Oahu Skip: 10 Small Towns Worth Visiting on Maui (2023)

With Nicole Hansen

Enjoy the sandy beaches, cultural attractions and lush tropical forests of Hawaii away from the crowds on Oahu with the best small towns on Maui.

Oahu Skip: 10 Small Towns Worth Visiting on Maui (1)

Wailea Beach Resort, Marriott, Maui, Wailea Alanui Drive, Wailea, Hawaii, USA

A tropical vacation is a dream for travelers around the world, and Hawaii is one of the most beautiful destinations of all.Oahu is a bucket list destinationin Maui that attracts year-round visitors thanks to its unique cultural museums, scenic hikes and iconic beaches such asthe historically significant Pearl Harbor. Unfortunately, this beauty and popularity often means large crowds, especially in the hotspots, which makes it difficult to really relax and enjoy the view.

Fortunately, those planning a Hawaii vacation don't have to submit to the crowds to enjoy the wide variety of natural and cultural attractions that Maui has to offer. Many of the surrounding towns have equal access to the stunning beaches and rainforests that make the island famous, with far less crowds and more affordable options than big city destinations.

Each of these small towns has fewer than 25,000 permanent residents, according to the2020 census. Don't let their small size fool anyone. These unique towns are filled with enough natural wonders, sandy beaches, and unique historical and cultural attractions to make their own day trip, if not their own Hawaii vacation.

Related:Oahu Vs Kauai Vs Maui: Comparing the Best Islands in Hawaii



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10 Hannah

Oahu Skip: 10 Small Towns Worth Visiting on Maui (2)

Red Sand Beach along the Hana Highway in Maui, Hawaii, USA

Hana is home to less than 1,000 residents and miles and miles of beautiful scenery. For those looking to enjoy the great outdoors, Hana on Maui is a must-see Hawaiian destination. The famous road to Hana, also known as theThe Hana Highway offers a unique tour of the island's geological and ecological history, withstops on the way to Hana, including waterfalls and beachesas well as delicious food options.

Visitors can explore the ocean shores at Hamoa or Black Sand Beach, or head inland and enjoy the Hana Lava Subway or Waiʻānapanapa State Park. In town, the Hana Cultural Center and Kahanu National Botanical Garden offer even more for visitors.

  • Why you should visit Hana:Road to Hana, Hamoa Beach, Black Sand Beach, Hana Bay Beach Park, Hana Lava Subway, Wai'anapanapa State Park, Hana Cultural Center, Kahanu National Botanical Garden

Guests can tootake a Road to Hana road tourfor an expert-led experience while enjoying the comfort of someone else doing all the driving and navigation.


9 Waters of Destruction

Oahu Skip: 10 Small Towns Worth Visiting on Maui (3)

The dramatic forest landscape of Iao Valley State Park, Wailuku, Hawaii, United States

With just over 17,000 people, Wailuku is one of Maui's best small towns that offers the perfect vacation for those who want easy access to major Hawaiian attractions without being in the middle of a tourist town. There are many tours available throughout the city, including zip line tours and scuba diving tours.

Wailuku is also the gateway to Iao Valley State Monument and Maui Tropical Plantation. Wailuku is also known as the home of Hawaii's aquarium, the Maui Ocean Center. Complemented by a variety of unique local restaurants and shops, Wailuku has attractions to rival even Oahu itself.

  • Why Wailuku is worth visiting:Μνημείο Iao Valley State, Maui Tropical Plantation, Maui Ocean Center, Ziplining, Scuba Diving, Maui Historical Society, Maui Swap Meet
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8 Married

Oahu Skip: 10 Small Towns Worth Visiting on Maui (4)

Waipi'o Lookout, Honokaa, Maui, Χαβάη

For a more relaxed Hawaii vacation, a visit to the small town of Honokaa is just what travelers are looking for. Wagon tours, the Mauna Kea Tea Farm, and farmers markets give the town a more relaxed feel during your Maui vacation. Guests can stay at Honokaa while visiting Waipiʻo Valley Lookout, Kalopa State Recreation Area, or Hiilawe Falls.

Those looking for a little more excitement can also take one of the many zip-line tours that take place around town, ensuring that everyone can enjoy the best views of Hawaii's paradise.

