Exploring the Sunshine State: My Ultimate Florida Road Trip Adventure

From the our first stop after crossing the Florida state line  the enchanting beauty of the Keys, my Florida road trip was nothing short of magical.

Join me as I travel from the Florida Panhandle down to the Keys, sharing highlights, travel tips, and unforgettable moments.

Each destination has a clickable link that will take you to more information about each location.

DAY 1

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GENERATIONS SEAFOOD AND PRODUCE

 

Generations Seafood and Produce

Address: 30233 Overseas Hwy, Big Pine Key, FL 33043
Phone: (239) 784-0169

THREE WATERS RESORT IN ISLAMORADA, FLORIDA (FORMERLY POSTCARD INN RESROT)

Postcard Inn Beach Resort & Marina became Three Waters Resort & Marina in the fall of 2024.  It offers a distinctive blend of relaxation and adventure across its 15 oceanfront acres. As part of the Islamorada Resort Collection, this family-friendly destination provides guests with a variety of amenities and experiences.

AMARA CAY RESORT, ISLAMORADA , FLORIDA

 

Nestled along the beautiful shores of Islamorada, Amara Cay Resort stands as a beacon of luxury and relaxation in the heart of the Florida Keys. Whether you're seeking a tranquil escape or an adventurous getaway, this tropical haven offers everything you need and more.

Smathers Beach: A must see beach in the Florida Keys

 

As the largest public beach in Key West, Smathers Beach offers over half a mile of soft, white sand and crystal-clear waters. 

CURRY HAMMOCK STATE PARK IN THE FLORIDA KEYS

Nestled along the beautiful blue waters of the Florida Keys, Curry Hammock State Park is a hidden gem, located midway between Key Largo and Key West.  

Exploring Sombrero Beach, Florida: A Visitor's Guide

Nestled in the heart of the Florida Keys in Marathon, Sombrero Beach is a tropical paradise that offers stunning views, pristine waters, and a relaxing atmosphere. Whether you’re traveling solo, with a partner, or as a family, Sombrero Beach is a must-visit destination. Here’s everything you need to know before you go.

Why Fort Zachary Taylor Historic State Park Should Be Your Next Destination

If you're planning a trip to the tropical paradise of Key West, Florida, there’s one destination you absolutely cannot miss: Fort Zachary Taylor Historic State Park. Tucked away at the southernmost tip of the island, this gem offers a perfect blend of history, nature, and recreation. Here’s why Fort Zachary Taylor should be at the top of your Key West itinerary.

Visiting Harry Harris Park, Florida: What You Need to Know

 

Located in the heart of Tavernier in the Florida Keys, Harry Harris Park is a hidden gem perfect for visitors seeking a family-friendly atmosphere, stunning ocean views, and outdoor fun. Here's a guide to help you plan your visit.

Guide to Bahia Honda State Park

 

If you're looking for a serene escape filled with natural beauty, crystal-clear waters, and a touch of history, Bahia Honda State Park in the Florida Keys is a must-visit destination. Nestled on Big Pine Key, this gem of a park offers visitors a chance to experience the unspoiled charm of the Keys without the hustle and bustle of the more touristy areas.

ROBBIE'S OF ISLAMORADA - VOTED #1 PLACE TO VISIT IN THE KEYS

 

You can't go to the Florida Keys without stopping at Robbie’s in Islamorada.  Discover the thrill of hand-feeding tarpon, engage in exhilarating water sports, and explore charming local shops offering handcrafted souvenirs. Indulge in fresh seafood, sip on signature cocktails or local draft beer.  

GILBERT'S RESORT & TIKIBAR - KEY LARGO

 

Visiting Roberts Resort and Tiki Bar in Key Largo provides a true Florida Keys experience with its tropical ambiance and waterfront views. If you're planning a trip to the Keys, make sure to include this stop on your itinerary. There's a fantastic restaurant for lunch, but if you're pressed for time (service can sometimes be slow), simply take a moment to stretch your legs and soak in the relaxing atmosphere.

ISLAND HOME NURSERY & GARDENIA'S BISTRO

If you have yet to visit Island Home Garden and the amazing Gardenia’s Bistro located within, your missing out!

We were headed to the Florida Keys when we saw the nursery. Of course, we immediately pulled over.

WORTH THE STOP - ANNE'S BEACH IN THE FLORIDA KEYS

 

If you are headed down to the Florida Keys and looking for a place to get some great photos, Anne's Beach in Islamorada is a great place to stop and explore. It was was devastated by Hurricane Irma but reopened in 2019 with new boardwalks pavilions.

LA SIESTA RESORT & MARINA ~ ISLAMORADA, FLORIDA

  

On my recent road trip to the Florida Keys, we stayed three nights at the beautiful La Siesta Resort in Islamorada.  When you stay at La Siesta Resort, you can also visit three other sister resorts (Amara Cay, Postcard Inn, and Pelican Cove) and enjoy all of their amenities and watersport rentals.  

La Siesta in Islamorada, is located on 6-acres of oceanfront accessible by the historic Overseas Highway at mile marker 80.  The resort is less than 90 minutes from Miami and about 1 1/2 hour drive to Key West.