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Your Best Place to Retire Might Be… in a City

Category: Best Retirement Towns and States

December 9, 2015 — For a surprising number of baby boomers the ideal retirement is not in an active community with a golf course, tennis courts, swimming pool, or clubhouse. Neither is it a small town, nor a postcard pretty burg with a college as its centerpiece. Instead, many surprise their friends by moving from the suburbs to of all places – a city. While an unexpected choice, there are any number of good reasons to make this move, akin to a salmon swimming upstream. This article will explore the many advantages and disadvantages of an urban retirement lifestyle, and then we will provide a list of 10 great cities where you can retire.

As we are fond of saying, retirement is a chance at a do-over on life. Lets say you have regrets about some choices you made during adulthood – like where you chose to live or what you did for a living. Now that you are
retired – so what! If you have the resources, once you retire you can do anything you want. And if moving to a city is your dream, we say go ahead and do it!

So many advantages
Cultural choices. Perhaps the biggest plus of living in the city is having so many choices of what to do. Everyday in the city you face a plethora of opportunities – which museum, gallery, sporting event, concert, lecture, book talk, walking tour – etc. should you experience? Or, you could just explore new neighborhoods on your own – on foot or your bike.

Perhaps you are crazy about food. Most cities have far more restaurants than you could ever sample, but you could try! New ones open up all the time with every type of ethnic cuisine, and they don’t necessarily have to be expensive. There are always interesting bars and wine bars to explore. Or, if you like to cook, there are always great markets where you can buy high quality and unusual ingredients to use in your home cooking adventures.

Indian Dish from Thalia in New Haven

Indian Dish from Thalia in New Haven

Shopping that never ends. One of the great things about a vibrant city is the range and quantity of shops. Whether it is department stores, or those that specialize in antiques, rugs, jewelery, bric-brac, books, art, clothes – whatever – you can enjoy amazing variety and quality. You don’t necessarily have to buy what tempts you – but you might!

Socialization. In the city you are likely to find many kindred spirits. You will live in a building where you will be at least in nodding acquaintance with many. You’ll get to know local shopkeepers and neighbors, along with people in the local restaurants or cultural venues. While you might have socialized with your neighbors in the suburbs, you will have a chance to meet people who might be very different and more interesting than you are used to.

Transportation without the automobile. In the suburbs getting in the car to go everywhere can be quite tiresome. While maybe not exactly on your timetable, in the city you can enjoy using a subway, bus, or high speed rail to get to your destination, and not have to worry about finding a parking space. As you age and driving becomes problematic, public transportation insures you can still get out and about safely. You will find walking to the things you need in the neighborhood is a lot nicer than having to drive everywhere.

Low maintenance. Chances are you will be living in a condo or rental apartment in the city, or a development close by. The exterior of the building is not your responsibility, so no need to worry about finding a roofer, someone to clean out the gutters, shovel snow, cut grass, or paint the house. Inside your own walls, you can usually call the super for help or advice on who to hire.

Livability. All of the things we have mentioned so far add up to livability – the ability to live your life with a minimum of hassles and a maximum of enjoyments. For many who choose an urban retirement lifestyle, better livability is the most pleasurable thing about it. And unlike living in the suburbs or community where you tend to be removed from your neighbors, the livability advantages in the city increase as you age.

Some Disadvantages too
Unfortunately, living in the big city usually comes with a fairly big price tag. Some cities like New York and San Francisco are out of range except for people with ample resources. But there are many livable cities where a modest apartment can be purchased or rented for about the same as what you might get for your house in an affluent suburb. And, you will probably save on maintenance and transportation costs to help out.

Crowding, noise, smells
Living in the city isn’t for everybody. Some people can’t get used to people everywhere, or the noise and strange smells. But others find those inconveniences a small price to pay for an exciting lifestyle.

You will probably feel safer in a small town or suburbs than in a big city. But, if you choose your neighborhood carefully you probably have no worries, unless you like to walk around in the middle of the night. Crime figures can be very hard to decipher – violent crime and gangs tend to be in certain neighborhoods you might never visit.

10 Great Cities for Retirement
Here are links to Topretirement profiles of some of the best “best retirement cities”. We didn’t include some very large cities that are fantastic places to retire, like Chicago, New York, Washington because they are quite expensive. Fortunately most of the same amenities can be found in a lesser scale in mid-size to smaller cities as well, which we are including here. You should also check out the cities listed in our recent article, “10 Great Places for LGBTs (and Everyone) to Retire“, because they are interesting retirement cities to consider too.