  • Why you should visit Honokaa:Mauna Kea Tea Farm, Waipi'o Valley Lookout, Kalopa State Recreation Area, Hiilawe Falls, Ziplining, Horseback Riding, Wagon Tours

7 It is nice

Oahu Skip: 10 Small Towns Worth Visiting on Maui (5)

Sunset on a beach in Kihei, Hawaii

If experiencing Hawaii's wildlife is on the agenda, the small town of Kihei is a must. This beach town is one of the prettiest small towns Maui has to offer and is perfect for those planning a day trip away from the big city of Oahu, with opportunities for humpback kayaking, snorkeling at one of the many beaches or just relax on the shore and watch the birds and ocean life.

Kihei is most famous for the Humpback Whale National Marine Sanctuary, whose mission is to protect and monitor whales in the wild. Through the Sanctuary at Kihei, visitors can take a whale watching tour or go kayaking, snorkeling, and even scuba diving near these giants.

  • Why Kihei is worth visiting:Humpback Whale National Marine Sanctuary, Kealia Pond National Wildlife Refuge, Kamaole Beach Park, Kealia Coast Boardwalk

Humpback whales migrate through Kihei between November and April, so those hoping to book a tour specifically to see the whales should plan strategically. Those visiting outside of this time frame can still enjoy kayaking, snorkeling and diving with a variety of other ocean natives.

6 Sacred

Oahu Skip: 10 Small Towns Worth Visiting on Maui (6)

The Harbor Village of Maalaea on the west coast of Maui, Hawaii, USA

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With less than 300 permanent residents, Maalaea is Hawaii's quintessential small town. Maalaea is best known for its harbor, giving locals and tourists alike the perfect place to get out on the water via any of the boat or independent tours (many of which are snorkeling and whale watching tours).

For those hoping to get a little more up close, snorkeling and diving spots are also accessible from this small seaside town. Maalaea is another access point for the Maui Ocean Center Aquarium, whose address is in Wailuku but crosses the city border.

  • Why you should visit Maalaea:Maui Ocean Center Aquarium, Boating, Snorkeling, Diving, Maui Golf and Sports Park

5 Careful

Oahu Skip: 10 Small Towns Worth Visiting on Maui (7)

Located on the slopes of Haleakala Volcano, the town of Makawao in Maui, Hawaii is one of the most charming small towns in Maui

About 8,000 people call Makawao home, but the number of cultural attractions and the city's historic center give it the feel of a much larger city. Travelers can enjoy the arts at the Hui No‘eau Visual Arts Centre, a mansion built in 1917 that now houses an art gallery and classes, or at Hot Island Glass, a glass-blowing gallery.

For a more meditative experience, travelers recommend wandering through the Sacred Garden of Malikos. Meanwhile, on the outskirts of town, visitors can find a classic Hawaiian tourist activity, the pineapple farm tour.

  • Why you should visit Makawao:Hui No‘eau Visual Arts Center, Hot Island Glass, Sacred Garden of Maliko, Hali'imaile Pineapple Farm, Haliimaile Distilling Company, Historic Downtown

4 Care

Oahu Skip: 10 Small Towns Worth Visiting on Maui (8)

While fields may not be the first thing that comes to mind when visitors plan their trip to the Hawaiian Islands, the small town of Kula fully displays this lesser-known side of Maui. Visitors can wander the lavender fields at Ali'i Kula Lavender Farm, take a full-day tour of Ocean Organic Vodka Farm and Distillery, or enjoy some coffee at O'o Farm.

Those planning a trip to Coola can also enjoy tours through the Surfing Goat Dairy Farm, which produces more than two dozen varieties of award-winning goat cheese. On the edge of Kula is Haleakalā National Park, completing the perfect Hawaii vacation in this hidden Maui gem.

  • Why you should visit Kula:Ali'i Kula Lavender Farm, Ocean Organic Vodka Farm and Distillery, O'o Farm, Surfing Goat Dairy Farm, Haleakalā National Park

Related:Sunrise in Haleakalā National Park: How to get the most exciting start to your Maui day

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3 Water

Oahu Skip: 10 Small Towns Worth Visiting on Maui (9)

Maui coast along the Wailea Beach Trail, Hawaii, USA

Every aspect of Hawaii is beautiful, but its world-famous beaches are perhaps the biggest draw for the millions of visitors who flock to the islands each year. Wailea is home to just over 6,000 people and some of Maui's best beaches, easily earning a coveted spot on our list of the best small towns Maui has in store for visitors.

