Your Ultimate Maui 5 Day Itinerary and Travel Guide

How to Spend 5 Days in Maui: A Complete Travel Guide

I have been to Maui three times over the years, and each time I am sad to leave. There are so many things to see from the Road to Hana, Haleakala National Park, luaus, seasonal whale watching, to beach and ocean activities. Maui is the second-largest Hawaiian Island; however, it feels quite small compared to the Big Island of Hawaii. Its size makes it easy to fit in all the activities you want to do during your stay. My top recommended activities for couples who are first-time visitors are all included in this itinerary, and it still leaves time for taking it all in, enjoying the beaches and scenery, and relaxing.

This Maui 5 day itinerary will help you make the most of your time on this beautiful island.

Key Travel Tips Before You Go

In my opinion, there is no wrong time of year to visit Maui. Many people stay in West Maui near Kaanapali, South Maui around Wailea, or Napili Bay. All areas are excellent places to stay in both summer and winter. Kaanapali is on the leeward side of the island, which is the area that tends to have less rainfall than the windward side. It also tends to be warmer and drier in the winter months. There are many condos there, which can be quite cost-effective if you do not want to stay at a hotel and eat out for every meal.

There may be some more rain showers in the winter months, but chances are, your week on Maui is going to be filled with beautiful weather, no matter what time of year. Similarly, Wailea is on the south leeward side of the island, which tends to have much calmer waters in the wintertime. Napili Bay is generally sheltered but calmer in the summertime and is good for snorkeling.

Car rentals are a must, no matter where you stay. It can be cost-effective to book in advance and find a deal. If you belong to Costco, search their travel site to compare up to four different rental car companies at Maui’s airport: Kahului. It is also worth checking out Expedia and Kayak. All of the car rental companies are centrally located. You can walk from the arrivals and baggage claim or take a little trolley shuttle.

Day 1: Arrival on Maui, Relax and Explore Near Your Vacation Rental

Day 1 might look slightly different depending on where you are flying in from: the mainland or another Hawaiian Island. If you are flying in from the mainland, chances are, you will arrive in the early to late afternoon. This is a great time to come because you only have to fight off the jet lag for a few hours.

After claiming your bags and picking up your rental car, it’s time to do some food shopping for your condo. Stop at Costco or Safeway to pick up essentials for your week. You will save a lot of money by having breakfast, happy hour snacks, and drinks at your place. Sign up for a Safeway rewards card to get deeper discounts at the supermarket. At this point, you should be ready to check into your lodging and have plenty of time to unpack, head to the beach or pool, and take in your first Maui sunset. You will undoubtedly go to sleep early, so you will be well-rested for day 2.

If you are flying to Maui from a neighbor island, you may arrive anytime in the morning through evening, but I would recommend a similar daytime arrival. If you are on another island, you will have to check out by 11 am or so anyway, so why not head to Maui during the day and drive around a bit to take in the scenery? The drive from Kahului Airport to Kaanapali is full of scenic shoreline views. That gives you an afternoon on the beach where you are staying and either dinner in your condo or at a restaurant nearby.

Day 2: Visit Haleakala National Park

Your first day on the island! It’s a good idea to get one of the best places to see in Maui done today. That will give you a buffer of time between days 2 and 4 for relaxing activities like swimming, snorkeling, or shopping. I would recommend visiting Haleakala National Park today, which can be a shorter half-day or a longer stay, depending on how much hiking you want to do.

A lot of people like to go to Haleakala for the sunrise, which now requires a reservation that needs to be booked 60 days in advance. Then, two days in advance of the desired date, there is another opportunity to book last minute. Those with reservations can enter the park anytime after 3 am on the reservation date. Keep in mind that if you go for the sunrise, it will be crowded and cold.

The time needed to reach the summit of Haleakala depends on where you are staying:

Kahului – 2.5 hours
Wailea – 3 hours
Lahaina – 3.5 hours

Personally, I have never felt the need to drive in the dark for the sunrise and have enjoyed all of my daytime visits for scenery and hiking opportunities. The drive up isn’t particularly scary, but there are a lot of steep, winding roads. There are also tour companies that can take you if you want to sit back and enjoy the scenery instead. Be aware that sunrise and sunset times are popular and will be more crowded.

The advantage of going to Haleakala during the day is driving and hiking in daylight hours. It is never too crowded in parking lots or on trails, either. Check out the official National Park website for more information to plan your visit. Park entry costs are per vehicle. A private vehicle entrance fee is $30. There is a $1 fee for any dates reserved for a sunrise reservation.

My hiking recommendation for a casual visitor would be the Sliding Sands Trail. The trailhead begins at the visitor center and is an out-and-back trail. Visitors can hike to the first overlook, which is a short .5 miles (.8 km) round-trip. Be aware that you are hiking downhill, so the return trip to the parking lot will be all uphill. This trail continues even further downhill for a total of 5.7 miles. There are many more trails and descriptions on the official website. Of course, you can always wait and visit a park ranger for recommendations and up-to-date information when you get there.

