There are two things I love and that is traveling and living in what I consider a “lifestyle” town or city. Of course where you live or what you do doesn’t guarantee happiness, but all else equal, living in a nice town and being able to easily travel is a real perk. My love of travel prompted this article on the 25 best small to mid-sized towns for traveling.
The requirements were that the town be relatively close to an airport and that the town itself be walkable and offer all the amenities one needs for meeting the necessities of life (i.e. healthcare, groceries, dining out, culture, etc.). Here’s the list and when possible, I chose an aerial photo just because I love aerial photos lol.
25. Naples, Florida
Naples is a paradise for retirees who crave luxury living with a laid-back vibe. The town’s pristine beaches and elegant shopping make it a top choice for those who want the best of both worlds.
Its charming, walkable downtown brims with art galleries, high-end restaurants, and cultural events, offering plenty of activities within a short stroll. With excellent healthcare facilities and a strong community of like-minded retirees, it’s easy to settle in. Even better, Southwest Florida International Airport (RSW) is just 30 miles away, making global travel a snap for those who love to jet off at a moment’s notice.
24. Asheville, North Carolina
Asheville brings together a rich arts scene, farm-to-table dining, and the stunning Blue Ridge Mountains, making it a haven for retirees who want beauty and culture in equal measure. The walkable downtown is lined with galleries, breweries, and quirky shops, perfect for a day out on foot.
Healthcare here is first-class, with major hospitals nearby. For travel, Asheville Regional Airport (AVL) is just 16 miles away, with easy connections to Hartsfield-Jackson Atlanta International Airport for quick access to international flights.
23. Boulder, Colorado
Boulder offers an unbeatable mix of small-town charm and access to the outdoors. With its walkable downtown, renowned for its eco-friendly ethos, retirees can enjoy a healthy, active lifestyle—whether it’s hiking the Flatirons or sipping coffee in one of the town’s many cafes.
The city is home to excellent healthcare and is a hub of intellectual energy thanks to the University of Colorado. Denver International Airport (DEN), just 44 miles away, is one of the busiest and best-connected airports in the world, perfect for retirees who want easy access to international travel.
22. Carmel-by-the-Sea, California
This stunning coastal town feels like something out of a storybook. Carmel’s ocean views, Mediterranean climate, and artistic atmosphere draw retirees looking for tranquility with a side of culture. Its walkable streets are filled with boutique shops, art galleries, and cozy restaurants, perfect for slow, scenic strolls.
Healthcare in nearby Monterey is solid, and you’re only 7 miles from Monterey Regional Airport (MRY), which offers easy connections to San Francisco International Airport for global travel when you want to trade the coast for more distant shores.
21. Sedona, Arizona
Known for its dramatic red rock landscapes and spiritual vibe, Sedona is perfect for retirees who want peace, beauty, and wellness. The town is small and walkable, with art galleries, new age shops, and healthy eateries dotting the streets.
With top-tier hiking and wellness retreats nearby, retirees can stay active and relaxed. While healthcare is solid in Sedona, major services are a short drive away. When it’s time to travel, Phoenix Sky Harbor International Airport (PHX) is about 120 miles down the road, offering access to international destinations in no time.
20. Traverse City, Michigan
Traverse City combines lakeside living with small-town charm, offering retirees the best of both worlds. Its downtown area is walkable, full of cozy cafes, breweries, and local shops, making it easy to enjoy the slower pace of life.
Lake Michigan’s stunning shoreline provides plenty of opportunities for outdoor activities. The town has excellent healthcare facilities, and Cherry Capital Airport (TVC), just 4 miles away, connects to major hubs like Chicago O’Hare, giving you the flexibility to travel internationally without hassle.
19. St. Simons Island, Georgia
St. Simons Island offers a mix of coastal beauty and Southern hospitality, ideal for retirees looking to slow down in style. The island’s quaint downtown area is highly walkable, filled with unique shops, historic sites, and plenty of outdoor activities.
It’s easy to get around by foot or bike, and the close-knit community makes settling in a breeze. Healthcare is top-notch, and Jacksonville International Airport (JAX), 70 miles away, provides easy access to international flights, keeping the world within reach.