Makena State Park, Keawakapu Beach, Polo Beach and more offer the perfect white sand experience for travelers. Guests can also enjoy ocean views from the coastal golf course or kayak on the water itself. Even with more than 80 accessible beaches on Maui, the small town of Wailea manages to stand out from the crowd.

  • Why you should visit Wailea:Makena State Park, Makena Beach, Keawakapu Beach, Polo Beach, Little Beach, Wailea Beach Path, Ulua Beach, The Shops at Wailea

If you are planning a visit, tourists should definitely add at least a few of themtop things to do in Waileaon their itineraries.

2 Printed

Oahu Skip: 10 Small Towns Worth Visiting on Maui (10)

Paia Town, Maui, Hawaii, USA

Located along Maui's North Shore, Pa'ia offers just the right balance of small-town charm combined with accessibility for out-of-towners passing through. Local restaurants and inns make this an affordable Maui vacation town, while attractions like Ho'okipa Beach Park, Kaulahao Beach, and Pa'ia's Secret Beach ensure travelers can experience this true Hawaiian landscape.

In town, there are many surf shops, art galleries and local cafes that cater specifically to tourists hoping to make the most of their visit to Pa'ia.

  • Why you should visit Pai'ia:Baldwin Beach Park, Kaulahao Beach, Ho'okipa Beach Park, Lower Pa'ia Park, Pa'ia Secret Beach, Maui Dharma Center

Related:10 Cheap Hawaii Vacation Spots You Must Visit This Summer

1 Lahaina

Oahu Skip: 10 Small Towns Worth Visiting on Maui (11)
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The colorful streets and buildings of the former missionary town of Lahaina on Maui, which was the capital of Hawaii before Honolulu and the center of the world's whaling industry.

Lahaina, once the capital of Hawaii, may be the largest city in West Maui, but with just over 13,000 residents, its small-town charm is alive and well. Being one of the prettiest small towns Maui has to offer, visitors here have plenty to experience, such as enjoying popular beaches like Hanakao'o Park, Baby Beach, and Ka'anapali Beach, as well as enjoying the attractions of the city itself. Throughout the city there are many churches of various denominations, including the Lahaina Jodo Mission, a Buddhist temple.

Historic buildings like the Baldwin Home Museum and the Old Lahaina Courthouse, which houses the Lahaina Heritage Museum (easily one of thebest museums in maui), are also worth exploring, while contemporary attractions like the Outlets of Maui and Front Street offer shopping opportunities for those hoping to recreate a big-city feel without having to battle the Oahu crowds.

  • Why you should visit Lahaina:Hanakao'o Park, Baby Beach, Ka'anapali Beach, Baldwin Home Museum, Old Lahaina Courthouse, Outlets of Maui, Front Street, Lahaina Banyan Court, Lahaina Harbor


Oahu Skip: 10 Small Towns Worth Visiting on Maui? ›

Lahaina: A Maui Hotspot

Lahaina is the most popular town to visit on the island. That's because there are so many things to do and see! The historic whaling village boasts top-notch art galleries, shops, eateries, and live entertainment. There's also a wide range of events to attend throughout the year.

What is the coolest town in Maui? ›

Lahaina: A Maui Hotspot

Lahaina is the most popular town to visit on the island. That's because there are so many things to do and see! The historic whaling village boasts top-notch art galleries, shops, eateries, and live entertainment. There's also a wide range of events to attend throughout the year.

What is better Oahu or Maui? ›

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.

How many days in Maui is enough? ›

So, How Many Days Do You Need in Maui? If Maui is the only Hawaiian island you'll be visiting, you'll want at least 7-10 days to explore the island. That will give you enough time to do some day trips, take a few tours, check out the beaches, and have plenty of time to relax and unwind.

Is it better to go to Honolulu or Maui? ›

Hawaii is a stunning location with plenty of fun things to do, no matter which island you visit. If you're in the market for a beachy, relaxing vacation, you may want to head to Maui. Otherwise, consider Honolulu for its abundance of hotels, things to do and plentiful flight connections to other U.S. cities.

