Boston, Massachusetts
Boston is like stepping back in time and enjoying modern city living! The city is exceptionally pedestrian-friendly, especially in its historic core, with excellent public transit. While a bit pricey, its rich history and top-tier healthcare make it a cultural and health hub for retirees.
Philadelphia, Pennsylvania
Philly offers the perfect blend of historic charm and surprising affordability. Enjoy neighborhoods like Rittenhouse Square, excellent transit, and incredible tax benefits for retirees. It's a fantastic choice for those seeking a vibrant city life without the hefty price tag.
Portland, Oregon
Nature lovers, rejoice! Portland boasts high bikeability and good transit, with a growing focus on pedestrian-friendly design. Although the cost of living is slightly above average, its unique culture and commitment to age-friendly health systems make it a Pacific Northwest gem.
Haven’t found your perfect fit? One of the next few might be it!
Haven’t found your perfect fit? One of the next few might be it!
Minneapolis, Minnesota
Minneapolis offers all four seasons in a highly accessible Midwestern setting. With streets designed for walking or biking, a vibrant cultural scene, and excellent transport options, it boasts a lower cost of living than many major metropolitan areas.
Savannah, Georgia
Experience Southern charm in Savannah's historic and Victorian districts, which are perfect for strolling. Its historic and Victorian districts invite slow, meandering strolls, while downtown offers a rare car-free lifestyle. This, coupled with the low cost of living and tax-friendly policies for retirees, makes it one of the perfect retirement destinations.
Washington, D. C.
The nation's capital offers exceptional pedestrian access and transit, allowing for a car-free lifestyle amidst monuments and museums. While expensive, D.C. fully exempts Social Security from state tax, making it an engaging and active urban choice for many.
Intrigued by these accessible havens? We’re just getting started…
Intrigued by these accessible havens? We’re just getting started…
Chicago, Illinois
The Windy City is surprisingly retiree-friendly, boasting streets designed for easy walking and excellent public transit. Chicago is financially accessible compared to other major cities, and Illinois is exceptionally tax-friendly, exempting all retirement income from state tax. Sounds tempting.
San Francisco, California
A pedestrian's dream with a Walk Score of 89 and strong transit, San Francisco offers unparalleled urban exploration. However, its extremely high cost of living and less-friendly tax policies do require a substantial retirement fund.
Denver, Colorado
Enjoy the Rocky Mountain views while strolling through Denver's increasingly pedestrian-friendly neighborhoods. With rising scores for easy travel, plus a generous state tax deduction on retirement income, it’s a great option for active, outdoor-loving seniors.
Which city is catching your eye for retirement?
Which city is catching your eye for retirement?
Raleigh, North Carolina
Raleigh offers a charming downtown with exceptional pedestrian access, good transit, and a lower-than-average cost of living. North Carolina is also moderately tax-friendly for retirees, making this vibrant Southern city an attractive and affordable choice.
Pittsburgh, Pennsylvania
The revitalized city of Pittsburgh is a hidden gem for retirees, famous for its tremendous affordability and highly tax-friendly state policies. While overall pedestrian access varies, Pittsburgh offers a rich cultural scene and excellent senior services.
Providence, Rhode Island
Providence is a compact, historic city with a high rating for easy pedestrian travel and strong transit options. Though the cost of living is high and tax policies are less friendly, it offers specialized geriatric care and a vibrant urban core.
Your ideal retirement-friendly city could be just ahead…
Your ideal retirement-friendly city could be just ahead…
Tampa, Florida
Bask in the Florida sunshine in Tampa, a top retirement spot with a very accessible downtown and good transit. It boasts a low cost of living and is exceptionally tax-friendly, with no state income tax on any retirement benefits.
Madison, Wisconsin
Enjoy a high-quality life in Madison, one of the safest and most welcoming cities for pedestrians, with extensive lakeside trails and vibrant cultural offerings. Wisconsin is a very tax-friendly state for retirees, with significant exemptions on retirement income as of 2025.
Seattle, Washington
Seattle allows you to experience the best of the Pacific Northwest in a highly pedestrian-friendly and transit-rich city. Despite a high cost of living, Washington is very tax-friendly, with no state income tax on any retirement income.
There are still a few more fantastic cities to consider…
There are still a few more fantastic cities to consider…
Portland, Maine
This charming coastal city is an AARP-ranked gem, offering excellent livability for active seniors. Easy-to-stroll streets, delicious seafood, and a vibrant arts scene in a picturesque New England setting. What more could one want?
Lawrence, Kansas
A quintessential college town, Lawrence offers a safe environment and high bikeability. It also provides a relaxed pace of life with cultural amenities, making it a friendly and engaging option for retirees seeking community.
Greenville, South Carolina
Greenville is a popular and affordable retirement destination with a growing downtown. Residents can enjoy a vibrant atmosphere, a charming main street, and direct access to the beautiful Blue Ridge Mountains.
Just a couple of more dream retirement cities left…
Just a couple of more dream retirement cities left…
Rochester, Minnesota
Home to the world-renowned Mayo Clinic, Rochester is a top choice for retirees prioritizing exceptional healthcare. The city also has a keen focus on pedestrian-friendly design, offers a supportive and welcoming community environment, and provides a slower pace of life that appeals to many.
The Villages, Florida
This unique 55+ community is a nationally recognized retirement destination designed for active adults. Offering unparalleled amenities and a golf cart-friendly environment, it is a paradise for retirees looking to spend their golden days in the best environment.
