 6 to 9pm, on Morada Way in Islamorada, and has run since 2011. Morada Way Arts & Cultural District: Art Walk Information
• The Morada Way Arts & Cultural District says its Art Walk is every third Thursday, but its upcoming events page still shows older dates (October 17, November 21 and December 19). The third Thursdays for late 2026 are November 19 and December 17, which the Chamber calendar matches. Morada Way Arts & Cultural District: Upcoming Events

Immerse Yourself! talks: every third Wednesday

The History of Diving Museum holds a free “Immerse Yourself!” presentation on the third Wednesday of every month at 7 p.m., in person and on Zoom. On those nights it stays open late and sells its last admission at 6:45 p.m. The museum is at 82990 Overseas Hwy.

• The museum hosts its free "Immerse Yourself!" presentation the 3rd Wednesday of every month at 7 pm, in person and on Zoom, with extended hours and last admission sold at 6:45 pm. History of Diving Museum: home page
• The History of Diving Museum is at 82990 Overseas Hwy (MM 83), Islamorada, FL 33036, phone 305-664-9737, on the bayside of US 1. History of Diving Museum: Location & Hours

Holiday Fest: Friday, December 4, 2026

The Chamber says the 22nd Annual Islamorada Holiday Fest runs from 4 to 10 p.m. on the Great Lawn at Founders Park, with the Holiday Parade at 7:30 p.m. Snow Mountain comes back with 30 tons of snow, and snow blows from a 35-foot holiday tree. The Chamber’s listing also mentions Santa photos, a holiday bazaar and an ornament auction. A few things we could not pin down. The Chamber gives no separate tree lighting time. We found no holiday boat parade on the Village or Chamber sites; the only parade posted is the Holiday Fest parade around the Great Lawn. And the Chamber’s page shows two different parade themes, so we print neither.

• The Chamber says the 22nd Annual Islamorada Holiday Fest is Friday, December 4, 2026, 4 to 10 p.m. on the Great Lawn at Founders Park, with the Holiday Parade at 7:30 p.m. Islamorada Chamber of Commerce: Holiday Fest 2026
• The Chamber says Holiday Fest features Snow Mountain with 30 tons of snow and snow blowing from a 35-foot holiday tree. Islamorada Chamber of Commerce: Holiday Fest 2026
• The Chamber's Holiday Fest page describes snow from a 35-foot holiday tree but does not list a separate tree lighting time for 2026. Islamorada Chamber of Commerce: Holiday Fest 2026
• We did not find an Islamorada holiday boat parade for 2026 on the Village or Chamber sites when we checked on October 21, 2026. The Chamber's Holiday Fest parade circles the Great Lawn at Founders Park. Islamorada Chamber of Commerce: Holiday Fest 2026
• The Chamber's Holiday Fest 2026 page shows two parade themes: "Everglades Holiday Magic, Deck the Glades" at the top and "A Season for Kindness… to Every Creature Great and Small" in the parade section. Islamorada Chamber of Commerce: Holiday Fest 2026

Islamorada Sailfish Tournament: December 5 and 6, 2026

The organizer says its 63rd annual tournament fishes on Saturday, December 5 and Sunday, December 6, and that festivities start on Friday, December 4, the same day as Holiday Fest. It is the main fundraiser of the Islamorada Charter Boat Association, and it opens the 2027 Florida Keys Gold Cup. The organizer’s page does not name a tournament headquarters. See the tournament site.

• The Islamorada Sailfish Tournament says its 63rd annual event fishes December 5 and 6, 2026, with festivities starting Friday, December 4; it is the primary fundraiser of the Islamorada Charter Boat Association. Islamorada Sailfish Tournament: home page

Lignumvitae Christmas: Saturday, December 5, 2026 (not confirmed)

The Chamber lists Lignumvitae Christmas from 9:00 a.m. to 3:00 p.m. at Lignumvitae Key Botanical State Park. The organizer, Friends of the Islamorada Area State Parks, showed no upcoming events when we checked, so we treat this one as not confirmed. Florida State Parks says the island can be reached only by boat or kayak.

