Retirement is supposed to be the reward at the end of a long career. The years you spend finally doing things on your own terms, choosing where to live and how to live. Yet every year, thousands of seniors pack up their savings, move to a so-called dream destination, and find themselves staring at bills they never expected. The reality of retirement geography is much harsher than the travel brochures suggest.
Some places look irresistible on paper. Warm weather, famous skylines, stunning coastlines. But when you actually run the numbers and factor in taxes, healthcare access, crime, and daily costs, the picture changes fast. These are the eight destinations that seniors are increasingly calling out as simply not worth it. Be surprised by what makes the list.
1. New York City, New York – Where Retirement Dreams Meet Financial Reality
Let’s be real: New York City is one of the most iconic places on Earth, but iconic does not pay the bills. In 2023, nearly 24,000 people aged 60 and over packed up and left New York City, while only about 6,800 moved in. That net loss of roughly 17,000 retirees was three times larger than any other American city. That is not a coincidence. That is a mass exit.
According to the Council for Community and Economic Research’s Cost of Living Index, New York is the most expensive place to live in the United States. The borough of Manhattan holds the top spot as the most expensive urban area in the nation, with a cost of living index of 232, compared to the national average of 100. Think about that for a moment: more than double the national average.
WalletHub ranked New York City as the priciest city to retire in. In New York State, you can expect to need around 1.3 million dollars in savings to retire, while in California you will need about 1.6 million. For seniors on fixed incomes, those numbers simply do not add up. And property taxes do not help: New York’s property taxes rank among the highest in the country, averaging 1.64% of a home’s value statewide.
The state’s average combined sales tax rate sits at 8.26%, and property taxes are likewise fairly steep. Toss in costly winters, the noise, and the relentless pace of city life, and it becomes obvious why so many seniors are voting with their feet.
2. Hawaii – Paradise Has a Price Tag That Most Seniors Simply Cannot Afford
Honestly, no destination captures the imagination quite like Hawaii. The sunsets, the beaches, the trade winds. But here is the thing: paradise has a price tag that would make most retirees faint. Retirement Living, a national platform for seniors planning to retire, ranked all 50 states for the best and worst places to retire in 2025, and Hawaii ranked last.
Hawaii scored third highest for quality of life, yet fell desperately short in affordability, causing the state’s descent to last place. Hawaii retirees need about 2.2 million dollars to cover basic living expenses for 25 years when retiring at 65. That is not a typo. Roughly 2.2 million dollars, just for the basics.
Besides the cost of living, Hawaii has one of the lowest numbers of healthcare facilities, with roughly 1,240 facilities per 100,000 seniors. This can lead to seniors needing to fly to the continental United States to get specialized care, which adds even more to their overall living costs. The median home price in 2025 is around 1.5 million dollars on Oahu, Maui, and Kauai.
Hawaii residents face utility bills that are nearly 94.4% above the national average, a disparity that adds approximately 5,000 dollars annually to retirement expenses. Hawaii’s grocery prices are some of the highest in the nation, costing about 15 to 30% more compared to the national average. The dream is real. The math, unfortunately, is not.
3. California – Golden State, Golden Price Tag
California is beautiful, diverse, and bursting with things to do. Retirees know this. That is exactly why so many of them tried to move there, and then left in droves. At the state level, California lost more retirees than any other state, with a net 56,858 people aged 60 and over leaving in 2023. That is an extraordinary number.
It is no shock to anyone that California is one of the most expensive places to retire. In The Motley Fool’s study, California ranked fifth-worst in cost of living. It has the second-highest cost of housing and the fifth-highest tax burden of all 50 states. California taxes pensions, although it does not tax Social Security benefits, and the state is also known for having some of the highest personal income tax and sales tax rates in the country.
The nation’s five most expensive retirement towns all have one thing in common: they are in California. From Silicon Valley to the Southern California coast, the price of real estate alone is enough to derail most retirement plans. The median home sale price in San Jose was 1,368,700 dollars as of October 2025.
Los Angeles came in second for retiree losses with a net outflow of over 3,000 seniors. San Diego followed closely. Oakland and San Jose also suffered significant losses. That put four California cities in the top 10 for retiree exodus. Sometimes a place is just too expensive to love, no matter how beautiful it is.
