Two Week Maui Itinerary
You should set aside at least 5-7 days to visit Maui. More the better. We usually spend two weeks on the island, and it is never enough. Check out this suggested two week itinerary. You can use this as good starting point and improvise.
DAY 1: Arrival & Visiting Kapalua Beach
After checking in to your hotel, rest a bit, and then head for Kapalua Beach. Don’t overdo the sun on your first day. After an hour or two at the beach, drive to Lahaina and spend a couple of hours walking the historic old town. Go to the Old Lahaina Luau at sunset to immerse yourself in the Hawaiian culture.
Day 2: Going Up a 10,000-Foot Volcano & Down Again
You’ll likely wake up early on your first day in Hawaii, so take advantage of it and head up to the 10,000-foot dormant volcano, Haleakala. You can hike in the crater, speed down the mountain on a bicycle , or just wander about the national park. Try to be at the top for sunrise. It is painful, but completely worth it. On the other hand, you don’t have to be at the top for sunrise; in fact, it has gotten so congested at sunrise that you may be too busy fighting the crowds to have an awe-inspiring experience. Instead, I suggest heading up any time during the day. On your way back down, stop and tour upcountry Maui, particularly the communities of Kula, Makawao, and Paia. Plan for a sunset dinner in Paia or Kuau.
Pack a lunch and spend the entire day driving the scenic Hana Highway . Pull over often and get out to take photos, smell the flowers, and jump in the mountain-stream pools. Wave to everyone, move off the road for those speeding by, and breathe in Hawaii. Plan to spend at least 2 nights in Hana (You will need to book a hotel.)
DAY 4: Spending a Day in Heavenly Hana
You have an entire day in paradise and plenty of things to see. Take an early morning hike along the black sands of Waianapanapa State Park ; then explore the tiny town of Hana. Be sure to see the Hana Cultural Center & Museum, Hasegawa General Store, and Hana Coast Gallery. Get a picnic lunch and drive out to the Kipahulu end of Haleakala National Park at Oheo Gulch. Hike to the waterfalls and swim in the pools. Splurge on dinner in the dining room at the Hotel Hana-Maui. Spend another night in Hana.
DAY 5: Enjoying Wine, Food & (Hawaiian) Song
Check to see if the road past Hana is open (roads can be closed due to flooding or debris); if it is, continue driving around the island, past Kaupo and up to the Ulupalakua Ranch and the Tedeschi Vineyards and Winery. Stop at Grandma’s Coffee House for a cup of java, and then head down the mountain, with a stop for lunch at Haliimaile General Store. Spend the afternoon at the Maui Ocean Center, in Maalaea, checking out the sharks and other marine life. Have dinner in Lahaina and see the drama/dance/music show Ulalena. If the road past Hana is closed, go back along the Hana Highway the way you came, stopping for lunch at Haliimaile, and then follow the rest of the itinerary from there.
DAY 6: Sailing to Lanai
Trilogy offers the best sailing/snorkeling trip in Hawaii, so don’t miss it. You’ll spend the day (breakfast and lunch included) sailing to Lanai, snorkeling, touring the island, and sailing back to Lahaina. Plus, you still have the afternoon free to shop or take a nap.
DAY 7: Relaxing & Shopping
Depending on how much time you have on your final day, you can decide to relax on the beach, get pampered in a spa, or shop for souvenirs. Spagoers have a range of terrific spas to choose from, and shopping aficionados should check out many interesting stores in the island. Check out Iao Valley.
DAY 8: Flying or Ferrying to Molokai for a Mule Ride
Head over to the “Friendly Isle” to experience the Molokai Mule Ride down into the Kalaupapa Peninsula. This is an all-day experience that you will remember for the rest of your life. You can either take the ferry over or fly; either way, don’t miss this opportunity.
DAY 9: Snorkeling in an Old Volcanic Crater
Take a day to see the fish inside the Molokini Crater. Go in the morning before the wind comes up. If it’s whale season and you’re lucky, you may spot whales on the way over or back.
DAY 10: Gliding over the Water in a Kayak
Kayaking is so easy that you will be paddling away within a few minutes of lessons. One of the best kayak places is Makena—it’s calm, the water is so clear you can see the fish, and you’re protected from the wind. After a couple hours of kayaking and snorkeling, stop for a picnic lunch at Makena Landing and then explore this area. If you still have energy to spare, hike over to La Pérouse Monument, along the rugged shoreline.
DAY 11: Taking an Off beat Tour
Plan at least one off-the-beaten-path tour while you’re on Maui. If you love good food, book the tour of Chef James McDonald’s O’o Farm, which includes lunch. Cheese aficionados will love visiting Surfing Goat Dairy and sampling its cheeses. For a really exotic experience, take the Combo Tour at Alii Kula Lavender, which includes a tour of the farm and lunch made with lavender products.
DAY 12: Seeing Maui from a Helicopter
The feeling of suddenly lifting off straight up in the air and then floating over the island of Maui in a helicopter is a memory that will stay with you forever. Of all the helicopter companies, I recommend booking with Blue Hawaiian Helicopters for the most comfortable, informative, and fun tour in the air. After the tour, take some time to explore old Wailuku town, wander through the shops, stop at the Bailey House Museum, and then take in Waikapu, Kahului, and Puunene.
DAY 13: Walking Back in Time in Lahaina
Plan to arrive in this historic town early, before the crowds. Eat a big breakfast, and then put on your walking shoes and take the self-guided historic walking tour of the old town. Plan to do some browsing in the quaint stores, watch the surfers skim the waves in front of the library, and pop over to Kaanapali to the Whalers Village Museum. Then drive around the head of the island on the Kahekili Highway, stopping to see the ancient Hawaiian village of Kahakuloa and the Halekii and Pihanakalani Heiau on the Wailuku side.
DAY 14: Enjoying Your Last Day
After 13 days of exploring Maui, spend your last day doing what you loved best: beachcombing, snorkeling, hiking, shopping, or whatever your favorite Maui activity is. Pick up a lei before you go to the airport, so you will have a little bit of Maui with you as you say aloha.
Check out other sample itineraries too.