Let’s cut to the chase: what puts Florida on the global map, the tourism map, and the retirement map is its 825 miles of sandy beaches. That topographical blessing, coupled with the state’s tropical and subtropical climates (it’s a big state), has always been its indelible draw as one of the best places to live.
Florida has also served as a haven for tax refugees: according to TurboTax, it has the fifth-lowest overall tax burden in the nation, owing, in large part, to the absence of a state income tax. (Read our Florida State Tax Guide).
During the COVID-19 pandemic, those realities were just some of the reasons for the so-called Great Migration, when hundreds of thousands of people — including a posse of ultra-high-net-worth individuals — headed south from colder, higher-tax states, and marquee businesses relocated or expanded their operations in the Sunshine State.
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Florida’s burst of growth and activity has made it even more enticing to retirees, whether you crave the Atlantic or the Gulf Coast, an urban lifestyle or a chill vibe.
1. Miami Beach, best for sand, sea, and sightseeing
- Population: 82,890 [Census]
- Cost of living: 50% higher than the U.S. average [ERI]
- Average single-family home price: $513,208 [Zillow]
- Average rent: $3,350 [Zillow]
There is a common misconception that Miami Beach is a neighborhood within the city of Miami proper, but this coastal resort icon is actually a city in itself, located on one main barrier island — and some small, highly exclusive manmade isles that dot Biscayne Bay.
Miami Beach’s shoreline inarguably counts as one of the world’s finest urban beaches, with miles of powdery white sands; clear, turquoise waters, a winding biking and walking path, and numerous outdoor workout stations.
The most famous and picturesque part of Miami Beach is South Beach, which is human-scale and home to one of the highest concentrations of art deco and midcentury buildings on the planet. The so-called Art Deco District was the first 20th-century neighborhood to be recognized by the National Register of Historic Places. Miami Beach teems with nightlife and dining options.
2. Coral Gables, best for an affluent environment with top-tier shopping and recreation
- Population: 49,248 [Census]
- Cost of living: 53% higher than the U.S. average [ERI]
- Average single-family home price: $1,491,894 [Zillow]
- Average rent: $3,600 [Zillow]
Miami-Dade County’s expertly planned community, known for its ubiquitous Mediterranean Revival architecture and some of the nation’s wealthiest zip codes, is home to several significant landmarks, including the highly rated University of Miami; the century-old Biltmore Hotel, which features an 18-hole golf course and one of the country’s biggest swimming pools; and the quirky Venetian Pool, a whimsical marvel filled with grottos and waterfalls.
But Coral Gables is more than a residential enclave; it is rapidly diversifying and drawing businesses to its lush streets. Miracle Mile functions as the city’s main drag, replete with dining, entertainment, and shopping, while the Shops at Merrick Park boasts such luxury brands as Gucci, Neiman Marcus, and David Yurman. Several condo-hotels, such as Cassia Residences and The Avenue, are in progress and within walking distance of this chic indoor-outdoor mall.
3. Naples, best for showing off your Ferrari, hitting the links, and retiring in style
- Population: 19,704 [Census]
- Cost of living: 34% higher than the U.S. average [ERI]
- Average single-family home price: $576,169 [Zillow]
- Average rent: $5,900 [Zillow]
For those drawn to Florida’s Gulf Coast, Naples is synonymous with wealth and the good life, and with an ample population of retirees. Parks, golf courses, and pickleball courts abound, not to mention the enduring attraction of its beaches, with their soft sands, calm waters, and spectacular sunsets.
As evidenced by its annual Cars on 5th Concours, which is sponsored by the Naples Chapter of the Ferrari Club of America, the city is an epicenter for luxury auto enthusiasts. But when the Ferraris, Lamborghinis, and Porsches roar away, Fifth Avenue — which counts as the city’s main street — returns to walkable normalcy, and is rife with cafes, bars, and more than a dozen art galleries.
4. Palm Beach, best for hobnobbing with the rich and famous
A Florida homestead
- Population: 9,258 [Census]
- Cost of living: 434.4% higher than the U.S. average [Bestplaces]
- Average single-family home price: $2,127,973 [Zillow]
- Average rent: $13,000 [Zillow]
Known as one of the most exclusive resort destinations in the world, Palm Beach, located on a barrier island across from West Palm Beach, is anchored by the Breakers Palm Beach. The owners insist upon the full name — The Breakers Palm Beach — because the brand is more than a historic hotel featuring four swimming pools and a half-dozen dining venues: the company has also invested mightily in adjacent real estate, spreading the wealth to revitalize Royal Poinciana Way, with its charming boutiques and eateries.
The locals who drink and dine at Buccan, La Goulue, and Sant Ambroeus (a popular offshoot of the New York-based chain) live in pricey condos — or mansions valued in the tens of millions, whether they front the Atlantic Ocean or the Intracoastal Waterway.
The most well-heeled homeowners and visitors stay for the cooler months of “the season,” then flee the summer humidity for the Hamptons or to make jaunts to Europe.
5. Key West, a laidback island that encourages creativity and eccentricity
Key West, Florida
- Population: 25,103 [Census]
- Cost of living: 80% higher than the U.S. average [ERI]
- Average single-family home price: $1,061,463 [Zillow]
- Average rent: $5,000 [Zillow]
After conquering the Overseas Highway, a roughly four-hour drive from Miami (five, if you stop for steamers at Lazy Days), you’ve arrived at an end-of-the-world kind of place, with its own eccentric customs and rituals. The nation’s southernmost city proved a draw for Ernest Hemingway (his former home is a museum and National Historic Landmark that bears his name), Tennessee Williams (who also inspired an eponymous museum), and President Harry S. Truman, who maintained a winter White House here that you can also visit.
Most of the island’s business happens on the 1.25-mile-long Duval Street, which is packed with seafood eateries and shops. The strand passes near the vibrant waterfront setting of Mallory Square, with its outdoor entertainers, sunset views, trolley tours, and cruise ship docking.
People visit and settle down in Key West for its Caribbean flavor and its arty, come-as-you-are vibe — and it remains one of Florida’s most distinctive places to retire.
6. St. Petersburg, best for a thriving arts scene as well as a suntan
High rises along a waterway in St. Petersburg
- Population: 263,553 [Census]
- Cost of living: 17% higher than the U.S. average [ERI]
- Average single-family home price: $360,584 [Zillow]
- Average rent: $2,200 [Zillow]
Located in the Tampa Bay area and known for its sunny weather and namesake pier (which is full of attractions), St. Pete’s is also a heavy hitter in terms of culture. The city is home to one of the world’s few museums devoted to surrealist artist Salvador Dalí, in addition to the encyclopedic Museum of Fine Arts, the Palladium Theater (which features concerts, dance, and Broadway-style shows), and the Morean Arts Center (offering exhibits and classes), which boasts a permanent collection of the work of glass artist Dale Chihuly. If the pieces by Chihuly leave you wanting more, the Imagine Museum is devoted to glass art from around the world.
Unlike some other Florida cities, St. Pete’s boasts an acclaimed downtown. Colorful Central Ave. is loaded with boutiques, vintage shops, restaurants, and bars, so if you want access to all that downtown offers, note that some of the city’s loveliest homes (including historic houses), dot nearby Beach Drive, which extends in a northeasterly diagonal past a series of waterfront parks.
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