The Top 10 Cities to Retire to in 2020

Retirement is one of the most exciting and rewarding milestones you can achieve. You’ve spent most of your life in school and at work, perhaps even raising a family, and now finally you have an opportunity to reap the rewards and relax during your golden years. If you’re nearing retirement age, you’ve probably started a list of all of the places you want to visit or settle down in. We have a list of our own to share! 

US News recently compiled the 2020 top ten list of the best places to retire. They ranked each city by examining 6 indexes: Housing Affordability, Job Market, Desirability, Health Care Quality, Happiness, and Retiree Taxes. 

But the rankings and statistics don’t tell the whole story, so we’ve put together profiles of each city so that you can be the judge and maybe add these great cities to your list!

10. Dallas-Fort Worth, Texas

The Dallas-Fort Worth area (often referred to as the DFW Metroplex), is located in Northeast Texas, about 200 miles from the Oklahoma border. DFW encompasses 9,286 square miles and is home to approximately 7.5 million people. Don’t let the numbers scare you! Although Dallas-Ft. Worth seems crowded, there is plenty of room to spread out. 

DFW enjoys a booming economy thanks to a large influx of coastal companies relocating to the area in pursuit of lower taxes and fewer business regulations. This in turn allows residents to enjoy a lower cost of living. The average price of a home in Dallas is $215,000, which is 4% below the national average. 

There’s no shortage of things to do in Dallas-Fort Worth. Dallas boasts a number of critically-acclaimed museums, and the region is home to several amusement parks, water parks, and sports attractions (perfect for visiting grandkids)! Did we mention BBQ? You’ll never get tired of it! The food scene is explosive, with some of the top chefs in the country fanned out across the region.


So what do you say, partner?

9. Grand Rapids, Michigan

Located to the east of Lake Michigan, Grand Rapids is a craft beer-enthusiast’s dream town! Known for their breweries and art scene, Grand Rapids is the right balance of vibrant city and peaceful suburbia. At last census count in 2017, Grand Rapids has a population of just under 200,000, while the greater metropolitan area is home to just over 1 million people. 

It’s true, it does get quite cold and snowy in the winter months, but summers are generally mild (rarely breaking 90 degrees) and offer plenty of opportunity to get out and explore the city on foot. Pub crawl, anyone? Grand Rapids has you covered.

Looking for things to do? Look no further! Grand Rapids has museums, zoos, and ample nature areas to explore. 

The real estate market in Grand Rapids is accessible to many, with homes averaging $197,000. 

Grand Rapids is an ideal spot for snowbirds to set up shop during the comfortable summer months, then return south to avoid the winter.

8. Nashville, Tennessee

Even if you’re not considering a move, make sure to put Nashville on your list of “must visit destinations.” A place some might call quintessentially American, Nashville is home to legendary country music venues such as the Grand Ole Opry House, and museums that pay tribute to storied musicians like Johnny Cash.

Just over 690,000 people call Nashville home, and many more make the journey to this historic city to enjoy the numerous live music venues, the bustling downtown scene, Music Row district, and incredible food culture. 

Are you a fan of whiskey? Lynchburg is just a short drive south of Nashville, and is home to Jack Daniel Distillery. Visitors can watch how this world-renowned whiskey is made, and learn the history behind one of America’s oldest brands.

While you’re there, be sure to take a break from the hustle and bustle and visit Radnor Lake State Park, home to over 1,300 acres of serene trails and lake views.

7. Winston-Salem, North Carolina

Located in Forsyth County, Winston-Salem is home to 244,605 people. This city draws much of its appeal from its friendly “small town” vibe, affordable real estate and recent surge in revitalization. Nicknamed the “Camel City” because of its history of involvement in the tobacco industry, Winston-Salem has also served as the backdrop of many films and TV shows.

The median home value in Winston-Salem is $142,000, with a steady upward trend in value over the prior years. Forecasters predict a 5.1% rise in home value over the coming year. Whether you’re looking to rent or own, your dollar stretches in Winston-Salem!

Enjoy the heat? North Carolina has you covered! Summer months in Winston-Salem are often hot and humid, with winter bringing cool to cold temperatures. If you’re adverse to seriously cold weather, Winston-Salem offers a nice compromise of hot and cool.

History buffs will appreciate the numerous historic homes and museums in Winston-Salem, many dating back to the 18th century.

6. Jacksonville, Florida

Buckle up! We’re about to take a long and winding tour through Florida. Several Florida cities appear in the top ten list, with Jacksonville coming in at # 6.

Jacksonville is one of Florida’s northernmost cities, and the most populous city in the state. At the last census poll in 2018, Jacksonville’s population was estimated at 903,889. 

