Best Places to Retire

Best Places to RetireWhat are some of the best places to retire? I don’t know if we’ll move from our current location (#RVA) when we retire, but just in case I’m creating a running list of the best places to retire. The list is based on several factors. One factor important to us is the cost of living for retirees, such as taxes in retirement.

First, the big question: Where do I want to live?

We plan to downsize within the next few years. Our current home has way more space than we need (~3,500 sq. ft.) and far too much maintenance for our anticipated lifestyle in retirement.

What are we considering with respect to a move?

  • A place that’s stimulating with nearby access to cultural activities
  • Club house, community center, and/or a university nearby
  • Coffee shops, restaurants, and fitness facility within walking distance
  • Access to excellent health care
  • Active, engaging community with walking paths near or on the water (i.e., lake, ocean, canals, etc.)
  • Lower than average cost of living for retirees
  • Smaller home with low maintenance
  • Mild climate
  • Above average energy efficient home with modern amenities (i.e., solar power, smart home, etc.)

Best Places to Retire

So, you followed the SMART Path to Financial Independence and now you are ready to move. Some of us boomers will find a retirement community, some will  downsize or up-size to make room for grand kids, and others may rent. With so many options, we need to create at least two lists. One, the criteria and desired amenities, such as active retirement community, great walking/biking paths, social activities, pet friendly, scenic view/water view, club house or activity center and so on. The second list includes the possible locations.

The amenities offered by each location will help us create a wish list based on the available options. A pet friendly, active retirement community is high on our list for sure.

The retirement areas are based on reading articles about the Best Places to Retire and republishing those that look interesting. On another note, I’m adding active retirement communities to the list on a regular basis.



I’m a fan of Florida for retirement, but how much will it cost to retire in Florida? According to, This Is What a Comfortable Retirement Will Cost You in Every State, you need at least $1,224,926 to retire comfortably in Florida. The annual cost of living in Florida is ~$49,000 and a few of the cheapest places to retire are located in Florida. Another article on the same website suggests the cost in Florida is about $1,000 per month more for a comfortable retirement!

“A comfortable retirement costs $61,246.30 a year in Florida.” Although Florida is NOT among the states where a comfortable retirement costs the least, there is no income tax in Florida and healthcare costs are a little below average. Other expenses are in line with national averages. A comfortable 20-year retirement in Florida might cost you around $1,225,000. [2019 stats]


We currently live in Virginia. How much do we need to retire in Virginia? According to the article mentioned above, we’ll need at least $1,265,000 to retire in Virginia. Housing costs average ~$18,600 per year and healthcare is around $6,700. All added up, annual expenses average $50,600; that seems to be a low estimate to me. And, another retirement cost article claims it is a bit more to live in Virginia during retirement.

A comfortable retirement costs ~$63,200 a year in Virginia. Virginia has an overall consumption index 2% above the national average, but transportation costs in Virginia are the second-lowest in the nation; $6,717 per year. Other costs all run above average. It is estimated you’ll need slightly more than $63,000 in annual retirement income, or ~$1,264,000 in savings to cover expenses for 20 years of retirement in Virginia. [2019 stats]


[AUGUST 2019]
Population: 18,656 | Cost of living: 98.2
Median home price: $230,000
Median condo/townhome price: $172,500
Share of population 65+: 55.3%

Historically, Punta Gorda appeals to retired folks; a majority of its population is 65 plus. Why? There are 55 miles of canal-front homes as well as numerous retirement communities that are restricted to people age 55 and older. Lots of golfing, a Fishermen’s Village waterfront complex with 30 shops and restaurants. Also, the Harborwalk along Charlotte Harbor is just a portion of the 18 miles of bike trails and pedestrian pathways you can enjoy.
(Source: 7 Great Places to Retire in Florida, August 2019)

Shared Use Paths: Running south from Linear Park at Shreve Street the Punta Gorda Pathways connects the heart of the city to neighborhoods to the south.  At the southern end of Shreve Street the path joins Tamiami Trail (US 41) and continues south for four more miles.

The Fitness Zone(s) at Linear Park  are located between W. Retta Esplanade and W. Olympia Avenue.  There are three (3) outdoor gym areas that contain multiple pieces of adult fitness equipment (17 total pieces) with activities designed to target the upper body, core, lower body and the cardiovascular system and is safe for use for persons 14 years of age and older, regardless of ability.

Been there and I like it! Nice place . . . .

There are 42 miles of sand on St. John’s Atlantic coast; something for everyone. St. Augustine Beach is located 10 minutes from downtown. The downtown area includes laid-back restaurants, plenty of fresh seafood, and retired folks in flip-flops.

