27 Unique & Fun Things to Do in Islamorada at Night & Afternoon | 2024 (with Photos)

James A. Smith

James A. Smith - Chief Editor

Last Updated: March 25, 2024

Hey there! I'm James, an avid traveler who love exploring unique experiences and hidden gems in different destinations. I'm excited to share my recommendations and insights on the hidden gems of Islamorada at night and in the afternoon.

Unique & Fun Things to Do in Islamorada at Night & Late Afternoon

Welcome to Islamorada, a captivating destination in the Florida Keys with a rich history and an array of attractions.

Discover the fascinating past of Dade County as you explore the historic locations and landmarks that dot the area. Dive into the vibrant culture and city life, immersing yourself in the bustling county.

Indulge in the culinary delights of the Mar Bar and enjoy fresh seafood at the renowned Green Turtle Inn. From feet-deep diving adventures to thrilling water sports, Islamorada offers a multitude of outdoor activities.

With amazing hiking trails, day trips, and captivating sea lion shows, this charming destination is worth visiting for an unforgettable experience.

Most Recommended Thing to Do

Theater of the Sea

Top Choice Hotel

Cheeca Lodge & Spa

Our Top Choice Restaurant

Our Top Choice Bar for Nightlife

Best Time to Visit

Beautiful beaches and sunny weather await in Islamorada.

Average Temperature

Warm and tropical climate with moderate temperatures year-round.

Transportation Options

Car, bicycle, walking, public bus, taxi, rideshare, boat, trolley.

Average Cost ($, $$, $$$)


My Top Recommendation

Indulge your senses in the serene beauty of the city's captivating beaches and crystal-clear waters - immerse yourself in the warm waves and bask in the sun-kissed shores, creating cherished memories that will last a lifetime.

Furthermore, don't miss the opportunity to explore the vibrant marine life that inhabits the city's captivating coral reefs - embark on a snorkeling or scuba diving adventure in the pristine waters, where you'll encounter an array of colorful fish and fascinating underwater creatures, making for a truly awe-inspiring and personal encounter with nature.

What You'll Need to Bring

  1. Swimming essentials
  2. Comfortable shoes for walking
  3. Insect repellent

What Not to Miss

  1. Islamorada Fish Company
  2. Theater of the Sea
  3. Anne's Beach
  4. Morada Bay Beach Café
  5. Founders Park

What to Avoid

  1. Crowded areas during peak tourist seasons.
  2. Interacting with wild animals or feeding them.
  3. Engaging in illegal activities, such as drug use.

1. Experience the Vibrant Nightlife in Key West

Duval Street

Key West, the southernmost city in the continental United States, is known for its laid-back vibe and energetic nightlife. 

The city's rich history, colorful character, and unique island charm come alive as the sun goes down, turning it into a hotspot for night owls.

Downtown Key West is brimming with lively bars, like the famous Raw Bar, nightclubs, and live music venues, offering a variety of options for an entertaining night out. One of the most popular spots in town is the world-class Florida Keys Brewing Company.

In Downtown Key West, you can sample a variety of locally brewed beers and enjoy live music performances that regularly take the stage. 

This brewing company's beer garden offers an atmosphere that encapsulates Key West's relaxed and fun-loving spirit.

The Green Turtle Inn, another local gem, serves up tasty late-night bites alongside a varied selection of cocktails.

For those with a taste for the supernatural, the city's ghost town reputation means you can also enjoy a guided tour of some of Key West's most haunted spots, revealing a different, more chilling side of Florida Keys history.

2. Taste Authentic Key Lime Pie at a Local Café

Lazy Days Restaurant

Key Lime Pie is synonymous with the Florida Keys. This beloved dessert, with its distinctive tart flavor and creamy texture, is a must-try for anyone visiting the area. 

As you embark on a walking tour of the city, stopping by a local café for a slice of this iconic pie is one of the best things to do in Islamorada

In the heart of the city, along the bustling Overseas Highway, you will find numerous cafés and bakeries offering their take on the classic Key Lime Pie. 

Each establishment has its unique recipe, but all share the same basic ingredients: key lime juice, sweetened condensed milk, and a crumbly graham cracker crust.

One of the best places to sample this traditional dessert is the locally renowned Blond Giraffe Key Lime Pie Factory.

