The Best Small Towns in Hawaii to Chill Out (2023)

The Best Small Towns in Hawaii to Chill Out (1)

Whether to find a nice, quiet beach to read a favorite book, a quaint restaurant to taste some local seafood and produce, or the most exhilarating surfing or snorkeling to be experienced in America, Hawaii is a place that can make that happen. Hawaii can accommodate travelers with some of the most beautiful waters, allowing everyday stress to melt away. Here are some of the best towns in Hawaii to do just that, to be able to chill out, alone or with family and friends, to relax and recharge.

MetropolisesTake a trip to one of the 10 Largest Cities in Hawaii

Lanai City

The Best Small Towns in Hawaii to Chill Out (2)

Situated in the center of the island of Lanai, Lanai City possesses a quaint charm that makes it the perfect spot for getting away from the hustle and bustle. Downtown Lanai offers a variety of activities, while not being like some of the more touristy places found in Hawaii. Dole Park may perhaps be the most common visiting spot in town, as it is surrounded by several restaurants and shops, like the Blue Ginger Café and the Lanai Culture and Heritage Center. There are also some beaches near Lanai, offering swimming, fishing, boating, snorkeling, and surfing. Hulopoe Beach is south of town, Polihua Beach can be found at the far northeast end of the island, and Shipwreck Beach is straight north.


The Best Small Towns in Hawaii to Chill Out (3)

Makawao is a quaint town located on the northwest slope of Haleakala, or the East Maui Volcano, on the northeastern side of Maui. As it only has a population of around seven thousand people, Makawao is a great place to chill out and relax for the day. There are several opportunities to accommodate this, like visiting the Sacred Garden of Maliko, checking out Makai Glass, famous for glass sculptures inspired by the sea and volcanic formations, or taking a walk through Makawao Park. Another relaxation from the anxieties of big-city life would be the several Mountain Bike tours, including the Haleakala Downhill Self-Guided tour, the Haleakala Day tour from 6500 feet to sea level, and the Haleakala Sunrise tour.


The Best Small Towns in Hawaii to Chill Out (4)

Haleiwa is located on the island of Oahu, on Waialua Bay, at the mouth of Anahulu Stream. With two prominent parks, Haleiwa Beach Park and Haleiwa Alii Beach Park, there are several options for chilling out in Haleiwa, whether visitors plan to stay for the weekend or the entire summer. Haleiwa Beach Park offers the Aloha Circle Island tour, a full-day adventure of snorkeling and swimming, and GLOW Stand-Up Paddle at Twilight, which is a great way to see Hawaiian Green Sea Turtles in their natural habitat. At Haleiwa Alii Beach Park, the Luxury Convertible tour and the Jeep tour are there to check out. If exercise is a preferred choice of leisure, the Ke Ala Pupukea bike path runs from north to south, through the entirety of downtown Haleiwa.

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The Best Small Towns in Hawaii to Chill Out (5)

Located on the far western side of the scenic island of Kauai, the town of Kapaa offers several great opportunities to relax and unwind. Downtown Kapaa offers visitors and residents alike access to the Kauai Path, which is about four miles in length and runs from one end of town to the other, with restaurants along the way to be able to grab some lunch. Also, with Kealia Beach north of town and Wailua Falls to the south, there are a variety of natural attractions to see in the area. Wailua Falls, a two-tiered, eighty-foot tall waterfall, and famous for being featured on Fantasy Island—easily accessible and a spectacular sight to share with friends and family.

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The Best Small Towns in Hawaii to Chill Out (6)

Hana is situated on the far western side of the island of Maui, past the Haleakala National Park and abutting the south Pacific Ocean. While Hana Bay, Pailoa Bay, and Honokalani Black Sand Beach are all within traveling distance, downtown Hana also offers several opportunities for being able to chill out for the weekend, the week, or even the entire summer! There is the Hana Cultural Center and Museum and the Hana Coast Gallery to visit. If outside adventure is more your cup of tea, Hana also has the Red Sand Beach, Hana Bay Beach Park, Twin Falls, Upper Waikani Falls, and the Pipiwai Trail. The Pipiwai Trail is a four-mile-long hike that passes the Makahiku Falls and Waimoku Falls.


The Best Small Towns in Hawaii to Chill Out (7)

Just northeast of Kapaa, on the island of Kauai, Hanalei boasts a population of less than five hundred people. While this signifies an ability to get away from the bustle of the big cities, it doesn’t mean there aren’t several opportunities for exciting adventure as well. Along with the typical breathtaking sights offered in many parts of Hanalei, like sight-seeing tours, airplane and helicopter tours, and bike tours, there are also several opportunities to chill out and grab something to eat with the family, including a variety of restaurants offering ultra-fresh seafood. To meet tourists’ surfing and swimming needs, visitors are welcome to visit the Hanalei Beach and Hanalei Bay, whose crescent-shape is one of the reasons the town was named Hanalei.

