THE ISLAND TIMES

Make the most of your time in Islamorada with our insider's guide to navigating the neighborhood. From lively dive bars to local dive shops, we’ll let you in on our favorite places to drink, dine, shop, and explore.

October in Islamorada

Turn your October into a month-long celebration. There are always...

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October in Islamorada

Turn your October into a month-long celebration. There are always tons of exciting events going on in Islamorada, but this month we get a little more festive. Check out some of our favorites, listed below. 

Leave your bathing suit and pack your lederhosen, it’s time for Oktoberfest in Islamorada. Brush up on your German, because there will be beer chuggin’, pretzel eatin’, and Oompa singin’. This completely free event is family-friendly and a great way to spend your afternoon.

Calling all nightcrawlers! Join the gang on the third Saturday of this month in your best zombie attire for the 5th Annual Zombie Pub Crawl. There will be a costume contest and tons of “boos” to go around. 

Pack your pups so you can raise your cups on the last weekend in October for Barktoberfest! Join Islamorada for a pet-friendly Halloween celebration, and be sure to pick out a clever costume for your furry friends because the best-dressed pet leaves with barking rights and a great prize! 

Take a Drive

Did you know that the main road that connects the...

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Take a Drive

Did you know that the main road that connects the Florida Keys to the mainland of the United States, Highway US-1, goes all the way from here to Maine? This highway is one of the longest in the entire country, stretching 2,369 miles from the north to the south.

This very long and important road connects most major cities on the East Coast, and makes its final stop right here in the Florida Keys. The "Mile 0" sign in Key West happens to be one of the most photographed highway signs in the whole state of Florida. Although some might say that Fort Kent, Maine, and Key West, Florida are the most important stops on Highway 1, we actually think the only one you have to remember is Mile Marker 85.5 — right here at the Postcard Inn! 

Kick it Kokomo style at the Pool Bar

Have you stopped by our famous pool bar? Kokomo is...

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Kick it Kokomo style at the Pool Bar

Have you stopped by our famous pool bar? Kokomo is the ultimate hangout spot at the Postcard Inn.

This pool area has some of the most spectacular views of the ocean without getting you all salty from the sea. It’s the best of both worlds. Kick it pool- and beachside with the gang and a Piña Colada in hand. Sway your hips at the pool bar to the sounds of Islamorada, whether it be our cool local bands or great radio jams. 

The Postcard Inn at Holiday Isle has been known for our tropical cocktails, local food, and tiki bar-style for decades—it’s what we do best. Grab a float and a floater and meet us at the Kokomo Poolside Bar, we know the Beach Boys would be proud. 

PADI Celebrates Women Divers

Scuba diving is a popular activity around Islamorada and the...

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PADI Celebrates Women Divers

Scuba diving is a popular activity around Islamorada and the Postcard Inn. Every July at the Islamorada Dive Center on-site, we like to celebrate all the women who take part in this environmentally important practice. We invite you to participate in Women's Dive Day anually in July. The typical day's events include starting your morning off at the History of Diving Museum to see and celebrate women in diving. Then, cap the afternoon off with a local dive or with Sailfish Scuba to learn even more about environmentally friendly diving practices. July is meant for women exploring the water— so here's to you ladies! 

Indian Key Historic State Park

Spend your morning getting lost in paradise. Even though “paradise”...

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Indian Key Historic State Park

Spend your morning getting lost in paradise. Even though “paradise” is only a half-mile off-shore from Islamorada, it feels like a place that's eons away. Indian Key Historic State Park is just a short kayak ride away but will make you feel like you are stepping back in time.

This little island was the very first county seat for Dade County and has been an important part of the Florida Keys since 1836. A small community on Indian Key created a tiny empire in the 1800s by salvaging wrecked ships and collecting their goods—this lucrative business opened up many doors for this small but mighty island. Although Indian Key was heavy in business for many decades, the tides have definitely shifted for this island getaway. Ironically, many people flock to the island now to escape work and focus on play. Indian Key is a great spot to snorkel, hike, swim, fish and to simply see the nature lurking beneath the ocean's surface.

Islamorada Sand Bar

Everyone flocks to the Florida Keys for the hypnotizing water...

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Islamorada Sand Bar

Everyone flocks to the Florida Keys for the hypnotizing water with a splash of the laid-back lifestyle. There are not many places in the world that replicate the feeling of being in Islamorada.

One of our favorite things to do is take the boat, kayak, or jet ski out to meet everyone at the Islamorada Sandbar for Islamorada’s best ocean parties. The sandbar is located less than a mile offshore from the Postcard Inn and once the crowds start gathering, it can be seen for miles and miles. Hundreds of boats and people become one with this unique geographical phenomenon that is right in our backyard. Lather on the sunscreen, pack up the snacks and booze, blow up the floaties, and hitch a ride to Islamorada’s most popular parties on the sandbar. 