Boulder, Colorado. We will confess, Boulder is expensive, but it is also very nice. Live downtown in a mixed use development like One Boulder Plaza – take the elevator down to a restaurant!

Pittsburgh, Pennsylvania. The scale and layout of this western PA city makes it so attractive. Along with multiple universities and affordable living. We know people who love retirement here.

New Haven, Connecticut. You have Yale, Long Wharf Theater, wine bars and restaurants. Bored – hope on Metro North and arrive in Grand Central Terminal an hour and half later! Our friends love living in a downtown high rise rental.

The Queen Mary, docked in Long Beach

Long Beach, California. Long Beach, with its population over 600,000, has many resources including an active convention center. It also has miles of beaches and commuter trains to LA. It enjoys a very high walkability score.

Portland scene

Portland, Oregon. Chances are you know someone who has moved to either Portland or Seattle for the lifestyle. Restaurants, recreation, bookstores (think Powells), coffee, and unbelievable biking.

Mission in Santa Barbara

Santa Barbara, California. This California city mid-way up the coast is especially beautiful, with a fantastic main street that ends at the ocean. Thanks to the nearby wineries, it is a foodies’ paradise.

View of Sarasota skyline

Sarasota, Florida. Just today we had a friend tell me how much he loves Sarasota – always something going on in this city with walkable neighborhoods. Outstanding museums and a circus heritage!

Tulsa, Oklahoma. If there is a top candidate for most under-rated city, this could be it. Tulsa is considered Oklahoma’s cultural and arts center, as it is home to two world-renowned art museums, along with professional opera and ballet companies.

The waterfalls in downtown Greenville

Greenville, South Carolina. Your editor hears lots of good things about retirement in Greenville, and knows of several people planning on retiring to the area. The downtown has been the subject of intense and successful redevelopment efforts It won Great American Main Street awards from the National Trust for Historical Preservation in 2003 and 2009. It is a small city but many people live in the surrounding area.

Portland Harbor, courtesy of Wikipedia

Portland, Maine. We just spent a fair amount of time in Portland, and must confess the urge to move here (seasonally) was strong. It is a foodie’s paradise with great restaurants all over, the fabulous Maine coastline. Whole Foods and Trader Joes are practically within snowball (oops, there go get winters here!) distance of each other.

Bottom Line
It’s your retirement, so why not live it to the fullest. If you want to live life at the center of the universe, the urban retirement lifestyle just might be for you. Why not take a mini-vacation and stay in a few cities and see how you like it. Don’t forget, might be a good way to do that.

For further reading
Check Out A New Urbanism Retirement
These College Towns Make for a Great Retirement
Accidental New Yorkers: The Grandparents

Have you thought about retiring to a city? Any places in particular? Please share your experiences and opinions in the Comments section below.

Posted by Admin on December 8th, 2015


  1. Interesting, i was in NYC yesterday. While the noise was horrific and don’t even mention the crowds in the subway, my husband and i enjoyed a long walk through Central Park, saw shop windows beautifully decorated for the holidays on 5th Ave, and if we had the time, could have gone to the Metropolitan Museum of Art. All right there! Upon entering the subway, a woman i had never seen before listed all the reasons why it’s better for an old person to retire in the city than the suburbs. Although i’d never think about retiring in NYC, nor could i afford to; i thought this article’s appearing today oddly serendipitous!

    by ella — December 9, 2015

  2. This is a concept that is very attractive to me. Right now I’m in an active adult community, golfing, tennis, hiking, pool, etc. I’ve thought a lot about this recently and think that when I’m a bit older and all of these physical sports and the like no longer are that compelling I may want to seek a very urban, downtown lifestyle. Not needing an automobile, using a bus and having easy access to what is important to me. I had done a little research to figure out if this is really possible and the biggest negative I found was cost…cost of condo or apartments in the best areas of a well developed downtown city.

    by ljtucson — December 9, 2015

  3. There’s another factor that is contributing to the popularity of city living. In some cities (such as Phoenix, where I live), the downtown area is being revitalized with new urban condos. I know Washington, DC and Pittsburgh have undergone urban makeovers over the past couple decades and become much more livable.

