October 16-18, 2026 · Weekend Guide
What To Do This Weekend in the Florida Keys: October 16-18, 2026
Executive Summary. Welcome to a weekend that shows off everything the Florida Keys do best. Key West kicks off Fantasy Fest with the Bahama Village Goombay Festival and the What I Did Fur Love Royal Coronation, Key Largo hosts REEF Fest for divers, snorkelers and anyone who loves the ocean, and Islamorada blends two fishing-focused weekends with family-friendly Halloween fun. Here is your day-by-day guide to October 16-18, from Key Largo to Key West.
Weekend at a Glance
- Fantasy Fest kickoff: The free Bahama Village Goombay Festival (noon-midnight Friday and Saturday) and the What I Did Fur Love Royal Coronation at Coffee Butler Amphitheater launch the weekend in Key West.
- REEF Fest in Key Largo: Diving and snorkeling, seminars at the Ocean Exploration Center, and Saturday's For the Love of the Sea Celebration at $125 per person with sunset views on Blackwater Sound.
- Islamorada's fishing weekend: The Casting for Cats Backcountry Tournament (October 16-17) and the Ladies, Let's Go Fishing! Keys Saltwater Weekend (October 16-18) both get underway.
- Family-friendly Halloween picks: The free Witches Paddle & Costume Swap at Green Turtle Hammock on Saturday (11 a.m.-2 p.m.) and Witches in the Hammock at Crane Point that evening.
- Lower-key Sunday: The free Fantasy Fest Artisan Market at Higgs Beach (10 a.m.-2 p.m.) is the best daytime choice, with two 10 a.m. REEF Fest experiences in Key Largo.
Friday, October 16
Friday opens the weekend with Fantasy Fest's launch in Key West, REEF Fest in Key Largo, and the start of two major fishing events in Islamorada.
Key West: Bahama Village Goombay Festival
Noon-midnight | Bahama Village | Free
The Goombay Festival launches Fantasy Fest weekend in historic Bahama Village with Caribbean-inspired music, food, arts and crafts. The main stage is at Petronia and Emma streets. Friday's schedule includes Blue Heaven Stage performances beginning at 4:30 p.m., followed by additional music into the evening.
Source: Fantasy Fest
Key West: What I Did Fur Love Royal Coronation
Doors 6 p.m.; show 7 p.m. | Coffee Butler Amphitheater
The Florida Keys SPCA's 2026 What I Did Fur Love Royal Coronation officially kicks off Fantasy Fest's King and Queen competition. The event includes a two-hour stage show and a three-course plated dinner.
Source: Fantasy Fest
Key Largo: REEF Fest
10 a.m.-5 p.m. at the Ocean Exploration Center; 4 p.m. happy hour
REEF Fest continues Friday with Ocean Exploration Center hours, afternoon seminars, a 4 p.m. Happy Hour Social, and a 5 p.m. seminar. Morning diving and snorkeling experiences are also available through participating operators.
Source: Reef
Islamorada: Fishing weekend begins
Two major fishing-focused events get underway:
- Casting for Cats Backcountry Tournament, Oct. 16-17. The tournament welcomes ladies, co-ed and junior divisions and combines backcountry fishing with community fundraising for local animal welfare.
- Ladies, Let's Go Fishing! Keys Saltwater Weekend, Oct. 16-18. The program combines education, hands-on fishing skills and optional inshore/offshore fishing. Its organizers describe Friday as the networking/kickoff portion, Saturday as the main educational day and Sunday as fishing/tournament day.
Source: Florida Keys & Key West
Saturday, October 17
Saturday, October 17, offers the biggest variety of activities across the Keys.
Key Largo: REEF Fest + “For the Love of the Sea”
Morning through evening
REEF Fest continues with morning diving/snorkeling opportunities, Ocean Exploration Center hours from 10 a.m.-4 p.m., seminars from 2-4 p.m., then the headline For the Love of the Sea Celebration from 5-8:30 p.m.
The celebration is at a waterfront property on Blackwater Sound near Mile Marker 103.6 and includes dinner, drinks, a silent auction and sunset views. Tickets are currently listed at $125 per person.
This is probably the strongest Saturday option for ocean lovers.
