The Complete Guide
The Best Places to Retire in Florida
Eight Florida cities, scored the same way on the same ten things, with the downsides left in. No state income tax is the easy part. This is the honest version of where to actually land, and who each place is wrong for.
Florida is not one retirement decision. It is at least four: the exclusive Gulf resort, the walkable arts city, the value coast, and the historic town. The brochures blur them together under palm trees and a zero on the income-tax line. We pulled them apart and scored eight cities across the dimensions that actually shape a retirement, then wrote each one up with the catches included. Two things are true of every Florida city below, so we will say them once here: there is no state income tax (a real, recurring advantage), and every one of them is a hurricane city with home-insurance estimates around $7,136 a year and coastal addresses far above. After that, they diverge hard.
All eight, side by side
Typical home value, our budget and key dimension scores (0–10), and the one-line identity of each. Sorted by typical home value, most to least. Tap any city to read the full profile.
| City | Typical home | Budget | Healthcare | Walk | Safety | Resilience | The identity |
|---|---|---|---|---|---|---|---|
| Naples | $549K | 3/10 | 10/10 | 5/10 | 9/10 | 2/10 | The exclusive resort |
| St. Augustine | $432K | 5/10 | 8/10 | 7/10 | 8/10 | 3/10 | The historic showpiece |
| Sarasota | $413K | 5/10 | 10/10 | 6/10 | 5/10 | 2/10 | The arts capital |
| Tampa | $377K | 6/10 | 10/10 | 6/10 | 6/10 | 2/10 | The complete metro |
| St. Petersburg | $352K | 6/10 | 7/10 | 8/10 | 6/10 | 2/10 | The walkable arts city |
| Delray Beach | $340K | 6/10 | 5/10 | 8/10 | 7/10 | 2/10 | The Atlantic main street |
| Fort Myers | $312K | 7/10 | 9/10 | 3/10 | 6/10 | 1/10 | The Gulf value play |
| Pensacola | $266K | 7/10 | 7/10 | 4/10 | 6/10 | 2/10 | The Panhandle bargain |
Scored 0–10 against the 100 cities in our database; higher is better, including Resilience (higher = less hurricane and insurance exposure). Typical home values are Zillow-style citywide figures as of June 2026; coastal and historic-district addresses run higher. Data: RetireMeHere city database.
Start with what you actually need
The right Florida city depends on the one or two things you refuse to compromise on. Here is where each priority points, straight from the scores.
Pensacola & Fort Myers
The two highest budget scores (7 of 10) and the two lowest typical homes ($266K and $312K). Pensacola is the outright cheapest with a historic downtown and the Navy; Fort Myers adds stronger healthcare and a better airport for a little more. Both ask the hardest hurricane questions on this list, Fort Myers especially.
Compare them head-to-head →Naples, Sarasota & Tampa
The three perfect 10s. Naples has NCH, rated Florida's #1 hospital multiple years; Sarasota has a perfect-rated Sarasota Memorial; Tampa pairs Tampa General and Moffitt Cancer Center with a perfect-10 airport. Fort Myers (9) and St. Augustine (8, with Mayo Clinic 40 minutes north) are the value-tier honorable mentions.
See the healthcare ranking →St. Petersburg & Delray Beach
The two 8s, and the only Florida cities here where you can genuinely live without a car. St. Pete has Florida's highest Walk Score and an arts downtown; Delray has Atlantic Avenue and the best airport access in our entire database. St. Augustine (7) is the walkable historic alternative.
Read the St. Petersburg profile →Naples & St. Augustine
Naples scores 9 of 10, the 97th percentile of every city we score, and St. Augustine follows at 8. Both buy an unusual degree of everywhere-feels-fine, which matters most for retirees living alone or walking in the evening. The trade is price: these are two of the pricier cities on the list.
Read the Naples profile →Sarasota & St. Petersburg
Both score 9 of 10 for community and culture, two different ways. Sarasota has the classical institutions: opera, ballet, symphony, the Ringling. St. Pete has the contemporary scene: the Dalí, Chihuly, and the SHINE murals. Delray and St. Augustine also score 9, with main-street and historic-district character respectively.