Here, the pie is made from scratch every day, using fresh key limes, and is served with a generous dollop of whipped cream on top.

3. Take a Night Tour of the Fascinating Diving Museum

Diving Museum

For an intriguing peek into the rich maritime history of the Florida Keys, plan a visit to the Diving Museum in Islamorada.

This world-class museum offers a fascinating journey through the evolution of diving, showcasing a variety of diving helmets, hand-operated air pumps, and other diving equipment, including a collection of armored suits that look like they belong in a science fiction novel.

The Diving Museum hosts an array of self-guided tours, allowing you to explore the museum at your own pace.

4. See Islamorada by Moonlight on a Boat Tour

Boat Tour

If you're looking for a different way to experience the beauty of the Florida Keys at night, a moonlit boat tour in Islamorada offers a breathtakingly unique perspective.

During the tour, you'll sail past some of Islamorada's most iconic landmarks, including the historic Alligator Reef Lighthouse. 

You'll also have the chance to see the Florida Keys' abundant marine life. Keep an eye out for sea turtles, sea lions, and a variety of other marine life that often makes an appearance on these nocturnal adventures.

Most boat tours also include a stop at a secluded beach or hidden cove, where you can enjoy a peaceful swim or simply relax on the shore. Some tours even offer night-time snorkeling, giving you a unique opportunity to see nocturnal sea creatures in their natural habitat.

5. See the City from the Overseas Highway at Night

Overseas Highway

The Overseas Highway, stretching from Key Largo to Key West, offers unparalleled views of the breathtaking Florida Keys landscape.

Driving along the Overseas Highway at night is a unique experience, offering a different perspective of Islamorada and its surroundings. 

Each bend and turn reveals a new vista, from the silhouettes of palm trees against the moonlit sky to the lights of distant islands dotting the horizon.

Making a pit stop at the popular Postcard Inn Beach Resort, which is beautifully lit at night, is a sight to behold. Here, you can stretch your legs, sip on a refreshing cocktail at the tiki bar, and enjoy the balmy tropical evening air.

6. Experience History at the Overseas Railroad Historic Site

Overseas Railroad Historic Site

For history buffs visiting Islamorada, a night visit to the Overseas Railroad Historic Site is an absolute must.

This remarkable site stands as a testament to the incredible engineering achievement of constructing a railroad across the vast expanse of the open sea, connecting the Florida Keys to mainland Florida.

Each step taken within this hallowed ground unveils stories of resilience, ingenuity, and the untamed beauty of the Florida Keys.

A night visit to this historic Site offers a unique and unforgettable experience for those seeking to connect with the fascinating history of Islamorada and the extraordinary human endeavor that shaped the region.

7. Visit Alligator Reef Lighthouse

Alligator Reef Lighthouse

A trip to Islamorada would be incomplete without immersing yourself in the captivating beauty of the iconic Alligator Reef.

Renowned for its vibrant marine ecosystem, this reef is a haven for divers and snorkelers seeking an up-close encounter with a diverse array of sea life.

However, it is during the nighttime that the Alligator Reef truly transforms into a mesmerizing spectacle.

The majestic Alligator Reef Lighthouse, standing as a stalwart guardian against the darkened sky, takes on an enchanting allure. Its powerful beam of light pierces through the darkness, casting a radiant glow upon the surrounding waters.

Whether observed from the comfort of a boat or the serenity of the shoreline, the illuminated reef paints a picture of pure magic, encapsulating the mystique and allure of the Florida Keys.

8. Enjoy a Late-Night Bite at a Food Truck

Garbo's Grill

The culinary scene in Islamorada is diverse and vibrant, with many options to satisfy late-night cravings. One of the unique features of the local food scene is the array of food trucks parked along the Overseas Highway.

These mobile eateries offer a variety of mouthwatering options, from succulent seafood to flavorful local dishes.

Whether you're in the mood for a classic Key Lime Pie or a deliciously fresh seafood taco, these food trucks offer a casual and relaxed dining experience.

Paired with the warm Florida night and the enchanting view of the nearby ocean, enjoying a late-night bite at a food truck along the Overseas Highway is a quintessential Florida Keys experience.

9. Take a Night Dive

Night Dive

Islamorada, known as the "Sport Fishing Capital of the World," is also a hot spot for divers. The island's rich marine life, coral reefs, and clear waters make it a diver's paradise.