18. Greenville, South Carolina
With its revitalized downtown, Greenville has become one of the most attractive small towns for retirees in recent years. The town’s walkable streets are lined with parks, shops, and restaurants, making it easy to get around without a car.
There’s also plenty of art and culture, with museums, galleries, and theaters to explore. Healthcare here is excellent, and the Greenville-Spartanburg International Airport (GSP), just 14 miles away, makes it simple to hop on a flight to international destinations.
17. Sarasota, Florida
Sarasota is the perfect blend of artsy culture and beachside living. Retirees flock here for the white sand beaches and the array of cultural venues, including theaters, opera houses, and art galleries.
The town’s walkability is a major plus, with downtown Sarasota offering plenty of opportunities to stroll to local cafes, parks, and shops. Healthcare is top-tier here, making it a great place for retirees. For frequent travelers, Sarasota-Bradenton International Airport (SRQ) is only 6 miles away, offering a quick escape to global adventures.
16. Santa Fe, New Mexico
Santa Fe’s historic charm, coupled with its laid-back lifestyle, makes it a standout destination for retirees. The town’s unique adobe architecture, thriving arts scene, and vibrant food culture ensure there’s always something interesting happening.
Santa Fe is highly walkable, especially around its Plaza, where retirees can explore galleries and local markets. Healthcare is strong here, and Albuquerque International Sunport is just 60 miles away, offering a direct link to the world.
15. Bend, Oregon
For the retiree who craves outdoor adventure, Bend is an ideal choice. Nestled in the Cascade Mountains, this town offers endless opportunities for hiking, fishing, and skiing, all within a short distance. Downtown Bend is small but highly walkable, filled with cafes, breweries, and boutique shops.
The healthcare system is excellent, catering well to its growing retiree population. Redmond Municipal Airport (RDM), only 18 miles away, provides easy connections to larger international airports, ensuring travel remains convenient.
14. Flagstaff, Arizona
Flagstaff offers retirees a cool mountain retreat, complete with access to the Grand Canyon and other natural wonders. This small town’s walkable downtown is charming, with historic sites, art galleries, and plenty of local eateries to explore.
The healthcare options here are top-notch, with Flagstaff Medical Center providing excellent care. Phoenix Sky Harbor International Airport is about 150 miles away, making global travel accessible, especially for those who enjoy scenic road trips before taking off.
13. Palm Springs, California
Palm Springs is a classic destination for retirees, offering warm weather, a mid-century modern vibe, and stunning desert landscapes. The town is exceptionally walkable, with plenty of high-end shops, restaurants, and galleries to explore. Healthcare is excellent, with top-rated hospitals nearby.
Palm Springs International Airport (PSP), just 2 miles from downtown, makes it easy to stay connected to the rest of the world, allowing retirees to travel internationally without the hassle of long drives to an airport.
12. Burlington, Vermont
Burlington is a charming lakeside town that offers a relaxed yet vibrant lifestyle for retirees. Nestled on the shores of Lake Champlain, its walkable downtown features local boutiques, cozy cafes, and a thriving arts scene.
The town is perfect for nature lovers who enjoy hiking, boating, or simply taking in the picturesque views. Burlington is known for its excellent healthcare, and for those with wanderlust, Burlington International Airport (BTV) is just 3 miles away, providing convenient access to major international hubs.
11. Galveston, Texas
Galveston offers retirees a unique combination of history, culture, and beachside living. Known for its Victorian architecture and walkable Strand Historic District, Galveston has plenty of activities, from museums to live music and seafood restaurants.
With healthcare services in the area and a mild climate, it’s a top choice for those looking for a vibrant yet relaxed lifestyle. William P. Hobby Airport (HOU) is just 40 miles away, offering excellent connections for international travel, especially via Houston’s George Bush Intercontinental Airport.
10. Hilton Head, South Carolina
Famous for its pristine beaches and world-class golf courses, Hilton Head is a dream retirement spot for those who love the outdoors. The island’s network of walking and biking paths makes it easy to get around without a car, while its vibrant community offers plenty of activities from boating to dining in waterfront restaurants.
