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City Hopping in Florida: A Local’s Top Travel Guide

Welcome to the Sunshine State, where each city holds its own unique charm and allure. If you’re seeking an adventure that transcends the ordinary, look no further than Florida’s vibrant urban landscape. As a seasoned local, I’ve traversed the length and breadth of this peninsula, uncovering hidden gems and experiencing the pulse of its cities firsthand. In this comprehensive guide, I invite you to join me on an exhilarating journey through Florida’s most captivating urban destinations.

From the electric energy of Miami’s South Beach to the historic streets of St. Augustine, and the eclectic culture of Key West, Florida offers an array of experiences to suit every traveler’s taste. Whether you’re a beach bum, a history buff, a foodie, or an art aficionado, there’s something here for you. So pack your bags, buckle up, and get ready to embark on an unforgettable city-hopping adventure through the Sunshine State.

Key West: A Tropical Paradise with a Bohemian Soul

Nestled at the southernmost tip of the Florida Keys, Key West is a tropical paradise like no other. With its laid-back atmosphere, vibrant culture, and breathtaking natural beauty, it’s no wonder that Key West has long been a magnet for artists, writers, and free spirits seeking inspiration and refuge. Join us as we explore the eclectic charms of this enchanting island oasis and uncover the bohemian soul that sets Key West apart.

Historic Landmarks

Key West is steeped in history, with a treasure trove of historic landmarks waiting to be discovered. Wander through the streets of Old Town, where you’ll find beautifully preserved Victorian homes, quaint cottages, and charming bed and breakfasts. Don’t miss the opportunity to visit the Ernest Hemingway Home and Museum, where the legendary author lived and wrote during the 1930s. Marvel at the six-toed cats that still roam the property and explore the lush gardens that inspired Hemingway’s writing.

 Duval Street

The heartbeat of Key West, Duval Street is a lively thoroughfare lined with colorful shops, eclectic galleries, and lively bars. Stroll down Duval Street and soak up the vibrant energy of this bustling strip, where live music spills out from open-air venues and locals and visitors alike gather to revel in the island spirit. Stop by iconic landmarks like Sloppy Joe’s Bar, a favorite haunt of Hemingway, and soak in the laid-back atmosphere that defines Key West’s nightlife scene.

 Sunset Celebrations

No trip to Key West is complete without experiencing its world-famous sunset celebrations. Head to Mallory Square, where each evening, locals and tourists gather to witness the breathtaking spectacle of the sun sinking below the horizon. Street performers, artists, and vendors line the square, creating a festive atmosphere as the sky explodes in a riot of colors. Grab a cocktail from one of the nearby bars, find a spot along the seawall, and prepare to be dazzled by nature’s nightly show.

Water Adventures

With its crystal-clear waters and vibrant marine life, Key West is a paradise for water enthusiasts. Explore the colorful coral reefs that surround the island on a snorkeling or scuba diving excursion, where you’ll encounter a dazzling array of tropical fish, sea turtles, and other aquatic creatures. For a more leisurely experience, embark on a sunset cruise aboard a historic schooner or hop aboard a kayak and paddle through the mangrove forests of the nearby backcountry.

Eclectic Cuisine

Key West’s culinary scene is as eclectic as its culture, with a diverse array of dining options to satisfy every craving. Sample fresh seafood at waterfront restaurants overlooking the Gulf of Mexico, indulge in Caribbean-inspired cuisine at cozy cafes tucked away on side streets, or savor traditional Cuban fare at local haunts frequented by Key West’s Cuban community. Be sure to try conch fritters, a local delicacy made from the island’s beloved queen conch.

Jacksonville: Florida’s Hidden Gem

City Hopping in Florida: A Local's Top Travel Guide

Nestled along the northeast coast of Florida lies a hidden gem waiting to be discovered – Jacksonville. While often overshadowed by its more famous counterparts in the Sunshine State, Jacksonville boasts its own unique charm, offering visitors a captivating blend of Southern hospitality, natural beauty, and urban allure. Join us as we uncover the treasures of Jacksonville and reveal why it’s deserving of the title “Florida’s Hidden Gem.”