7 Mile Bridge Run

The Florida Keys is a sacred destination for locals and...

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7 Mile Bridge Run

The Florida Keys is a sacred destination for locals and tourists alike. One of the things that makes our sweet home so special is that it inhabits a true island lifestyle.

The Caribbean water makes up much of what we know to be our home, and it wouldn’t be possible to keep our keys connected without an elaborate series of bridges. One of the most iconic structures in the Keys is the 7-Mile Bridge. This particular bridge was built to connect the middle keys, but unlike a traditional overpass, it had to stretch for seven miles without any true anchor but the sea. A fun way to celebrate this incredible feat is by cheering on the runners of the 7 Mile Bridge Run. Each April marks the Annual Bridge Run, which began when the new bridge first opened. It's the only run that is completely surrounded by water from start to finish and it's a great way to spend your Saturday morning in the Florida Keys! 

Winter Lionfish Derby

Did someone say lionfish? It seems like this spiky, striped...

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Winter Lionfish Derby

Did someone say lionfish? It seems like this spiky, striped fish has struck up quite the conversation among those living in the warmer waters of the Caribbean in the past few years.

This particular species has been labeled as an invasive fish that is growing quickly in numbers in our local waters. Who knew that the solution would be to eat them? The lion-fish has become the latest delicacy and apparently has a lot to offer in the taste-buds department. 

One of the ways to limit their growth is by literally removing them from the sea and eating them for dinner. A fun way to get involved is by fishing or feasting at this year's Winter Lion Fish Derby. Come try your hand at lionfish farming or just try a piece for a good cause at our annual event with Reef Environmental Education Foundation (REEF).  

Festive in February

There is nothing better than the Florida Keys in February....

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Festive in February

There is nothing better than the Florida Keys in February. The weather is just right, the island is bustling with people from all over the world, and there is so much to do! We wanted to give you the inside scoop here first. 

Up first on the list is the Big Kahuna Corn Hole Tournament benefitting the Good Health Clinic where you can try your hand at a corn-hole-in-one while raising money for a good cause.  

Next up is a little more involved. The Whale Harbor Bridge Run is a very short half-mile run, meant to bring out fun and support the local community. The proceeds that are made during this run go to scholarships for students at Coral Shore High School. 

Last but not least, one of our favorite things to do is drink beer, and our second favorite is to support our local brewery. Islamorada Beer Company is celebrating their anniversary each February. Join in all the birthday party fun!

Food & Wine Festival

If you’re planning a trip to Islamorada in January, you...

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Food & Wine Festival

If you’re planning a trip to Islamorada in January, you are required to pack your taste buds in your carry-on. 

January is already a great month in the Florida Keys because of the delicious weather and clear blue waters, but on top of everything that makes these islands great, it's the Key Largo & Islamorada Food & Wine Festival that makes it even better. For ten whole days of the month, the Upper Key’s will be “Uncorked” and scattered with delicious bites and booze all over the place. There are over 35 different events taking place starting the second week of January and there is an option for every palate and budget throughout the festival. And the best part is that Grand Tasting will be taking place right here at The Postcard Inn. What a great way to start off the new year! 

Holiday Events in Islamorada

Be sure to make time for the Annual Islamorada Holiday Fest...

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Holiday Events in Islamorada

Be sure to make time for the Annual Islamorada Holiday Fest to celebrate another great holiday season at Founders Park. There is nothing quite like a lot of snow on a very sandy beach. Bring your kids, bring your family, and bring your friends for this Florida winter celebration. The Parade kickoff and Holiday Gift Bazaar will begin the first weekend in December. Don’t miss out on Santa’s Sweet Shop, with all the delectable goodies that will be offered throughout the entire evening — and if you’re interested in a little healthy competition, be sure to check out the annual Ornament Competition by 50 local artists, all competing for the best ornament design on the island. Holiday Season is here and we couldn’t be more excited to celebrate it here in our hometown!

Jet Skiing in the Florida Keys

Calling all adrenaline junkies, it's time to get your feet...

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Jet Skiing in the Florida Keys

Calling all adrenaline junkies, it's time to get your feet wet and feel the wind in your hair by hopping on one of the Florida Key’s favorite past times, jet skiing!

A jet ski is like a motorcycle on the water, but instead of streets, you can glide across the open blue ocean. This fun activity is a more affordable way to get your ocean fix than renting a larger boat. You are still able to skip over waves, explore intimate passageways of the mangroves, follow the tide pattern, ride from island to island and race around the Atlantic Ocean all by yourself or with a few close pals. Guided island-hopping tours are available for those who would like to see all parts of the Florida Keys and not just from a hammock. Pick your favorite Waverunner to try out this fun, action-packed ocean activity today. 

