Best 5-Day Itinerary in wonderful Maui, HI

If you are reading this post, you probably have just booked flights to Hawaii and you’re now wondering how to make the most of your time there. Or you are strongly thinking about booking this amazing trip and looking for confirmation this is the place to go. Either way, I can guarantee you are making the right choice going to Maui, it is such a wonderful place to visit with so much to see and do!

Maui is the second biggest island of the Hawaiian archipelago after Hawai’i (Big Island) and the second most visited after O’ahu (where Honolulu is). Between the diversity of the tropical rainforest on the road to Hana, the beautiful sandy beaches by Kihei or the magmatic breathtaking Haleakala crater, Maui has it all to seduce you!

The weather is tropical with wetter winter months and dryer summer months, but overall warm and sunny year round. Prices tend to go up around national holidays (Thanksgiving, Christmas and spring breaks) but you will find a wide range of accommodations, restaurants and activities for all budgets.

We went in mid April as it was what was the most convenient for our group of four friends, and after a lot of research and considerations, we came up with this 5-day itinerary, a perfect combination of sportive hikes, wilderness experience, relaxation and sightseeing! 

The crew at OGG airport – adventure begins now!

DAY 1 – Getting there

Although there is a direct flight from Denver Airport to Maui, it was quite pricey so my partner and I opted for a cheaper option with a connection in Los Angeles (LAX). From there, it is a quick and easy 5h30 hour flight to Kahului airport (OGG), the main city of Maui island. 

I’d recommend renting a car, it will make it a lot easier to get to the different sides of the island, especially if you’re looking to do some exploring in less touristy areas. If you are spending all your time at the same hotel though, you can probably get by with taxis and Ubers, available at the airport and in all the main cities. We booked ours with Turo, which was more affordable than typical car rental companies. 

Since we landed mid afternoon, we didn’t plan much for our first day in Maui, we just wanted to relax after the flight and settle in. We decided to stay in Kihei/Wailea, which is only 20min from the airport so we could be in the ocean before sunset!

Where to stay in Kihei: We booked 2 nights at Kamaole Castle Sand (https://www.castleresorts.com/maui/kamaole-sands/), which was on the higher end for accommodations during our trip. Most apartments in resorts in Hawaii are actually privately owned as time shares, managed by the hotel. On the positive side, our apartment came with a lot of beach equipment: beach towels, beach chairs, umbrella, body surfs…etc  

Castle Resort – Room View

Where to have dinner in Kihei: after checking out the beach, we didn’t want to take the car again, so we walked around the neighborhood and discovered a great local restaurant: Coconut’s Fish Cafe (https://coconutsfishcafe.com/). They have good poke bowls (although you might want to ask for the sauce on the side), but their best deal is the ahi tuna steak. 

While you are in the area, I’d recommend you stop at Whalers General Store, they sell absolutely delicious homemade papaya bread, pineapple bread and coconut bread that we enjoyed a lot for breakfast the next day.

DAY 2 – Relax and Beach

After a nice cup of Hawaiian coffee on the apartment’s terrace, we set for the beach in front of the resort. There are several beaches in Kihei/Wailea, and most of them have a lifeguard on duty. The nice perk of having jet lag and waking up early is that we got to enjoy Kamaole Beach Park without any tourists and families, and it felt like a private beach between 7 and 9am. Super relaxing!

Early morning swim at Kamaole Beach

Where to have a pastry in Kihei: I’d recommend the Cinnamon Roll Place (https://www.cinnamonrollplacemaui.com/), it’s a mom and pop bakery that offers great (and massive, don’t hesitate to share!) cinnamon rolls among other treats and coffee. 

