9 Smart Places to Retire

St. Augustine and the surrounding St. John’s County offer more than just surf and sand wedges.

St. Augustine Beach, located 10 minutes from downtown, is backstopped by laid-back restaurants serving up the day’s catch to folks in flip-flops. If a peaceful hammock is more your vibe, chill with the local wildlife on the secluded beaches of 1,600-acre Anastasia Island State Park.

A short drive north will land you in Ponte Vedra Beach, replete with ritzy beach clubs and golf courses. Here you’ll find TPC Sawgrass, home of The Players Championship, one of the PGA’s most prestigious annual events. The area is also home to the World Golf Hall of Fame and the PGA Tour Academy—for golf legends both real and aspiring.

You can’t walk very far in St. Augustine without being reminded that it is the oldest European-established city in the U.S.; the town square dates to 1573. The city is still very much alive, however. Pedestrian-only St. George Street, lined with bistros, boutiques and bars, bustles all day and well into the night.

Also keeping the city young: Flagler College, where retirees can take in free lectures, plays, musicals, concerts and art exhibitions.

Living costs in greater St. Augustine aren’t cheap by national standards, but Florida is among the tax-friendliest states in the country for retirees. There is no state income, estate or inheritance tax.

Savannah isn’t your typical college town, but if you enjoy the arts—from film to fashion—this city might be for you.

The private Savannah College of Art and Design doesn’t have a traditional campus. Rather, it operates out of historic buildings it has renovated, mostly in the downtown area. Many school-sponsored activities are open to residents. One of the most popular is the annual Savannah Film Festival. It features more than 100 films, some from Hollywood studios, that haven’t yet hit theaters.

Savannah is also home to Savannah State University and the Armstrong Campus of Georgia Southern University, public institutions that offer free tuition for residents age 62 and older. But you don’t need to sit in a classroom to learn history here, because it’s all around. Savannah, founded in 1733, has one of the largest National Historic Landmark Districts. Spanish moss hangs from massive live oaks in its parks, including Forsyth Park and its iconic fountain.

Hot and steamy summers are a drawback. But many here escape the heat by heading 18 miles east to Tybee Island’s beach.

Georgia is one of Kiplinger’s top 10 tax-friendly states for retirees. Social Security income is tax-exempt, and so is up to $65,000 of most types of retirement income if you’re 65 or older (up to $35,000 if you’re 62 to 64).

Richmond is historic and southern, but it’s anything but sleepy. Around town, you’ll find a mix of magnolias and colorful murals, preppies in pastels and bohos with turquoise hair and tattoos.

The centers of the city’s intellectual and creative life are Virginia Commonwealth University, a state university; the University of Richmond, a private school; and Virginia Union University, a private, historically black university. Relocating retirees are often alumni or discovered the city when their children attended college there.

Because Richmond is also the state capital, cultural offerings are plentiful. On the city’s west end, the University of Richmond’s Modlin Center for the Arts attracts retirees with programming that includes music, dance, theater, visual arts, live broadcasts, lectures and more.

The city straddles the James River, which offers some respite on hot summer days. At Belle Isle, accessible via a pedestrian bridge, you can walk on shady paths and watch great blue herons glide down to rocks midstream. Bicyclists, runners and walkers enjoy the Virginia Capital Trail, which runs 52 miles between downtown Richmond and the Jamestown Settlement near Williamsburg. Retirees can visit or volunteer at Maymont, a gilded-era home and 100-acre property with gardens and a nature center.

Virginia is tax-friendly for retirees. It doesn’t tax Social Security benefits, and residents 65 and older can deduct up to $12,000 per person of income from IRAs, pensions and other retirement accounts, subject to income eligibility limits.

