Retiring Soon? These 7 Cities Are Perfect If You Want Your Grandkids to Visit Again and Again

Let’s be real—when you think about retirement, you’re probably not just dreaming of golf courses and quiet mornings with coffee. You’re also picturing birthday parties, noisy weekends, and grandkids running through the house. Because for a lot of retirees, it’s not just about finding a place to live—it’s about finding a home that feels close to family, especially those little ones who light up your world.

So, if you’re planning your next chapter and want to make sure there’s plenty of room (and entertainment) for grandkids to visit, here are some cities that check all the boxes: affordable, fun, and family-ready.

What Makes a City Grandkid-Friendly?

Choosing where to retire isn’t just about saving money—it’s about the life you want to build. And if you’re expecting regular visits from your grandkids, here’s what matters most:

• A reasonable cost of living so your retirement savings go further

• Access to good healthcare, because peace of mind matters

• Family-friendly activities—think parks, zoos, and museums

• Nearby airports or travel options so family can visit easily

• Safe, walkable neighborhoods you’ll feel good living in

We’ve looked at it all—from tax perks to playgrounds—to help you find the right fit.

Cities That Are Great for Grandparents and Grandkids

Pittsburgh, Pennsylvania

Affordable, full of charm, and lots to do with the kids

Pittsburgh is one of those cities that might not be on your radar—but it should be. It’s affordable, full of history and culture, and has top-rated hospitals. Plus, it’s loaded with fun places for the grandkids: science museums, a great zoo, and plenty of green spaces to explore.

• Median rent is around $1,300 a month

• Great public transit and healthcare

• Perfect mix of quiet living and kid-friendly fun

Sarasota, Florida

Beach town living, sunshine all year, and no state income tax

If you love warm weather and want to be somewhere that practically begs your grandkids to visit, Sarasota’s a top contender. You’ll find beautiful beaches, marine life, and places to explore with kids. And with no state income tax, it’s easier on your budget.

• Beaches like Siesta Key are stunning and family-friendly

• The Mote Marine Lab is a must for visiting kids

• You can enjoy outdoor life almost every day of the year

Des Moines, Iowa

Quiet, affordable, and full of Midwestern charm

Des Moines is one of those cities that feels like a hidden gem. It’s peaceful and affordable, with a cost of living about 13% below the national average. It’s got great healthcare, plus plenty of activities for families—like a zoo, science center, and art museums.

• Simple, stress-free living

• Great for retirees who like culture without the crowds

• Kid-approved attractions and wide-open spaces

Raleigh, North Carolina

Lush parks, top-tier healthcare, and a relaxed lifestyle

Raleigh offers a great balance—it’s got a slower pace, good weather, and excellent medical care. There are also tons of parks, family activities, and nearby universities that give the area some youthful energy. If your grandkids live on the East Coast, it’s super accessible.

• A good-sized city without big-city stress

• The Marbles Kids Museum and Pullen Park are local favorites

• Clean, green, and welcoming

Biloxi, Mississippi

Coastal charm, super low costs, and relaxed living

If you want to live near the water without spending a fortune, Biloxi is worth a look. It’s quiet, low-cost, and has no state tax on Social Security or retirement income. There’s also a beautiful waterfront and kid-friendly places to visit like the local aquarium and lighthouse.

• Median rent around $1,245

• Affordable beachfront living

• Slower pace with just enough fun for visiting family

Madison, Wisconsin

Lakeside living, good healthcare, and a strong sense of community

Madison has a cozy, small-town feel even though it’s a capital city. You’ve got lakes, parks, walking trails, and excellent hospitals. It’s easy to get around, and there’s plenty to do with kids, like free visits to the zoo and outdoor markets.

• Family-friendly vibe with year-round community events

• Nice mix of nature and city comforts

• Great for active grandparents who love being outside

San Antonio, Texas

Cultural landmarks, great food, and plenty of places to explore with kids

San Antonio is full of life—and so much fun for families. The River Walk is great for a stroll, and there are lots of spots your grandkids will love like LEGOLAND Discovery Center and SeaWorld. The cost of living is decent, and there’s no state income tax.

• Warm weather and rich cultural history

• Plenty of public parks and family attractions

• A good choice if you want something vibrant and budget-friendly

Bonus: Easy Access Makes a Big Difference

If your kids and grandkids live in different states, a city with a solid airport is a big help. Cities like Raleigh, Madison, and Pittsburgh all have good flight connections and manageable airports—no chaos, just convenience.

Retirement doesn’t mean slowing down—it means doing what matters most. And for many, that means staying close to the ones who call you Nana, Papa, or Grandma and Grandpa.

Luckily, you don’t have to choose between affordability and family time. There are plenty of cities where your money stretches, your health is in good hands, and your weekends can still be filled with finger painting, story time, and hugs that make everything worth it.

So go ahead—choose a city that lets you live your best life and welcome the grandkids with open arms and maybe a cookie or two.