I would also recommend driving all the way to the summit and then making stops on the way down. There are different parking and lookout areas, some with short trails, that you can visit along the way. The visitor center at the entrance also has a shop with souvenirs like t-shirts and magnets, as well as hiking supplies and some snacks.

Depending on how long you stay in the park, you could potentially have an afternoon at the beach or go out to lunch afterwards. This does not have to be a whole day event but there is also a lot to see here. The good thing about this itinerary is that it is a starting point for planning your trip and is easily editable.

Day 2 Bonus Activity: Luau

A Maui luau is a rite of passage for any first-time visitors to Hawaii. Upon arrival, you are given a fresh lei to wear. Luaus feature a buffet feast with a traditional Kalua pig roast. There is often an opportunity to view the removal of the pig from the imu (which is an oven built underground). Vegetarian food is also available. As a vegetarian myself, I have found that there were plenty of options for me to eat there.

After the buffet dinner around sunset, the real show begins. This is when the traditional Polynesian hula dancing, sometimes narrated by an MC, tells a story of Hawaiian history and culture. There is something quite magical about it all: sitting under the stars with a fading glow off the ocean and a gentle breeze. Listening to the music and seeing the traditional attire and graceful dancing is a real treat. I always encourage visitors to learn more about the culture and history of places they visit, and a luau is an excellent way to immerse yourself in Hawaiian history.

I can recommend two luaus on Maui since I had first-hand experience with both: the Old Lahaina Luau and the Maui Nui Luau.

First, here are some details about the Old Lahaina Luau. Sadly, I was not able to visit this luau on my recent trip because of the devastating fires that took place in Lahaina. However, this luau is now reopened. The community of Lahaina needs our support now more than ever. This luau is often cited as the best and most authentic luau in Maui. It is located on the ocean at Front Street in Lahaina and operates 7 days per week.

There are different seating options, including tables and chairs, and sitting cross-legged on cushions at low-set tables. The low-set tables are the ones that are directly in front of the stage. Tables have 8 guests and will be shared with others if you are in a smaller party size. Tickets are around $220 plus tax and include food and drinks.

The Old Lahaina Luau begins with a fresh lei and tropical drink. You are escorted around the grounds and shown your seats by one of the hosts. This is a casual time where you can take portraits, visit cultural crafters, and view the imu presentation. After that, a cultural presentation is shared on the stage. When I visited, there was a buffet dinner, but now, there is a four-course meal which is provided to each table. Any requests for vegetarian, vegan, or gluten-free meals should be provided in advance. Once the sun sets, the show begins. The show follows the history of the Polynesian migration and shows the ancient Hawaiian hula, followed by a more contemporary style hula.

My second recommendation is the Maui Nui Luau at the Sheraton Kaanapali. This one takes place on Mondays, Wednesdays, and Fridays, along with some seasonal Saturdays. Unlike the Old Lahaina Luau, this one has two different options: the VIP seating and buffet package and the standard seating. In the VIP package, you are given preferred seating near the front and are ushered to the buffet dinner before everyone else. With the standard option, you are given standard seating and are able to visit the buffet after the VIP users have gotten their food.

The seating is similar to the Old Lahaina Luau, with large round tables, so you will be seated with other people who are not in your party. One note about this seating is that you could be facing away from the stage and have to turn your chair around away from the table to see the show. This shouldn’t be an issue if you are done eating.

The arrival here is casual. Women are given a fresh flower lei, and men are given a wooden carved necklace upon arrival. There is a casual happy hour where you can take pictures and view traditional crafts. The imu presentation occurs here as well. The buffet follows, which features options for vegetarians. Then, the sunset provides for some photo opportunities as you are right on the beach. The show begins, which tells the story of the Hawaiian demigod Maui. The end of this show features a fire dance, which is quite spectacular.

The other difference in this one is that at some point, visitors will be invited up to the stage to dance with some of the men and women in the show. If you are introverted, like me, keep this in mind if you sit in the VIP section. I was invited up to the stage, but I declined because that is not something that I thought I would enjoy. The cost of this one is around $228 plus tax for the adult VIP ticket and $198 plus tax for the standard adult ticket.

You will have a great time at any Maui luau you choose. These are the ones that I have personally visited and can recommend from experience.

Day 3: Beach, Snorkeling and/or Ocean Tour Day

I am a big believer in spacing out my itinerary for a week’s vacation. There is nothing worse than needing a vacation from your vacation! After a day of tours, hikes, and activity, it’s nice to rest and recover. For this reason, day 3 is a day to do an ocean activity of your choosing. Seasonally, I would highly recommend a whale watch. I wrote about the best Maui whale watches in a separate post here. The best times to see humpback whales are during the winter months. If you are visiting another time of year, you can also choose a snorkeling tour from the same companies that offer whale watches.

Napili Bay is a great spot for snorkeling year-round. It is known for having calm waters and a healthy Hawaiian sea turtle population. It is considered one of the best places to see sea turtles. You will need to bring your own snorkel gear or rent it from a place nearby. A popular Hawaiian chain is Snorkel Bob’s, and they have many locations that you can rent from. The beach is beautiful here as well. I would recommend arriving early to secure street parking and spending the morning here. There are plenty of restaurants along the bay that you can eat lunch at as well.