    I talked to a retired couple recently who owned both a small condo downtown and a cabin in Payson, about an hour or so northeast of Phoenix where the elevation is higher and it’s a lot cooler. They stay in the condo when they want to enjoy city life (theatre, museums, restaurants, etc.), and they head to the cabin when they want peace and quiet (and cooler temperatures).

    Dave Hughes

    by Dave Hughes — December 9, 2015

  4. Anyone tried Philly? I think I would like it, but probably not on my retirement income.

    by elaine — December 9, 2015

  5. We retired to downtown Chattanooga for all of the above reasons. It is a great life however, none of our kids live in the area. If just one of them would move here, I think I would be very happy!

    by LisaJ — December 9, 2015

  6. Philly is a great city but expensive, high crime, and snows a lot.

    by Jasmine — December 9, 2015

  7. I want to retire either in San Diego or Asheville depending on which I can afford.

    by Jasmine — December 9, 2015

  8. Interestingly, many of the places on this list are known for being high crime or are outrageous for the cost of living.

    by Denny — December 9, 2015

  9. This article is perfect. I call myself an Urban Chick. After I retired in NE Ohio I moved to Albuquerque, NM March, 2014. Unfortunately this was a poor choice; not big enough. Albuquerque has a small town attitude and very ethnic which does not fit with this Urban Chick. I would’ve settled in the Phoenix area but didn’t think I could handle the high heat. So I’ll check rentals in all of the places you mention here. Thank you.

    by KieraD — December 9, 2015

  10. New Haven, CT??? HUH?????

    No way! I live in another part of CT and just about every day/night there is a shooting there! Same with Hartford, CT and Bridgeport, CT. Bridgeport is so bad we have heard there are areas the cops won’t even go to. The only good thing about New Haven is Yale New Haven Hospital and Metro North.

    The cost of living in CT is horrendous. They tax you to death and the State budget is so out of whack it would make your head spin! One minute they promised the tax payers a $55 refund due to excess money in the budget now only months later the budget is in a $350 million dollar deficit! How does that happen? Oh, and we never did get the $55 refund! LOL!

    by Louise — December 9, 2015

  11. I agree with Louise. New Haven is not a safe place to be for anyone, especially senior citizens. I can’t believe anyone who has been there recently would recommend living there to anyone at all.

    by Mary B — December 10, 2015

  12. Eaine – I have a kid working in Philly near where the Pope visited. She reports very high crime and lots of homeless people. She just laughed at me when I asked her about Philly as a retirement city. I absolutely agree with Louise about the CT cities too.

    And saying that “Pittsburgh” has city housing is not completely accurate. There’s very little housing downtown. However, there are urban neighborhoods around the outside of the city, like Oakland where the University of Pittsburgh is located (as long as you don’t mind thousands of college kids and apartments catering to that crowd) or the South Side where residents complain about bar clientle urinating on their homes and taking all the parking. Some of those urban neighborhoods are being rehabbed and becoming trendy, such as in Lawrenceville. Some urban neighborhoods have always been trendy, like Shadyside. Some of these neighborhoods have few stores. Many of them are extremely hilly, which can be challenging when snow and ice arrives. When shopping for a city location in Pittsburgh, it’s critical to get guidance from a realtor who knows the quirks of each small urban neighborhood. A single street can make a big difference.

    by Kate — December 10, 2015

  13. Regarding Philly, I live within the city limits and hate it. City services are poor, there’s a high crime rate, your car insurance rates will go through the roof, and overall it’s not a friendly environment. I have stayed because my daughters were in school and my job is close by in Montgomery County, but I’ve been planning my departure for quite some time. I can’t wait to get the heck out.

    by Linda — December 10, 2015

  14. A thought on Philly and maybe some other cities I’m less familiar with: Philly has had a lot of problems for a very long time but consider living in one of the cities on the Main Line. There are still commuter trains that can take you to museums and events for day trips and the odd overnight in the city can be fun. Not exactly the same ambiance but an option.

    by Shumidog — December 10, 2015

  15. The divergence of opinion on city living in these comments is interesting. My wife and I have lived in the suburbs and in cities in several states over the years and we’ve come to like the urban environment a lot more. We have noticed less tolerance for noise & grime as we’ve aged but, would not characterize all cities or city neighborhoods as noisy, grimy or dangerous. In fact, we’ve found that kind of generalized ‘paint it all with the same brush’ thinking would have caused us to miss out on several opportunities to live in wonderful urban environments, had we bought in to it.