What is one thing not to miss on Maui? ›

No trip to Maui is complete without visiting the island's many shorelines, such as the famous black sand beach at Wai'anapanapa State Park. There are also more traditional white sand beaches like Ka'anapali Beach, Wailea Beach and the pristine Big Beach at Makena State Park.

What is the least touristy city on Maui? ›

For a more authentic feel, skip the mega-resorts of West and South Maui and head to the North Shore, East Maui, or Upcountry, where you're more likely to interact with locals than with tourists. Upcountry is the least touristy area.

Is Maui less touristy than Oahu? ›

On one hand, Oahu is the most crowded of the two and boasts a happening tourist scene. Since it's geared toward tourists, it has more touristy attractions to try. Maui has a more laid-back vibe, perfect for those who like to laze around in paradise.

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 prettiest Hawaiian island to visit? ›

Kauai's lush greenery makes it, in my opinion, the most beautiful of all the Hawaiian islands. It is home to waterfalls, hiking trails and a variety of eco-adventures. Most travelers seek out Kauai to avoid the hustle and bustle of Oahu and Maui and have a more unplugged vacation experience.

What is best month to go to Maui? ›

The best time to visit Maui, taking into consideration the weather, demand for accommodations, and how crowded, or not, the island is, are the month(s) of April, May, August, September, and early October. Some call these Maui's 'off-season periods' or the 'shoulder months.

What is the busiest tourist month in Maui? ›

According to data from the Hawaii Tourism Authority, if you want to visit Maui with the fewest crowds, you should visit in January, February, September, October, or November. The busiest months on Maui are March, June, July, August, and December.

Are there a lot of things to do in Maui? ›

TOP 25 Things To Do in Maui
  • Learn to surf.
  • Witness a Haleakala sunrise.
  • Transform into a mermaid.
  • Explore the Road to Hana.
  • Visit Molokini Crater.
  • Combine snorkeling & kayaking.
  • Paia Town.
  • Go whale watching.

Which is the cheapest Hawaiian island to visit? ›

Due to the abundance of hotels, activities, tours, and attractions, Oahu is the cheapest Hawaiian island to visit. Between the competitive prices and myriad of things to do, those looking for a budget vacation to Hawaii will find that Oahu is exactly what they've been searching for.

Is Oahu worth going to? ›

Located in the middle of the Pacific Ocean, Oahu is one of the most popular tourist destinations in the world. Whether you're looking for outdoor adventures, Polynesian cultural experiences, or just a relaxing vacation, Oahu has something for everyone. One of the best things to do in Oahu is to hit the beach.

What is the cheapest week to go to Hawaii? ›

April thru June and mid-August thru mid-September are Hawaii's "low seasons," and airfares are lower then. No matter what time of year you travel, you may be able to score better deals if you travel midweek.

What to stay away from in Maui? ›

23 Things NOT To Do While Visiting Maui
  • Don't touch/get too close to wildlife. ...
  • Don't forget the reef-safe sunscreen. ...
  • Don't ignore ocean warning signs. ...
  • Don't leave your shoes on when entering someone else's house. ...
  • Don't call your slippers “flip flops.” ...
  • Don't over plan. ...
  • Don't stand on the reef.
May 1, 2022

What are the tourist problems in Maui? ›

Maui suffers from beach erosion, drought, water rights, and more. Maui was mentioned as an area impacted by water crises for these problems. Some Maui residents have had conservation orders to avoid non-essential water usage.

Are there places to avoid in Maui? ›

Don't swim in the mouths of rivers or streams or in any murky areas. Murky waters attract predators (think “shark”), and you don't want to be mistaken for a fish or turtle when they are looking for a snack. You'll find more Maui ocean safety tips here!

What is the best walkable area in Maui? ›

Kaʻanapali is one of Maui's largest, most walkable tourism hubs. A collection of hotels and resorts are perched directly on the golden sand at Kaʻanapali Beach. Here, restaurants, shops, and activities abound.

What is the most walkable neighborhood in Maui? ›

The Lahaina area is best suited for those who enjoy walking from place to place. Those with access to a vehicle will find many hidden gems in Upcountry Maui, which is away from the hustle of tourist towns. Stop to see the vintage rooms at the Paia Inn near Hana Highway.

What is the hippie town near 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.