Maui is known for its beautiful beaches, and there is no shortage of options. Ka’anapali Beach is considered one of the best beaches in Maui. It has a long stretch of white sand and plenty of amenities. Black Rock, on the northernmost section, has calmer waters and is good for snorkeling. There are lifeguards, restrooms, and places to eat right off the boardwalk that runs down the beach.

Wailea Bay has calm and clear waters. This is considered a luxury area as many of the most expensive resorts are located here. There is also a beach walk here, allowing you to walk past hotels, shops, and restaurants right along the water. There are plenty of amenities such as bathrooms, showers, and free parking.

Again, you can’t go wrong with Maui’s beautiful beaches. It may be best to visit one near your vacation rental and have a relaxing day there, and catch a sunset dinner at a local restaurant.

Day 4: The Road to Hana

The road to Hana is a scenic drive that takes place along the Hana Highway. This is a long drive because of frequent one-way sections and a winding road. There are also frequent places to stop and view waterfalls, scenic viewpoints, and black sand beaches. There are two options: driving yourself or taking a tour. Either one will be a full-day trip.

I have driven this road twice in a rental car, and if I did it again, I think I would choose a guided tour van. I read that locals were overwhelmed with the return of tourists after the closures from the covid pandemic. It might be more sustainable in the future to choose tour vans that help to limit the number of cars that will be on the road at one time. There is also an option to stay overnight in Hana and return the next day. The best time to do this is early morning. Give yourself an early start and avoid having to drive back in the dark.

Your first stop should be the historic Paia town. This is the hub of the North Shore of Maui. It is a very cute town with an eclectic artistic vibe to it. Fun fact: My sister once saw Woody Harrelson here at the local market, Mana Foods. Mana Foods is also where I would stop and get snacks and drinks for the drive. They have options like sandwiches and wraps that you can take and eat on a picnic table somewhere along the route. Walk around the town a bit and then head over to Mana Foods to pick up your lunch before embarking on the rest of your road trip.

There are audio tours that you can use while driving along the Road to Hana to add to your experience.

Do some research and get a rough idea of the places you want to stop. Things can pass by quickly, so if you are not aware of a waterfall stop, you may drive right by it.

There have been a number of changes in recent years with locations requiring reservations, which are $5 per person. The last time I drove this highway, I was unable to visit Waianapanapa State Park, otherwise known as Honokalani Black Sand Beach. Even though it was a quiet day, they require reservations. Since you likely will not have wifi access, you will be unable to go online and reserve a spot when you arrive here. There are other stops that are worth taking the time for, such as Twin Falls, the Kaumahina State Wayside Park, and the Kahanu Garden.

Last time we drove this route, we stopped at the end at Hamoa Beach Park, which had picnic tables and bathrooms. This was a nice spot to eat the lunch we bought earlier in the day, before making the trek home.

The last thing to note about this tour is that there is a back loop. Instead of turning around and driving back the way you came, you can drive the backside of Haleakala. This allows for a visit to the Pipiwai Trail in Haleakala National Park. There are some things to note about this route, however. There are rumors that it is not allowed with certain rental car companies. I do not think that is true, but check your agreement ahead of time.

There was a period of time when this road was closed due to severe storms that occurred in January of 2024. Check this out in advance. Lastly, some of the road is gravel and can be rough and slow going. Make sure you give yourself plenty of time if the road is open and you do decide to do it.

I hiked part of the Pipiwai Trail, and it is a wonderful hike to a bamboo forest. The entire trail is 4 miles round-trip and can take between 2-4 hours. This is a lot to tack onto an already long day, and adding that to our packed itinerary was pretty tiring. We did not hike all the way to the waterfall for that reason. It was a wonderful hike, but I don’t think I would do that again. By the time we returned to the west side near Kaanapali, it was dark out. This may be a better option by splitting up the Road to Hana into two days and doing this hike the second morning.

Day 5: Culture and Relaxation

Wow, day 5 already! This itinerary has hit all of the best things to see on Maui. Since it is your last day on the island, this is another day that you will want to take it easy. I would recommend visiting either Lahaina Town or heading back to Paia. Lahaina has reopened and needs support as it rebuilds. Be respectful as there may be places that are still cleaning up and closed to visitors. I recommend supporting local whenever you can. This is a great site that offers some suggestions for shopping, dining, and other local companies. Explore local shops, get some shave ice, and have a relaxing afternoon enjoying this beautiful Hawaiian island before you leave.

Conclusion

This flexible itinerary provides some of the best options to spend your 5 days in Maui. The days and activities can be adjusted to suit your needs. Even on a short trip to Maui, you can still have time for leisure activities without feeling rushed. If you have more or less time, you can adapt this itinerary as well. This 5-day itinerary covers Maui’s highlights: beaches, waterfalls, Haleakala National Park, and the Road to Hana.