Where to have dinner in Wailea: Monkeypod Kitchen (https://monkeypodkitchen.com/dine_wailea)! The best restaurant we experienced in Maui, we got the recommendation from 5 different locals, and can only approve of it! It has great cocktails, good food and appetizers and awesome vibes. Out of four dishes tried, our favorite was the Organic Macadamia Nut Crusted Fresh Fish – delicious!
I’d recommend making a reservation, but don’t worry if it shows fully booked online, we learned they reserve tables for walkins, so don’t be shy to just show up. We didn’t wait more than 20min to get a table for 4, and there are some shops around to keep you busy, such as Sweet Paradise Maui Chocolatier (https://sweetparadisemaui.com/), that sells very cute chocolates, worth a try for dessert. 

DAY 3 – Haleakala National Park

If, like us, you are planning a camping trip, you’ll likely need gas since you can’t fly with it from the mainland. The Safeway store will be your best bet for gas and any other missing gear. The drive to Haleakala National Park Visitor Center takes about 1h15min from Kahului, or 1h30min from Kihei, and you’ll likely go through the clouds that hang on the side of the mountain, making for gorgeous views once you get above those clouds! I’d recommend going in the morning as the weather tends to darken in the afternoon, although there is never an absolute guarantee. 

Haleakala National Park is very popular, yet big enough the hiking trails are not overcrowded. If you’d like to overnight camp, you will need to get a permit, that you can book online: https://www.recreation.gov/camping/gateways/2751 In addition to the campsites, there are also 3 cabins you can reserve, ideal if you don’t want to carry a tent and still enjoy the wilderness. 

We had a 3 days and 2 nights trip planned, our itinerary started from the Visitor Center, then Paliku campsite the first night, and Holua campsite the second night. However, the weather conditions made us change our plans last minute; thunderstorms were on the radar and the rangers recommended against going to Paliku as it is further down in the crater. We hiked downhill into the crater and headed towards Kapaload Cabin, from there we went north around the different craters and mounts, saw Kawilinau bottomless pit (a 150 feet deep hole) and set up camp in Holua. The next morning, we hiked up to Halemau’u trailhead, from where one of us hitchhiked up the road to get our car. 

DAY 4 – Road to Hana

Since the storm chased us a day early from Halaekala, we booked a campsite by the water in Wai’anapanapa State Park and got to start the Road to Hana a day earlier and felt less rushed along the way.

The Road to Hana (Hana highway) starts in Haiku Pauwela and goes along the tropical north east coast of the island. In addition to the super scenic views, there are many waterfalls and viewpoints worth stopping along the way. Be careful where you stop though, as most waterfalls are in a blind turn with a bridge crossing the river and parking is limited. You can swim in a few natural pools, as a rule of thumb the least parking spaces you see, and the more remote the waterfall is, the more magical the experience will be. 

Here is a list of stops I can recommend, there are many more and you could take the entire day driving the Road to Hana! 

  • Maui Garden Grove Cafe: we stopped for a fresh smoothie, it’s not the only cafe, there are several on the road with viewpoints. 
  • Eucalyptus Rainbow Trees: one of our favorite stops! Those massive and very tall eucalyptus have a bark colored like a rainbow, it is very pretty and impressive. Parking is fairly easy too. 
  • Haipua’ena Falls: only a handful of parking spots, if you’re lucky enough to find one, it is worth the 5 minute hike to see the waterfall. As we had the pool for ourselves, we took a quick swim to cool off – amazing! (Barbara swimming Picture)
  • Nu’yenle’e Waterfalls – another very cool waterfall worth a look – and pictures!
  • Ke’ane Arboretum: another strong recommendation! This arboretum has species from all over the world, it is free of charge, with easy parking. It is fairly big, we spent almost 45 min walking up and down the path. Don’t go to the other one (Garden of Eden), it is more touristy, with a $20 entrance fee.
  • Ke’ane Peninsula: the road has a pretty view of the ocean and only adds about 10-15 min of driving. Note this is not a full loop though, you will have to come back to rejoin the Road to Hana. It would be perfect for a picnic stop. 
  • Upper Waikani Falls – another very pretty waterfall worth a look!