Read the Sarasota profile →St. Augustine
The single most important honest note on this page: no Florida city is low-risk, but St. Augustine's 3 of 10 is the gentlest resilience score we give in the state, on a northeast coast our database flags as somewhat less surge-exposed. It still flooded in Matthew and Irma. "Less exposed" is the most any Florida coast can honestly claim.
Read the St. Augustine profile →The one thing the brochures never price
Every city on this page sits between a 1 and a 3 of 10 for climate resilience. That is not a knock on Florida; it is the cost of the coast, and it is real money and real planning, not a disclaimer. Budget the insurance line (roughly $7,136 a year on a $300K dwelling, far more near the water), read the flood map for the specific address before the specific offer, and have an evacuation plan. Hurricanes Ian, Milton, Matthew, Irma, Ivan, and Sally all appear in these eight profiles because they all actually happened to these eight places. The retirees happiest in Florida are the ones who priced this in from the start, not the ones who discovered it in year two.
Still torn between two? Read the head-to-head.
When the choice comes down to a specific pair, our comparison pages score them row by row with an honest verdict. The six Florida matchups, by region:
Gulf Coast
Oldest-city matchup
Retiring in Florida: the questions people actually ask
What is the best place to retire in Florida?
There is no single best; it depends on your top priority, and the scores point cleanly. For elite healthcare and safety, Naples. For value, Pensacola or Fort Myers. For walkable city life, St. Petersburg or Delray Beach. For arts and culture, Sarasota or St. Petersburg. For history and the gentlest storm exposure, St. Augustine. For the most complete all-around package, Tampa, which holds perfect 10s for both healthcare and airport access. Every one of these is scored on the same ten dimensions, so the comparison is apples to apples.
What is the cheapest place to retire in Florida?
Of the cities we cover, Pensacola, at a $266,000 typical home and monthly retiree budgets from about $3,000. Fort Myers is next at $312,000. Both score 7 of 10 on our budget dimension, the highest in our Florida coverage, and both sit in budget tier 2. The trade-off is real: Fort Myers carries the heaviest hurricane exposure on the list (a 1 of 10 resilience score as Hurricane Ian's 2022 ground zero), and Pensacola has genuine Panhandle winters rather than peninsula warmth.
Does Florida tax retirement income?
No. Florida has no state income tax, which means Social Security, pension, and retirement-account withdrawals are not taxed at the state level. Every city in this guide scores 9 of 10 on tax friendliness for that reason, with a typical property tax rate around 0.78%. The offset that retirees underestimate is home insurance, which runs high statewide because of hurricane risk, around $7,136 a year on a $300,000 dwelling and considerably more near the coast.
Which part of Florida has the least hurricane risk?
None is low-risk, but in our coverage the northeast Atlantic coast around St. Augustine scores best, a 3 of 10 for climate resilience versus the 1s and 2s of the Gulf and South Florida. Our database flags that stretch as somewhat less surge-exposed. It is a relative edge, not safety: St. Augustine's historic district still flooded during Hurricanes Matthew (2016) and Irma (2017). Anyone retiring anywhere in Florida should budget hurricane insurance, check the flood zone for the exact address, and keep an evacuation plan.
Is it better to retire on Florida's Gulf Coast or Atlantic Coast?
The Gulf Coast holds more of our cities and the calmer, warmer water; the Atlantic side offers walkability and, around St. Augustine, slightly lower storm exposure. Our Gulf cities (Naples, Sarasota, Tampa, St. Petersburg, Fort Myers, Pensacola) range from exclusive resort to Panhandle bargain. Our Atlantic cities (Delray Beach, St. Augustine) lean walkable and historic. Winters are warmest on the peninsula (both coasts) and noticeably cooler in the Panhandle. The honest tiebreakers are usually price, walkability, and which specific city's character fits, not the coast itself.
Not sure which fits you?