The Best and Worst Cities for Retirees to Visit

Published April 12, 2022

title card for best cities for retirees
We spend years and years of our lives working and dreaming of retirement. But when retirement comes, what’s there to do?! The world is your oyster, and you’re given the perfect opportunity to travel to new places and see new things! That being said, it can be overwhelming to figure out where to start, so we found the best cities in the U.S. for retirees to visit based on ranking factors such as: accommodation cost, average cost of food and drinks, and the number of entertainment opportunities available!


To find out, we here at Coventry developed our own way to rank the 50 most populous U.S. cities by the average cost of a stay and opportunities for events and entertainment. We judged several factors, including:

  • Average Cost of Accommodation (Typical Double-Occupancy Hotel Room)
  • Average Transportation Cost Per Day (Taxis, Local buses, Subway, etc.)
  • Average Cost of (Meals For One Day)
  • Average Cost of Drinks (Per Day)
  • Average Cost of Entertainment (Entrance tickets, shows, etc.) Per Day
  • Airfare Cost
  • Number of Upcoming Art/Theater Events
  • % of Retiree Population

We then subjectively weighted these factors based on how much we felt they affected the trip for a retiree, for better or worse:

  • Average Cost of Accommodation (USD)| Weight: 2.00
  • Average Transportation Cost Per Day (USD) | Weight: 2.00
  • Average Cost of (Meals For One Day) | Weight: 2.00
  • Average Cost of Drinks (Per Day) | Weight: 1.00
  • Average Cost of Entertainment (Entrance tickets, shows, etc.) Per Day | Weight: 1.00
  • Airfare Cost | Weight: .75
  • Number of Art/Theater Events Near City | Weight: .25
  • % of Retiree Population | Weight: 1.00

This led to each city being given a score from 0-50, with a score closer to 0 meaning it’s worse for retirees, and a score closer to 50 meaning it’s better!
We wanted to note that Indianapolis has a pretty severe outlier in the data for accommodation cost which accounts for their low ranking.

The Top 20 Best U.S. Cities for Retirees to Visit

table of best cities for retirees

Our top three best U.S. cities for retirees to visit have two popular Florida vacation spots which commonly have a high percentage of retirees. Miami and Tampa come in at the first two spots with scores of 39.4 and 38.7 respectively out of a possible score of 50. These beach towns are known for their warm weather and older population. 17% of Miami’s population are retirees, and it’s almost 19% for Tampa! Phoenix, another warm weathered city, rounds out our top 3 spots with an overall score of 38.69, just barely missing the second spot by a tenth of a point.

While the majority of the cities in the top 20 list are located in warmer climates year-round, cities like Baltimore, Detroit, Cleveland, Seattle, and a few others make the list. Hopefully, retirees will be visiting in the warmer months, although there are still a lot of things to do in these cities. Baltimore, Philadelphia, Providence, San Diego, and San Francisco all boast a high number of art and theater events.

The Top 10 Worst U.S. Cities for Retirees to Visit

table of worst cities for retirees

Cost was a big factor when ranking these cities with 6 out of our 8 ranking factors analyzing this metric, so it’s no surprise cities like Las Vegas and New York make the top 10 worst cities for retirees to visit. The accommodation costs alone in Las Vegas are $147 more than the number one spot, Miami.

The Best and Worst U.S. Cities for Retirees to Visit

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Wondering where your city ranks? The table above provides a list of the cities that we researched and the data for each of the ranking factors.

Final Thoughts

If you are already retired or it’s in your near future, what does retirement look like for you? Will you focus on traveling, spending time with family, or move to a different state? However you decide to spend your future, Coventry Direct is here to help uncover more retirement income. Find out if you qualify to sell your life insurance.

Editorial Disclaimer: Coventry Direct, a member of the Coventry group of companies, educates policyowners and insureds interested in learning about life settlements. Resources and publications are researched, written and updated by in-house experts to reflect the most up-to-date industry knowledge.

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