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The Best Small Towns in Hawaii to Chill Out (8)

There are several must-see attractions in the town of Hawi. Situated to the west of the community of Kapaau, in the district of North Kohala, on the island of Hawaii, Hawi provides access to Keokea Beach Park, which offers snorkeling, swimming, and surfing, Lapakahi State Park (constructed from the ruins of an ancient village), and the Original King Kamehameha Statue, which is located in Kapaau. Along with these spectacular sights, Hawi also offers visitors opportunities to check out the Pololu Valley Lookout, which has a stunning view of the valley and the ocean, as well as stop in at the Hawi Farmers Market, which boasts local produce from Hawi as well as other villages nearby.

Volcano Village

The Best Small Towns in Hawaii to Chill Out (9)

Almost due south of Hawi, at the southern end of the island of Hawaii, lies Volcano Village. With a population of less than three thousand people, Volcano Village is a great place to unwind and relax, either for the weekend or longer. There are several stunning natural attractions in and near Volcano Village, as it is surrounded by the Hawaii Volcanoes National Park, which covers over five hundred square miles of land. Along with the National Park and the famous Kilauea volcano, offering opportunities for hiking, camping, and photographic experiences, there is the rustic village and its accommodations and restaurant choices, far away from the traffic, crowds, and the hectic confusion found elsewhere.

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So, whether the idea of chilling out entails relaxing on the sand, experiencing the latest culinary dish, surfing a gnarly wave, or exploring the crater of a volcano, these towns of Hawaii may be a good option. Offering peace, quiet, a quaint outlook on the detriments of societal stress, along with a keen sense of adventure and excitement, they are each a secluded piece of heaven in a world of chaos and calamity.

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What is the best island to chill in Hawaii? ›

Kauai is the best Hawaiian island for travelers who like hiking, relaxing, and a quieter vibe.

Where is the best place in Hawaii for relaxation? ›

If you're looking for a little bit of everything; relaxing beach days, adventurous hikes to waterfalls, a nightlife, lively coral reefs, and resorts, than Maui is truly the ideal tropical paradise. Most first-time Hawaii visitors travel to Maui due to its diversity and popularity.

What are the least touristy parts of Hawaii? ›

Molokai is the least visited island of Hawaii. With about 65,000 visitors, the island attracts only a fraction of all the tourists that visit the island group each year. The island is more rural and doesn't have resorts. Molokai is most definitely a destination off the beaten path.

Which Hawaiian island is less touristy? ›

LANAI ISLAND - THE PLACE TO RELAX Lanai entices the sophisticated traveller with a handful of exclusive luxury resorts and championship golf courses. It's the least visited Hawaiian Island, small in size and slow in pace those that travel to Lanai, by air or on the ferry from Maui, are forced to rest and relax.

What Hawaiian island has the calmest beaches? ›

Oahu Beaches are the Best for Calm Waters

If you are looking for the best beaches in Hawaii for swimming, Oahu is the place to go. South Oahu, from Honolulu to Ko Olina has calm waters year-round. For the best beaches for swimming due to calm waters, check out Ala Moana Beach Park just outside of Waikiki.

What is the calmest beach in Hawaiian Islands? ›

Lanikai Beach

Loved by both locals and tourists, Lanikai is largely considered the best swimming beach in Hawaii thanks to its calm waters. This is attributed to the coral reef which also makes this a great spot for snorkelling in Hawaii.

What is the most relaxing city in Hawaii? ›

Lahaina is a small and relaxed Hawaiian city to visit. Lahaina is the perfect destination for relaxation and adventure on the west side of Maui.

What is the quietest island to stay in Hawaii? ›

Today, Molokai is the least populated of the islands, with over half of its population 100 percent native Hawaiian.

What is the most peaceful part of Hawaii? ›

Oahu's east and north shore are much more peaceful. On average there are roughly 200,000 tourists on the islands on any given day: 100,000 on Oahu, 48,000 on Maui, 29,000 on the Big Island, and 22,000 on Kauai. For more information see our guide on the best time to visit Hawaii.

What is the number 1 vacation spot in Hawaii? ›

Oahu is the most visited of all the Hawaiian islands, at nearly 4.7 million visitors annually. Oahu is primarily defined by the state capital of Honolulu, as well as Pearl Harbor and the famous beach known as Waikiki. These areas attract tourists by the thousands daily.

