Hawaii can be a little overwhelming to plan…which island to visit, where to stay, should we visit more than one island? I’ve done Hawaii three times, each in a little different way. For Maui, I think there’s enough to do that you should just spend a full week there, and come back another time to see some of the other islands. I’ve done Maui as a family when my kids were 11 and 14, and with my husband on a couple’s getaway. This itinerary is a combination of the best of both. As far as time of year to visit, the weather doesn’t change much throughout the year, but dry season is April to October, and rainy season is November through March. And if you want to go whale watching, the best time to see them is generally December through May. This is a pretty full itinerary, so you can certainly eliminate some things you’re less interested in and spend more time at the beach!
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Here is a sample itinerary for 6 days in Maui, any time of year, and good for anyone!
DAY 1: ADJUST TO TIME CHANGE, BEACH, AND SNORKEL TRIP TO MOLOKINI CRATER:
First, where to stay? There are a few areas of Maui that you can stay in (the main resort areas are generally along the West coast where the beaches are), but most stay in Kaanapali, Lahaina, Kihei, or Wailea. Given the recent fires in Lahaina, I’m not sure what the status of staying in that area is currently. There are lots of options for Air BnB rentals if you prefer to stay in a home or apartment. I prefer resort-style lodging, so I stayed in Wailea on both of my visits, and highly recommend that area. The first time we stayed at the Fairmont Kea Lani, which was a very nice, sprawling property, right on the beach, toward the South end of Wailea. The second time we stayed at the Wailea Marriott, also very nice, newly-renovated and set back from the beach a bit, on the North end of Wailea. The Marriott was a better location (lots of options for walking to restaurants and shopping), but the beach was a pretty long walk from the main hotel rooms. Both are along a really nice walkway that runs past all of the resorts in Wailea, right along the water. It’s about a mile long one way, and is perfect for sunrise or sunset walks.
Transportation…this is a tough one. We rented cars both times, and it is really expensive in Hawaii. We found that we didn’t use the car that much, and sometimes ended up taking an Uber because we didn’t want to deal with the traffic. If you have a smaller group (4 or less), you can probably get away with just taking Uber, especially if you’re staying in an area that has a lot of restaurants in walking distance. With that said, if you do most of the excursions on this itinerary, you will need a car.
For most travelers, you’ll probably arrive in Maui pretty late in the day (especially in whatever time zone you’ve come from). The goal is to stay awake until a normal bed time in Hawaii so that you can sleep as late as possible. The first morning you will probably wake up really early either way, and will get pretty tired by dinner time. For the first day I’d suggest spending the morning at the hotel beach or pool, and taking a walk down the path that runs along Wailea to get familiar with the area (there’s a Starbucks in the Marriott on the North end of the trail…place your order in advance though because it’s super busy!). Then in the afternoon, consider doing one of these snorkel trips to Molokini Crater.
The snorkel trips depart from Ma’alaea Harbor not far from Kihei, so I’d suggest getting dinner in that area after your trip. There’s a great restaurant called Seascape in Ma’alaea (a little more upscale with harbor views), or for more casual fare check out Dina’s Sandwitch restaurant in Kihei, and add your own dollar bill to the wall!
DAY 2: ROAD TO HANA
The Road to Hana seems to be polarizing…people love it or hate it. Personally, I think it’s a must do at least once! You can drive it yourself using a self-guided tour like this one, but I would recommend doing it with a guide. I truly think you’ll get more out of the experience, and it will take the stress out of driving (it gets very hairy in spots!) so the entire group can sit back and relax. We booked a private tour through Viator similar to this one, and it was amazing. Our guide picked us up at our hotel in a clean, air conditioned van, equipped with water and soda for the day. We stopped at a black sand beach, at waterfalls, did cliff jumping, swam and climbed through a cave, saw amazing landscape, and ended with a visit to a beach where there were a number of Green Sea Turtles basking in the sun.
We stopped several times for quintessential Hawaiian food along the way as well. Banana bread and coffee at a local bakery to start the day, followed by lunch at Braddah Hutts BBQ (a barbecue food truck), and dessert in the afternoon at Coconut Glen’s vegan and dairy-free ice cream (made with coconut milk)!
DAY 3: BIKE DOWN THE HALEAKALA VOLCANO AND DINNER IN WAILEA
This activity is not for the faint of heart, but it’s actually not as scary as it might seem at first. It’s a 15 mile bike ride down the Haleakala volcano, with the bike ride descending from 6,500 feet! I was a little uneasy about it the first time I did it, especially given that my youngest was 11. Note that the minimum height to ride is 4 ft 10 inches. I’ve done the tour twice, both times with Bike Maui. There are several options for the the ride, so check out the websites and decide what works best for your group. If it’s your first time, it’s worth going to the very top to see the Volcano (often above the clouds at 10,000 ft), but it does add an hour or so to the day. You’ll get 30 minutes or so to see the volcano, take pictures, and tour the visitors center, and then your guide will take you back down to 6,500 ft and send you on your way!