The diving culture here is vibrant and welcoming, with many opportunities for both novices and seasoned divers.

To truly immerse yourself in this culture, join a night dive expedition. A night dive in Islamorada offers an entirely different experience compared to a daytime dive.

10. Visit the Florida Keys Brewing Company

Florida Keys Brewing Company

Unwind at the Florida Keys Brewing Company, located in the heart of Islamorada. Known for its laid-back atmosphere, artistic surroundings, and of course, its craft beer, this local brewery is a great place to spend an evening.

As the night settles, the brewery comes alive with twinkling lights, live music, and a lively crowd. Tour the brewing facilities and learn about the craft beer-making process, then head over to the tasting room to sample some of their specialty brews.

With a diverse selection of beers that encapsulates the flavors of the Florida Keys, there's something to suit every palate.

11. Catch a Live Performance at the Sea Theater

Sea Theater

An evening in Islamorada wouldn't be complete without a visit to the renowned Sea Theater. This captivating venue has earned a reputation for its exceptional live performances, captivating audiences with a variety of engaging shows.

Step into the world of marine entertainment as you witness the incredible seals' performances that showcase the intelligence and agility of these magnificent creatures.

The theater also hosts dramatic theater productions that transport viewers into captivating storylines, filled with emotion and talent.

Whether you're enjoying the show with your family, friends, or a loved one, the theater offers an evening of entertainment that combines creativity, passion, and the natural beauty of Islamorada.

12. Experience the Flora and Fauna at a Coral Reef

Coral Reef

For an adventure off the beaten path, consider a nighttime exploration of a local coral reef. Nighttime offers a unique opportunity to see nocturnal marine life that hides away during the day.

Even the coral itself changes from the dark. Many coral species exhibit polyp extension, a feeding behavior where polyps extend out from the coral to capture microscopic organisms called zooplankton.

This natural wonder transforms the reef into a dynamic and active ecosystem, revealing a side of Islamorada's underwater world that is rarely seen.

It's a spectacular and unique experience that should not be missed when visiting Islamorada at night.

13. Have a Beach Bonfire and Cookout at Anne's Beach

Beach Bonfire

Anne's Beach is an idyllic spot nestled in the Florida Keys and a popular destination for locals and tourists alike.

With its white sandy beaches and clear, turquoise waters, it's a picture-perfect spot to spend an evening.

Engage in lively conversations, share stories, and enjoy the relaxing sounds of the waves lapping on the shore.

14. Learn about Florida Keys History at the Visitor Center

Visitor Center

Start your evening with a visit to the Visitor Center, an important stop to get acquainted with Islamorada's history and culture.

This place is a treasure trove of fascinating historical information about the Florida Keys.

The second part of your visit can involve exploring the various exhibits that feature artifacts and memorabilia.

Each piece tells a story of the people, places, and events that have contributed to the unique heritage of the Florida Keys.

This engaging and informative experience is a must-do for history buffs visiting Islamorada.

15. Stargaze from the Islander Resort Beach

Islander Resort Beach

Islamorada's remote location makes it a prime spot for stargazing. At the Islander Resort Beach, the soft sand and soothing ocean sounds create the perfect environment for a serene night under the stars.

As darkness descends, the sky becomes a canvas of twinkling lights. Lay back on a beach blanket and marvel at the beauty of the cosmos.

To make the evening more educational and interesting, bring along a star chart or use a stargazing app.

These tools can help you identify constellations and planets. The tranquility, combined with the awe-inspiring sight of the night sky, makes stargazing at the Islander Resort Beach a truly magical experience.

16. Discover the Fascinating Marine Life at Robbie's Marina

Robbie's Marina

An evening trip to Robbie's Marina offers a unique opportunity to interact with the abundant marine life of the Florida Keys.

The marina is home to a large population of tarpon, also known as "silver kings" due to their large size and shiny scales.

Visitors can feed these impressive creatures right from the dock, a thrilling experience that is both fun and educational.

The second part of your visit could involve a nighttime boat tour. Guided by the moonlight and your guide's expert knowledge, you'll get a glimpse of the diverse marine species that call the waters around Robbie's Marina home.

