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

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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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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!

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.

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.

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.

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.

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.

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.

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.

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.

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.

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 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.

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 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.

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.

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.

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 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.

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 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.

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. '

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.

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

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.

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).

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.

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.

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.

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.

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.

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.

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.

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.

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.