A Minnesota College Town Nicknamed 'The Island City' Is One Of The Best Places For Retirees

Retirees frequently look for a calm environment where they can enjoy a low cost living with access to quality basic amenities. Some U.S. states are better than others in this regard, and the same is true internationally for those looking to expatriate. Looking to the northern U.S., Winona, Minnesota — sometimes called "The Island City" — is an affordable and engaging hub tucked between limestone cliffs and the Mississippi River.

Winona has a notable landmark called Sugar Loaf Bluff that towers around 500 feet above Lake Winona; it's hard to miss. At the top, you will see a jagged limestone peak that juts into the sky. As it is a busy college city, Winona has a lively vibration, thanks to the campuses of Winona State University and Saint Mary's University. They bring new life to the city, accompanied by the welcoming cafés, theaters, and a variety of community events that keep the city lively and engaging.

Also, per the 2019 to 2023 U.S. Census Bureau, American Community Survey (ACS), interpreted via Neilsberg, 15.45% of the population is aged between 65 to 84. That is one in six and a half (or about 1 in 6.5 people). World Population Review puts Winona's population at 26,061, therefore, 15.45% is over 4000 elderly at Winona, a great selling point for retirees who want to foster a sense of community in their later years.

A single person in Winona, Minnesota can cover the basics on about $2,067 a month or roughly $24,800 a year. For a couple, the ballpark budget rises to $3,360 a month, or about $40,320 a year. Winona's cost‑of‑living index sits at 81.9, says BestPlaces.net, putting everyday expenses about 18% below the U.S. average. The Economic Research Institute echoes that. In its March 2025 update it found life in "The Island City" is 14% cheaper than the national average and 10 % below the Minnesota average.

Furthermore, the median house here is $210,100 and rent for a two-bedroom is approximately $760 per month. According to Census Reporter American Community Survey (ACS) for 2023, houses owned by residents in Winona fall within an average of $193,500 in value. When you compare this to the national median, which is closer to $338,000, it is not far-fetched to believe people spend less in Winona. 

Winona's calendar stays busy year‑round. One week you're catching live music at Two Fathoms Brewing; the next you're browsing fresh produce at the Levee Park farmers' market. Retirees have options for assisted living, too. There are five senior living communities — one ranked among the nation's best by U.S. News — that offers built-in support and plenty of activities. Lifelong learning is part of the city's DNA. Through Winona State University's Senior University, adults 55‑plus can enroll in four to six‑week, non‑credit classes on everything from social science and politics to creative writing and literature.

Beyond the school, if a retiree has an interest in outdoor activities, they can explore the bluff-top forest paths moving on the Mississippi, or Garvin Heights that has a view of the river valley that extend everywhere. Also, they could visit the Sugar Loaf Bluff and the Mississippi River that draw nature lovers of all ages. These locations, and the rest of Winona, have received reviews and even been described as an amazing city with amazing people and a perfect place to raise a family or enjoy retirement, by a longtime resident. So if you want to retire, consider The Island City, Minnesota.