Best Things to Do in the Florida Keys This Weekend, November 13–15, 2026
Weekend Highlights
Key West Oyster Fest · Fishing Tournaments · Live Music · Local Art Walks · Theater Performances · Waterfront Adventures
If you're looking for the best things to do in the Florida Keys this weekend, November 13–15, 2026, there's plenty happening throughout the island chain.
From fresh oysters and live entertainment in Key West to fishing tournaments in Islamorada and Sugarloaf Key, this weekend offers a combination of local festivals, outdoor adventures, and opportunities to experience the laid-back Florida Keys lifestyle.
The biggest highlight is the inaugural Key West Oyster Fest on Saturday, November 14, bringing together seafood lovers, local chefs, oyster farmers, and live musicians at the Historic Seaport.
Whether you're planning a weekend getaway, looking for family-friendly activities, or simply want to explore the local community, here are some of the best ways to spend your weekend in the Florida Keys.
1. Attend the Inaugural Key West Oyster Fest
Date: Saturday, November 14, 2026
Time: 5:00–10:00 p.m.
Location: Half Shell Raw Bar, Key West Historic Seaport
Admission: Ticketed event
One of the biggest attractions this weekend is the inaugural Key West Oyster Fest.
Hosted by Half Shell Raw Bar and Everglades Oysters, the waterfront festival celebrates oyster farming, local seafood, and the culinary traditions of the Florida Keys.
Visitors can enjoy:
- Fresh raw and grilled oysters.
- Seafood creations from local chefs.
- Oyster shucking demonstrations.
- Live music by The Farm Boys.
- A premium open bar until 8 p.m. with admission.
- Special appearances and culinary experiences.
The festival also highlights oyster-shell recycling and coastal conservation, connecting the local food scene with efforts to protect marine ecosystems.
Why Visit: If you love seafood and waterfront dining, this is one of the weekend's standout experiences. It's also a wonderful opportunity to discover the culinary side of Key West.
Event information: Key West Oyster Fest
2. Watch the Cheeca Lodge All-American Backcountry Tournament
Dates: November 12–14, 2026
Location: Islamorada
Islamorada is known as the Sportfishing Capital of the World, and this weekend brings another exciting fishing competition to its waters.
The Cheeca Lodge All-American Backcountry Tournament celebrates backcountry fishing while honoring military veterans.
Anglers participate in a catch-and-release competition targeting popular Florida Keys species, including:
- Snook.
- Redfish.
- Bonefish.
- Tarpon.
- Permit.
The event benefits Bonefish & Tarpon Trust, an organization dedicated to conserving important flats fisheries.
Why Visit: Even if you're not competing, the tournament offers a glimpse into the fishing culture that makes Islamorada such a special destination.
Event information: Cheeca Lodge
3. Explore the Sugarloaf Showdown Fishing Tournament
Dates: November 12–14, 2026
Location: Sugarloaf Key, Lower Keys
The Lower Keys Guides Association hosts its 13th Annual Sugarloaf Showdown this weekend.
This conservation-focused tournament brings together professional fishing guides, anglers, and younger participants through several fishing divisions.
Target species include:
- Bonefish.
- Permit.
- Barracuda.
The competition supports the Florida Keys Guides Trust Foundation, which helps strengthen the local fishing community.
Why Visit: It's an excellent opportunity to experience the Lower Keys' fishing heritage and learn more about the people who help preserve its marine resources.
Event information: Sugarloaf Showdown
4. Experience First Fridays on Fleming in Key West
Date: Friday, November 13, 2026
Time: 6:00–9:00 p.m.
Location: Fleming Street, Key West
Admission: Free
Looking for a relaxed evening activity? First Fridays on Fleming is a great way to explore Key West's creative community.
During this monthly event, Fleming Street comes alive with local artists, galleries, independent shops, and neighborhood businesses.
Visitors can enjoy:
- Local gallery openings.
- Artisan pop-up shops.
- Live music.
- Local shopping.
- Food and drink tastings.
Why Visit: It's a wonderful alternative to the typical tourist attractions and offers a chance to discover the local personality of Old Town Key West.
Event information: Key West Attractions Association
5. Watch Destroying David at Waterfront Playhouse
Dates: November 12–14, 2026
Friday Showtime: 7:30 p.m.