What is the most walkable city in Hawaii? ›

Waikiki has an extremely high Walk Score of 90 out of 100, making it one of the most walkable cities in all of the Aloha State (and one of the top 5 most walkable neighborhoods in Oahu itself).

Where can I avoid crowds in Hawaii? ›

Kahana Bay Beach Park, Oahu

Kahana Bay Beach Park is one such place. Because this location doesn't have any lifeguards or the usual beach facilities, it attracts fewer crowds while still being a great beach location. This beach park is ideal for wading, fishing, kayaking, and even hiking.

What's the prettiest island in Hawaii? ›

Kauai is the winner

In our opinion, Kauai takes the throne as the prettiest Hawaiian island. It has a variety of views and terrain to see. Rocky coastlines, beautiful beaches, lush jungles, and mountains and valleys. There is so much to see and do.

What is the least busy place in Hawaii? ›

Molokai. The most local of the main Hawaiian Islands, Molokai also receives far fewer visitors than the other islands and will have the least touristy feel. What is this?

What is the locals only island in Hawaii? ›

Quite amazingly, Niihau is the only place in the world where people still speak Hawaiian as their primary language. The residents have their own dialect called Olelo Kanaka Niihau.

What is the least crowded beach in Hawaii? ›

Waimea Beach, Kauai

With just one primary lodging option, Kauai's dry, sunny west side is by far the island's least crowded coast accessible by road. Waimea Beach has fine brown-black sand that is great for beachcombing and leisurely strolls, and it offers views of the island of Niihau across the channel.

Which Hawaiian island is more affordable? ›

Oahu is the cheapest Hawaiian island to visit, with a total cost of $2,625. A Ko Olina Resort lagoon on Oahu. Maui is the most expensive island to visit, coming in nearly $1,000 more expensive, with a total cost of $3,600.

Which Hawaiian island is best for introverts? ›

Molokai: The Introvert

You want to avoid the crowded beaches and resorts, and live like a local. Molokai has remained mostly untouched by throngs of tourists and offers a magical escape for those who want solitude and a rural escape—without a single stoplight.

What time of year is the water the calmest in Hawaii? ›

Summer is the best time to take a dip in the warm Hawaiian waters. The ocean temperature hovers around 82°, and the wind and surf are reliably low. Visitors of any experience level can enjoy snorkeling in the clear, calm summer sea.

What is the most relaxing beach in Oahu? ›

Pokai Bay. Pokai Bay is known to be the safest beach if you're traveling with kids. This beach on Oahu is renowned for its tranquil seas and mild waves. The water is shallow and has a sandy bottom, making it the ideal family beach and one for rookie swimmers.

What Hawaiian island is known as the friendly island? ›

Molokaʻi (The Friendly Isle)

This laidback little island got its nickname from the people who live there.

What is the friendliest place in Hawaii? ›

Why move to Molokai? Among the Hawaiian Islands, Molokai is known as the Friendly Isle, and those who live there would consider it the best island to live on by far. With many longtime families and few visitors living on remote Molokai, it is one of the most secluded Hawaiian Islands.

What Hawaiian island is best for relaxing? ›

If you are looking for to relax under the swaying palms of a gorgeous resort, then Maui is the best island to visit in Hawaii. With its amazing beaches, most luxurious resorts and world-class spas, Maui is the perfect destination for any traveler looking to unwind and enjoy some quality time in paradise.

What is the most safest island in Hawaii? ›

If you're just looking at the sheer number of incidents on each island, Kauai is the safest island to live on.

What are the happiest cities in Hawaii? ›

Love and Garboden also found that wealthier neighborhoods – places like Kailua, Waialae/Kahala, Hawaii Kai and Kaimuki – were among Oahu's happiest places. Part of that might have been the result of an “area premium.” A particular place might make people happier because it's close to the beach, they said.

What is the hippie town in Maui? ›

Since the 1970s, Paia Town has gotten plenty of recognition as the laid back, surfer hippie town of Maui. While most people breeze by on their early morning drive to explore the Road to Hana, we recommend taking the time to discover one of Hawaii's coolest small towns.

Which side of the island of Hawaii is best to visit? ›

The short answer: Go to Maui if you want to be pampered at a resort with all the amenities. Book Oahu if you want to see Pearl Harbor and the famous Waikiki Beach. Visit Big Island if you want to hike Volcanos National Park (and maybe see flowing lava). Head to Kauai if you want to experience wild, untamed Hawaii.

What is the least traveled month to Hawaii? ›

Hawaii ON/Off peak periods

To avoid crowds, try planning your trip for after July as the number of visitors drops off down to September and October, which are the quietest months for tourists.