There is a sunrise option that starts at 3:30AM (!!) where they bring you to the top of the volcano to catch the sunrise before heading down the mountain. There are also guided options where a guide stays with you the entire time, or you can guide yourself. For my first time with the kids, we went to the top, and then went out on our own the rest of the way…totally manageable. For my second time with just my husband, we skipped the volcano viewing and just did the ride down ourselves.
You’ll need to drive yourself to the bike shop (45 minute drive from Wailea – this is when it’s good to have a car) to get suited up and start your tour. Be sure to pack water and snacks (in a small backpack), and wear layers. It starts very chilly at the top and you’ll be sweating by the end! They will get you geared up with a bike (with hydraulic brakes…WARNING….be sure not to hold down on the brakes for long periods of time or you will not be able to stop!) and a hard-core helmet, and you’ll be on your way. Note there are no bike paths – you are sharing the road with the cars and it’s tight, so be sure everyone in your party is comfortable on a bike.
The tours all start in the morning, and I believe you get 3 or 4 hours to make your way down the volcano and back to the bike shop. It’s plenty of time. Your guide will take give you recommendations of where to stop along the way, especially for lunch. I highly recommend stopping at the Kula Lodge (be sure to map it out so you don’t miss it!) and ask for a table outside. The views and gardens outside are amazing, and the food is great too. Overall, this is a really memorable experience and I recommend it to everyone!
Since you should wrap up with the bike ride and be back to the hotel by mid-afternoon, I’d suggest grabbing dinner at one of the restaurants in the hotel area of Wailea. A couple of our favorites there were Monkeypod, a short walk from the Marriott, and Humuhumu….(longest name ever!) at the Grand Wailea hotel. If you’re looking for good ice cream during your visit, check out Lapperts. And for shave ice, Uluanis in Kihei gets the best ratings!
DAY 4: HELICOPTER TOUR AND KAANAPALI BEACH
This is another adventure that might not be for everyone, but a helicopter tour is a really wonderful way to see parts of Maui that you’d never see otherwise. The views are spectacular, and it’s actually very relaxing! You’ll want to book in advance, and I’d suggest booking a morning time slot so that you can fit all of the other activities in the afternoon. Again, you’ll need a car for this day, as it is about a 30 minute drive to the helicopter departure point.
We took a 60-minute tour through Air Maui. There are several options to choose from; we did the West Maui and Molokai tour. The helicopter seated two of us in the front (complete with clear floor so we could see below) along with the pilot, and then four more in the back. The pilot will play music throughout the flight, point out all of the landmarks, waterfalls, etc. and you have the option to buy the recording of your ride at the end. All in all a really great experience.
After the helicopter tour, head toward Kaanapali (about a 50 minute drive). If you’d like to do some boogie boarding, pick one up at the store along the way. They are inexpensive to buy at a “normal” store (versus a tourist shop), you can use it throughout the week, and then just leave it behind when you head home. In Kaanapali I recommend going to Duke’s for lunch! From my other posts you’ll see that wherever there’s a Duke’s, I like to grab a meal there. Great Mai Tai’s, fresh fish, and the Hula Pie for dessert! After lunch, find a good spot to park along the beach and spend the afternoon on one of the beaches in Kaanapali swimming, relaxing, and boogie boarding!
DAY 5: ‘IAO VALLEY HIKE AND SUNSET CRUISE
If you are up for a challenging hike, or just want to explore the mountains and valleys of Maui, take the 40 minute drive from Wailea to the ‘Iao Valley State Monument. The views alone are worth it. There are a couple of options for hikes (one short and steep, and one longer and steep…ha!). We went with the longer one, the Waihe’e Ridge Trail, which is 4 miles and 1,400 ft of elevation gain. It was a wet and muddy hike, but a nice change of pace from the desert hikes that we typically do, and the views at the top are pretty amazing.
This would be a great night to reserve a ride on a sunset cruise. We did this champagne cruise out of Lahaina Harbor (as of October 2023 the website shows that they plan to resume charters from Lahaina starting in January 2024). When we took this cruise in December, we happened to see a lot of whales which was an added bonus!
DAY 6: BEACH DAY AND LUAU
For the last day, I like to keep the day open just in case there are cancellations earlier in the week that need to be rescheduled. This itinerary is very packed, so there isn’t much room for error. Normally, especially with kids, I’d plan for a couple more down days in between the excursion days. For the last day, I’d recommend going out for breakfast (check out Honolulu Coffee Company if you’re on the North end of Wailea) and then just relaxing by the pool or on the beach at the hotel for the day. At the Fairmont, the water is usually pretty calm and you can snorkel right off of their beach.
If you would like to do a Luau, it’s worth doing at least once. We didn’t do one in Maui since we had done one on the Big Island on another trip, so we decided to skip it this time. But, based on my research, the best Luaus on Maui are at the Westin Kaanapali, the Sheraton Kaanapali, and the Marriott Wailea. A Luau would be the perfect way to end your Hawaiian vacation!
Great post! I have done the Marriott Wailea Luau and agree with your endorsement. On my next trip, if I do another luau it would be this one.
Good to hear, Ken!