    Our experience has been as follows:
    – Focus on the neighborhood (just as you would in the burbs but, usually for schools)
    – Choose a city that’s recently redeveloped/redeveloping; you get most of the good & usually lower cost
    – Don’t be fooled by crime statistics for ‘the city’; look closer @ the data for your neighborhood/area, talk to the local police to get the real story.
    – Don’t forget mid-sized cities; they have lots to offer & are usually less expensive than NY, SF, and the like
    – If you can find a great urban environment with a university nearby, it might be perfect for you; being around young people is good for you.
    – Walk everywhere you can; the places you discover & people you meet will enrich your life in ways you couldn’t have imagined.

    We have also lived in some suburbs (including a planned community) that we enjoyed but, it’s not our first choice because of the isolation and homogeneity of that environment. In fact, of the six suburbs in six different states that we lived in over the years, the typical environment was one where you had to drive everywhere, everyone drove in/out of their garage without speaking to their neighbors, and the similarity of everyone there was stifling. While all suburban neighborhoods are not like that, many (most?) are, and that has to be included in any coversation about urban versus suburban living. You could look at the choice this way:

    Live in the city & risk losing your purse or, live in the burbs & risk losing your mojo.

    by Mark — December 10, 2015

  16. I was surprised to see only mid-sized cities in your list. Yet before reading here, I was already thinking even smaller — Chapel Hill, NC would probably be a major option (just so much ties us here and I love the atmosphere). But any small city with a university, restaurants and senior capable housing within short walking distance of good shopping is a candidate.

    Our case is a little different. More than 20 years ago we built and moved to our planned retirement home in a very rural (almost remote) part of central NC just south of Chapel Hill. We have had exactly what we wanted , but creeping age has been turning my thoughts elsewhere for several years. I keep a regularly updated, detailed annual budget (extends until my wife an I reach 110 years old!). When doing the regular prep for next year (2016) a couple of days ago, I noticed that if we moved away to a place that did not required that WE personally manage or do all the upkeep (house, yard, appliances, etc.), we would immediately have an expected $10,000 annual savings. And most of those upkeep things are quickly becoming problematic for us at 68 (this month).

    Sure there are cost implications, but there are more trade-offs too. (No necessary car expense for example.) And to consider just minimizing an annual rent/lease contract with $10,000 in home upkeep makes this really jump out at us. (And we do realize that there are still possible maintenance fees.)

    So we are once again thinking along the lines of this article and considering not only Chapel Hill, but Asheville, Greenville SC, Chattanooga TN and many other small cities in the SE. (For various reasons including health, we have already determined that our last years will be in the Southeast — we can always plan to travel where we want.)

    by Rich — December 10, 2015

  17. My feelings about New Haven echo many of the ones already expressed. The last thing I want to do is get myself locked into a life care environment where I do not trust the neighborhoods around the facility may become more dangerous in a 5-10-15 year window.

    What may be reasonable today can change rapidly, especially due to the outrageous State of Connecticut. I think that fees will rise more rapidly due to the state effect on costs, taxes, etc.

    I’ve lived in CT for most of my life. When my husband can retire, we are taking a fast track out of the state. We may stay in a cold environment, but not here.

    Unfortunately all the boomers are headed out and my property value will diminish quickly, despite the fact I live in a small town in a beautiful neighborhood.

    by Trappercat — December 12, 2015

  18. My husband and I moved to Miami Beach, population about 100000, a year ago, for the reasons cited above. So far we love it! We walk, bike and take a trolley or local bus everywhere. We have quick access by car to Miami and its airport, Key Biscayne and the keys. We live in a high-rise condo with a bay view we never tire of. We love Miami’s beautiful new art museum and MB’s New World Symphony offerings. We can walk to both the regular movie theater and the art cinema. We are slowly making friends — it’s not like living in an over-55 community where everybody is like us, but we like that. We feel safe walking everywhere. Our community police officer said her biggest problems are drunk driving and keeping tabs on the homeless population (northern cities, she says, give homeless people free one-way bus tickets to Miami!). We do not have to deal with the summer heat, however; we sold our big suburban home and bought a smaller house in Newport RI and the aforementioned Miami Beach condo. Our property taxes with two new properties are still cheaper than the one suburban house (and as FL residents we no longer pay income taxes). We’re thinking in five-year chunks, and so far we like this chunk!

    by Pam — December 16, 2015

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