Naples – Best for Luxury and Nature

Nestled along the Gulf of Mexico, Naples is synonymous with upscale living and pristine beaches. Snowbirds seeking the perfect blend of luxury and natural beauty will find themselves at home in this southwest Florida gem. With world-class shopping, dining, and cultural attractions, Naples offers a more sophisticated winter retreat.

Sarasota – Best for Arts and Culture

Sarasota is known for its vibrant arts scene and cultural events, Sarasota attracts snowbirds with a flair for creativity. The city boasts numerous theaters, galleries, and museums, including The Ringling, making it an ideal destination for those who appreciate the finer things in life. The stunning beaches and diverse dining options add to Sarasota’s appeal.

St. Augustine – Best for Historic Charm

Snowbirds with a penchant for history and charm will find St. Augustine, the nation’s oldest city, irresistible. Cobblestone streets, historic architecture, and a rich colonial past make this northeast Florida city a unique winter haven. Explore the Castillo de San Marcos, stroll along St. George Street, and immerse yourself in the city’s captivating history. Provides more of a small town experience.

Miami Area – Best for Tropical & Spanish Culture

For snowbirds seeking an electrifying urban experience, Miami is the ultimate destination. The Magic City is synonymous with glamour, vibrant nightlife, and a diverse cultural scene. From the iconic South Beach to the trendy neighborhoods of Wynwood (Where the creative locals like to live) and Brickell, Miami offers a dynamic winter experience filled with excitement and style.

Miami Beach was my gateway city to snowbirding in America! I have escaped to Miami Beach every February for the last handful of years. For all of the Hostel Travelers out there, I recommend the Freehand Miami (Caveat: It has a lost some of it’s convenient features and je ne sais quoi after Covid). It’s a super walkable location. The beach is 2 blocks away and there’s a local bodega 1 block away with a delicious deli that all the local workers use. Lots of people like the Generator as well. The best value being an Airbnb so you can cook your own food. We will feature our tips for enjoying Miami/Miami Beach area in another post.

Orlando – Best for Family-Friendly Fun

Orlando, the theme park capital of the world, is an obvious choice for snowbirds traveling with family. Beyond the enchanting world of Disney, Orlando boasts a plethora of attractions, including Universal Studios and SeaWorld. The city’s diverse dining options and entertainment make it a perfect winter destination for families. I stayed with a family in Orlando and experienced this location first hand. See my post on Exploring Orlando like a local.

FYI Orlando is one of The Most Visited Cities in the World.

Fort Myers – Best for Relaxed Coastal Living

Situated along the Caloosahatchee River, Fort Myers provides a laid-back coastal experience for snowbirds seeking relaxation. With waterfront dining, charming historic districts, and easy access to the barrier islands, Fort Myers offers a tranquil retreat with a touch of Florida’s natural beauty.

We were in Florida this past October for a conference and hung out in Boca Raton. We went out to dinner with a colleague who was from Ft. Meyers. He thought Boca was a bit too one-dimensional for him and Ft. Meyers had more of the dynamics he enjoys.