Florida Keys Weekend Guide: October 24-26, 2026
Fantasy Fest Parade Weekend, Halloween events, waterfront experiences and a Hunter's Moon dinner
Saturday, October 24 through Monday, October 26, 2026
This is one of the busiest October weekends in the Keys, with the main Fantasy Fest parade in Key West, family Halloween events in Key Largo and Islamorada, a full-moon kayak experience in Big Pine, and a luxury waterfront dinner at Little Palm Island on Monday.
Weekend at a Glance
- Saturday, October 24: The biggest day of the weekend, with the Fantasy Fest parade in Key West, family Halloween events in Key Largo and Islamorada, and a full-moon kayak in Big Pine.
- Sunday, October 25: Fantasy Fest closing day, with family activities including Children's Day at Bayview Park and the Sheriff's Animal Farm Open House.
- Monday, October 26: The Hunter's Moon dinner at Little Palm Island brings a luxury waterfront finish to the weekend.
Saturday, October 24
Saturday, October 24, is the biggest day of the weekend in the Keys.
1. Fantasy Fest Parade: the biggest event of the weekend
7 p.m. | Duval Street, Key West
The Deep Eddy Vodka Fantasy Fest Parade takes place Saturday night at 7 p.m., winding through Key West's famous Duval Street. The official parade route begins at Truman Waterfront Park/Southard Street and finishes back near the waterfront.
Source: Fantasy Fest
The City of Key West says Duval Street closes at 6 p.m., with rolling closures around the route, so visitors should expect significant traffic delays and plan to arrive early.
Source: City of Key West
The official Fantasy Fest Street Fair also runs Saturday, with food and vendors along Duval Street from noon into the early morning hours.
Source: Fantasy Fest
Why go: This is the centerpiece of Fantasy Fest 2026 and the weekend's biggest draw.
2. A Halloween Saturday across the Keys
There are several options beyond Fantasy Fest.
Key Largo: Haunted Lagoon
6-8:30 p.m. | MarineLab Undersea Park
MarineLab's annual Haunted Lagoon is a free family Halloween event featuring spooky science, games, treats and an optional nighttime snorkeling experience. MarineLab says the event is a fundraiser supporting free programs for Monroe County students.
Source: MarineLab
Address: 51 Shoreland Drive, Key Largo.
Islamorada: Trunk or Treat
6-8:30 p.m. | Founders Park
The Village of Islamorada's 8th Annual Trunk or Treat takes place at the Great Lawn. Expect decorated car trunks, candy, a bounce house, obstacle course, pumpkin decorating, dancing, face painting and a costume contest.
Source: Florida Keys & Key West
Address: 87000 Overseas Highway
Parking: $15
Key West: Screaming Green Halloween
10 a.m.-2 p.m. | Key West Tropical Forest & Botanical Garden
The garden's Screaming Green Halloween includes trick-or-treating and age-group costume contests. The organizers encourage costumes made from natural or recycled materials. Admission is $5 per child or $10 per family, with members admitted free.
Source: Florida Keys & Key West
Best for: Families looking for a more traditional Halloween experience rather than an adults-only Fantasy Fest event.
3. Big Pine: Full Moon Kayak Tour
5:15-7:15 p.m. | Old Wooden Bridge, Big Pine Key
The Florida Keys Wildlife Society lists a Full Moon Kayak Tour for Saturday, October 24, launching from the Old Wooden Bridge at 1791 Bogie Drive.
Source: Florida Keys Wildlife Society
This is a particularly nice alternative for visitors who want a quieter, water-based evening rather than spending the night in Key West.
Best for: Couples, paddlers, photographers and visitors interested in the Lower Keys.
Sunday, October 25
Sunday, October 25, is Fantasy Fest closing day, with family activities across the Keys.
4. Fantasy Fest Closing Day + Family Activities
Sunday marks the closing day of Fantasy Fest 2026, and the schedule shifts toward recovery, pool parties, family activities and the festival's final events. Fantasy Fest officially runs through October 25.
Source: Fantasy Fest
Children's Day
12-5 p.m. | Bayview Park, Key West
Key West's official calendar lists Children's Day at Bayview Park, with family-focused activities on Sunday afternoon.
