August Is One of Key West's Best Kept Secrets
Most people think winter is the only time to visit Key West.
Locals know August has a charm all its own.
The crowds are lighter, sunsets seem to last forever, the water is crystal clear, and the island settles into a relaxed rhythm without slowing down. Restaurants are easier to enjoy, fishing is outstanding, and the community calendar remains packed with festivals, live music, culinary experiences, and local traditions.
Whether you're planning a vacation or you're lucky enough to call Key West home, August offers countless opportunities to experience the island like a local.
Here's what's happening around Key West this month.
🦞 August 5 through 9
Key West Lobsterfest
One of Key West's favorite summer traditions celebrates the opening of Florida's regular lobster season.
For five delicious days, the island comes alive with fresh seafood, waterfront parties, live entertainment, local vendors, and plenty of Caribbean flavor. Restaurants throughout Key West feature fresh Florida lobster while visitors gather to celebrate one of the Keys' most iconic culinary events.
Highlights include:
- The Lobster Boil at the Historic Porter Mansion
- The Duval Street Lobsterfest Street Fair
- Fresh Florida lobster served throughout the island
- Live music
- Local vendors
- Beats & Brunch at First Flight Island Restaurant & Brewery
Whether you're a seafood lover or simply looking for an authentic Key West experience, Lobsterfest is one of the island's signature summer celebrations.
Dates: August 5 through 9, 2026
Official Website: https://keywestlobsterfest.com/
🛍️ August 9
Key West Artisan Market and More | Lobsterfest Edition
The final day of Lobsterfest begins with a special edition of the Key West Artisan Market from 10:00 AM until 2:00 PM at the Southernmost Beach Resort parking lot.
Browse local artists, handcrafted goods, fresh produce, specialty foods, and delicious lobster inspired dishes while enjoying live entertainment in a relaxed waterfront setting.
After the market, continue the celebration with a Lobster Brunch at First Flight Island Restaurant & Brewery, followed by the Closing Pool Party at Southernmost Beach Resort from 1:00 PM until 4:00 PM, featuring the popular Lobster Roll Eating Contest beginning at 2:00 PM.
It's a fantastic way to wrap up one of Key West's biggest summer weekends.
Date: August 9, 2026
Official Website: https://keywestlobsterfest.com/
🐴 August 9 & 23
Monroe County Sheriff's Animal Farm
One of Key West's best hidden gems opens to the public only on the second and fourth Sundays of each month from 1:00 PM until 3:00 PM.
Admission is completely free, although donations are always appreciated.
Originally created as a safe haven for homeless animals, the Animal Farm began with Muscovy ducks, chickens, and a blind horse named Angel. Today it has grown into a beautiful park featuring miniature horses, goats, pigs, rabbits, chickens, reptiles, a large aviary, and many other domestic and exotic animals.
Families with children absolutely love this experience, and many locals make it part of their monthly routine.
Dates: August 9 & 23, 2026
Hours: 1:00 PM until 3:00 PM
Official Website: https://www.keysso.net/animal-farm
👨🍳 Monday Through Saturday
Key West Cooking Show
If you enjoy great food, local history, and interactive experiences, the Key West Cooking Show is one of the island's newest must do attractions.
Located inside the historic Navy Building Number One at 291 Front Street, this unique dining experience blends live chef demonstrations, storytelling, and a multi course meal inspired by the diverse culinary traditions of Key West. As talented chefs prepare each course before your eyes, they share the stories behind the island's Cuban, Bahamian, Caribbean, Spanish, and New England influences, creating what they call Dinnertainment™.
Beyond the signature cooking show, guests can also enjoy Key Lime Pie demonstrations, rum cocktail classes, mixology experiences at Bar 1, and special culinary events throughout the week. Whether you're visiting Key West for the first time or you're a longtime local looking for something different, it's a memorable way to experience the flavors and history that have shaped the island.
Open: Monday through Saturday
Closed: Sundays
Location:
291 Front Street
Key West, FL 33040
Official Website:
Key West Cooking Show
🎨 August 20
Walk on White
Every third Thursday, White Street transforms into one of Key West's most creative neighborhoods.
Local galleries, artist studios, boutiques, and businesses open their doors for an evening celebrating the island's vibrant arts community. Meet painters, photographers, jewelers, sculptors, and other talented local artists while enjoying one of Key West's most walkable neighborhoods.
If you're looking for an evening that's a little quieter than Duval Street but full of local culture, this is one of the best events of the month.
Date: August 20, 2026
Official Website: https://www.walkonwhitekeywest.com/
🥃 August 10 through 16
Key West RumFest
Few places pair with rum quite like Key West.
RumFest celebrates the island's Caribbean heritage with a full week of premium rum tastings, distillery showcases, cocktail competitions, educational seminars, mixology classes, waterfront parties, and special dinners hosted throughout the island.
Whether you're an experienced rum enthusiast or simply curious to discover new flavors, RumFest offers countless opportunities to meet master distillers, learn about rum production, and sample handcrafted cocktails at some of Key West's most iconic venues.
Dates: August 10 through 16, 2026
Official Website: https://rumfestkeywest.com/
🌴 August 12 through 16
Tropical Heat
One of Key West's signature LGBTQ+ celebrations returns for another unforgettable week.
Hosted by the Key West Business Guild, Tropical Heat welcomes visitors from around the world for five days of pool parties, clothing optional events, sunset cruises, happy hours, themed dance parties, nightlife, and social gatherings across many of Key West's most popular venues.
While Island House serves as one of the festival's central locations, events take place throughout the island, creating an exciting and welcoming atmosphere that celebrates the diversity Key West is known for.
Whether you're attending one event or spending the entire week in town, Tropical Heat has become one of the island's most anticipated summer festivals.
Dates: August 12 through 16, 2026
Official Website: https://gaykeywestfl.com/tropical-heat/
🎭 Throughout August
Live Music, Comedy & Theater
There is never a shortage of entertainment in Key West.
Throughout August you'll find concerts, comedy shows, theater productions, and live music nearly every night of the week.
Favorite venues include:
- Key West Theater
- Comedy Key West
- Green Parrot Bar
- Rick's Bar
- Tennessee Williams Theatre
Whether you're looking for nationally touring musicians or local performers, you'll find something happening somewhere on the island almost every evening.
🌅 Every Single Evening
Mallory Square Sunset Celebration
No visit to Key West is complete without experiencing sunset at Mallory Square.
Every evening you'll find:
- Street performers
- Live musicians
- Local artists
- Food vendors
- Handmade crafts
- Incredible waterfront sunsets
No two evenings are ever exactly alike, which is one of the reasons both visitors and locals continue coming back.
Watching the sunset over Key West Harbor remains one of the island's most iconic experiences.
Official Website: https://www.mallorysquare.com/
Who You Work With Matters
One of the things we love most about Key West is that there is always something happening. From Lobsterfest and Tropical Heat to local art walks, waterfront sunsets, live music, and community traditions, every month offers another reason to get outside and experience island life.
Whether you're planning your next vacation or thinking about making Key West your permanent home, understanding the lifestyle is just as important as finding the right property. As local real estate advisors, we're always happy to share our favorite neighborhoods, restaurants, festivals, and hidden gems that make living here so special.
Who You Work With Matters,
THE SPOTTSWOOD TEAM
Terri Spottswood, John Spottswood, Ted Stewart
305-432-4848
[email protected]
Truman & Co. Real Estate