Alligator Reef Lighthouse

Grab your snorkel and dive right into the fresh waters...

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Alligator Reef Lighthouse

Grab your snorkel and dive right into the fresh waters of Islamorada, Florida. There is no better way to cool off than by swimming in the coastal shores of the Florida Keys. One of our favorite spots to dive at is Alligator Reef Lighthouse because this unique diving spot is home to hundreds of fish. The bright blue water surrounding Alligator Reef is crystal clear, and it's a guarantee that you will spot Parrot Fish, Barracudas and Sargent Majors. And, if you're one of the lucky ones, you might just get a glimpse of one of the turtles that hang around the lighthouse. You can only reach Alligator Reef by boat, so guests of the Postcard Inn can contact the front desk to arrange a charter or rental. Enjoy the refreshing water of the Keys while taking in the gorgeous sites of Alligator Reef Lighthouse.

Lobsters during Mini Season

Every year, the end of July signals that it's Mini Season...

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Lobsters during Mini Season

Every year, the end of July signals that it's Mini Season around Islamorada. If you’re not familiar with Mini Season, let us explain:

It is the most anticipated two days of the entire lobster season — it just happens to fall a few days before the regular lobster season opens from August to March. These two days are always on the last consecutive Wednesday and Thursday in the month of July, just in time to get your fresh lobster fix. People from all over the country flock to the Florida Key waters to try their hand at lobster catching. Mini Season is typically the most plentiful time to grab your lobsters, as the crustaceans have had a few months of R&R. All you need to participate in this two-day event is a valid recreational saltwater fishing license and lobster permit, your tickle stick, a lobster bag, a few pals and a little bit of butter for the after party! 

Independence Day for The Conch Republic

If you have ever visited the Florida Keys, you would...

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Independence Day for The Conch Republic

If you have ever visited the Florida Keys, you would know already that it's a place like no other.

But did you know we act under our own name as the Conch Republic? Yes, it's true — we are just a bunch of conchs! On April 23, 1982,  the Conch Republic was established in response to a United States Border Patrol Blockade that had been set up on highway U.S.1 between the Florida Keys and the mainland. Local residents and officials of Key West were so astonished that they later marched to Federal court in Miami and declared on television that they would be seceding from the Union. The secession only lasted for one minute before the Mayor surrendered, however, this became the revolution of the ‘conchs’ that now extends throughout the entire Florida Keys. No matter where you are on April 23rd, please help us celebrate our independence with a cocktail in hand and a little Jimmy Buffet on the stereo!

Sailfish Tournament

Grab your rods and reels, and wade through the open...

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Sailfish Tournament

Grab your rods and reels, and wade through the open waters, it's time for the Islamorada Fishing Clubs Annual Sailfish Tournament.

The kick-off for this competition is January each year, and the competition will be fierce. Grab your best angling friend and try your hand at some good old catch and release of these giant beauties. Sailfish are the fastest fish in the ocean and mostly enjoy swimming in the colder waters that fall upon the islands in January. They are notorious for their large bills and always put up a tough fight for the person on the other end of the rod; this attribute makes them great competition and a pretty awesome trophy fish. You can put your lines in the water right at 8:00 am, but be sure to have them out by 5:30 pm. Do you think you have what it takes to fight your way to the top?

Cocktails at Home

Take the essence of the Florida Keys back home with...

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Cocktails at Home

Take the essence of the Florida Keys back home with you any time of year!

Especially when the weather begins to turn up north, it's impossible not to dream about the turquoise waters and breezy afternoons of Islamorada, wishing with every bone in your body that you were sitting at the Postcard Inn’s Tiki Bar. Trust us, we know its tough — but to help you through those tough days, we have compiled a list,—recipes included—of our top three favorite local cocktails that will bring you right back to island time! Try your hand at making the Goombay SmashRum Runner and Hurricane — all mixed with rum, all tropical, and all extremely satisfying. These cocktails are sure to warm you up like the South Florida sun, but be sure to sip slowly because a rum punch like this will sneak up on you in all the right places!

Grand Prix of the Sea

Calling all adrenaline junkies — this month is all about...

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Grand Prix of the Sea

Calling all adrenaline junkies — this month is all about you! Come on over to The Postcard Inn and experience the Annual Islamorada Grand Prix of the Sea, put on by our very own hotel and P1 Aqua X in August.

Let your heart thump while listening to the powerboats race up and down the crystal clear waters of the Florida Keys. This year marks the first ever P1 races, and we feel so honored to be included in this Florida & Pro Series event. P1 Aqua X is proud to bring their world-renowned racing community to our home front — this completely free event is perfect for people of all ages! If you love a good thrill and want to be part of something new to Islamorada, be sure to claim a spot early right outside your hotel door, or stop by our famous tiki bar for a rum runner and burger while you wait for P1 to START THEIR ENGINES!