Location: Waterfront Playhouse, 407 Wall Street, Key West
For visitors who enjoy theater and the performing arts, Destroying David is another weekend highlight.
The Florida premiere is part of the Waterfront Playhouse Spotlight Series. The production explores art, identity, and the legacy of Michelangelo's famous David.
Why Visit: It's a distinctive cultural experience for couples and visitors who want to explore more of Key West beyond its beaches, restaurants, and nightlife.
Event information: Waterfront Playhouse
6. Celebrate Sea Turtle Conservation at Sea Turtle Shell-E-Bration
Date: Saturday, November 14, 2026
Time: 6:00–8:00 p.m.
Location: Key West Aquarium
Marine-life enthusiasts and families can enjoy an evening dedicated to sea turtle conservation.
The Sea Turtle Shell-E-Bration marks the close of the sea turtle nesting season and highlights the importance of protecting these marine animals and their habitats.
Visitors can learn more about the marine environment and conservation efforts that help preserve the Florida Keys.
Why Visit: This is a meaningful activity for families, children, and anyone interested in marine wildlife.
Event information: Florida Keys Official Event Calendar
7. Attend A Tribute to the Songs of Pete & Wayne
Date: Saturday, November 14, 2026
Location: Key West Theater, 512 Eaton Street, Key West
If live music is more your style, consider spending Saturday evening at Key West Theater.
A Tribute to the Songs of Pete & Wayne brings together music, storytelling, and entertainment in a performance celebrating the songs of Pete & Wayne.
Why Visit: It's a great option for visitors who prefer a relaxed musical evening rather than a busy festival atmosphere.
Event information: Key West Theater
8. Make Your Own Mexican-Inspired Tin Ornaments
Date: Saturday, November 14, 2026
Time: 10:30 a.m.–1:00 p.m.
Location: The Studios of Key West
For something creative and hands-on, The Studios of Key West is hosting an embossed tin ornament workshop with local artist Pam Hobbs.
Participants can learn traditional metal-embossing techniques and create decorative ornaments to take home.
Why Visit: It's a fun opportunity to explore local art and craftsmanship while creating a unique souvenir from your Florida Keys visit.
Event information: The Studios of Key West
9. Explore the Key West Historic Seaport
Location: Key West, Old Town
The Historic Seaport is worth visiting even if you don't have tickets to a specific event.
This waterfront district is filled with boats, marinas, restaurants, and shops, offering a glimpse into Key West's maritime heritage.
Things to enjoy include:
- Walking along the harbor.
- Watching boats come and go.
- Exploring waterfront restaurants.
- Browsing local shops.
- Enjoying scenic marina views.
- Taking photographs along the waterfront.
The seaport is also the location of Saturday's Oyster Fest, making it an ideal place to explore before the evening celebration.
Why Visit: It's one of the best places to experience the waterfront atmosphere that defines Key West.
10. Enjoy the Sunset Celebration at Mallory Square
Location: Mallory Square, Key West
Best Time: Late afternoon and sunset
No Florida Keys weekend would be complete without experiencing a Key West sunset.
Mallory Square is famous for its Sunset Celebration, where visitors gather along the waterfront to watch the sun disappear over the Gulf of Mexico.
The evening atmosphere typically includes:
- Street performers.
- Local artists and vendors.
- Live entertainment.
- Food stands.
- Beautiful sunset views.
Why Visit: It's one of Key West's most recognizable experiences and a great way to end a day exploring Old Town.
11. Go Kayaking or Enjoy a Backcountry Eco-Tour
Location: Key West and the Lower Keys
If you prefer spending time on the water, November is a wonderful opportunity to explore the Florida Keys' natural surroundings.
Consider a guided kayak or eco-tour through mangrove channels and shallow backcountry waters.
Possible activities include:
- Guided mangrove kayaking.
- Paddleboarding.
- Snorkeling excursions.
- Wildlife observation.
- Sandbar trips.
- Private boat tours.
One local option is Lazy Dog Adventures, which offers guided and self-guided paddling experiences around Key West and Stock Island.
Another option is Get Up And Go Kayaking at Sugarloaf Marina, which offers clear-kayak experiences in the Lower Keys.
Why Visit: These activities allow you to experience a quieter side of the Florida Keys while appreciating its unique coastal ecosystems.
Tour information:
12. Visit Robbie's of Islamorada
Location: 77522 Overseas Highway, Islamorada
Robbie's of Islamorada is a popular waterfront destination known for its tarpon feeding experience, marina, restaurants, and local market.