4. New Jersey – The Worst State for Retirees, and It Is Not Even Close
New Jersey is often dismissed as a state people pass through on the way to New York or Philadelphia. But for retirees, the bigger problem is not the reputation. It is the finances. New Jersey is the worst state to retire, driven by its high cost of living and income tax rate of 10.75% for top earners. That is one of the steepest rates in the entire country.
States might be considered less desirable for retirement due to high costs of living, high taxes including income, property, and sales taxes, harsh climates, lower-quality healthcare systems, and safety concerns. New Jersey checks many of those boxes. It is not one problem. It is a whole pile of them stacked on top of each other.
New Jersey lands in the middle of the pack when it comes to the size of its older community at 17.7%, its Supplemental Security Income payment of 660 dollars, and the availability of arts and recreational facilities at 268 per 100,000 older adults. Average at best, outrageously expensive to live in. That combination is a tough sell for anyone on a fixed income.
California, Connecticut, Massachusetts, New Jersey, New York, Rhode Island, Montana, and Vermont are among the worst states to retire in for taxes, factoring in tax rates on retirement income and property tax bills. Being in such distinguished company for all the wrong reasons says a lot about what New Jersey offers retirees.
5. New Mexico – High Crime, Sparse Healthcare, and Brutal Summers
New Mexico gets romanticized for its sunsets and adobe architecture. And honestly, it does look stunning in photos. The trouble is, retirement involves more than scenery. New Mexico takes the top spot for worst places to retire in The Motley Fool’s 2026 study. Not second. Not third. First.
New Mexico has the second-worst crime rate nationwide, with a crime score of just 2 out of 100. The state also received a low quality-of-life score. Its healthcare score was 40 out of 100. According to FBI data, New Mexico has one of the highest rates of violent crime against older adults in the nation.
On average, violent crimes against seniors in the state occur at a rate of 212.2 per 100,000 individuals. That is a striking and sobering figure. While New Mexico is rich in culture and boasts beautiful landscapes, crime can be high and medical facilities are sparse, especially in rural areas. That means retirees may need to travel long distances to access specialized care.
Overall, New Mexico has good weather with warm summers and mild winters, but harsh weather conditions such as strong winds, dust storms, and wildfires are common. It is the kind of place where the lifestyle looks appealing until reality sets in. And for seniors who need reliable healthcare nearby, the rural healthcare gaps alone are a dealbreaker.
6. Oregon – Beautiful Scenery, Beautiful Taxes
Oregon is genuinely gorgeous. The Pacific coastline, the forests, Portland’s food scene. It is the kind of place that shows up on every “best places to live” list for younger people. For retirees, though, the picture is considerably less rosy. Oregon ranks low for retirement in the 2026 WalletHub study, placing 40th overall, largely due to high costs and limited affordability.
The state’s cost of living is higher than the national average by about 10 to 13%, driven by rising housing prices, expensive healthcare, and steep state income taxes on most retirement income, including pensions, IRAs, and 401(k)s, though Social Security is exempt. This combination can strain fixed incomes, making it tough for budget-conscious seniors.
Additional drawbacks include air quality issues from frequent wildfires, rainy weather in much of the state, higher crime rates in some urban areas, and limited access to specialized senior healthcare outside major cities like Portland. The wildfire smoke alone has become a serious seasonal health concern for older adults with respiratory conditions. I think that point often gets buried under Oregon’s more glamorous reputation.
7. Boston, Massachusetts – Historic, Prestigious, and Wildly Expensive
Boston has a certain magnetism. World-class universities, incredible hospitals, rich history. But magnetism costs money, and Boston charges a premium for every square foot. There are few cities in America as iconic as Boston, but this is also part of what makes living there so expensive. This historic city scores a cost of living index of 144.8.
According to Zillow, the average home in Boston costs 760,717 dollars as of January 2026, easily 200,000 dollars over the national average. The average rent for a one-bedroom apartment in Boston is 3,429 dollars per month, nearly double the national average. Those numbers hit hard when you are living on retirement savings.
The Bureau of Labor Statistics reports that the average Boston resident spent 13,515 dollars on food alone in both 2023 and 2024, while the nation’s average annual food expenditure that year was over 3,000 dollars lower. According to the Massachusetts Health Policy Commission, state healthcare costs have risen by 5.2% per year since 2019, and the state’s health insurance premiums are ranked the second highest in the country.
