My Favorite Road Trip from Miami to the Middle Florida Keys

Dynie Sanderson - NapaFoodGalTravels

My Favorite Road Trip from Miami to the Middle Florida Keys

by Dynie Sanderson

At least once a year, when I visit my family in Miami, we try to organize one of our favorite pilgrimages down to Islamorada and Marathon in the Florida Keys. We were unable to make our planned road trip this year as the Keys have been closed or partially closed to visitors since early March 2020. They are slowing putting out their welcome mats to visitors. These laid-back tropical islands off of the southern tip of Florida are ready to welcome you back as they are re-opening up their doors again. Time to start planning our next road trip there.

Miami, Florida to Marathon in the Florida Keys – The Route

Only 89 miles to your destination in Marathon, you will discover that driving south from Miami provides a relaxing drive south along US 1. You will actually feel yourself unwind, and your day to day tensions drift away as you embark into the gateway of the upper keys at Key Largo. During our journey along the Overseas Highway (US 1) to our final destination in Marathon, we experience aquatic vistas on both sides of the islands with the Atlantic Ocean to the left (east) and the waters of the Gulf of Mexico and Florida Bay (west) to your right.

First Stop – Alabama Jacks

A must stop along the way is stepping back in time to the renowned old-school beach bar, Alabama Jacks, where you find their infamous Conch Fritters and tropical beverages. And being the Conch Fritter junkie that I am, Alabama Jacks is absolutely one of my favorites for fritters. It’s just a detour east off of the direct route of US Hwy 1. Just south of Homestead, you will merge onto Card Sound Road (CR 905) just before crossing the Card Sound Bridge to North Key Largo. You will find Alabama Jacks a rustic and lively waterside spot for seafood, live music, and a breezy atmosphere. Be sure and have one of their Margarita's. 58000 Card Sound Road, Key Largo: 305-248-8741 They don’t have a website, but you can check them out on Facebook.

What’s Magical About Cruising Down the Overseas Highway

For me, this Florida road trip is a much about indulging in the freshest of Florida seafood as it is about getting away from it all and chillaxing in this unspoiled and unpretentious seaside paradise. Next stop, we are off to Islamorada, the Village of Islands, which boundaries are from mile marker 90 down to mile marker 72. These six islands of Islamorada are informally known as the Sport Fishing Capital of the World. Much of the area is preserved in State Parks. You can rent a boat, charter a boat, participate in a guided tour to fish, snorkel, scuba dive, and swim with marine life. Places to be sure and check out are The Theater of the Sea featuring dolphin encounters; The History of Diving Museum where you will see a 16th century treasure chest. Windley Key Fossil Reef Geological State Park; Lignumvitae Key Botanical State Park has a tropical forest; Key Historic State Park – a tiny island with 1800’s ruins. There are many sportfishing operations and dive operators in the area.

Dining Scene in the Upper Keys

The dining scene in Islamorada is renowned, and here as well, the fresh seafood is the reigning star of the area's divine regional cuisine. A must-do is take a stop off at one of the areas many tropical-themed bars for a full Florida Keys experience. Two of my favorite stopovers is the Morada Bay Keys Beach Café and Bar located at Mile Market 81.6, which was also the location where the Netflix series Bloodline was filmed. Another must-stop is the world-famous Tiki Bar at the Holiday Isle Resort, Mile Marker 84, which has been a popular island stopover since 1969. They are known for their signature Rum Runners; you must try one. They knock it out of the park with their Conch Fritters, other fresh seafood, and raw bar. It is truly a quintessential Florida Keys experience.

When in the Keys it is all about the fresh seafood and just about every dining establishment has their own version of conch fritter. And if it is Stone Crab season, be sure to indulge. Stone Crabs, Conch Fritters and the abundance of fresh caught season is one of things I miss most about Florida. As I tell everyone, being a tried and true Florida Girl that relocated West – “You can take the girl out of Florida, but you can never take the Florida out of the Girl!”

