Where are the best places to live and retire in the United States near a Trader Joe's, airport, university, coast / beach, and Costco? I asked ChatGPT.

Phew! That was one tall order for ChatGPT when I decided to put it to the task. 

The more my little AI sidekick churned through data from across the internet, the more interested I became in tweaking the question based on various factors.

ChatGPT looked at data from Niche.com plus Trader Joe’s’ official store directory, and prioritizde towns by the following factors — which are important for everyone to consider!

1. healthcare access
2. proximity to an airport
3. access to a university, if you enjoy in-person lectures and extension classes or maybe plan to go to college. Plus college towns tend to have vibrant, affordable restaurant and cafe scenes not to mention young people in learning mode.
4. proximity to a Costco — because while you can order many things from Costco online, who doesn't love to get Costco gas, produce, cheeses, free samples, wine, and all the other good stuff we depend on from Costco? Yes, toilet paper!
5. near or on a coast

Weather, political climate and laws, and cost of living did not factor into this query about the best places.

It is very important to research trends in hospital closures and medical facilities opening when deciding where to live.

It is also important to know that despite the "intelligence" of artificial intelligence, this data really depends on what the AI finds online.

Thinking about the San Francisco Bay Area, which checks the boxes of the criteria used for this analysis, I am surprised that the Marina Bay community of Richmond, California did not appear on the list. Marina Bay is by the water, has a ferry to San Francisco, and a range of condos, townhouses and single family houses, many with pools and gyms, just a few  miles from Berkeley and even closer to Costco.

Read my article about Marina Bay and why so many people from the Bay Area downsize to this lovely community. (I have no stake in Marina Bay...just an observation about why this list is preliminary and not conclusive!)

I am more than happy to tailor a search to the perfect places for you based on what it is important to you! Ask for a custom search for the best places to live and retire.

What are the best places to live in the United States or abroad based on what's important to you? Get free ideas from realtor Susie Wyshak and her AI friends.

Interpreting the data...

ChatGPT cited the main sources it used and explained the methodology as well as pointing out the strongest matches (best fit for all four priorities).

Interestingly, at first anyway, while ChatGPT included mileage to Trader Joe's, I knew — having driven many times from places like Camden, Maine to Trader Joe's in Portland, Maine — that 40 miles does not a 40-minute drive make.

So if you are a several time a week Trader Joe's shopper, be sure to check the actual driving time if you're thinking of living in a small coastal town. On the other hand, you might be surprised how close there is a Trader Joe's as they have landed in some locations I never would have imagined. 

Top 25 coastal small towns (prioritized for healthcare, airport, university, Costco — with Trader Joe’s nearby)

The AI tool grouped towns into Top Matches (strong on all 4 priorities), Very Good Matches (strong on most priorities), and Good Matches (retirement-appeal + TJ’s plausible but one priority weaker). After the list I add 2–3 example citations for representative towns.

Note from Susie: Why coastal areas outside of Portland, Oregon, Portland, Maine, and in Washington state did not appear on the list are a mystery to me. There are so many places that I would consider livability whether retiring or not. 

This post is also interesting in how it shows that numbers do not always tell the story. It's important to talk to (human) locals and also tap into community forums. (Sites like Reddit are anonymous so in my opinion, opinions should be taken with  grain of salt since you don't really know who's raving about or criticizing a place. The latter could be a real estate investor hoping values go down so they can scoop up property!)

Top Matches — Best fit across all 4 priorities

#CaliforniaLove

1. Santa Barbara, CA (and nearby small towns: Carpinteria / Summerland) — excellent hospitals, SB airport (SBA), UC Santa Barbara nearby (in Goleta), multiple Trader Joe’s and Costco in the metro area. (Trader Joe's Store Directory)

2. Pismo Beach / Avila Beach / Grover Beach, CA — SLO County has strong healthcare (French Hospital in SLO), SLO airport (SBP) / San Luis Obispo area, Cal Poly (San Luis Obispo) within easy drive, Trader Joe’s in San Luis Obispo. (Niche lists Pismo/Avila/Cambria among the best places to retire in SLO County.) (Niche)