Visitors can:
- Feed giant tarpon from the marina.
- Browse local shops.
- Enjoy waterfront dining.
- Book fishing and boating excursions.
- Explore nearby water activities.
The marina provides a fun stop for families and visitors traveling through the Upper and Middle Keys.
Why Visit: It combines several quintessential Florida Keys experiences in one location.
Website: Robbie's of Islamorada
13. Enjoy Live Music Throughout Key West
Dates: November 13–15, 2026
Location: Various venues throughout Key West
Key West has a lively music scene, with performances taking place throughout the weekend.
Visitors can explore local venues such as:
- Sloppy Joe's Bar.
- Schooner Wharf Bar.
- Irish Kevin's.
- Smokin' Tuna Saloon.
- Key West Theater.
From acoustic performances to energetic bar entertainment, there's something for different musical tastes.
Sunday Highlight: The Garcia Project
On Sunday, November 15, The Garcia Project returns to Key West Theater with special guests Jess & Jill.
It's a great way to close the weekend with a tribute to the music of the Jerry Garcia Band.
Event information: Key West Theater
Where to Eat in the Florida Keys This Weekend
November is an excellent time to enjoy seafood and waterfront dining throughout the Florida Keys.
Here are some ideas for your weekend food itinerary.
Fresh Oysters in Key West
Make the Key West Oyster Fest your Saturday evening destination for oysters, seafood dishes, and live entertainment.
Stone Crab Season
Florida stone crab season runs from October 15 through May 1.
November is a great time to look for fresh stone crab claws at local seafood restaurants.
Waterfront Dining in Islamorada
Enjoy a meal overlooking the water while exploring Islamorada's restaurants and marinas.
Fresh Local Seafood in Key West
Look for restaurants serving locally available seafood, including fish, shrimp, and seasonal specialties.
Suggested Florida Keys Weekend Itinerary
If you're planning to explore several activities over three days, here's one way to organize your weekend.
Friday, November 13 – Discover Key West
- Morning: Explore Old Town Key West.
- Afternoon: Visit local shops and galleries.
- Evening: Attend First Fridays on Fleming.
- Night: Enjoy live music or a theater performance.
Saturday, November 14 – Food, Art & Waterfront Experiences
- Morning: Attend the embossed tin ornament workshop.
- Afternoon: Explore the Historic Seaport.
- Late afternoon: Enjoy waterfront dining and sightseeing.
- Evening: Attend the Key West Oyster Fest.
Sunday, November 15 – Outdoor Adventures & Local Entertainment
- Morning: Take a scenic drive along the Overseas Highway.
- Afternoon: Explore Islamorada or the Lower Keys.
- Evening: Catch The Garcia Project at Key West Theater.
Tips for Visiting the Florida Keys This Weekend
Before heading out, consider these helpful tips:
- 1. Book popular events early. The Oyster Fest and theater performances may have limited ticket availability.
- 2. Plan your route. The Florida Keys stretch across multiple communities, so allow enough travel time between Key Largo, Islamorada, Marathon, and Key West.
- 3. Check the weather. November is a pleasant time to explore the Keys, but boating and outdoor activities remain weather-dependent.
- 4. Make dining reservations. Popular waterfront restaurants can become busy during weekends.
- 5. Explore beyond Key West. Islamorada, Marathon, and the Lower Keys each offer their own attractions, dining experiences, and outdoor activities.
- 6. Confirm event details. Schedules, admission prices, and availability can change. Check with event organizers before visiting.
Why November Is a Great Time to Experience the Florida Keys
November offers an appealing combination of outdoor activities, local festivals, and seasonal dining.
The weather is generally more comfortable than during the hotter summer months, making it a great time to explore the islands, enjoy the water, and spend time outdoors.
It's also an opportunity to experience the local community before the busiest winter travel season arrives.
Whether you're enjoying fresh oysters in Key West, watching fishing tournaments in Islamorada, or kayaking through mangrove channels, the Florida Keys offer something for every type of visitor.
And that's what makes life in the Keys so special: there's always another waterfront restaurant to discover, another island to explore, and another reason to enjoy the coastal lifestyle.
Thinking about making the Florida Keys your home? Discover local communities, waterfront properties, and real estate opportunities with Conley Group Florida.
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