Islamorada is a village of six islands on mile marker 88 of the Florida Keys just ninety miles from both Miami and Key West. This island paradise is known as the Sport Fishing Capital of the World and offers visitors an up-scale yet small-town atmosphere, scenic views in every direction, fishing, fresh seafood, and an abundance of quaint shops and art galleries.
This popular Keys destination may just be the only place on Earth where you can catch a sailfish offshore then snag a tasty catch in the waters of the backcountry in the same day. With 24 miles of canals throughout the islands, there’s ample opportunities to explore the mangroves as sea life frolics around you.
There’s no shortage of delicious seafood straight off the boat, tasty frozen drinks, live music, sandy beaches and crystal clear water perfect for snorkeling, paddle boarding and swimming.
We interviewed our Destination Manager Chelsea to learn how she would spend five perfect days in this pristine village of Islands.
DAY 1: Road Trip to Key West 
A stunning drive south down the Overseas Highway, also known as Route 1, will lead you through 90 miles of sea and sun to mile marker 0 where a fun day awaits in festive Key West. Before you hit the road, pop into the Midway Café (just .3 miles from the residence) for a freshly baked pastry, homemade quiche or refreshing breakfast smoothie.
In under two hours you’ll find yourself in Key West where endless activities fill your roster. Start your day relaxing on Smathers Beach where you can bask in the white sand and take a dip in the turquoise water. When the sun works up your thirst, cool off with a delicious daiquiri at the Flying Monkeys Salon.
For lunch you’ll love Key West’s favorite tapas restaurant, Santiago’s Bodega, where the laid-back ambience is enhanced with custom artwork. Located just off Duval Street, it’s in the thick of the best people watching and serves mouthwatering tenderloin alongside a variety of “small plates” guaranteed to fulfill.
After lunch, the Hemingway House tour is a must. Then savor the flavor of Duval Street either by foot or rent a bike or scooter. Art galleries, live music, unique vendors, and colorful people pepper the popular corridor. End your Duval Street tour at Mallory Square for a front row seat to an amazing sunset and evening entertainers.
For dinner, you’ll enjoy a fresh grouper sandwich and a live band at Schooner’s Wharf. This “last little piece of Old Key West” is at the foot of the historic harbor walk where you’ll embrace the true meaning of Conch life while checking out the boats.
DAY 2: Fish On!
Café Moka is an upbeat local coffee shop in Islamorada and a delicious way to start the day with French pastries, sandwiches & coffee or espresso before heading to Bud & Mary’s Marina where we’ve booked your offshore or inshore (backcountry fishing) charter. Offshore catches include sailfish, marlin, kingfish, wahoo, dolphin (mahi-mahi) and tuna. Backcountry hooks yield tarpon and bonefish.
Captain Larry brought our investors huge success in reeling in dinner over the years, and we are happy to book your charter with him. The world-famous World Wide Sportsman Store is minutes from the house where you can get outfitted with everything necessary for your fishing adventure.
If your charter is in the morning, enjoy lunch at The Islamorada Fish Company. Their fresh ahi tuna salad is delicious, and you’ll love dining outdoors in the soft bay breeze as you overlook the Florida Gulf Coast.
Back at the Islamorada residence, take an afternoon dip or sip a cocktail by the pool. For dinner, grill your fresh catch of the day at the cabanas and enjoy the sunset, hot tub and company of your friends and family.
DAY 3: Kayak, Paddle Board and Enjoy Wildlife 
Enjoy coffee on the deck overlooking the serene sunrise over the Atlantic. Your local host stocked the home with all your favorite foods prior to your arrival, so whip up a delicious breakfast before you head out for the day.
This morning you’ll head to Back Country Cowboy where we’ve arranged a kayak or paddle board tour of the intricate mangroves. Dolphins, birds, turtles, sting ray, manatees and sharks are ready and waiting for you to observe on your journey. If you’d rather hit the pavement, they also rent bikes and can suggest some amazing rides nearby.
For lunch, the Square Grouper is calling with its fresh seafood, craft cocktails and unbeatable location overlooking the bay. Their fresh mahi is delicious and the patio offers prime views of the Gulf and all its action.
Back at home, the pool is calling for you to relax before heading to Morada Bay for a fabulous sunset and cocktails. This festive beach bar offers signature drinks and bay breezes guaranteed to please. Your Local Host made reservations next door at Pierre’s Restaurant, the iconic white mansion on the bay, for dinner. At dusk the beach offers a romantic backdrop to the most mouth-watering French fusion cuisine. With your feet in the sand and perfectly paired wine in hand, this will be one of your most memorable meals on the island.