Where to stay in Hana: Hotels in Hana are limited and often a little pricey, likely because they know you won’t do the out and back drive the same day. Since we had our camping gear, and changed plans last minute, we booked a night at Wai’anapanapa State Park for camping. We understood it is usually better to book in advance as it is really popular but since we came during the off-season we were able to find a spot. Reservations can be made online here: https://dlnr.hawaii.gov/dsp/parks/maui/waianapanapa-state-park/

Honestly, we couldn’t have dreamed of more perfect conditions for camping! Tents can be pitched on the grass within walking distance to the Black Sand Beach, it has bathrooms and showers, and picnic tables. Since the park closes at 6pm, we enjoyed having the beach almost for ourselves from 5 to 6pm as people were leaving. The beach is sandy and offers easy water access, while being protected by cliffs so the waves don’t get too high, even in the winter.

DAY 5 – Hana / Haiku

There are so many hiking trails and beaches near Hana that are amazing it is hard to pick one! Since we were already in Wai’anapanapa state park, we chose the coastal hiking trail that is past the Black Sand Beach. The trail gets really rocky, so I’d recommend wearing real hiking shoes or at least closed shoes if you want to make it far. The scenery is absolutely beautiful, and it is not too busy of a hike. Reward yourself with a swim at the Black Sand Beach afterwards!

Where to have lunch in Hana: Continuing towards Hana there is a shared food truck area with at least 10 different options for food and drinks. We ordered from Poke Bob’s for ahi tuna poke, from the truck next door for fresh juice, and from a third truck for coffee. The location of this delicious stop is here!

Had we had more time, we could have explored more beaches and hiking trails in Hana, but as we had already spent a night in Wai’anapanapa state park, we made our way back to Haiku. On the way back we stopped at the arboretum and other waterfalls we had missed on the way in. 

Where to stay in Haiku: We booked an Airbnb called Haiku Sanctuary, nothing amazing but it was good for the price and fit our needs coming back from Hana. Since our flight was at 2pm the next day, it also got us closer to Kahului airport. 

Where to have dinner in Haiku: Our Airbnb host recommended Nuka (https://www.nukamaui.com/), a Japanese restaurant for sushi, and it was really good. In general, getting recommendations directly from the locals is the way to go to ensure you have the most updated info! While waiting for our table to be ready, we had a drink at Colleen’s At the Cannery (https://colleensinhaiku.com/), which had a younger crowd but decent vibe and had the advantage of being within walking distance. 

LAST DAY – Leaving Maui

Already our last day in Maui and it is time to head to the airport OGG! We were flying to Kaui next with Hawaiian Airlines, bags cannot be checked online but it is really easy to do so at the airport, and going through security was a breeze. If you have a couple of hours to kill though, here is the last bit of our itinerary:

In the morning we looked for a beach on the north shore to swim. In the winter/spring season, the waves are a lot bigger on the north shore as they are in Kihei (or the protected Black Sand Beach), and at the first beach we went to, Ho’okipa beach, a life guard told us this was for experienced surfers only, and currents were too strong. We kept driving down the coast until Kuau Cove, which is a great sand beach, a little hidden, with a reef that breaks the waves and current. It’s also perfect for snorkeling, and we saw all kinds of marine life! It is located next to Mama’s Fish house, a restaurant that had also been recommended to us by several locals and tourists alike, but unfortunately we didn’t have the chance to try it. The restaurant opens at 11am, so the beach is really quiet and peaceful before that time.

Where to have lunch in Paia: continuing our drive towards the airport, we stopped in Paia for lunch and ate a last poke ball at Tobi’s Poke & Shave Ice (https://tobispokeandshaveice.com/), I’d recommend the tasty garlic flavor! Paia also has a post office if you need to buy stamps and send postcards before leaving Maui. Post lunch, treat yourselves with an ice cream from Artisan ice Cream on Baldwin Avenue, https://www.artisanpaia.com/ they are delicious!

I hope you enjoy your trip to Maui as much as we did!