3. Carmel-by-the-Sea / Monterey / Pacific Grove, CA — good regional hospitals (Salinas/Monterey), Monterey Regional Airport (MRY), CSU Monterey Bay / nearby universities, Trader Joe’s in Monterey/Salinas area. (Trader Joe's Store Directory)

4. Laguna Beach / Dana Point, CA — Irvine / Orange County medical centers nearby, John Wayne Airport (SNA) close, UC Irvine a short drive, Trader Joe’s & Costco in nearby Laguna Niguel / Irvine. (Trader Joe's Store Directory)

5. Encinitas / La Jolla / Del Mar (North San Diego coast), CA — excellent hospitals (Scripps/UCSD), San Diego International (SAN), UC San Diego nearby, Trader Joe’s & Costco in north San Diego county. (Trader Joe's Store Directory)

While deciding where to live based on Trader Joe's may seem silly, if you are a huge fan it's important to think about if you will miss not being close to a store. You've probably heard stories of people begging their friends to transport Trader Joe's food to them when visiting.

Very Good Matches — strong on most priorities

Note from Susie: Many part of Florida have become strong buyers' markets in 2025 for various reasons. If you would consider moving there, here are a few places ChatGPT came up with. I know some great realtors that focus in each of these areas. Get in touch if you would like some connections to get further advice from local experts.

6. Siesta Key / Sarasota, FL — Sarasota Memorial Hospital (regional hub), Sarasota Bradenton Int’l Airport (SRQ), University of South Florida Sarasota-Manatee nearby and University of South Florida (Tampa) within reach, TJ’s & Costco in Sarasota area. Niche ranks Siesta Key highly for retirees. (Niche)

7. St. Pete Beach / Redington Beach / Madeira Beach, FL (Tampa Bay area) — strong healthcare (Bayfront Health/St. Pete), St. Pete–Clearwater Int’l (PIE) / Tampa Int’l (TPA), University of South Florida (Tampa) / USF St. Petersburg campus, Trader Joe’s & Costco in Tampa/St. Pete metro. (Niche)

8. Highland Beach / Boca Raton area, FL — Boca Raton Regional and Palm Beach hospitals nearby, PBI/FLL airports within drive, FAU (Florida Atlantic University) in Boca Raton, Trader Joe’s & Costco in Boca/Delray. (High Niche retirement ranking.) (Niche)

9. Naples, FL — good regional healthcare (NCH - multiple campuses), Naples Airport + RSW (RSW in Fort Myers) nearby, Florida Gulf Coast University (FGCU) in Fort Myers a drive away, TJ’s & Costco in Naples / North Naples. (Trader Joe's Store Directory)

10. Milford, CT (Connecticut shore) — Niche-noted for retirees and coastal lifestyle, Yale-New Haven Hospital / Bridgeport hospitals within a reasonable drive, Bradley/Bradley Field and TF Green farther but New Haven is well-connected, Trader Joe’s in New Haven area, Costco locations in the region. (Niche)

Good Matches — retirement appeal + TJ’s nearby but one or two priorities may be weaker

11. Cape Cod area (Falmouth / Hyannis / Chatham), MA — Cape Cod Hospital (Hyannis), Barnstable Municipal Airport, UMass Dartmouth / local community colleges, Trader Joe’s in Hyannis / Barnstable; Costco in nearby Hyannis/Falmouth area. (Some towns are seasonal; healthcare access concentrated in Hyannis.) (Trader Joe's Store Directory)
    Note from Susie: The markets outside of Boston have become really hot. You can see why, with all of the areas that come up on this list.

12. Cayucos / Cambria / Morro Bay, CA — beautiful SLO coastal towns; healthcare & TJ’s centralized in San Luis Obispo but within reasonable drives; airports and universities (Cal Poly San Luis Obisbo) reachable. (Niche) 
    
    Note from Susie: My friend moved to Arroyo Grande ("AG") and really loves it. Both Cayucos (which has my beloved Brown Butter Cookie Company) and Cambria are more coastal and smaller-feeling communities than AG and Morro Bay which are pretty close to SLO. 

13. Santa Cruz area towns (Capitola / Santa Cruz) — Dominican / Watsonville hospitals nearby, San Jose / Santa Cruz metro airports, CSU Monterey Bay / UC Santa Cruz access, TJ’s and Costco in Santa Cruz / Capitola area. (Trader Joe's Store Directory)
    
    Note from Susie: I love the Santa Cruz area! The coast is beautiful there which explains why real estate has skyrocketed in lockstep with the tech industry, which is just over the hill.

