Beginner’s Guide to Hawaii: Maui, Lanai, and Molokai

Maui

First-time visitors to Hawaii can be overwhelmed when planning their trips. After all, the state has six tourist islands—which is the right one to experience? It’s easy to fall into the trap of thinking Waikiki Beach and Honolulu should be the first stops, especially because most of the direct flight options land on Oahu. Though Oahu has its draws, it really shouldn’t be the first stop for new visitors; Honolulu is a big city with lots of traffic and loads of tourists, and it doesn't accurately reflect what other islands have to offer.

We’ve compiled a three-part series on how to see Hawaii for the first time, and it starts with Maui, which has the perfect mixture of tourism and culture, plus two lesser-known islands: Lanai and Molokai, both of which are easily accessible from Maui and can provide an authentic Hawaiian experience.

Maui

Maui

Maui is just as popular as its sister island of Oahu and can be reached via direct flights from the mainland. What sets Maui apart is that although there are central tourist areas on the island, there’s a lot left to explore and discover beyond that. The island is large, and getting from one side to the other can be daunting, so planning your itinerary with specific locations in mind will help decrease time spent behind the wheel. Maui is for lovers, families, and even groups of friends looking for an escape. As with all the islands, the weather depends on the season, but the Wailea side tends to see the most sunny days. But all it takes is some good planning to get the most out of any weather.

If you are going to Maui, you have to wake up early on the first day and head to Haleakala to catch the stunning sunrise from the top of the crater. Depending on where you are staying on the island, the drive can take some time, especially with traffic. (Make sure to bring warm clothes, as it’s a lot colder at the higher altitudes.) To get a bird’s eye view of the island, Proflyght Paragliding has a two flight options, great for all levels of jumpers because they are tandem jumps. Additional activities in the area include tastings and tours at Surfing Goat Dairy Farm or Tedeschi Vineyards and Winery.

Maui

For the more adventurous travelers, Maui Easy Riders offers a downhill bicycle tour of the Haleakala volcano, and Skyline Eco Adventures has zip lines that overlook Maui’s historic Lahaina town and boast incredible views of West Maui. When it’s time to wind down a bit, Atlantis Submarine Tours has 45-minute rides that depart from Lahaina Harbor and provide a one-of-a-kind view of the ocean floor. Gemini Sailing Charters has many options for visitors, but their two-hour sunset cruise with a complimentary bar is not to be missed. 

Finding good food on Maui is fortunately not a problem, and there is an abundance of great restaurants scattered throughout the island. Some places not to miss include Mama’s Fish House on the North Shore, Ferraro’s Bar e Ristorante at the Four Seasons Maui, Humuhumunukunukuapua’a at the Grand Wailea Resort, The Plantation House in Kapalua, Ka’ana Kitchen at the Andaz Maui at Wailea Resort, Star Noodle in Lahaina, Cuatro in Kihei, and newcomers to the food scene Cow Pig Bun (535 Lipoa Pkwy.; 808-875-8100) and Joe’s Nuevo Latino (131 Wailea Ike Pl.; 808-875-7767), both garnering much well-deserved attention.

Where To Stay

Grand Wailea, A Waldorf Astoria Resort is one of the most stunning family-friendly resorts in Wailea, with award-winning dining, spa, and amenities and one of the best coastlines in all of Maui.

The Westin Maui Resort & Spa recently completed a multi-million dollar refresh and offers many ways to rejuvenate, including its 87,000-square-foot aquatic playground.

Sheraton Maui Resort & Spa is on Kaanapali Beach at the foot of the legendary Black Rock, which means it boasts breathtaking views of the Pacific Ocean from every guest room.

Lanai

Lanai

Lanai is currently accessible via Expeditions Ferry from Lahaina Harbor in Maui. Fortunately, the island provides a unique experience that doesn’t require advanced planning if you’re heading over for a day of snorkeling in Manele Bay. A quick hike to view Pu’u Pehe (Sweetheart Rock), which represents an ancient Hawaiian legend of lovers, is a must; nearby are the tidal pools of Hulopoe Bay. For the best tour of the island, Rabaca’s Limousine visits the Lanai Culture and Heritage Center, Keahiakawelo (Garden of the Gods), and Kaiolohia (Shipwreck Beach). For more active visitors, archery at Lanai Pine Sporting Clays is a highly coveted secret on the island.

The heart of Lanai City is Dole Square, dotted with local boutiques, galleries, and places to eat. Dis 'N Dat is the most unique and most visited boutique in the city; it isn’t hard to find thanks to the bright yellow car proudly parked on the front lawn. Amazing dining options are available at the hotels on the island, but for more local cuisine, check out Blue Ginger Café, Canoes Lanai Restaurant (419 7th St.; 808-565-6537), and the Lanai Ohana Poke Market.

Where To Stay

Four Seasons Resort Lanai at Manele Bay is situated on the cliffs of Manele Bay. This newly renovated property rivals the best Maui hotels and is providing cutting-edge technology conveniences for guests.

Four Seasons Resort Lanai, The Lodge at Koele provides a completely different atmosphere from Manele Bay. It's the more rustic, yet luxurious, lodge of the Four Seasons. Shuttle service between the two properties is available.

Molokai

Molokai

Molokai is one of the least visited islands of Hawaii but can be reached via daily flights from Maui and Oahu, as well as ferry service from Maui. The island remains true to its island roots, as there are no traffic lights and a lot of aloha spirit. The harbor town of Kaunakakai is where fisherman fish and farmers showcase fresh-picked produce. Molokai is also the birthplace of the hula and home to one of the most sacred spots in Hawaii, Halawa Valley, which can be visited by setting up a private tour with the family who resides there. Visitors can also descend 1,700 feet by mule to the remote settlement of Kalaupapa. Molokai is a very spiritual experience, and it’s important to be respectful of the locals. They have only recently begun accepting visits from tourists, unlike the rest of the islands, which have been doing so for decades.

Where to Stay

Hotel Molokai offers a a mix of authentic Hawaiian traditions (like live ukulele on Friday nights) and modern accommodations.

Molokai Shores helps bring guests closer to nature with its ocean views and four acres of lawn. 

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