“Oceanfront condos with pools in St. Augustine Beach run about $500,000, compared with $1 million or more in Miami or Fort Lauderdale, she says. She recently showed a 2,222-square-foot, four-bedroom, three-bath house in nearby South Ponte Vedra Beach for $520,000. Residents can walk through a tunnel under the adjacent highway straight onto the beach.” (Source: July 2019: St. Augustine, Fla.: A Smart Place to Retire).

Port St. Lucie, Florida [Oct. 2019]

Population: 454,482
Share of population age 60+: 32%
Median monthly mortgage cost: $1,392
Median monthly rent: $1,074

Located on the Atlantic coast, Port St. Lucie includes a reasonable cost of living; high marks for desirability and scores well on the happiness metric (Gallup survey). Ocean beaches, freshwater marshes (Savannas Preserve State Park), boardwalk trails (Hillmoor Lake Park), NY Mets spring training (First Data Field). (Source: Best Places to Retire in 2020, Oct. 2019 article). The Top 10 Best Places to Retire according to the article; 4 of the 10 are in Florida:

  • Fort Myers, Florida
  • Sarasota, Florida
  • Lancaster, Pennsylvania
  • Asheville, North Carolina
  • Port St. Lucie, Florida
  • Jacksonville, Florida
  • Winston-Salem, North Carolina
  • Nashville, Tennessee
  • Grand Rapids, Michigan
  • Dallas-Fort Worth, Texas


No state income tax, great weather and beaches, more than 50 parks; Coral Springs. Less than 30-minutes from Boca Raton and Fort Lauderdale, considered “one of the safest” nationwide, according to


(Source: 50 Great Places for Early Retirement in the U.S., June 2019)

RETIRED COST OF LIVING: 9.3% below national average
MEDIAN INCOME, AGE 45 TO 64: $68,759

You can find plenty of great places to retire in Florida, as the scores of resident retirees can tell you. But this area ranked best with us for young retirees, driven mainly by its particularly affordable living costs and younger-skewing population. Tampa is actually one of three major cities that make up the Tampa Bay area, which also includes St. Petersburg and Clearwater. The latter tends to be the most popular among seniors, with seniors making up 21.4% of the population, compared with just 17.7% in St. Petersburg and 12.2% in Tampa.


Loretto, Florida
(Less than 20 miles south of Jacksonville)
City’s median listing price: $210,000
Neighborhood’s median listing price: $185,000

Bayside West, Florida
(Within the city limits of Tampa)
City’s median listing price: $309,900
Neighborhood’s median listing price: $233,900

SOURCE: CNBC 10 Best Neighborhoods for Retirement (December 2018)

Happiest Places to Retire (U.S. 2019)

Charleston, S.C. 

COST OF LIVING FOR RETIREES: 2.1% above the national average

City living with Southern charm and a rich history. Plenty of nearby beaches and the Preservation Society of Charleston is the oldest community-based historic preservation group in the country. Charleston’s cobblestone streets feature numerous restaurants. Activities readily available include: surfing, paddle boarding and kayaking, as well as boating and fishing.

Charlottesville, VA

COST OF LIVING FOR RETIREES: 0.2% below the national average

Thomas Jefferson laid the foundation for the well-rounded city. University of Virginia, artists on the downtown promenade, the Charlottesville community is a blend of Southern charm and liberal edge. You’ll find plenty of options for outdoor recreation: the Blue Ridge Mountains and more than 100 miles of the Appalachian Trail in nearby Shenandoah National Park.

SOURCE: Happiest Places to Retire in the U.S. 2019

Retirement Communities to Consider:

The Villages Florida – Prices begin around $115,000 and go up to over $1 million. Stay active during retirement, big focus seems to be health and wellness: softball fields, polo grounds, golf, exercise classes, etc. Article: Retiring in These Luxe Communities Carries a Steep Price

Sawgrass Villa, Florida – Sawgrass Villa Country Club, retirement community mentioned on HGTV lottery show.

Tips for Retiring in Florida


  • Determine the insurability of the house you want to buy, before buying it! Annual premiums can be several thousand dollars more than you were expecting to pay.
  • The risk of hurricanes makes insuring your home in Florida complex and expensive. Expect to pay a higher deductible for hurricane damage; generally, 2% or 5% of your coverage amount for damages caused by a hurricane. Keep enough money in your emergency fund to cover this potential expense if you retire in Florida.
  • Wind Mitigation Inspection (before buying a home): There are special construction features that help a home withstand high winds. The cost to insure a home without wind mitigation features might be four times higher than a home with wind mitigation. (SOURCE: Ten Things You Must Know Before Retiring to Florida)

Best Places to Retire Articles

States That Don’t Tax Social Security Benefits (includes Florida, Georgia, Virginia, etc.)

State-by-State Guide to Taxes on Retirees – Kiplinger article