Which island to visit for first time in Hawaii? ›

If it's your first trip to Hawaii

Chances are, the Big Island of Hawaii has everything you're looking for. But depending on what you want to do, one of the other islands accessible from the mainland — Maui, Oahu or Kauai — could be a better fit.

What is the busiest month to visit Hawaii? ›

December (except for the first week), January and February are the busiest months, when prices for airfare and accommodations are at their highest. In particular, the last two weeks of December and the first week of January are prime times for travel, and hotels and flights are often booked to capacity.

What is the prettiest city in Hawaii? ›

10 Of The Most Beautiful Cities In Hawaii
  • 8 Kane'ohe, Oahu.
  • 7 Makaha, Oahu.
  • 6 Ka'anapali, Maui.
  • 5 Kihei, Maui.
  • 4 Lahaina, Maui.
  • 3 Honomu, Big Island.
  • 2 Kealakekua, Big Island.
  • 1 Wailua, Kauai.
Dec 27, 2022

What is the most beautiful street in Hawaii? ›

Kalakaua Avenue, Honolulu, Oahu Hawaii

Kalakaua Avenue is located alongside Waikiki beach with stunning views of Diamond Head. With it's overhead palm trees and location next to a world famous beach, it's no wonder it attracts approximately 85,000 visitors daily.

Where is the best place in Hawaii to visit without a car? ›

Generally speaking, the best Hawaiian island to visit without a car is Oahu. This is because the bus system goes throughout much of the island and it's convenient enough to take the Oahu bus to different places, and there's also a bus from the Honolulu airport.

What is the most tourist friendly Hawaiian island? ›

Oahu - The Gathering Place

Oahu is the most visited of all the Hawaiian islands, at nearly 4.7 million visitors annually. Oahu is primarily defined by the state capital of Honolulu, as well as Pearl Harbor and the famous beach known as Waikiki. These areas attract tourists by the thousands daily.

Is Maui or Kauai better? ›

Stunning coastlines, towering mountains, and lush jungles abound on both islands. However, the main difference between the two islands comes down to the variety in the landscapes, which Maui wins by a narrow margin. Maui: All in all, the scenery on Maui is more accessible than what's found on Kauai.

What's the funnest island in Hawaii? ›

Oahu is the most famous Hawaii island when it comes to sightseeing. You can tour Pearl Harbor, hike Diamond Head, and snorkel Hanauma Bay. The good news is that there are many great day tours available on every Hawaiian island for boat tours, snorkeling, kayaking, zip lining, and scenic drives.

Is Oahu or Maui better? ›

If you're looking to hole up at your hotel for the entire vacation, pick Maui and its sprawling oceanfront resorts. But if you're looking for adventure, to really experience the Hawaiian Islands and make the most of your well-earned vacation, Oʻahu should be your choice.

Which Hawaiian island is most walkable? ›

Oahu is the easiest island to get around. There are several car rental companies at the Honolulu Airport if you'd like to drive the island. If you're looking to save a few dollars on transportation, the Oahu bus system can get you within walking distance of almost anywhere on the island.

What is the most outdoorsy Hawaii Island? ›

Kauai offers up pure paradise to anyone who loves the great outdoors. Kauai is the oldest of the major Hawaiian Islands and has certainly earned its nickname of the "Garden Isle." Beautiful flora and fauna abound around the island. As the oldest Hawaiian Island, Kauai is also home to some of the world's best beaches.

Why is Kauai so popular? ›

Perhaps more than any of the other islands, Kauai is known for its natural beauty and its dramatic, beautiful sites. These include Waimea Canyon, the Coconut Coast and much more. You'll find gorgeous mountains and waterfalls, white sand beaches, sugarcane fields, and beachside cliffs such as those on the Na Pali coast.

When not to visit Kauai? ›

Hurricane and tropical storms are historically rare events on Kauai, but it's still important to be prepared for storms if you visit during Hawaii hurricane season - June through November.

Is it more expensive to stay on Maui or Kauai? ›

However, it's true that generally speaking Kauai is a bit cheaper. In terms of accommodation, there isn't a huge difference between both islands but when it comes to shopping and eating Maui can be slightly more expensive as it's more touristy.

How many days should I vacation in Hawaii? ›

While many vacations are five to seven days long, we recommend staying for at least 10 days to enjoy your Hawaiian vacation. The time change is difficult to adjust to at first and takes about 3 days to get fully acclimated. So, allowing a couple days to get over the jet lag is important.

Is there a ferry from Oahu to Maui? ›

Oahu and Maui are only 100 miles apart, but there is no ferry service linking the two islands. Today, you have to fly between Honolulu and Kahului. (Or rent a charter boat, but that's not a cheap option.)


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