Healthcare is readily available on the island, and Savannah/Hilton Head International Airport (SAV), just 40 miles away, makes traveling to global destinations seamless.
9. Williamsburg, Virginia
Williamsburg blends small-town charm with a rich historical backdrop, offering retirees a peaceful and cultured lifestyle. The colonial-era architecture and beautiful walking paths give the town a storybook feel.
It’s easy to explore on foot, and retirees can enjoy museums, performances, and a strong sense of community. Williamsburg has top-tier healthcare options, and Newport News/Williamsburg International Airport (PHF) is just 20 miles away, providing quick access to major international connections.
8. Charlottesville, Virginia
Charlottesville offers retirees a vibrant mix of history, education, and natural beauty. Located in the foothills of the Blue Ridge Mountains, this walkable town has a thriving downtown, home to unique shops, restaurants, and live music venues.
Its proximity to the University of Virginia ensures excellent healthcare and plenty of cultural events. For international travel, Washington Dulles International Airport (IAD) is 100 miles away, making it easy to plan trips abroad while living in a peaceful, scenic setting.
7. Fort Collins, Colorado
Fort Collins is known for its friendly, laid-back atmosphere and beautiful surroundings. Retirees love the highly walkable downtown, filled with craft breweries, farm-to-table restaurants, and cultural events.
With nearby Rocky Mountain National Park, there’s no shortage of outdoor activities. Healthcare services in Fort Collins are top-notch, and Denver International Airport (DEN), about 70 miles away, provides a convenient gateway to international travel.
6. Savannah, Georgia
Savannah’s charming cobblestone streets, oak-lined squares, and historic architecture make it one of the most picturesque towns in the U.S. Retirees can stroll through its walkable historic district, enjoy the vibrant arts scene, and dine in exceptional restaurants.
Savannah is also known for its healthcare services, and with Savannah/Hilton Head International Airport (SAV) just 10 miles from downtown, traveling abroad is easy and convenient.
5. Charleston, South Carolina
With its stunning historic homes, walkable waterfront, and renowned food scene, Charleston offers retirees a mix of Southern charm and vibrant city life.
The town’s tight-knit community and rich cultural offerings make it a popular spot for retirees. Charleston’s healthcare is excellent, and Charleston International Airport (CHS) is only 12 miles away, offering easy access to international flights.
4. Boise, Idaho
Boise is an emerging retirement destination, offering a mix of urban sophistication and outdoor adventure. The downtown area is highly walkable, with plenty of parks, coffee shops, and cultural activities, all set against the backdrop of the Boise River.
Retirees enjoy a thriving arts scene, affordable living, and excellent healthcare. Boise Airport (BOI), located just 4 miles from downtown, offers convenient access to international travel via connections to major hubs.
3. Santa Barbara, California
Santa Barbara’s Mediterranean climate, stunning coastline, and walkable downtown make it a prime retirement spot for those seeking beauty and culture. Retirees can enjoy wine tasting, art galleries, and year-round outdoor activities like hiking and beachcombing.
With excellent healthcare facilities and easy access to Los Angeles International Airport (LAX), just 90 miles away, Santa Barbara combines the best of small-town living with global travel opportunities.
2. Madison, Wisconsin
Madison offers a vibrant, intellectually stimulating environment for retirees, thanks to its university presence and lively arts scene.
The town’s walkable downtown, surrounded by lakes, offers plenty of outdoor activities, from biking to sailing. Healthcare services are world-class, and with Dane County Regional Airport (MSN) just 5 miles away, retirees can travel internationally with ease via connecting hubs.
1. Portland, Maine
Portland is the perfect blend of New England charm and coastal living, making it a top choice for retirees. Its historic Old Port district is highly walkable, filled with quaint shops, seafood restaurants, and galleries.
Retirees can enjoy the vibrant arts scene and easy access to outdoor adventures along the rugged Maine coastline. Portland International Jetport (PWM) is just 3 miles away, providing convenient access to international travel via connections to major airports, making this scenic, friendly town a great spot for retirees who love to explore the world.