Is Maui as crowded as Oahu? ›

Oahu, home to capital city Honolulu, is generally more crowded than Maui. It boasts the best-known destinations in Hawaii. You can book one of the many hotels on Waikiki Beach, visit the U.S.S.

Is Maui more relaxing than Oahu? ›

Because Maui is more secluded and far from city life, you can expect more peaceful views of the island's beautiful beaches. On the other hand, you can find most of the Oahu resorts in Waikiki. And the rooms also feature views of the white sand beaches and busy nightlife.

Which Hawaiian island is best to visit not crowded? ›

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.

What is the slowest month for tourism in Hawaii? ›

Spring and Autumn are the “low” or “off” season in Hawaii. April through mid-June, and September through mid-December see the fewest tourists. This can result in a wider variety of options for you when it comes to hotels, transportation, and attractions.

What is the least busiest month to visit Hawaii? ›

The Fewest Crowds in Hawaii

January, February, September, and October have the fewest people on the Hawaiian Islands. To avoid the crowds, these months are the best time to visit Hawaii. September and October are the least crowded as visitor counts drop to the islands after Labor Day.

What is Maui most known for? ›

Maui, known also as “The Valley Isle,” is the second largest Hawaiian island. The island beloved for its world-famous beaches, the sacred ʻĪao Valley, views of migrating humpback whales (during winter months), farm-to-table cuisine and the magnificent sunrise and sunset from Haleakalā.

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.

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 most laid back Hawaiian island? ›

Kauai is best-known as “the Garden Isle” thanks to its lush green landscape that stands out among the Hawaiian Islands. But “the Laid-Back Isle” is a fitting name too, as the pace of life just feels much slower here than you'll find on other major islands.

What is the rainiest month in Maui? ›

What is the rainy season in Maui? In general, the wettest periods on Maui occur during the winter months of November to March, although Wailea benefits from being on the leeward side of Maui, which means the weather at Grand Wailea is generally drier (and warmer) than the rest of the island, even during the winter.

What month is the coldest on Maui? ›


What is hurricane season in Maui? ›

The Central Pacific Hurricane Season officially runs from June 1 until November 30, though tropical cyclones can occur off season and storms can happen at any time of year.

How many nights in Maui is enough? ›

How much time do you need in Maui? We recommend at least one week in order to experience all that Maui has to offer. While you can get a flavor of Maui even if you just visit for a day or two, as a minimum, try to plan 3 to 5 days in Maui.

How far in advance should I book a trip to Maui? ›

Our advice here will help you with your Maui trip planning. We recommend booking six months in advance to secure the best prices for rental cars and hotels. Plus, you will be able to pick your preferred hotel room for the dates you want. Things do sell out on Maui so book ahead for peace of mind.

How far in advance should I book a Maui vacation? ›

3 to 6 months out is a sweet spot, but as mentioned above, you may want to consider booking a year in advance. Sometimes, you have to take a vacation when you can get the time off, and this may fall during a popular time of the year. If you book early enough, that won't be a problem.

What part of Maui is most popular? ›

Initially developed in the 1960s, West Maui remains one of the most popular destinations to stay and play on the island of Maui. Here you'll find the old whaling village of Lahaina. In addition, the resort area of Kaanapali stretches along the coastline here.

How do you avoid crowds in Maui? ›

5 Tips to Escape Tourist Crowds in Maui
  1. Skip the beach and head to the mountains.
  2. Take the Road to Hana and stay overnight.
  3. Experience local voluntourism.
  4. Try a local market or hole-in-the-wall restaurant.
  5. Find a secluded beach.
Jun 12, 2018

Is 5 full days in Maui enough? ›

How Many Days on Maui. You will never want to leave Maui, and there are enough beaches, hikes, road trips and adventures to easily fill a week or more on the island. At a minimum, though, I recommend three days on Maui if you are island hopping or five days on Maui if this is your only stop.

What is the most expensive island to go to in Hawaii? ›

The Cheapest Hawaiian Island to Visit and the Most Expensive

Maui is the most expensive island to visit, coming in nearly $1,000 more expensive, with a total cost of $3,600. The Grand Wailea in Maui, a luxury resort.

Which Hawaiian island is best 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.