17. Take a Moonlit Stroll in Tropical Gardens

Fairchild Tropical Botanic Garden

A moonlit stroll in Islamorada's Tropical Gardens offers a sense of tranquility that is both calming and inspiring.

As the moonlight filters through the lush foliage, the garden comes alive in a different way. Each leaf and flower is bathed in a soft glow, creating a magical landscape that beckons for exploration.

As you enjoy the serenity of the surroundings, take a moment to appreciate the beauty of nature under the gentle glow of the moon.

It's an experience that connects you deeply with the natural world and leaves you with a profound sense of peace.

18. Visit the Florida Keys Discovery Center

Florida Keys Discovery Center

The Florida Keys Discovery Center is a must-visit for anyone interested in the region's diverse ecosystems. 

The center frequently hosts evening lectures that delve into various topics, from marine biology to the effects of climate change on local wildlife.

These presentations, given by experts in their respective fields, offer deep insights into the complex web of life in the Florida Keys.

After the lecture, take a stroll through the center's exhibits. Each display is designed to be interactive and engaging, making the learning experience both fun and informative.

Whether you're a science enthusiast or simply curious about the natural world, an evening at the Florida Keys Discovery Center promises to be enlightening.

19. Explore Gems on the Mile Marker Walking Trails

Green Turtle Hammock Nature Preserve

The Mile Marker Walking Trails offer an excellent opportunity to explore the hidden gems of Islamorada.

Meandering through various landscapes, these trails are brimming with unique sights. As the moon casts its soft light, the paths take on a different persona, offering a tranquil yet adventurous night hiking experience.

The trails take you past several historical landmarks, providing glimpses into Islamorada's rich past. Whether it's a hidden cove or a scenic viewpoint, each trail has its surprises.

20. Appreciate Art at Local Art Galleries

Islamorada Art Gallery By Pasta

Islamorada's art scene is as vibrant as its landscapes, boasting a myriad of local art galleries that showcase the talent and creativity of the region's artists.

An evening spent hopping from one gallery to another is not only a feast for the eyes but also an immersion into the local art culture.

Each gallery offers a different perspective, showcasing works that range from traditional to contemporary art forms.

As you admire the art pieces, you'll also learn about the stories and inspirations behind each creation.

21. Try Out Night Fishing from the Key State Park Piers

Edward B. Knight Pier

If you're a fishing enthusiast seeking a memorable angling experience, why not try your hand at night fishing from the Key State Park piers?

As the sun dips below the horizon, casting an ethereal glow over the waters, the nocturnal atmosphere adds an element of excitement to your fishing adventure.

Set up your fishing gear on the sturdy piers that extend into the calm waters, providing a prime spot to cast your line.

Whether you're a seasoned angler or a beginner looking for a unique fishing experience, night fishing at the Key State Park piers offers a serene and captivating setting that is sure to create lasting memories.

22. Discover the Cultural District

Cultural District

As night descends upon the Cultural District in the Florida Keys, a vibrant and captivating atmosphere envelops the streets, enticing you to discover the rich tapestry of artistic expression.

Embark on an enchanting journey through this cultural hub, where creativity and imagination come to life under the moonlit sky.

Discover an array of galleries, each adorned with captivating works from talented local and international artists. Lose yourself in the vibrant colors, intricate details, and thought-provoking concepts that grace the gallery walls.

As you wander through the streets, you'll encounter live performances that ignite the senses, with music resonating through the night air and theatrical spectacles captivating audiences.

Indulge in the flavors of the region at charming restaurants, where culinary masterpieces are served, celebrating the unique fusion of flavors found in the Florida Keys.

23. Enjoy the Tennis Courts on Park Ave

Founders Park

For sports enthusiasts intrigued by Florida Keys's history, check out the tennis courts on Park Ave, located in the upper keys region of Islamorada, not far from the famed Overseas Highway.

Gather your friends after an engaging day at the discovery center or an enlightening visit to the hurricane monument, and challenge them to a spirited match.

24. Explore the Underwater World with Scuba Diving

Scuba Diving

Dive into an extraordinary adventure and explore the mesmerizing underwater world surrounding Islamorada through scuba diving. As the sun sets, the underwater realm takes on a whole new allure.