The St. John’s river snakes through the heart of the city, providing waterfront views from practically anywhere. Don’t forget the beach! Jacksonville Beach is a short drive from downtown, and is a popular tourist spot that’s perfect for a warm getaway.

Locals love Jacksonville for its authenticity and unique personality. Whereas other big cities in Florida have tourism at heart, and sometimes come across as “kitschy,” Jacksonville offers a myriad of attractions that celebrate local culture, art and history.

5. Port St. Lucie, Florida

Our next stop on our Florida tour takes us further down the coast to Port St. Lucie. This Atlantic coastal town is lush with flora that really exemplifies the beauty of Florida. From alligators to dolphins, you’ll encounter droves of wildlife!

Is Florida fishing on your retirement checklist? Look no further than Port St. Lucie. Boat rentals are widely available, as are chartered fishing excursions. 

If you love the heat, this is your spot. Port St. Lucie summers are long and hot. You’ll need to be comfortable with humidity and an overall “muggy” feeling. The best times to visit are early February to early summer, and again in late fall.

Looking to commit? The median home value is $232,931, meaning Port St. Lucie is more affordable than other south Florida coastal cities. 

4. Asheville, North Carolina

Let’s take a break from the Sunshine State and head back north to Asheville, North Carolina. At number 4 on the list, Asheville offers a vibrant downtown scene against a backdrop of the gorgeous Blue Ridge Mountains. Outdoor enthusiasts love Asheville because of the endless nature attractions. From zipline tours to treetop adventures, you’ll have plenty to explore in this North Carolina city.

Perhaps you’re looking for retirement activities that are a bit slower and a lot tastier? Asheville’s “Foodtopia” is a community of culinary icons who have joined their talents and passion to bring food adventures to the Blue Ridge Mountains. Explore farmers markets, culinary excursions, a thriving beer scene and more.

3. Lancaster, Pennsylvania

Located about 80 miles away from Philadelphia, Lancaster is considerably smaller than other cities on our list. 59,322 people call Lancaster home, but don’t let size fool you! This city has plenty to do and see. 

Lancaster rests squarely in Pennsylvania Dutch Country, and the architecture alone is worth the trip to see. A stroll through downtown takes you back to the early days of America, when homes and buildings embodied the old American spirit of industry. 

Lancaster offers a true Amish experience, with farm tours, villages and other Amish artistry and attractions to explore. Whether you have grandkids in tow, or you’re just a kid at heart, you’ll love the hands on museums, scenic train rides and workshops available year-round.

2. Sarasota, Florida

We’re back down south in Florida as we narrow in on our top 2 places to retire. We’re headed to the west side of the state to Sarasota, another coastal city with a big personality. Located south of Tampa, Sarasota is home to a number of cultural institutes, The Venice Symphony, museums, and plenty of oceanic adventures. 

Craving crab? Be sure to visit Sarasota in the fall, notably in October, when stone crab season kicks off. These extraordinarily tasty crabs are a local delicacy you can’t miss. 

Real estate in Sarasota is competitive but still affordable. There are homes available in many budget brackets, and no matter where you live in Sarasota, you’re never very far from ocean access.

1. Fort Myers, Florida

We’ve arrived at the number 1 city to retire to in 2020: Fort Myers, Florida. Located in southwest Florida and set slightly inland, Fort Myers sits along the Caloosahatchee River. This bright and cheerful city is home to around 82,000 people, and has a storied past. Fort Myers was built in the 1830s during the American Indian Wars, and served as a base against the Seminole Indians. It wasn’t until after the Civil War that Fort Myers became an established city. For more fascinating historical facts about Fort Myers, click here.

So what makes Fort Myers so desirable to retirees? Its close proximity to beaches makes it a popular site for boaters and ocean-enthusiasts. Fort Myers is also consistently warm, with an average temperature of 84.3 degrees. Perhaps most attractive to residents and newcomers alike is the lack of state income tax

Getting around town is also a breeze! Downtown Fort Myers is on-foot-friendly, and the city’s bus system provides easily accessible service for those who want to embrace a vehicle-free retirement.

As more and more people discover the beauty and benefits of Fort Myers, real estate prices have steadily risen over the last several years. If you’re on the fence, now is the perfect time to make a move, before home prices climb in the coming years.

We’ve counted down the top ten places to retire in 2020, and it’s too hard to choose just one! We hope you found this guide helpful in crafting your retirement travel plans. You’ve definitely earned a trip to all ten!

Share this post

Share on facebook
Share on google
Share on twitter
Share on linkedin
Share on pinterest
Share on print
Share on email
Scroll to Top