Senior Resources » 5 BEST Small Towns for Retirees to Visit in Hawaii

5 BEST Small Towns for Retirees to Visit in Hawaii

If you want to get away from the buzz of tourism and big-city lights, take a stroll through some of the most scenic small towns in Hawaii. While you won’t find Honolulu on the list, you will discover some hidden gems that offer pristine beaches and unique attractions. Here are the top 5 BEST small towns to visit in Hawaii!


Paia, Maui

surf boards lined up on a fence in Hawaii

Once a plantation community, the hip little surfing town of Paia, Maui is the island’s hub for the sport. Surf shops line the streets and give rise to the hippest and most casual mix of restaurants, cafes, and shops. Visit some eclectic boutiques and art galleries or go learn about Tibetan Buddhism at the Maui Dharma Center. The town of Paia is a destination for retirees who enjoy a mix of adventure, spirituality, and outdoor activities.

Lahaina, Maui

The scenic town of Lahaina offers a historic shopping district that is old-world charm meets modern. Architecture in the town brings the charm of the plantation community to life by preserving what once stood among the backdrop of the island’s unique beauty. There is a modern mix of eateries, retailers, and nightclubs that lure tourists in by droves. Surprisingly enough, the town never seems over-crowded!


Hawi, Big Island

Located on the Big Island of Hawaii, Hawi is often overlooked but offers a peaceful appeal that can only be found in one of the best small towns in Hawaii. Found along the Northern Kohala peninsula, the lush scenery is a huge draw. Tourists love the small community because of its well-preserved boutiques, shops, and unique stops—like, The Bamboo Restaurant and Gallery. The storefronts have been reconstructed over the years to their natural state and offer a rich history. Bookstores and galleries line the streets. Check out Tiffany’s Art Agency!

Haleiwa, Oahu

Hawaii Beach

Located along the North Shore, the small town of Haleiwa came about in 1898 when a businessman named Benjamin Dillingham constructed a Victorian Hotel named Haleiwa. The area became a prestigious weekend getaway for residents of Honolulu. Today, the town is a gateway to much of the surfing community along the North Shore. Surf shops, shaved ice stands, and ice cream parlors line the streets and give rise to a diverse group of residents and tourists. Are you an adventurous retiree? Try snorkeling with sharks or scuba diving!

Hanalei, Kauai

Located far from the buzz of the city lights of Honolulu or any other large community in Hawaii is the picturesque town of Hanalei. The town is found along the North Shore of Kauai and can only be entered from the single-lane bridge known as the Hanalei River Bridge. The town boasts unusual shopping retailers and anything from sushi to burgers in its restaurants and food trucks – check out Trucking Delicious! The surrounding landscape has everything to offer its tourists. The backdrop contains valleys that drop low into the earth and cliffs that seem to glide up into the heavens. The white sand beaches are breathtaking in this resort-free town!

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Originally published January 30, 2024


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