• The Islamorada Chamber lists Lignumvitae Christmas on Saturday, December 5, 2026, 9:00 a.m. to 3:00 p.m., but the organizer (Friends of the Islamorada Area State Parks) showed no upcoming events when we checked on October 21, 2026. Friends of the Islamorada Area State Parks: Events
• Florida State Parks says Lignumvitae Key is accessible by boat or kayak only; the listed address is 77200 Overseas Highway, Islamorada FL 33036. Florida State Parks: Lignumvitae Key Botanical State Park

January to April 2027

Sailfish tournaments

Fish for Holly says its 9th Annual Fish for Holly Sailfish Tournament runs Friday, January 8 to Saturday, January 9, 2027 at Islander Resort, Islamorada. It is held in memory of Holly Given and raises money for domestic abuse prevention and scholarships. Details: Fish for Holly.

The Gold Cup series site lists the Islamorada Fishing Club Sailfish Tournament on Wednesday, January 20, 2027 and the Cheeca Lodge Presidential Sailfish Tournament on Saturday and Sunday, January 23 and 24, 2027. We could not confirm either date on the host’s own page. That same site lists the Islamorada Bartenders Sailfish Open on Monday, February 1, 2027 and Al Flutie’s Over the Hill Rip-off Sailfish Tournament on Wednesday, February 10, 2027, and neither is confirmed by a host page. We found no 2027 dates from any organizer for an Islamorada bonefish tournament.

• Fish for Holly says its 9th Annual Fish for Holly Sailfish Tournament is January 8 to 9, 2027 at Islander Resort, Islamorada. Fish for Holly Sailfish Tournament: Tournament page
• The tournament site says the Islamorada Sailfish Tournament opens the 2027 Florida Keys Gold Cup, followed by the Islamorada Fishing Club Sailfish Tournament on January 20, 2027 and the Cheeca Lodge Presidential Sailfish Tournament on January 23 and 24, 2027. Islamorada Sailfish Tournament: home page
• The Islamorada Fishing Club and Cheeca Lodge Presidential sailfish dates come from the Gold Cup series site; we did not confirm them on each host's own page when we checked on October 21, 2026. Islamorada Sailfish Tournament: home page
• We did not find 2027 dates posted by an organizer for an Islamorada bonefish tournament when we checked on October 21, 2026. Islamorada Chamber of Commerce: Events calendar

Island Fest: Saturday and Sunday, April 10 and 11, 2027

The Chamber says the 35th Annual Island Fest runs from 10 a.m. to 5 p.m. both days at Founders Park, mile marker 87 bayside. It includes the Plantation Yacht Harbor Arts and Crafts Show with about 100 artists, a Smoked Fish Dip Contest and a vintage car show, plus live music on the beach stage and food trucks. If you come across a Chamber page still advertising March 28 and 29, 2026, that was the 34th festival, which has already happened. Details: Island Fest.

• The Chamber says the 35th Annual Island Fest is Saturday and Sunday, April 10 and 11, 2027, 10am to 5pm at Founders Park, mile marker 87 bayside. Islamorada Chamber of Commerce: Island Fest
• The Chamber says Island Fest includes the Plantation Yacht Harbor Arts and Crafts Show with approximately 100 artists, a Smoked Fish Dip Contest and a vintage car show. Islamorada Chamber of Commerce: Island Fest

Summer 2027, and dates nobody has posted yet

FWC lists the 2027 spiny lobster sport season as Wednesday, July 28 and Thursday, July 29, 2027, which are the last consecutive Wednesday and Thursday of July. During the sport season the daily bag limit in Monroe County is 6 per person, and night diving for lobster is prohibited in Monroe County. The regular season runs August 6 to March 31. FWC’s possession line still shows 2026 dates, so check FWC before the season.

