The Best Retirement Destinations for Single Boomers
Retirement as a single baby boomer is a fresh start—a chance to live exactly how you want, in a place that keeps life interesting. With no job tying you down, the world is yours to explore. This guide will take you through a curated list of retirement destinations hand-picked for single boomers!
Naples, Florida
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Once you live here, you’ll understand why it’s called the Golf Capital of the World. Naples is polished, full of golf carts zipping between clubhouses, and home to some of Florida’s best beaches. But the real appeal is the built-in social network. Between the country clubs, yacht gatherings, and endless events, you’re never short on people to meet.
Prescott, Arizona
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Prescott attracts boomers who appreciate a historic downtown but aren’t quite ready for the typical Florida shuffleboard scene. The art galleries, bluegrass festivals, and outdoor cafes are just as appealing as the surrounding pine forests and hiking trails. Unlike the sweltering heat of Phoenix, Prescott stays comfortable year-round for outdoor activities.
Fort Collins, Colorado
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Some cities cater to retirees; Fort Collins makes you forget you’re even retired. There’s always something happening—live music, outdoor festivals, and more breweries than you’ll ever get through. The Colorado State University connection keeps things fresh, and with the Rockies in your backyard, the “lazy retirement” idea doesn’t exist here.
Sarasota, Florida
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Sarasota isn’t just about the beaches (though, yes, Siesta Key sand is as soft as they say). This city doubles as an art and music hub, with year-round festivals, a professional ballet, and even an opera scene. If you like your retirement with a little sophistication—and maybe some waterfront dining—this is the place.
Santa Fe, New Mexico
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If retirement for you means quiet mornings, mountain air, and conversations that go deeper than the weather, Santa Fe delivers. The city is an artist’s paradise, with Pueblo-style homes, cozy coffee shops, and a wellness culture that embraces everything from sound baths to hot springs. It’s not just scenic—it’s soul-filling.
Charleston, South Carolina
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In Charleston, you’ll find cobblestone streets and old-fashioned Southern charm, but also waterfront bars, farmers’ markets, and enough live music to fill your calendar. It’s a city where people actually talk to each other—perfect for anyone who’s not trying to spend retirement in solitude.
Austin, Texas
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Austin isn’t your typical retirement town, and that’s exactly the point. The energy is infectious—live music pours out of nearly every corner, tacos are practically a religion, and the social scene is effortless. It’s also one of the few places where retirees and young professionals mingle seamlessly. No state income tax doesn’t hurt, either.
Asheville, North Carolina
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If you want mountains, music, and a built-in creative community, this is where you retire. People in Asheville spend their days hiking the Blue Ridge Parkway and their nights at intimate music venues or breweries. With a university-backed lifelong learning program, it’s also one of the best places to keep your mind sharp
Cape Cod, Massachusetts
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If you’ve ever imagined retiring somewhere where neighbors still borrow sugar and summer feels endless, Cape Cod is it. The coastal villages, lighthouses, and clam shacks create a postcard-perfect backdrop for a retirement that’s equal parts social and serene. It’s a little pricier, but for lifelong New Englanders, it’s worth every penny.
Palm Beach, Florida
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Palm Beach is for retirees who appreciate the finer things—pristine beaches, world-class golf courses, and an arts scene that includes everything from high-end galleries to the Kravis Center for the Performing Arts. If the idea of bumping into celebrities at brunch appeals to you, this is your kind of retirement.
Charlottesville, Virginia
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Charlottesville doesn’t try too hard—it doesn’t have to. This is where retirees get the best of both worlds: a laid-back small-town vibe with just enough action to keep things interesting. You can spend your days hiking the Blue Ridge Mountains or enjoying local wine tastings, and thanks to Virginia’s retiree-friendly tax policies, your wallet won’t take a hit.
San Francisco, California
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Yes, it’s expensive, but if you can afford it, San Francisco is retirement gold. You get world-class healthcare, unbeatable cultural experiences, and neighborhoods that cater to every personality—whether you’re drawn to the bustle of North Beach or the quiet elegance of Sea Cliff. The city’s public transit also makes car-free living easy.
Philadelphia, Pennsylvania
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If a big city calls to you, but you don’t want New York’s chaos, Philly is the answer. History, food, and culture collide here, creating an endlessly entertaining environment. You’ve got museums, theaters, and a restaurant scene that rivals any major city—without needing a retirement fund the size of a small fortune.
Chicago, Illinois
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Chicago’s lakefront parks, museums, and exciting food scene are for retirees who thrive in a fast-paced city. The L train means you can navigate easily without a car, and there’s no shortage of concerts, comedy shows, or deep-dish pizza nights to keep your social calendar full.
Miami, Florida
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If you want your retirement to feel like a never-ending vacation, Miami makes it happen. Whether it’s salsa dancing in Little Havana, exploring the murals in Wynwood, or just lounging by the water with a mojito, the energy is contagious. It’s warm, diverse, and perfect for anyone who thrives on excitement.