DAY 4: Snorkeling, Sandbars, Singing & Seafood
Rise and shine and make your way over to the hip, iconic Green Turtle Inn – just a two-minute drive or ten-minute walk from the house – for their famous breakfast burritos and lobster benedict.
We’ve made reservations at Aqua Blue Adventures where you’ll hop aboard a five-star charter boat to the Islamorada Sandbar, a snorkel adventure, or sightseeing excursions to Alligator Lighthouse (don’t worry – there aren’t any alligators). You can opt to stop by Publix and stock up on “Pub subs” and BYOB cocktails on the charter, or choose from dockside lunch menus for an all-inclusive experience. If you’re heading out in the afternoon, Wahoo’s Bar & Grill is a great choice for lunch before you board the charter.
This afternoon we’ve made reservations for you to be pampered in paradise at Cheeca Lodge & Spa. After a relaxing massage or facial, you’ll appreciate a cold drink at the tiki bar while snacking on their fresh smoked fish dip and watching another award-winning sunset.
For dinner, reservations at the waterfront Atlantic Edge Restaurant at the Cheeca Lodge will impress as you savor their blue crab stuffed yellowtail perfectly paired with the sommelier’s favorite wine. If you’ve got a craving for sushi, your local host will gladly reserve your table at Nikai Sushi Bar, also in the Cheeca Lodge. You can expect nothing short of delectably fresh sushi in the sportfishing capital of the world!
DAY 5: Swim with the Dolphins & Feed the Tarpon at Robbie’s Marina
Today there are a number of activities you can choose from to round out your perfect Keys vacation. Back at the Midway Café, your coffee and breakfast sandwiches are hot and fresh. If it’s an active day you seek, try your hand at a round of Tennis back at the Cheeca Lodge & Spa.
Calling all animal lovers at heart, the Theater of the Sea is a spectacular tribute to the sea life of Islamorada. Natural lagoons and tropical gardens are home to dolphins, sea lions, sea turtles, fish, sharks, stingrays, alligators, and birds. The dolphins are playful in their indigenous habitat, and you have the rare opportunity to meet, swim and paint with them. For the history buffs, the History of Diving Museum is a homage to the fascinating story of the brave pursuit to explore the depths of the sea.
An afternoon at Robbie’s Marina is akin to a waterfront amusement park with a tropical open-air market, parasailing, party boat fishing, restaurants and shopping. A “trailer trash Bloody Mary” from the Hungry Tarpon is a must-have on your visit. You can feed the tarpon, rent a paddleboard, or try your skills on a jet ski.
If you’ve worked up an appetite, the Florida Keys Brewing Company not only has a fun tasting room but also serves amazing fresh fish tacos. If you’re seeking live music on your last night out, ask your Local Host to see who’s playing at Islamorada Brewery & Distillery.
Indulge in an afternoon siesta back at the house where the refreshing pool and hot tub await. Your Local Host saved the best for last with reservations at the renowned Chef Michaels where if locals are catching or growing it, their chefs are cooking it. Start off with fresh conch fritters but make sure to save room for your entrée, either the tuna tataki or “off the boat” seafood with pasta. The menu will change based on available fresh catches, so be sure to ask your server for suggestions.
No trip to the Keys is complete without key lime pie, and for a real treat stop by Midway Café for their frozen key lime pie on a stick.
At Home in Islamorada with Equity Estates
This modern 3-bedroom, 3-bath luxury oceanfront penthouse is located within an exclusive, gated community. The home features panoramic views of the Atlantic from every room, as well as an array of amenities including a dock, pool, hot tub, cabanas and hammocks to make your stay special.
The light-filled, end unit home has been recently renovated, and boasts a spacious open kitchen with top-of-the-line Bosch appliances. For your convenience, there’s covered parking and an elevator that takes you up to an open veranda and right to your front door.
Just outside, you’ll find a resort-style community pool, hot tub, cabanas with outdoor grills and inviting hammocks. Click here to view the Islamorada residence.
About Sargassum
Please note that during summer months there is an influx of sargassum on the beaches of Islamorada. Sargassum is a marine alga, commonly known as seaweed. It grows in the Atlantic Ocean, Gulf of Mexico, and Caribbean Sea.
While the community works vigilantly to clean up the seaweed it can often limit the ocean access immediately behind the residence. Sargassum season begins in late May or June through hurricane season, which ends November 30th.