14. Newport, RI / Narragansett / Jamestown — good hospitals in Newport/Providence, T.F. Green in Providence, Roger Williams University in nearby Bristol/Providence region, Trader Joe’s in Providence area, Costco within the metro. (Trader Joe's Store Directory)

15. Old Saybrook / Mystic / Westbrook, CT — Connecticut shore small towns with Yale/Connecticut hospitals within driving range, TF Green/Boston accessible, Trader Joe’s & Costco in New London/Providence/Bridgeport corridors. (Niche)

16. Provincetown / Wellfleet (Cape Cod), MA — great coastal lifestyle, healthcare concentrated in Provincetown/Hyannis, TJ’s presence is in larger Cape towns; Costco & airport access via Hyannis. (Trader Joe's Store Directory)
    
    Note from Susie: These towns are SO on my "to visit" list. If you are interested in these coveted and beloved destinations, I know a great real estate agent who lives and focuses in this area. 

17. Portsmouth, NH (coastal NH / nearby small towns) — Portsmouth Regional Hospital, Manchester–Boston Regional (MHT) and Logan (BOS) reachable, University of New Hampshire in Durham nearby, Trader Joe’s in Portsmouth area. (Trader Joe's Store Directory)
    
    Note from Susie: I spent the summer in the Portsmouth area. It's one of my favorite cities in the U.S. with beautiful water views, charming brick-lined streets and lots of tax-free shopping along with fantastic dining. Boston is about an hour away, and there are some great towns within 30 minutes of Portsmouth with more affordable real estate. Kittery and Maine are walkable from Portsmouth. 

Ask me about Portsmouth, New Hampshire and Kittery, Maine. This is a view in December. Chilly yet so beautiful! (Photo by Susie Wyshak)

11. Saugatuck / South Haven / New Buffalo area (Lake Michigan coast, MI) — strong small-town appeal, hospitals in nearby Holland / St. Joseph, Detroit/Chicago airports are regional; Trader Joe’s in the region (Holland/Grand Rapids/Chicago corridor) — good for Midwest retirees wanting lakeshore + grocery access. (Trader Joe's Store Directory)

12. Rehoboth Beach / Lewes, DE — Beebe Healthcare (Lewes/Rehoboth), Salisbury/Ocean City hospitals nearby, Salisbury–Ocean City (SBY) airport regional, University of Delaware (Newark) a drive away, Trader Joe’s in nearby larger Delaware/Maryland towns. (Trader Joe's Store Directory)

13. Wrightsville Beach / Carolina Beach / Kure Beach (Cape Fear coast), NC — New Hanover Regional Medical Center (Wilmington), Wilmington Int’l Airport (ILM), UNC Wilmington nearby, Trader Joe’s in Wilmington area; Costco in Wilmington. (Trader Joe's Store Directory)

Additional coastal towns that often rank well for retirees and have TJ’s nearby

• Monterey / Carmel Valley — (if you prefer Carmel-by-the-Sea as a separate entry from Monterey). (Trader Joe's Store Directory)

• Carlsbad / Encinitas (further North San Diego coast) — excellent healthcare (Scripps), McClellan–Palomar & SAN airports, Cal State San Marcos / CSUSM nearby, TJ’s & Costco in Carlsbad area. (Trader Joe's Store Directory)
  
  Note from Susie: These towns on the coast near San Diego define California Dreaming. 

• Sanibel / Fort Myers Beach, FL — good hospitals in Fort Myers (Golisano Children’s/Lee Health), RSW airport, FGCU nearby, Trader Joe’s & Costco in Fort Myers/Naples area. (Trader Joe's Store Directory)

• Rehoboth / Dewey Beach (Delaware) — repeat region entry — (good small-town beaches, smaller hospitals nearby but good metro access). (Trader Joe's Store Directory)

• Milford / Stratford / Westport (CT coast cluster) — strong Niche retire ratings (Milford specifically highlighted), TJ’s & Costco in regional corridor, Yale-New Haven and Bridgeport hospitals nearby. (Niche)

Also noted...