  • Southern Charm and Hospitality: Despite being the largest city by area in the contiguous United States, Jacksonville exudes a warm and welcoming Southern charm. From its historic neighborhoods lined with oak-shaded streets to its friendly locals, visitors will feel right at home in this hospitable city.
  • Natural Beauty: Jacksonville is blessed with an abundance of natural beauty, from its pristine beaches along the Atlantic coast to its expansive parks and waterways. Explore the miles of unspoiled coastline at places like Jacksonville Beach and Neptune Beach, or escape to nature at the scenic Timucuan Ecological and Historic Preserve.
  • Cultural Diversity: Jacksonville’s rich cultural tapestry is reflected in its diverse neighborhoods, vibrant arts scene, and eclectic culinary offerings. Immerse yourself in the city’s cultural heritage by visiting historic sites like the Kingsley Plantation or sampling international cuisine in the trendy Riverside and Avondale districts.
  • Outdoor Adventures: Outdoor enthusiasts will find no shortage of adventures to embark on in Jacksonville. Whether it’s kayaking along the St. Johns River, hiking through lush nature trails, or teeing off at world-class golf courses, there’s something for everyone to enjoy amidst the city’s natural playground.

Jacksonville is much more than meets the eye – it’s a hidden gem waiting to be explored. From its Southern charm and natural beauty to its diverse culture and urban excitement, Jacksonville offers a truly unique and unforgettable experience for visitors. 

Sarasota: The Cultural Gem of Florida’s Gulf Coast

Nestled along the tranquil shores of Florida’s Gulf Coast, Sarasota beckons visitors with its blend of cultural richness, natural beauty, and laid-back charm. Often referred to as the “Cultural Gem” of the region, Sarasota boasts a vibrant arts scene, pristine beaches, and a wealth of recreational activities. Let’s embark on a journey to uncover the treasures that make Sarasota a must-visit destination.

Cultural Delights

Sarasota is renowned for its thriving arts community, attracting artists, performers, and art enthusiasts from around the world. Start your cultural exploration at The John and Mable Ringling Museum of Art, home to an impressive collection of European and Asian art, as well as the stunning Ca’ d’Zan Mansion. Continue your artistic journey at the Sarasota Art Museum, housed in a historic Sarasota High School building, showcasing contemporary art exhibitions that inspire and provoke thought.

Theatrical Wonders

Theater aficionados will delight in Sarasota’s vibrant performing arts scene. The Asolo Repertory Theatre, located on the grounds of The Ringling, offers world-class productions ranging from classic dramas to innovative contemporary works. For a taste of outdoor theater, don’t miss the annual Sarasota Opera Festival, where you can experience the magic of opera under the stars at the Sarasota Opera House.

Beach Bliss

No visit to Sarasota is complete without a day spent basking in the sun on its pristine beaches. Siesta Key Beach, with its powdery white sands and crystal-clear waters, consistently ranks among the top beaches in the world. Whether you’re lounging in the sun, swimming in the Gulf of Mexico, or partaking in water sports like paddleboarding and parasailing, Siesta Key Beach offers endless opportunities for relaxation and recreation.

Natural Escapes

Beyond its stunning coastline, Sarasota is home to a wealth of natural wonders waiting to be explored. Take a leisurely stroll through Marie Selby Botanical Gardens, where lush tropical gardens and stunning orchid displays create a serene oasis in the heart of the city. For a more adventurous outing, venture to Myakka River State Park, where you can kayak through mangrove tunnels, spot wildlife on a scenic airboat tour, or hike along miles of nature trails.

Culinary Delights

Sarasota’s culinary scene is as diverse as it is delicious, offering a tantalizing array of dining options to suit every palate. Indulge in fresh seafood at waterfront eateries overlooking Sarasota Bay, savor farm-to-table cuisine at trendy downtown restaurants, or sample international flavors at ethnic eateries scattered throughout the city. Be sure to save room for dessert and treat yourself to a slice of Sarasota’s famous key lime pie.


What’s Happening Florida” offers an invaluable resource for travelers seeking to explore the diverse landscapes and vibrant culture of Florida through city hopping. Our comprehensive guide showcases the best of what the Sunshine State has to offer, from bustling urban centers to tranquil coastal retreats. With a wealth of local insight and recommendations, we aim to enhance visitors’ experiences and ensure they uncover the hidden gems scattered throughout Florida’s dynamic cities. Let us be your trusted companion on your journey through this captivating destination.

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