• FWC lists the 2027 spiny lobster sport season as July 28 to 29, 2027 (the last consecutive Wednesday and Thursday of July), for residents and non-residents. FWC: Spiny Lobster recreational regulations
• During the sport season FWC sets the daily bag limit at 6 per person for Monroe County and Biscayne National Park, 12 per person elsewhere in Florida. FWC: Spiny Lobster recreational regulations
• FWC prohibits night diving for lobster in Monroe County only during the sport season. FWC: Spiny Lobster recreational regulations
• FWC lists the regular spiny lobster season as August 6 to March 31, with a daily bag limit of 6 per person. FWC: Spiny Lobster recreational regulations
• FWC's lobster page lists the 2027 sport season as July 28 to 29, 2027, but its off-the-water possession line still names July 29 and July 30, 2026. Check FWC before the season for the 2027 possession dates. FWC: Spiny Lobster recreational regulations

The Village had not posted a date for its 2027 July 4th Celebration & Fireworks at Founders Park when we checked. Its parks department also supports the Beats on the Bay & Bay Jam Music Series, but we found no dates for it.

• The Village had not posted a date for its 2027 July 4th Celebration & Fireworks at Founders Park when we checked on October 21, 2026. Islamorada, Village of Islands: Founders Park
• The Village says its parks department supports events including the Chamber Holiday Festival and Island Fest, the July 4th Celebration & Fireworks, and the Beats on the Bay & Bay Jam Music Series. Islamorada, Village of Islands: Founders Park

Seasons and closures that shape the calendar

FWC says stone crab season in state waters opens October 15 and runs to May 1, closing May 2. The National Hurricane Center gives the Atlantic hurricane season as June 1 to November 30. Under the Village’s code, sea turtle nesting season runs April 15 to October 31. And Indian Key Historic State Park has been completely closed since April 2026 while contractors rebuild its dock, a project Florida State Parks says is “slated to take up to six months.” When we checked, no reopening date had been posted.

• FWC lists the state waters stone crab season as open October 15 to May 1, closed on May 2. FWC: Stone Crab recreational regulations
• For the Keys, the season to plan around is the Atlantic hurricane season: June 1 through November 30 every year, as NOAA's National Hurricane Center defines it. NOAA National Hurricane Center: Tropical Cyclone Climatology
• The Village says its Code of Ordinances defines sea turtle nesting season as April 15 to October 31; nesting in Islamorada occurs mainly between mile markers 72 and 83, primarily on the Atlantic shoreline. Islamorada, Village of Islands: Sea Turtle Nesting Regulations
• Florida State Parks posts: "Effective April 2026: Indian Key Historic State Park is completely closed to the public while contractors rebuild the Park's dock. The project is slated to take up to six months." Florida State Parks: Indian Key Historic State Park
• Florida State Parks said in April 2026 that Indian Key would be fully closed for up to six months while its dock is rebuilt; no reopening date was posted when we checked on October 21, 2026. Florida State Parks: Indian Key Historic State Park

Founders Park, where most of these events happen

The Village describes Founders Park as 45 acres, open from sunrise to sunset, and the center of its park system. It has zero tolerance for alcohol and bans glass and smoking. Village residents and their guests get in free. The Founders Park page lists non-resident entry at $10.00 for adults (18 to 64) and $7.00 for youth and seniors (3 to 17), rising to $15.00 and $10.00 on summer weekends (Memorial Day to Labor Day) and on holidays. Details: Founders Park.

• The Village describes Founders Park as 45 acres, open sunrise to sunset, the center of the Village park system. Islamorada, Village of Islands: Founders Park
• Founders Park rules include zero tolerance for alcohol, no glass, no smoking, no fishing, no loud amplified music and no dogs on the beach, playground, picnic areas, soccer fields or pool area. Islamorada, Village of Islands: Founders Park Rules
• The Village says Village residents and their guests get free admission to Founders Park; park fees apply to non-Islamorada residents. Islamorada, Village of Islands: Founders Park Rules

Every dated event we hold

Islamorada events FAQ

Dates, rules and hours can change. The organisers have the final word: Village of Islamorada (official site)