Swarthmore College, one of the nation’s leading liberal arts colleges, occupies about a third of the town of the same name, and with more than 4,000 different kinds of plants stretching across 300 acres, it’s also a designated arboretum. The school has long welcomed town residents by making virtually all of its happenings—concerts, lectures, sporting events and more—open to the public. The town itself is walkable, with plenty of sidewalks and more than two dozen lushly forested trails. “You can’t live anywhere in Swarthmore that’s more than a 10-minute walk to town,” says Carrie Piccard, a local real estate agent since 2003. Add in free public transit for seniors, and “having a car just isn’t a necessity,” says mayor Marty Spiegel.

It doesn’t hurt that for all of its small-town charm, Swarthmore is a 20-minute train ride to Philadelphia, where you can take in museums, theater and every kind of cuisine. The train goes to Philly’s 30th Street Station, and from there, New York City and Washington, D.C., are less than two hours away by train (in opposite directions).

Because of its small size, the housing market can be tight, but residents say the situation is improving. Swarthmore’s city government recently lifted a zoning law that prevented more than a few unrelated people from living together in a family home—originally intended to prevent a dozen students from cramming into a house. That spells opportunity for retirees who want to give communal living a go.

Pennsylvania is tax-friendly for retirees. Social Security benefits, retirement plan withdrawals and pensions are exempt from taxes.

Hanover buzzes with a diverse mix of art, culture, and outdoor sporting and recreational activities year-round. Located along the Connecticut River bordering Vermont, the town is home to Dartmouth College. Founded in 1769, it’s the smallest of the eight Ivy League colleges, but it’s big on including all residents, especially active retirees, in its community.

Whether retirees are Dartmouth alums or transplants yearning to spend their retirement years in a bucolic college town, they have numerous opportunities to participate on campus committees, town boards and commissions, often alongside students and college staff. “Getting retirees at the committee level with Dartmouth students on various topics is something you see all the time,” says Julia Griffin, town manager.

“The campus is extremely porous, with no fences or gates to differentiate between what’s on or off campus,” says Julia Griffin, Hanover’stown manager. It’s typical to see retirees mingling with students at the coffee bar in Dartmouth’s Baker-Berry Library or on the Dartmouth Green, the vast quad located at the heart of the campus.

Hanover residents young and old participate in the college’s events and activities, from concerts and performing arts events at the Hopkins Center for the Arts—known as The Hop—to sporting events, especially ice hockey. Yes, hockey—winters are chilly and long. In January, for example, the average high is 28 degrees, with an average snowfall of 17 inches.

New Hampshire residents pay no taxes on Social Security benefits, pensions or distributions from their retirement plans. And there’s no sales tax.

Situated between Chicago’s city limits and its North Shore suburbs, Evanston is best known as the home of Northwestern University, but it’s hardly a simple college town. Whether you’re drawn to its classes, architecture, theater or music, this “City of Churches” is a rich cultural center with plenty to offer retirees.

Evanston is on America’s so-called Third Coast, Lake Michigan. The freshwater behemoth offers excellent views and miles of biking trails along the water and through town. But the cornerstone of Evanston’s retiree appeal is Northwestern itself. The Osher Lifelong Learning Institute—motto: “Curiosity Never Retires”—offers regular lectures, classes and study groups for any retiree looking for a sense of community and vibrant discourse.

Another draw is Evanston’s historic architecture. It received the attention of architectural greats such as Frank Lloyd Wright in the early 20th century, which earned it the moniker “City of Homes.” There are dozens of iconic structures, such as the Charles A. Brown House, dotting neighborhoods across town.

Illinois excludes most retirement income from state taxes, but sales taxes are steep. Property taxes are also high, but there are numerous homestead exemptions for seniors who qualify.

Looking for an active yet funky college town with a bit of southern hospitality? You will feel right at home in Fayetteville. A vibrant, economically and culturally diverse mecca in the Ozarks, Fayetteville attracts a variety of people from around the country, often retirees following their children—mid-career professionals who may work for local Fortune 500 companies such as Walmart, Tyson Foods and JB Hunt Transport Services.

