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The Complete Vacationers Travel Guide to Islamorada, Florida (The Florida Keys)


Islamorada is located minutes away from Key Largo and an easy drive from Fort Lauderdale/Miami and Key West airports. It’s an ideal destination for families but perfect for those that just want to go relax too! Islamorada is known for its clear and calm waters, towering palm trees lining sandy beaches, and breathtaking sunsets. Though it has long attracted sport fishermen, it’s an equally appealing spot for divers and snorkelers, thanks to a colorful variety of shallow coral reefs and shipwrecks in its surrounding warm waters. It’s just a super peaceful, calm, and relaxing vibe.

Plan a vacation to the casual key of Islamorada! Check out our complete travel guide below!

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Where To Stay

While we were there we visited Amara Cay Resort and fell in love with this lovely Florida Key. It was selected by Jetsetter as one of the 9 best hotels in the Florida Keys! It’s a casual ocean front resort where the vibe is come as you are (shoes are optional).

Read More: Our stay at Amara Cay Resort 

Postcard Inn Beach Resort & Marina is Islamorada’s favorite oceanfront playground! “This newly refreshed Florida Keys resort getaway is an iconic property that offers the retro, throwback feel of a nostalgic American beach vacation, combined with modern amenities, designer furnishings and a touch of whimsy. They are currently undergoing a ‘stem to stern’ refresh here on property, including event venues, sleeping rooms, front lobby, landscaping and exteriors.”

Where To Eat

You can’t go wrong wherever you go because the food is so good and so fresh! A few local favorites were The Whistle Stop, where we were told to order the tacos, burritos, or the pizza. Head to Lorelei or Morada Bay for the best sunsets, drinks and live music. If you’re looking for sushi head to Kaiyo from 5-7 for their half off specials! We were told by the best food and beverage director that for an upscale island dinner, Chef Michael’s was a must! It’s the best seafood on the island. Trying hog fish while you’re on Islamorada is a must! It’s a white flaky light fish that you can only find down here. Anytime you find it, you also need to try conch fritters and the cracked conch. If you’re looking for exquisite oceanfront dining you’re going to want to go to Lazy Days! They also cook your catch which is pretty cool! Another favorite local spot for apps and starters is Wahoo’s Bar and Grill on the water!

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Ciao Hound

Ciao Hound Italian Kitchen & Bar features classic Italian comfort food that pairs the iconic flavors of Tuscany with familiar, locally-sourced ingredients. They offer patio seating (even a spot for your pups called the pooch patio) and Edison-style bistro lights to enjoy a dynamic menu with dishes such as Grilled Mahi Mahi Puttanesca, Sweet Florida Shrimp Scampi, Chicken Parmigiana, Linguini Vongole and Garlic-Rosemary Basted Tuscan Sirloin Steak. I got the lobster ravioli and it was spectacular. You could tell the ravioli was handmade from scratch and it melted in your mouth.

Honestly, I would have never gone here if it wasn’t recommended to me because who wants Italian at the beach? Most people are just looking for fresh fish. Well, I couldn’t have been more wrong. This place was amazing! The food was delicious and the presentation was outstanding. By far the best food I had while I was in  Islamorada.

Located at mile marker 84, Ciao Hound offers a full-bar, wine pairings and an Italian-inspired cocktail menu featuring Limoncello Sunrise and Sangria of the Day developed by resort mixologists. Ciao Hound is open for dinner seven days a week from 5 -10 p.m. and 5 – 11 p.m. Friday and Saturday.

Raw Bar

The Oceanside Raw Bar is a go-to spot for sampling seafood favorites. “Fresh from the sea” steamers, crab legs, shrimp and oysters. These are just some of the specialties cooked fresh daily if you’re looking to experience the distinct taste of Islamorada. A casual open-air deck offers picnic table seating overlooking the water. Live entertainment and custom cocktails are available 7:30 – 9 p.m. Sunday through Thursday and 7:30 – 11 p.m. Friday and Saturday.

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Holiday Isle Tiki Bar

The Holiday Isle Tiki Bar was such a fun vibe. The staff was super nice and friendly. You can lounge around a fire pit over looking the water with a rum runner in your hand. The marina boats are behind you and you’re surrounded by water. The views are spectacular and it’s so chill. Tiki Bar offers Island specialties including fish tacos and sandwiches, conch chowder and conch fritters with cocktails flowing 7 days a week. Make sure to catch live entertainment on Friday and Saturday nights and a celebratory Rum & Reggae party each Sunday. A Tiki Bar tradition, Conch Blowing takes place each day at sunset to kick off happy hour with a round of complimentary shots. Tiki Bar has such a chill vibe because it’s outdoors.  They have pool, shuffleboard and foosball set up which is a ton of fun. The conch blowing was definitely my favorite part!

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Fun Fact: “The Tiki Bar opened in 1969 and is home to the original rum runner!  In 1972, the hotel’s owner challenged his manager, “Tiki John,” to create a drink using only the overstock liquor in the storeroom. So he concocted a mix of Bacardi Superior Rum, Blackberry Brandy, banana liquor, lime juice and grenadine, and the original Rum Runner was born and is still served to guests today using the same recipe.”

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Things To Do

Islamorada is a super relaxing place so I spent most of my time relaxing in the pool, lounging in the hammock by the water, or in the water taking a dip.

Ocean side is where you can find Florida Keys Brewing Co. They are a small micro brewery with an artsy island vibe and brewing close to 30 styles of beer annually. You can only buy FKBC beer in their tasting room! Head to The Lobster Trap Art Gallery, a unique gallery full of colorful art from local artists from the Florida Keys. It’s known as the epitome of “Island Life”. Definitely get out on the water and try some of the many water activities offered! One of the top favorites is snorkeling under the Alligator Reef Lighthouse. You’re able to jet ski, hop on a boat tour, or go fishing! I love being able to be on the water and Islamorada definitely offers that! A local favorite is Spray Water Sports.  But if you want to check out something really cool go to Robbie’s, home to the word famous tarpon feeding! They even have water sports, shops, and a restaurant on site.

When To Visit

The Florida Keys weather is nothing short of perfection all year-round:

        • Spring: High of 85, Low of 69
        • Summer: High of 90, Low of 79
        • Fall: High of 86, Low of 72
        • Winter: High of 77, Low of 65

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What To Wear

Keep it cool. I’d recommend long flowy maxi dresses or skirts or loose shorts. Because it’s quite hot but since you’re surrounded by water, it’s sometimes cool and windy. I always like to pack a hat to protect my skin from the sun. Islamorada has a very laid back vibe so dress comfortably. Summer dresses, rompers, and swim suits with sandals are my summer go to staples.