Source: Reef
Islamorada: Witches Paddle & Halloween Costume Swap
11 a.m.-2 p.m. | Green Turtle Hammock Nature Preserve | Free
Visitors can dress in costume, paddle the basin and participate in a costume swap at Green Turtle Hammock Nature Preserve. The event is organized around a family-friendly Halloween theme.
Good for: Families, paddlers and anyone looking for a less commercial Keys experience.
Source: Keys Weekly Events
Islamorada: Hoy Shanty Crew Sing-Along
6-8 p.m. | History of Diving Museum
The History of Diving Museum presents its Hoy Shanty Crew Sing-Along, exploring maritime songs and their connection to Florida Keys history. The event includes light refreshments and raffles; a $10 donation gets attendees a custom museum pint glass.
Source: Florida Keys & Key West
Marathon: Witches in the Hammock
6:30-9 p.m. | Crane Point Hammock
Crane Point's annual Halloween event includes a lantern walk, witches, a fire pit, hayride, games, a movie and food. Admission is listed at $15 adults / $7 children.
Source: Fantasy Fest
Key West: Goombay Festival continues
Noon-midnight | Bahama Village | Free
Saturday continues the Goombay celebration with music and Caribbean cultural programming.
There are also numerous Fantasy Fest partner events around Key West, including the Lip Sync & Lifeguard Pool Party at Blue Flamingo Resort from noon-4 p.m. and free live music at Sunset Pier beginning at 7 p.m.
Source: Fantasy Fest
Sunday, October 18
Sunday, October 18, blends art, ocean experiences and a slower finish to the weekend.
Key West: Fantasy Fest Artisan Market
10 a.m.-2 p.m. | Higgs Beach | Free
The Key West Artisan Market, Fantasy Fest Edition brings Florida Keys artists and makers to Higgs Beach. Visitors can shop locally made art and crafts, find Fantasy Fest merchandise, listen to live music and grab food from international vendors.
This is one of the best choices for a daytime, lower-key Sunday activity.
Source: Fantasy Fest
Key West: “Legends Never Die” Día de los Muertos celebration
3-7 p.m. | Elevate Skye Bar & Lounge at Opal Key Resort & Marina
The event combines Mexican and Latin-inspired food and drinks, art, dancing and music celebrating legendary performers.
Source: Fantasy Fest
Key Largo: REEF Fest closing experiences
Although the Ocean Exploration Center is closed Sunday, REEF Fest has two 10 a.m. experiences:
- Pennekamp Nature Walk at John Pennekamp Coral Reef State Park
- MOTE Coral Nursery Tour at Reefhouse Resort & Marina
Park admission applies to the Pennekamp walk; the MOTE tour is at the Reefhouse Resort & Marina site.
Source: Reef
Islamorada: Final day of Keys Saltwater Weekend
Ladies, Let's Go Fishing concludes with the Fishing Fever Tournament, with participants able to fish inshore or offshore. The event is designed to accommodate both beginners and experienced anglers.
Source: Florida Keys & Key West
Beaches & Water Activities
This weekend is particularly strong for visitors who want to combine events with time on the water.
- Key Largo: REEF Fest is the standout option for diving, snorkeling, coral conservation and marine education. REEF lists multiple participating dive/snorkel operators and special experiences during the festival.
- Islamorada: The fishing events make the Upper Keys particularly attractive for anglers, while the Witches Paddle adds a casual paddling option.
- Key West: Higgs Beach works particularly well Sunday because the Artisan Market is held there from 10 a.m.-2 p.m.
FAQs
Frequently Asked Questions
What's the best Saturday option for ocean lovers?
What free events are happening in Key West?
What fishing events are in Islamorada that weekend?
What should families do on Saturday?
What is REEF Fest in Key Largo?
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Resources
Official Sources for This Guide
- Fantasy Fest: Schedule
- Fantasy Fest: Partner Events
- REEF: REEF Fest
- Florida Keys & Key West: Ladies, Let's Go Fishing! Keys Saltwater Weekend
- Florida Keys & Key West: Casting for Cats Backcountry Tournament
- Keys Weekly: Witches Paddle & Halloween Costume Swap
- Florida Keys & Key West: The Hoy Shanty Crew Sing-Along
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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