• Pismo Beach / San Luis Obispo County — Niche lists Avila, Pismo, Cambria, Cayucos as “best places to retire” in SLO County; French Hospital Medical Center (San Luis Obispo) is the regional hospital serving these towns, and Trader Joe’s has a San Luis Obispo store. This makes Pismo/Avila a strong match for retirees who want coastal charm + healthcare + nearby university (Cal Poly) + TJ’s. (Niche)

• Siesta Key / Sarasota — Niche ranks Siesta Key highly for retirees; Sarasota Memorial Hospital is the major healthcare hub, SRQ airport serves the area, and Trader Joe’s + Costco have locations in the Sarasota metro. This alignment makes Siesta Key a top Florida pick. (Niche)

• Santa Barbara / Carpinteria — California has dense TJ coverage and Niche shows strong retiree appeal for Santa Barbara area towns; University of California Santa Barbara, multiple hospitals, SBA airport, Trader Joe’s and Costco are all within the metro region. (Trader Joe's Store Directory)
  
  Note from Susie: If you said "I'm giving you a house wherever you want, Susie" Santa Barbara would be at the top of my list. It really checks all the boxes. Nearby Montecito is a haven for the "rich and famous" while Oxnard and other nearby cities are also great options for living the dream. Speaking of living the dream, Oxnard has the only Costco I've seen that has a car wash!

AARP Livable Cities check for the 25 towns

ChatGPT checked all 25 towns againstAARP’s public Livability resources. Almost every town has an AARP Local page (AARP publishes local events/resources). Fewer towns are listed as formal LivableMap members / Community Challenge grantees (those that are appear on the LivableMap member pages). Where you want the towns flagged as formally designated / on the LivableMap, I’ve marked the ones I could confirm in the table above.

• AARP Local pages: Almost all 25 towns have an AARP Local page (events/resources) — i.e., AARP publishes local content for these places. Examples: Santa Barbara, Pismo Beach, Carmel, Encinitas, Siesta Key, St. Pete Beach, Milford, Hyannis, Cambria, Capitola, Newport, Old Saybrook, Provincetown, Portsmouth, Rehoboth Beach, Wrightsville Beach, Monterey, Carlsbad, Sanibel, Dewey Beach. (AARP Local)

• AARP LivableMap member/grantee (“official” AARP Livable Communities listing): Only a subset show up on the LivableMap public member/grantee listings or county-level pages (examples: Encinitas and Carlsbad are explicitly shown on California’s LivableMap member list; Barnstable (Hyannis/Cape Cod) and Santa Cruz show AARP Community Challenge/grantee activity; Sarasota County / St. Petersburg appear on Florida/state pages). Many towns have AARP local activity but do not appear as a separate LivableMap “member” page in the public directory. (livablemap.aarp.org)

I hate to be "that Califorian" but the ranking makes me proud. (That comment is from Susie, not ChatGPT) 🙂

Chat GPT's sources / methodology for the rankings

Here's what ChatGPT did to arrive at this data:

• Started from Niche.com retirement rankings (national + county-level lists for coastal counties) to get towns with proven retirement appeal. (Niche)

• Cerified Trader Joe’s coverage using Trader Joe’s official store directory / locator pages. (This is the canonical TJ’s source I used to confirm if a TJ’s is in or very near the town/state.) (Trader Joe's Store Directory)

• For the healthcare priority, sampled local major hospitals (example: French Hospital Medical Center for San Luis Obispo / Pismo Beach area) to show what defines “good healthcare access.” (Dignity Health)  Note from Susie: Medicare is changing in 2026 and beyond. There are important changes coming to some states with experiments in decisions on care. Be sure to research every state you might be considering moving to if you depend on Medicare or plan to.

ChatGPT offered the following notes / caveats: “Within 10 miles” is treated as approximate; for many small coastal towns the nearest TJ’s is in the closest larger nearby town (often within 10 miles in high-density TJ states like CA and FL, sometimes >10 in more rural states). If you want exact mileages and driving times for any subset, I can compute them immediately and show store/hospital/airport/Costco addresses.

What are the best places to live in the United States or abroad based on what's important to you? Get free ideas from realtor Susie Wyshak and her AI friends.