Stand-Up Paddleboarding

What's the best way to get out and enjoy the sapphire blue...

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Stand-Up Paddleboarding

What's the best way to get out and enjoy the sapphire blue waters of Islamorada? Grab a board and a paddle right here in Holiday Isle. The smooth island seas are perfect for gliding on the surface, perfecting your tan, and getting an up-close sneak peek at the sea life below. Overnight guests can visit us on the beach and we will get you set up with your complimentary paddle board. If you are looking for a bit more adventure we can set you up with our favorite team from Aquaholics for a half-day morning or afternoon expedition exploring the coastal waters. Take your tour to the next level and try a guided evening tour on our glowing paddle boards. The coolest way to unwind and get up close and personal with our most-loved island. 

Snorkeling Hot Spots

The Florida Keys are known for the spectacular reefs and...

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Snorkeling Hot Spots

The Florida Keys are known for the spectacular reefs and aquatic life underneath the ocean surface. Overnight guests can come talk to a concierge to plan your snorkeling adventure. No matter which reef you choose, you are bound to see a plethora of colorful fish, gorgeous coral, and the occasional sea turtle. A two-hour adventure out on the water will either include Chicken and Hen’s reef or Cheeca Rock Reef, any reef you end up at — even if it is just offshore of the hotel — will be incredible. Snacks, drinks and beer are all available for purchase, to cool off before or after your salty excursion.

Full Moon Party at Morada Bay

The moon is one of the most important elements on –...

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Full Moon Party at Morada Bay

The moon is one of the most important elements on  or should we say around  the planet.

It brings the tides in and out, it dances daily with the sun and it gives us a bright dewy glow every single month. Therefore we only think it is right to celebrate. When all the sun lovers go away for the evening, the moon worshippers will come out to play — we are celebrating with a Full Moon Party each May! After the summer sun sets, que the full moon for the party to begin. This evening festival will be headlined with live music, delicious food, and crafty cocktails. Take your evening slow and enjoy dinner and drinks in an Adirondack chair by the sea or party the night away with the Junkanoo band dancing in the moonlight. End the evening with a spectacular firework show and be sure to send your salutations to our beloved moon.

Original Marathon Seafood Festival

Lobster, sunshine and live music — have you ever heard...

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Original Marathon Seafood Festival

Lobster, sunshine and live music — have you ever heard three words more important to The Florida Keys?

The second largest event held in the Keys is The Original Marathon Seafood Festival held each March. For more than fourty years running this festival has taken on an identity of its own. The Seafood Festival started as a local event for the fishing community to spend time with their loved ones while enjoying the outcome of their hard work. Slowly it turned into an island sensation and everyone wanted an invite. The Organized Fisherman of Florida still take part in putting on this tasty event and are always sure to give back to the community by sharing part of the proceeds that are gained. Pull up a seat, shuck an oyster and grab a cold one — now this is what The Florida Keys are all about!

Island Fest

Spring may not mean as much in the Florida Keys,...

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Island Fest

Spring may not mean as much in the Florida Keys, where the weather’s always sunny and warm, but it does mean that it’s time for Islamorada’s fun-packed Annual Island Fest!

Located less than ten minutes from our Islamorada beachfront resort, visitors can enjoy live music from a variety of genres, gourmet cuisine from local restaurants, arts and crafts booth from both local and national artists, and even fun sand castle building competitions. There’s also a classic car show planned with free entry and unique, hand-crafted coconut awards for a range fun and goofy categories like "Keys-y Rider!" Fun for the whole family, Island Fest is a not-to-be-missed event that celebrates everything that makes the Keys and Islamorada such a great place to be! Plan to not miss this annual Spring event in late March or ealy April.

Address: 87000 Overseas Highway, Islamorada

Robbie's of Islamorada

Grab a ice-cold beverage and a bucket of bait, right off...

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Robbie's of Islamorada

Grab a ice-cold beverage and a bucket of bait, right off of US1 and have yourself a good ol' time.

You can’t come down to the Florida Keys without feeding the infamous tarpons at Robbie’s Marina and Bar. These monsters will jump right out of the water to snatch the bait right out of your hands, creating the most perfect photo opportunity! Right outside the marina is a group of vendors, selling everything from hammocks to fine artwork, in the magnificent sunshine. The Robbie’s experience is a complete treat and an authentic Florida Key’s establishment. The marina itself has been around for nearly twenty years and is a staple stop for many traveling throughout the islands. Make sure you take a second to admire the gorgeous view of the bay and staple a dollar bill to the bar to let the world know that you fed a fish named Scarface in the Florida Keys.