Two people are kayaking in a blue and white kayak on the water, with modern white buildings and palm trees visible in the background.

The Ultimate Islamorada Summer Bucket List

Published on May 7, 2025

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Dreaming of a summer packed with sun, sea, and unforgettable adventures — no passport required?
Look no further than Islamorada, the sparkling gem of the Florida Keys. Whether you're chasing thrills on the water, exploring hidden natural wonders, or simply soaking up that signature island serenity, Islamorada is the perfect place to write your summer story.

And when it comes to where to stay — make it as unforgettable as the journey itself.
The Islands of Islamorada offers private beachfront villas, elevated resort-style amenities, and personalized concierge services, so you can relax, recharge, and dive into everything the Keys have to offer — all from one extraordinary home base.

The Islands of Islamorada

Swim with Dolphins at Theater of the Sea

A true bucket-list experience! At Theater of the Sea, you can swim with dolphins, sea lions, or even rays. It's family-friendly, unforgettable, and a truly hands-on way to connect with Florida’s amazing marine life.

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A person is standing on a paddleboard, with a paddle splashing water, against a sunset backdrop.

Kayak or Paddleboard to Indian Key

Adventure lovers, this one’s for you. Indian Key Historic State Park is a deserted island you can only reach by kayak or paddleboard. Once there, explore the ruins of a 19th-century settlement and enjoy some of the best snorkeling spots around.

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Two people are parasailing with a bright yellow parachute against a clear blue sky.

Go Parasailing over the Atlantic

See Islamorada from a whole new perspective — soaring hundreds of feet above the sparkling waters. Parasailing offers incredible views of the islands, coral reefs, and maybe even a dolphin or two playing below.

A person in sunglasses examines jewelry at a colorful outdoor market, surrounded by various items on display on a table.

Stroll the Third Thursday Art Walk

Experience the creative side of the Keys! On the third Thursday of each month, head to the Morada Way Arts & Cultural District for the lively Third Thursday Art Walk. This open-air event features local and regional artists, live music, and delicious food and drinks — all under the twinkle of string lights. It’s the perfect way to meet the artists, browse galleries, and soak in Islamorada’s vibrant arts scene.

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A woman is selecting red cabbage at a farmers' market stall, surrounded by various fresh vegetables and shoppers.

Visit the Florida Keys Farmers Market

Every Sunday from 10 AM to 3 PM, head to 81001 Overseas Highway for the Florida Keys Farmers Market. You’ll find fresh local produce, handmade goods, food trucks, and live music — making it a great way to spend a laid-back weekend morning in the Keys.

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A person is snorkeling underwater, wearing a mask and snorkel, while taking a selfie in clear, blue water.

Snorkel at Alligator Reef Lighthouse

Some of the clearest waters in the Keys are found at Alligator Reef. Hop on a snorkeling charter and swim among colorful fish, corals, and maybe even a sea turtle or two.

The Islands of Islamorada

Reel in a Big Catch on a Fishing Charter

Known as the "Sportfishing Capital of the World," Islamorada is the place to try your hand at deep-sea fishing, backcountry fishing, or even a family-friendly sandbar trip.

The Islands of Islamorada

Try Local Favorites: Key Lime Pie & Fresh Seafood

Foodies, rejoice. Your summer isn't complete without tasting authentic Key Lime Pie and the catch of the day at a dockside restaurant. Look for spots with water views and a chill, island-style vibe.

Make it an all-day culinary adventure by hitting the Key Lime Culinary Trail — a delicious journey to explore unique key lime-inspired treats and dishes across Islamorada. From classic pies to creative key lime-infused cocktails, it's a fun way to taste your way through the islands.

Key Lime Trail
A serene sunset over the ocean, viewed from the side of a boat, with golden reflections on the water's surface.

Sunset Cruise (Or Drop Anchor at a Sandbar)

Nothing beats a Keys sunset — especially when you're out on the water. Book a sunset cruise for front-row views of the sky lighting up in shades of gold and coral (many include drinks and light bites). Or opt for a sandbar excursion earlier in the day, where you can wade in turquoise shallows, sip something cold, and soak up the island vibes from your own slice of paradise.

The Islands of Islamorada

Celebrate the 4th of July at Founders Park

Add a patriotic touch to your summer! Join the Independence Day Celebration at Founders Park on July 4th. Enjoy live music, local food vendors, family-friendly activities, and a spectacular fireworks show over the water.

Event Details:

Date & Time: July 4, 2025, from 5:00 PM to 9:30 PM
Location: Founders Park, Mile Marker 87
Admission: Free; $10 suggested parking donation

Tip: Bring chairs or a blanket — but leave coolers at home!

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