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)
Guide to retiring in Southwest Florida in 2026, comparing Naples, Fort Myers, Sarasota, and more on cost of living, taxes, healthcare, and 55+ communities.
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. Discover 400+ miles of canals, Gulf-access waterfront homes 40-60% below Naples prices & boating lifestyle.
Read GuideEnglewood
Complete guide to retiring in Englewood FL. Old Florida charm, affordable beach living, Lemon Bay kayaking & fishing, laid-back lifestyle below Venice prices.
Read GuideFort Myers
Discover why retiring to Fort Myers, Florida offers affordability, sunshine, and an active lifestyle.
Read GuideNaples
Retiring to Naples Florida? Our 2026 guide covers cost of living, 55+ communities, healthcare, golf, beaches, taxes & the best neighborhoods for retirees.
Read GuidePort Charlotte
Complete guide to retiring in Port Charlotte FL. Affordable waterfront living, world-class tarpon fishing, Fawcett Memorial healthcare & 40% below Naples.
Read GuidePunta Gorda
Complete guide to retiring in Punta Gorda FL. Walkable historic downtown, Charlotte Harbor fishing, waterfront homes 30% below Naples & boating lifestyle.
Read GuideSarasota
Complete guide to retiring in Sarasota FL. World-class arts, Ringling Museum, Siesta Key beaches, Sarasota Memorial healthcare & Lakewood Ranch 55+.
Read GuideVenice
Complete guide to retiring in Venice FL. Shark tooth beaches, walkable Italian downtown, Venice Theatre, 55+ communities & 15-25% below Sarasota.
Read GuideMarco Island
Complete guide to retiring on Marco Island FL. Exclusive barrier island living, pristine beaches, Ten Thousand Islands boating & Naples proximity.
Read GuideSanibel Island
Guide to retiring on Sanibel Island FL. Post-Ian recovery, world-famous shelling, Ding Darling Wildlife Refuge & nature-focused island living.
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 GuideRelated Retirement Resources
Quick 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.