Massachusetts has the nation’s second-highest cost of living, according to the Missouri Economic Research and Information Center, and a long-standing reputation for high taxes. Despite excellent healthcare infrastructure, the sheer cost of accessing it leaves many seniors running the math and then quietly booking a moving truck heading south.
8. San Diego, California – Sun, Sand, and Staggering Housing Costs
San Diego is one of those places that genuinely seems perfect from a distance. The weather is almost criminal in how pleasant it is. The beaches are world-class. The lifestyle is enviable. Just miles from Mexico, San Diego offers mild temperatures and low humidity year-round and is home to many beaches, hiking trails, and golf courses. However, it is also known as one of the most expensive places to retire in the country, with a cost of living index score of 146.1.
Housing affordability is a huge problem for San Diegans, much like the rest of Southern California. San Diego recorded a net outflow of 2,604 seniors in 2023 alone. Thousands of retirees who thought they would be spending their golden years watching the Pacific decided the price was simply not worth the view.
Think of it this way: imagine paying luxury hotel prices every single day for the rest of your life, just to live in your own home. That is what San Diego retirement can feel like on a fixed income. The worst places to retire tend to lag in quality of life, healthcare, and affordability, and while San Diego does not fail on quality of life, affordability makes the rest nearly irrelevant for most retirees.
A recent AARP study found that roughly one in five adults aged 50 and over have no retirement savings, and more than three in five are worried they will not have enough money to support themselves in retirement. Against that backdrop, choosing an ultra-expensive city like San Diego is a financial gamble that most seniors simply cannot afford to take.
The Bigger Picture: What These Destinations Have in Common
Step back and look at all eight destinations together, and a clear pattern emerges. These cities span different regions and climates, but they share one thing: high costs. A majority of the top cities that retirees are leaving are in states where you typically need over 1 million dollars in savings to retire comfortably. That is the common denominator.
States and cities are considered less desirable for retirement due to high costs of living, high taxes including income, property, and sales taxes, harsh climates, lower-quality healthcare systems, and safety concerns. High living expenses, particularly for housing and healthcare, can strain retiree budgets. It is a combination of factors, not just one flaw.
When you combine longer lifespans with rising costs, it becomes more critical than ever to retire in a place that is affordable, has accessible healthcare, and offers a strong community and social life for seniors. That framing matters. Retirement location is not just about where you want to be. It is about where you can sustainably afford to be for potentially decades.
What Seniors Should Look for Instead
Do not just choose a retirement location because it has low taxes or housing costs. Look at the overall cost of living, including property insurance, available services, and general living costs. It sounds obvious, but plenty of retirees skip this step and pay the price later.
According to the Employee Benefit Research Institute’s 2025 Retirement Confidence Survey, 67% of workers reported feeling at least somewhat confident they will have enough money to retire comfortably, but only 24% said they were very confident. That gap between “somewhat confident” and “very confident” is exactly where bad location choices tend to live.
Before you sell your home and pack up your life, try renting for at least several months in your planned destination. That way, you can figure out the good and the bad about living there. You can also start building your community so you will have a social circle if you actually move. It is genuinely the smartest piece of advice in all of retirement planning. Simple, but rarely followed.
The Conclusion: Your Retirement Location Is a Financial Decision, Not Just a Lifestyle One
The eight destinations on this list are not inherently bad places to live. Many of them are genuinely wonderful. The problem is that “wonderful” and “financially sustainable for a 20 to 30-year retirement” are two very different things. Significantly fewer retirees moved in 2024 compared to previous years, with rising home prices and high mortgage interest rates among the likely reasons for the slowdown. Seniors are getting smarter about this.
The most honest retirement advice anyone can give is this: fall in love with a place after you have checked the numbers, not before. When you combine longer lifespans with rising costs, it becomes more critical than ever to retire in a place that is affordable, offers accessible healthcare, and provides a strong community. Location shapes everything from your monthly budget to your access to a doctor to how safe you feel walking around your own neighborhood.
The no-go list is not permanent. Circumstances change, savings vary, and what is unaffordable for one retiree may be manageable for another. But the data is clear about which places consistently drain retirement savings faster than expected. Now the real question: does your dream retirement destination make this list? What would you do differently if it did?