Source: City of Key West
Sheriff's Animal Farm Open House
1-3 p.m. | Stock Island
The Monroe County Sheriff's Office Animal Farm is open the second and fourth Sunday of each month. On October 25, visitors can meet animals including capybaras, sloths, goats and birds. Admission is free, though donations of cash or fresh produce are appreciated.
Source: Florida Keys & Key West
Fantasy Fest closing-day parties
The official festival schedule includes several Sunday events, including:
- Reggae Rehab Pool Party: 1-4 p.m.
- The Hangover “But Did You Die?” Pool Party: 1-4 p.m.
- “The Fat Lady Sings” Tea Dance: 4-8 p.m. at La Te Da, listed as the final official Fantasy Fest event.
Source: Fantasy Fest
Monday, October 26
Monday, October 26, brings a quieter, upscale finish to the weekend.
5. Hunter's Moon Dinner at Little Palm Island
By reservation | Little Palm Island, Little Torch Key
For travelers extending the weekend, Monday brings a very different Florida Keys experience: the Hunter's Moon Full Moon Dinner at Little Palm Island Resort & Spa.
The official Florida Keys tourism listing describes an adults-only private-island dinner featuring seasonal coastal cuisine from Executive Chef Rodrigo Albornoz, with dining available on the oceanfront verandah or beneath the palms on the sand, subject to availability.
Source: Florida Keys & Key West
Non-resort guests 18 and older can attend by reservation. Complimentary boat transfers leave from the resort's Shore Station at 28500 Overseas Highway on Little Torch Key at the bottom of each hour; the crossing takes about 15 minutes.
Source: Florida Keys & Key West
The Hunter's Moon reaches full phase at 12:11 a.m. on October 26 in the Florida Keys/Key West area.
Source: Time and Date
Best for: Couples, luxury travelers and visitors looking for a quieter, upscale experience after Fantasy Fest weekend.
DINING: Taste the Keys is still going
October 24-26 falls within Taste the Keys, the Upper Keys' monthlong dining celebration running through October 31.
The official event currently lists 23 participating restaurants, with prix-fixe menus from $17 to $75 per person. The remaining trolley food tour after this weekend is scheduled for October 29.
Source: Taste the Keys
This gives you a useful dining angle for visitors who want to escape the Fantasy Fest crowds for a meal in the Upper Keys.
A Simple 3-Day Itinerary
Saturday: Big event day
- Morning: Key West Tropical Forest or local sightseeing
- Noon: Fantasy Fest Street Fair
- Afternoon: Explore Old Town / waterfront
- 7 p.m.: Fantasy Fest Parade
- Evening: Continue along Duval or head out of Key West for a quieter night
Sunday: Slow down
- Morning: Beach or brunch
- 12-5: Children's Day at Bayview Park
- 1-3: Sheriff's Animal Farm
- Afternoon: Fantasy Fest closing events
- Evening: Sunset dinner
Monday: Luxury finish
- Daytime: Relax, boat, beach or explore the Lower Keys
- Evening: Hunter's Moon dinner at Little Palm Island
What to Know Before You Go
Key West traffic: The City says Duval Street closes at 6 p.m. on October 24, with the parade starting at 7 p.m. Expect delays and avoid trying to drive directly through the parade area during the event.
Source: City of Key West
Fantasy Fest: The official festival says its schedule is subject to change as event partners update their details, so verify individual event information before publishing a final itinerary.
Source: Fantasy Fest
Family vs. adults: Fantasy Fest is a broad festival, but many individual events are adults-only or have age restrictions. For families, the official schedule and local tourism calendar provide separate family activities such as Children's Day and the Halloween events above.
Source: Fantasy Fest
FAQs
Frequently Asked Questions
What should you know before going to the Fantasy Fest Parade?
What family Halloween options are there on October 24?
What is the best way to experience the full moon in the Keys?
What is the Hunter's Moon dinner at Little Palm Island?
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Resources
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Ready to Take the Next Step?
Weekends like this one are why so many visitors end up calling the Keys home. If you are thinking about making the Florida Keys your everyday, Steve Conley can help you find the right place, from Key Largo to Key West.
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