The Best Hawaii Travel Destination for Retirees

While retirement brings with it many changes, one aspect of it that most retirees look forward to more than anything is the newfound freedom to explore the world at their own pace, going where they want, when they want. One US destination that features highly on the list of “must-visits” for the 60-plus crowd is Hawaii.

With its stunning vistas, consistently mild climate, and rich cultural experiences, America’s 50th state (it was the last to join the Union in 1959) is an ideal travel destination for retirees seeking a mix of adventure, relaxation, and beautiful scenery. From charming towns to perfect beaches, the best Hawaii travel destinations are well suited for retirees and offer incredible tropical island experiences, but with all the benefits of traveling within the US.

Kailua, Oahu

Kailua is a popular coastal town located on the windward (eastern) side of Oahu and is perfect for retirees seeking tranquility without being too far from urban amenities, with Honolulu, the state capital, just 20 minutes away by car. The town’s laid-back vibe along with beaches like the famous Lanikai Beach and Kalama Beach Park invite relaxing strolls along the shoreline or sunbathing beside its stunning turquoise waters.

Retirees can also enjoy outdoor activities like kayaking in Kailua Bay or exploring areas of outstanding scenic beauty such as the nearby Maunawili Falls. If you enjoy cycling, the Kawainui Marsh Bike Trail is a gentle three-mile route that takes around an hour to do, unless you stop for some birdwatching or fishing. Need a bike? Kailua Beach Adventures have a range of rental options, including bikes, kayaks, and paddleboards. The town’s farmers’ markets (there are three here) are also worth visiting and feature local producers and craft makers, so pick up a souvenir or two.

Waimea, Big Island

Located on the northern side of Hawaii’s Big Island, Waimea is a refreshing blend of pastoral beauty and Hawaiian “cowboy” culture. Known for its cool climate and wide-open spaces, Waimea is perfect for retirees who appreciate scenic drives and gentle hikes through lush valleys. The area’s most notable attraction is the historic Parker Ranch, the largest cattle ranch in Hawaii, where retirees can explore the history and culture of Hawaii’s paniolo cowboy tradition.

With its small-town charm and proximity to some of the state’s most spectacular mountains and coastlines, Waimea also presents visiting retirees a chance to explore historic sites like the Anna Ranch Heritage Center and enjoy a leisurely drive along Kohala Mountain Road with its stunning views.

Hana, Maui

Hana, on the remote eastern coast of Maui, is undoubtedly one of Hawaii’s most peaceful destinations. Retirees looking for solitude will certainly appreciate the town’s seclusion as it’s surrounded by lush rainforests and quiet beaches. It’s also famous for the scenic Hana Highway, a winding road boasting incredible views of waterfalls, cliffs, and the Pacific Ocean.

Hamoa Beach and Wai‘anapanapa State Park are also must-visits and are perfect spots for sunbathing and swimming with clear, calm, and safe shallow waters. And the beaches here are quite unusual and feature black sand, the result of erosion of volcanic materials, so take plenty of photos.

Koloa, Kauai

Historic Koloa is a charming town on the island of Kauai that once served as the center of Hawaii’s sugar industry. Vestiges of this impactful industry and the region’s rich sugarcane heritage can be seen at historical sites like the Old Sugar Mill, built in 1835 and the state’s first commercial sugar plantation. Though it closed 1996, you can still see ruins including the mill’s chimney along with a plaque marking it as a National Historic Landmark.

The 10-mile-long Koloa Heritage Trail takes in the sugar mill and other landmarks including the Old Sugar Mill Memorial dedicated to those who worked the sugarcane crops. Nearby Poipu Beach is perfect for retirees who enjoy sunbathing, snorkeling, or simply watching a great Pacific sunset.

Kailua-Kona, Big Island

Kailua-Kona, located on the western coast of Hawaii’s Big Island, is the perfect blend of relaxation and exploration. The town’s sunny weather and gentle coastal breezes make it an ideal place to enjoy outdoor activities like snorkeling at Kahalu'u Beach Park, an area that’s also known for its wildlife, including sea turtles.

Also fun is exploring Ali’i Drive, the town’s six-mile-long main drag. In addition to its souvenir shops and eateries, here you’ll find connections to Hawaii’s past in places like Hulihee Palace, built in 1838 as a vacation home for Hawaiian royalty and now a fascinating museum. Also worth seeing is Mokuaikaua Church, built in 1837 and the state’s first Christian place of worship.

Waikoloa Village, Big Island

Waikoloa Village is another Big Island destination that appeals to retirees. A peaceful, resort-style retreat located along the Kohala Coast, here you’ll find superb ocean views over Anaehoomalu Bay. It’s also a popular golfing destination, with places like the Village Course and Waikoloa Kings' Nine offering superlative experiences with lush fairways and ocean views.

This part of Hawaii has also become popular for its upscale accommodations, with notable properties like Mauna Lani and Hilton Waikoloa Village offering high-end vacations. There are some great beaches to relax on here, too, including Anaehoomalu Beach and Waikoloa Beach. Enjoy fishing? Hop aboard a charter or cast a line in Kuualii Fishpond or Kahapapa Fishpond, two well-stocked historic reservoirs between the beaches and the resorts themselves that have long been a source of food for locals.

Molokai

Molokai is often referred to as “the most Hawaiian island” due to its unspoiled scenery and its deep cultural heritage. This quiet island provides retirees with a truly tranquil experience that’s far removed from the crowds found in other, more tourist parts of the state. Fun things to do include exploring the island’s untouched beaches, the largest being Pāpōhaku Beach Park. Unspoiled by resorts or other construction, this magnificent, pristine beach is over 100 yards wide in places and is never crowded.

Kalaupapa National Historical Park is a must-visit for its outstanding natural beauty. Though something of a hike, you can book a fun mule ride to take you to some parts of the park. The Kapuaiwa Coconut Grove is another awesome spot to visit. Planted around 1860, it features hundreds of coconut palm trees and is a delight to explore and photograph.

Lahaina, Maui

For retirees who enjoy a mix of history, culture and giving back to local communities, Lahaina is a Hawaiian destination worth considering. This historic town on Maui’s west coast, once the capital of the Hawaiian Kingdom from 1795 to 1893, was devastated by a tragic wildfire in August 2023. While much of the town was destroyed, including the majority of its oldest heritage buildings, recovery, and rebuilding are underway, presenting an ideal opportunity for retirees to assist through donations and volunteer efforts.

Plans are underway to restore heritage buildings along Lahaina’s Front Street, including such landmarks as the Lahaina Courthouse, the Baldwin Home, and the Old Prison, all destroyed by the fire. One survivor, a 151-year-old banyan tree, is once again in leaf, a remarkable testament to the resilience of nature and the townsfolk here. Retirees can also help support the community by booking a whale-watching cruise with Makai Adventures, just one of a number of companies that sail out of Lahaina Harbor.

The Final Word

Hawaii offers plenty of excellent destinations for retirees looking to unwind, explore nature, and immerse themselves in culture. From the quiet charm of small towns to the scenic beauty of coastal areas and national parks, each location provides the kind of memorable experiences retirees crave. Add to this the fact Hawaii boasts a near-perfect climate, and 60-plussers simply won’t want to leave.