How many days in Oahu is enough? ›

How Many Days Should I Spend on Oahu? I recommend a minimum of three to four days on Oahu to check out the most popular sights and beaches. At least five days on Oahu is best if you want to spend some days at the beach, hike and explore different coasts of the island.

What month is best for Oahu? ›

The best time to visit Oahu, taking into consideration the weather, demand for accommodations, and how crowded (or not) the island is - are the months of early April, May, September, and early October. Some call these Oahu's 'off-season periods' or the 'shoulder months. '

Is 1 week in Oahu enough? ›

Four or five days in Oahu is even better if you want to hike, visit some cultural sights, go kayaking, or just slow down a bit. With seven days in Oahu, you should have enough time to discover your own favorite beach and get a little sampling of everything, from museums and historic sites to gardens and waterfalls.

What month is the most expensive to go to Hawaii? ›

Between mid-March and early-April 2023. This can also be one of the highest-priced times of year to visit Hawaii.

What time of year is it cheapest to fly to Hawaii? ›

Top tips for finding cheap flights to Hawaii

High season is considered to be June and July. The cheapest month to fly to Hawaii is January.

What is the cheapest day to fly? ›

Average domestic airfare price by day
  • Tuesdays and Wednesdays are the cheapest days to fly domestically.
  • Saturday and Monday flights can help you avoid the Sunday rush.
  • Wednesdays and Thursdays are the cheapest day to fly internationally.
  • Book one to three months in advance.
  • Set a price alert.
Apr 21, 2023

What is the hippie city 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.

What is the hippie town in Maui? ›

Paia is Maui's hippie and surfer town, with architecture from Maui's plantation era. Some say its residents are still living in the 70's, but visitors love its many interesting and unusual shops, galleries, and restaurants.

What is the nicest area in Maui? ›

The west area is likely the best place to stay in Maui for couples and luxury lovers. Budget options are still available here, however. Great restaurants and best nightlife are in West Maui. Many popular day tours leave from the Lahaina Harbor (like whale watching tours).

What side of Maui is best to stay on? ›

For most visitors who come to Maui, the island's western side hosts the most favorable accommodations, including most top resorts, long-stay condos, and Maui hotels with kitchens.

Where on Maui is Oprah's house? ›

According to a sales deed obtained by KITV4, Oprah has just purchased a whopping 870 acres of land in Kula, the central part of Maui, to the tune of nearly $6.6 million. The land was purchased from Ulupalakua Ranch, KITV4 reports.

Where does Oprah eat in Maui? ›

Hailimaile General Store-- a Bev Gannon restaurant off the beaten path in upcountry. Oprah's favorite (although she only gets takeout) and definitely one of ours as well.

Where do the rich people live on Maui? ›

The community of Kapalua can be found on the northwestern tip of Maui and is home to some of the most luxurious properties on the island. Whether you're looking for luxury houses by the beach or up on the hillside, you'll find your perfect home in Kapalua.

Where is Jeff Bezos Maui home? ›

The 14-acre property on La Pérouse Bay in Makena includes the remains of a Hawaiian fishpond, allowing Bezos to own a piece of the ocean. Bezos' newly acquired property on South Maui's La Pérouse Bay includes a Hawaiian fishpond, granting ownership of the ocean to the world's second richest man.

What is the oldest town in Maui? ›

Wailuku, 1904

Wailuku, with a current population of almost 17,000, was founded on the island of Maui in 1904. It is extraordinarily important in the history of Hawaii. It is the location where King Kamehameha won a decisive victory over other chiefs in 1790.

Where not to stay in Maui? ›

The West Maui beaches beyond Kapalua, like Mokuleia and Honolua, can be very dangerous, particularly with high winter surf. And Makena Beach (aka Big Beach) in South Maui is one of Maui's most scenic beaches, but notorious for rogue waves that knock people down, causing serious injuries.

What is the best month to go to Maui? ›

The best time to visit Maui, taking into consideration the weather, demand for accommodations, and how crowded, or not, the island is, are the month(s) of April, May, August, September, and early October. Some call these Maui's 'off-season periods' or the 'shoulder months.

Which side of Maui is expensive? ›

Maui's South Side is known for some of the island's most expensive real estate and its ultra high-end Wailea resorts. Nearby Kihei, just north of Wailea, is known for its relaxed beach town vibe and long stretch of sand. Both tourists and locals intermingle in Kihei.


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