Here are a few of my top favorites to dine in Islamorada

· Morada Bay Keys Beach Café

· Green Turtle Inn

· Cheeca Lodge – 4 Restaurants

· Pierre’s Lounge and Restaurant at Morada Bay

· Islamorada Fish Company and Market

· Marker 88

· Bayside Gourmet

· Lorelei Restaurant and Cabana Bar

· Tiki Bar

Great Places to Stay When Visiting Islamorada and Key Largo

· Postcard Inn Holiday Isle

· Cheeca Lodge

· The Moorings Village

· La Siesta Resort and Marina

· Amara Cay Resort

· Islander Resort

· Chesapeake Beach Resort

· Casa Morada

· Bayside Inn

· Islander Resort

· Topsider Resort

Cheeca Lodge and Spa

For a more refined and relaxing experience, chose to stay at the iconic Cheeca Lodge and Spa. It is romantic, serene, and dynamic. This award-winning resort offers lush accommodations, a golf course, snorkeling, sea kayaking, bicycling, scuba diving, and a state of the art spa. It is also a premier destination for serious anglers, where you can charter a boat and find over 500 species of fish just minutes from shore.

Marathon – The Middle Keys

Next stop and our final destination on our Florida Keys road trip is Marathon, a middle keys city, set on 13 islands known for their beautiful and serene beaches and their barrier reef. Known as The Florida Reef, it is the third-largest coral barrier reef system in the world (after the Great Barrier Reef and the Belize Barrier Reef). Marathon is located between mile marker 61 at Tom's Harbor Cut Bridge by Duck Key and the beginning of the 7-mile bridge, which was one of the longest bridges in existence when it was built and opened in May 1982.

The tropical climate and consistent offshore trade winds provide an inviting atmosphere to explore all of the area’s outdoor activities. A few of my favorite things to explore when I am in Marathon is The Turtle Hospital. There is also the Dolphin Research Center and the Florida Keys Aquarium Encounter. Of course, snorkeling and scuba diving opportunities are abundant. For the best beaches, Sombrero Beach is one of my favorites. And like all of the keys, getting out on a boat and fishing offshore is what it’s all about along these islands.

Isla Bella Beach Resort – Luxury in the Middle Keys

For some of the most pristine lodging and dining in Marathon, plan on staying at the Isla Bella Beach Resort, a brand new Florida Keys Luxury Resort, offering stunning ocean views from every room at their 24-acre oceanfront destination.

Top Places to Stay in Marathon and the Middle Keys

· Hawks Cay

· Isla Bella Beach Resort

· Tranquility Bay Resort

· Indigo Reef Resort

· Glunz Ocean Beach Hotel and Resort

· Hyatt Place Marathon Florida Keys

· Grassy Flats Resort and Beach Club

Here are a Few of My Favorites to Dine at in Marathon

· Castaway Waterfront Restaurant

· Island Fish Company

· Irie Island Eats

· Sparky’s Landing – Fish n Cocktails

· Burdines Waterfront

· Florida Keys Steak and Lobster House

· TJ’S Tiki Bar

· Sunset Grille

Keys Fisheries and The Sunset Grille

Now off to two of my favorite local eateries in the Marathon area – Keys Fisheries and The Sunset Grille and Raw Bar. There is nothing fancy about either of these two seafood eateries; however, they are absolute gems. Their fresh seafood offerings and "daily-catch just in from the boat" dishes are off the nautical charts. Keys Fisheries is really nothing to look at as you drive up, but when you head up to their second-floor rustic open-air perch, the panoramic views of the Atlantic Ocean abound, not to mention the array of fresh seafood displayed in ice-filled trays. What always catches my eye first is the gorgeous colossal fresh Stone Crabs that have my name on them to go along with their own signature hot sauce. I am in heaven, as Stone Crabs are my favorite delicacy from the seas of Florida.

To end up the perfect day in Marathon, we venture over to the Sunset Grille and Raw Bar, which offers the best sunset viewing in all of Marathon located at Mile Marker 47 at the crest of the 7-mile bridge. The fresh seafood, innovative tropical drinks, and spectacular sunsets create memories of your Florida Keys road trip to last a lifetime. And to top it all off a deliciously spectacular Florida Key Lime Pie! Yum!

by Dynie Sanderson - NapaFoodGalTravels

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Greetings and Welcome to NapaFoodGalTravels! My name is Dynie Sanderson and I am merely a “Wanderous” gal who just loves to travel and happens to live amongst the breathtaking rolling vineyards of the lush Napa Valley. The rest of the time I am in constant search of new sights, new sounds, and new flavors in this amazing world we live in. I welcome you to join me on my journey as I venture to the next spot on my list of Dynie’s Delicious Destinations. You will find great information on wine destinations around the US and the world, food and wine events, delicious recipes, road trips, day trips, Chef Profiles, what to do and where to go! Thanks for stopping by! See you again soon! Cheers and Happy Travels! come visit me at

Napa, CA

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