A major driver of the downtown region’s economy is the University of Arkansas. Founded in 1871, U of A’s Fayetteville campus is the flagship of the state university system. Arkansans age 60 and older can enroll in for-credit undergraduate and graduate courses tuition-free (based on space availability).

Social Security benefits aren’t taxed in Arkansas, and up to $6,000 of retirement income, including IRA distributions, is exempt from state income taxes. However, Arkansas imposes a 6.5% sales tax, and localities can add as much as 5.13%. Food is also taxed by the state at 1.5%, and localities can add their own taxes.

At an elevation of 7,000 feet, this mountain town swaddled by sweet-smelling Ponderosa pine trees has plenty to offer retirees by way of outdoor activities, top-tier dining, volunteer opportunities and seasonable weather. Snowbirds, take heed: This is not the sun-bleached Arizona you may be thinking of. Despite its crisp lack of humidity, it regularly receives about 100 inches of snow every winter.

Designated a “Bicycle Friendly Community” by the League of American Bicyclists since 2006, the city offers more than 130 miles of bike lanes and another 56 miles of multi-use “urban trails.” If skiing is your thing, Arizona’s tallest mountains, the San Francisco Peaks, are a 30-minute drive from the city. (If skiing isn’t your thing, take the chairlift for breathtaking views.) The Grand Canyon is roughly 90 minutes north by car. But don’t be fooled by downtown Flagstaff’s sleepy western vibe; it has more than 200 restaurants and award-winning craft beers in abundance along a “brewery trail.”

Northern Arizona University offers events year-round that are open to the public, including free summer seminars, symphony concerts with reduced admission for seniors, and community-welcome events staffed by NAU students for both new and longtime Flagstaff residents. But maybe the most compelling draw to the city can be found in a squat, beige building on Northern Arizona’s campus. Through NAU’s Civic Service Institute, retirees can find volunteering opportunities at any of the dozens of nonprofits that call Flagstaff home—everything from supporting Habitat for Humanity to tutoring elementary students. “A lot of new retirees find that getting involved in this kind of work is a great way to build community and find like-minded people,” says Erin Kruse, the senior program’s project director.

Arizona exempts Social Security benefits from state taxes, along with up to $2,500 in income from military or Arizona state and local pensions. Income from IRAs and other retirement plans is taxable at a top rate of 4.54%.

Claremont has critical college mass with seven colleges that make up The Claremont Colleges: Claremont McKenna College, Claremont Graduate University, Harvey Mudd College, Keck Graduate Institute, Pitzer College, Pomona College and Scripps College. They sponsor innumerable educational, cultural and sporting events. Eight times a year, the colleges publish and distribute a calendar of events open to the public, including live performances, lectures, art shows and more. Most are free or low-cost.

The walkable downtown, known as “the village,” is a major draw, with lots of independently owned businesses, restaurants and a public square where the Claremont Farmers and Artisans Market takes place once a week.

If you want to get outdoors, the city has 23 parks, including the Claremont Hills Wilderness Park. Located at the base of the San Gabriel Mountains and the Angeles National Forest, the wilderness park has plenty of hiking trails. The 86-acre Rancho Santa Ana Botanic Garden is dedicated to native California plants.

Claremont is almost always sunny. It can be hot during the day, especially in the summer. But it’s dry heat, it cools down at night, and it isn’t buggy, says Danielle Fontes, president of the Citrus Valley Asso­ciation of Realtors.

To get out of town without fighting L.A.’s notorious traffic, you can hop on a Metrolink train at the Claremont station. Ontario International Airport is about a 15-minute drive away.

Claremont also has four continuing care retirement communities. The oldest of them, Pilgrim Place, was founded in 1915 to serve missionaries returning from overseas.

California doesn’t tax Social Security, and residents over 65 can claim a tax credit of $118 from state taxes. But other retirement income is taxed at a rate of up to 13.3%.