Retire in Southwest Florida
Your complete guide to retiring in SWFL. Compare cities, explore 55+ communities, and find your perfect retirement destination.
Retiring to Southwest Florida (2026 Guide)
Complete guide to retiring in Southwest Florida 2026. Compare Naples, Fort Myers, Sarasota & more with cost of living, taxes, healthcare, 55+ communities & lifestyle info.
Retirement Guides by City
Each guide covers cost of living, healthcare, 55+ communities, lifestyle, and more.
Cape Coral
Complete guide to retiring in Cape Coral FL for 2026. Discover 400+ miles of canals, Gulf-access waterfront homes at 40-60% below Naples prices, Lee Health hospital, Sandoval 55+ community & boating lifestyle.
Read GuideEnglewood
Complete guide to retiring in Englewood FL for 2026. Discover old Florida charm, affordable beach living, Lemon Bay kayaking & fishing, uncrowded beaches & laid-back lifestyle 30% below Venice prices.
Read GuideFort Myers
Complete guide to retiring in Fort Myers FL for 2026. Discover Lee Health hospitals, River District downtown, Shell Point & Pelican Preserve 55+ communities, Edison Estates & 20-30% savings vs Naples.
Read GuideNaples
Complete guide to retiring to Naples, FL for 2026. Discover Pelican Bay beach access, NCH Healthcare, Fifth Avenue dining, 90+ golf courses & no state income tax savings.
Read GuidePort Charlotte
Complete guide to retiring in Port Charlotte FL for 2026. Discover affordable waterfront living, Sunseeker Resort entertainment, world-class tarpon fishing, healthcare at Fawcett Memorial & cost of living 40% below Naples.
Read GuidePunta Gorda
Complete guide to retiring in Punta Gorda FL for 2026. Discover walkable historic downtown, Charlotte Harbor fishing, waterfront homes 30% below Naples & active boating community.
Read GuideSarasota
Complete guide to retiring in Sarasota FL for 2026. Discover world-class arts at Ringling Museum & Asolo Theatre, Siesta Key beaches, Sarasota Memorial healthcare & top 55+ communities like Lakewood Ranch.
Read GuideVenice
Complete guide to retiring in Venice FL for 2026. Discover shark tooth beaches, walkable Italian downtown, Venice Theatre, 55+ communities & healthcare at Venice Regional—15-25% below Sarasota prices.
Read GuideMarco Island
Complete guide to retiring on Marco Island FL for 2026. Discover exclusive barrier island living, pristine beaches, Ten Thousand Islands boating, Hideaway Beach & Naples proximity—premium island retirement.
Read GuideSanibel Island
Complete guide to retiring on Sanibel Island FL for 2026. Post-Ian recovery status, world-famous shelling, Ding Darling Wildlife Refuge, insurance reality & whether nature-focused island living fits your retirement.
Read GuideBonita Springs
Guide to retiring in Bonita Springs FL for 2026. Affordable beach living between Naples & Fort Myers with golf courses, dining, nature preserves & more.
Read GuideEstero
Guide to retiring in Estero FL for 2026. Discover new 55+ communities, Coconut Point shopping, easy RSW airport access & cost of living near Fort Myers.
Read GuideQuick City Comparison
| City | Best For | Lifestyle | Guide |
|---|---|---|---|
| Naples | Upscale living, golf, fine dining | Luxury coastal | View |
| Fort Myers | Beach access, history, value | Active & diverse | View |
| Sarasota | Arts, culture, beaches | Cultural & refined | View |
| Cape Coral | Boating, affordability | Waterway living | View |
| Venice | Small-town charm, beaches | Relaxed coastal | View |
| Punta Gorda | Historic downtown, boating | Charming & quiet | View |
Ready to Explore Southwest Florida?
While you're planning your move, discover the best restaurants and activities in each city.