Hawaii's Best Small Town For Retirement
Long admired for its stunning scenery, warm, dry, sunny climate, and abundance of social and recreational activities, Wailea stands out as one of the nation鈥檚 premier retirement destinations. Nested on the leeward (dry) side of Maui, the topography is marked by gentle rolling hills that slope towards the Pacific Ocean. The region is lush and tropical, with volcanic rock formations and pristine sandy beaches. The dormant Haleakal膩 volcano makes for a dramatic backdrop. Wailea lies along the sun-kissed southwestern coast of Maui and offers residents and visitors upscale amenities, a rich cultural heritage, and all the modern conveniences seniors are looking for.
Wailea's Heritage
Wailea鈥檚 roots are deep, back to ancient times, when the now famous sweet potato farms graced the hillsides, and the fishermen dominated the shores. Later, in the 19th century, cattle farming became the main industry until the Second 海角社区 War, when the U.S. Marine Corps used the beachfront as a training ground. The latter half of the 20th century gave rise to growing American incomes and demand for travel. It did not take developers long to see the potential of turning Wailea into a luxurious resort destination. Today, tourism remains Wailea鈥檚 primary industry, and the region hosts some of the finest resorts on the island, such as the Four Seasons, the Fairmont Kea Lani, and the Grand Wailea.
Top Retirement Destination
There is a lot for one to consider when selecting the right retirement destination. Issues like overall quality of life, access to top-notch medical care, affordability, safety, convenience, culture, and activities are among the top concerns for many seniors. In 2024, niche.com ranked Wailea as the best place to retire in Hawaii. According to U.S. News, Maui is ranked among the top five best U.S. travel destinations and the top contenders globally. U.S.A. Today reports that Hawaii has the longest life expectancy of all 50 states. One can鈥檛 put a price on that.
Cost-of-living
Speaking of money, is Wailea affordable for retirees? The median home value in Maui County is a staggering $1,053,401 as of February 2025. Compared to the state average of $843,185, retirees will be paying 20% more to buy a home here. Thus, Wailea is not the least expensive place to retire; however, there are additional factors to ponder. Hawaii offers some money-saving incentives that have attracted silver hairs, such as limited taxation of retirement income and property tax exemptions for seniors. There is an argument to be made that Wailea is simply good for the soul.
The temperatures average in the mid-to-upper 70s throughout the year, there is little rainfall, and the island is home to 30 miles of golden, white, black, and green sandy beaches. Seniors need not struggle with winters full of backbreaking snow shoveling or cold weather causing flare-ups of achy arthritic bones. The mild climate further grants residents outdoor living options that few places can match, and many homes feature a lanai (covered outdoor space) that can maximize the livability of smaller homes and condos. There is a reason over 35% of Wailea鈥檚 population is 65 years and older. They can鈥檛 all be wrong.
On the other hand, if you鈥檙e willing to live nearby, Roselani Palace in Kahului is just half an hour away. This assisted living facility is a non-profit venture offering an affordable living alternative for seniors. It offers various living options, including independent living, assisted living, and memory care. Moreover, residents will enjoy 24-hour medical care, fitness classes, community events, and meal support.
Landmarks & Attractions
The historic landmarks and commercial attractions are plentiful. The Wailea Beach Path is a 1.5-mile paved walkway along the coastline with a spectacular view of the Pacific. The path is level and accessible for most levels of mobility. The Wailea Old Blue Golf Course and the Wailea Gold Course are some of the most celebrated by Golf Magazine, Golf Digest, and Conde Nast Traveler. Makena State Park is located just south of Wailea and is home to 鈥淏ig Beach,鈥� prized for its clear water and expansive shoreline.
For residents and their guests who desire a more culturally immersive experience, consider The Feast at Mokapu, with its traditional Hawaiian luau and performances, which are second to none. Tickets start at $140 for children, so it is best saved for special occasions. While Wailea lacks a traditional downtown, it does offer premier shopping with a mix of luxury boutiques and diverse dining options. The Shops at Wailea feature notables like Tommy Bahama, Tiffany and Company, Gucci, and Louis Vuitton. For a meal in town, opt for restaurants such as Wolfgang鈥檚 Steakhouse, Waikiki Brewing Company, and coffee shops.
Quality Healthcare
One might be concerned that a small island would not be able to offer access to the types of medical care that one needs as they age. The good news is Wailea has access to medical care provided by doctors and urgent care facilities. While the nearby (roughly half-hour drive) Maui Memorial Center is the only hospital on the island, it is ranked as a high performer in treating heart attacks, according to U.S. News Health. Further, Bestplaces.com ranks Wailea low in both violent and property crime, checking the safety box for those looking for a peaceful place to spend their golden years. For minor medical concerns, the Kihei-Wailea Medical Center is just ten minutes away, with friendly staff and short wait times.
Parting Thoughts
When envisioning the perfect retirement destination, Wailea, Maui, offers a compelling balance of beauty, comfort, and practicality. Its balmy breezes, pristine beaches, and rich cultural heritage provide an idyllic tropical setting. Beyond its scenic allure, Wailea ensures modern conveniences, excellent healthcare access, and a safe, welcoming environment for retirees. While the cost of living may be higher, the financial incentives for seniors, combined with Hawaii鈥檚 renowned longevity and healthy lifestyle, make it a worthwhile investment. For those seeking a vibrant, fulfilling retirement, Wailea stands out as a destination offering luxury and peace of mind.