Strap on your scuba gear and plunge beneath the surface to discover a world teeming with vibrant marine life, captivating coral formations, and hidden treasures. Illuminated by your dive light, the colors come to life, revealing a breathtaking spectacle of biodiversity.

Encounter graceful sea turtles gliding through the water, schools of colorful fish dancing in unison, and intricate coral reefs swaying to an invisible rhythm.

The silence of the deep creates a sense of tranquility as you navigate through this otherworldly environment.

Whether you're a seasoned diver or embarking on your first underwater expedition, scuba diving at night offers a unique perspective and a chance to witness the wonders that come alive beneath the surface after dark.

25. Visit the Fossilized Coral Reef

Fossilized Coral Reef

For an enchanting and ethereal experience, make your way to the fossilized coral reef in Islamorada and witness its captivating transformation under the cover of darkness.

As the moonlight casts an enchanting glow, the ancient coral formations reveal their intricate details, evoking a sense of awe and wonder.

This natural wonderland, preserved through time, offers a magical nighttime view that transports you to a bygone era.

As you walk along the reef, the moonlight reflecting on the fossilized remains creates a captivating play of shadows and highlights, emphasizing the unique shapes and textures of the coral.

26. Try Your Hand at Night Photography

Islander Resort

Embark on a unique journey under the moonlit sky, capturing the mesmerizing beauty and the Florida Keys history of Islamorada after dark.

Equipped with your camera and tripod, let the raw beauty of overseas Hwy Islamorada FL lead you through scenic spots, where the twinkling stars form a breathtaking backdrop.

Venture into the upper keys, and experience the allure of the trails that reveal hidden historic landmarks. Capture the gentle glow of the streets on key largo, reflecting off the tranquil waters, and use a long exposure to create dreamlike images of light trails illuminating the city life.

Explore the Indian Key, brimming with historic stories of the county, bathed in soft, ambient lighting, where the architecture takes on a new charm.

27. Enjoy Live Music on Commercial Street

Hog Heaven Sports Bar and Grill

Discover the vibrant nightlife of Islamorada and indulge in the soul-stirring melodies of live music at one of the local spots along Commercial Street.

As the sun sets and the town comes alive, the rhythmic beats and enchanting melodies fill the air, inviting you to sway, dance, and let the music take you on a journey.

From intimate jazz clubs to lively beachfront stages, the variety of venues offers a diverse range of musical experiences to suit every taste.

Whether you prefer soothing acoustic melodies, lively Caribbean rhythms, or energetic rock performances, the local music scene has something to captivate and entertain you.

FAQs: Fun Things to Do in Islamorada

In this section, we provide answers to some of the most common questions people have regarding the best things to do in Islamorada at night.

What is Islamorada famous for?

Islamorada is famous for its breathtaking natural beauty, pristine beaches, and world-class fishing. Known as the "Sport Fishing Capital of the World," it offers exceptional opportunities for anglers to catch a wide variety of fish species.

Can you see the sunset in Islamorada?

Yes, Islamorada is known for its stunning sunsets. The vibrant hues of orange, pink, and purple paint the sky as the sun dips below the horizon, creating a mesmerizing spectacle. Watching the sunset in Islamorada is a must-do experience that captures the essence of the Florida Keys.

Can you swim in the ocean in Islamorada?

Absolutely! Islamorada is blessed with crystal-clear turquoise waters, making it an ideal destination for swimming and various water activities. Visitors can enjoy swimming in the ocean, snorkeling along vibrant coral reefs, or simply lounging on the sandy beaches and soaking up the sun.

Summing up: Unique & Fun Things to Do in Islamorada at Night

As you can see, there is no shortage of fun things to do in Islamorada at night.

From its intriguing history to its captivating attractions, Islamorada in the Florida Keys offers a diverse range of experiences.

Whether you're looking for cultural insights, outdoor adventures, or a taste of the local scene, this destination has it all.

Discover the unique charm of Islamorada by visiting its attractions, such as the Rain Barrel Village and its vibrant art scene, or by exploring the fascinating historic sites that dot the area.

Dive into the waters and engage in thrilling water sports or embark on nature trails to witness the beauty of the natural surroundings.

With its rich heritage and the allure of city life, Islamorada promises an unforgettable journey into the heart of the Florida Keys. So, plan your visit and uncover the hidden treasures that await this remarkable destination.