The Ultimate Maui 5-Day Itinerary
And I’m not the only one. For over 15 years, the readers of the travel magazine “Condé Nast Traveler” choose Maui to be the best island. May it be the dreamlike beaches and sunsets or the numerous natural wonders, Maui is definitely worth a visit – even in just 5 days.
Long ago the harbor city Lahaina was the capital of Hawaii before the regency was relocated to Honolulu in 1845. The history of the island’s emergence becomes clear when you look at its topography. In the west, the 1.764 m (5.787 ft) high Puu Kukuiof rises for about two million years.
Its counterpart in the east is by far younger and much higher: the Haleakala forms the largest part of Maui with 3.055 m (10.023 ft) height. Both volcanoes are connected by Central Maui, a fertile valley that also forms the narrowest point of the island. Not even 15 km (9 mi) separate Kahului Harbor in the north from Maalaea Bay in the south.
Besides the breathtaking and diverse landscape of Maui, the numerous water sport activities are another wealth of the island. While in the southwest beautiful beaches attract the visitors, in the northwest divers, snorkelers and surfers populate the beaches. Especially the North Shore is a popular spot for adventurous surfers since there are one of the biggest waves during the winter months.
Now that you’ve learned a little bit about the Hawaiian island, let’s get to the most important part: what can you do in Maui in a 5-day itinerary, what is the best travel time, how to get to Maui and where to eat and stay? Let’s go!
Best travel time
Maui only has two seasons: a warm and dry summer and a mild and wet winter. While summer starts from April to October, winter is from November to March. During the summer months, you can expect pleasantly warm weather with average temperatures from 25-30°C (77-86°F). Maui’s winter starts with occasional storms and temperatures from 20-25°C (68-77°F). Ocean temperatures are always nice and warm. Although it can rain sometimes during the winter months, I recommend traveling to Maui from December to March. It’s the off-season and prices are lower than during peak season.
My boyfriend and I traveled to Maui in February and we only had one hour of rain and this was in the rainforest. So the rainy season is really no problem at all. Also, you should know that there are two different types of weather on Maui throughout the year. While the western side is dry most of the year, the south-eastern side of Maui (where the rainforest is) has lots of rainy days. But usually, tourists are staying on the western side as we did.
How to get to Maui
First of all, we stayed 5 full days on Maui. It doesn’t sound like much and it definitely isn’t. But most of you do island hopping and stay around the same days on one island. Of course, you can probably spend two weeks on Maui. However, even Maui in a 5-day itinerary is possible. So don’t worry, you can still see the most amazing places the island has to offer.
Our travel route started in Munich, Germany. From there we flew straight to San Francisco and then to San Diego. In the Californian city, we spent 4 days to get used to the time zone (9 hours time difference from Germany). From there we could fly straight to Kahului Airport (OGG), the international airport on Maui. The flight is about 6 hours from California and was operated by Hawaiian Airlines. On our way back we flew with Alaska Airlines. So there are several airlines that fly non-stop from California.
Unfortunately, we missed the flight to our last stop San Diego, because we stood 2.5 hours in the security queue. So here’s my tip: if you don’t have a direct flight, but the first layover in an American city as a foreigner, plan enough time so you won’t miss your flight to Maui.
If you come from far away (US east coast or Asia), the best and cheapest option is to fly into Honolulu International Airport (HNL). From there it’s just a 30-minute flight to Maui. If you fly in from Honolulu, you have the possibility to fly to one of the two other airports: Kapalua Airport (JHM) in West Maui and Hana Airport (HNM) in East Maui. If your hotel is closer to one of these airports, it’s better to fly to either one so you don’t have a long way to your accommodation in the end.
Travel Insurance for Maui
If you’re still looking for travel insurance – which you should if you plan to do lots of activities – with World Nomads you can find it. You can book insurance for any kind of vacation. Whether it is a diving tour or a surf trip, travel insurance will save you lots of money in case of an accident. So, I highly recommend it – especially when traveling to Maui in a 5-day itinerary.
Maui in a 5-day itinerary
One of the number-one highlights on Maui is the Haleakala. It’s not just the largest inactive volcano in the world, but also covers more than 75% of the island of Maui. Proud 3.055 m (10.023 ft.) high, its amber slopes are visible from every point of the island. So it’s impossible to miss it! A very touristic thing is to visit the volcano in the early morning to watch the sunrise. There are several tours to get up there (typical costs for a sunrise tour: $300 in high season).
But it’s not for long sleepers. Depending on your hotel location, you have to get up at 2 am to get on the peak before the sunrise, because it takes about 2 hours from the Lahaina area. An alternative is seeing the sunset. It’s as beautiful as watching the sunrise and you benefit from fewer tourists. My boyfriend and I wanted to do the sunset tour, but it was too expensive for us (typical costs for sunset tour: $350 in high season).
But we were lucky. One of our Uber drivers said, he does private tours and can take us up there for about $200. His name was Jamie and we can highly recommend him. He gave us helpful tips and he even took us to the Ho’okipa Beach on our way back. If you also want to save some bucks, send him a message: +1 (808) 214-0884.
If you rent your own car, make sure you will make a confirmed reservation two months in advance. It’s only necessary for the sunrise tour. For the sunset tour, you don’t need any reservations. The entrance fee for the Haleakala National Park is $25, which everyone with a vehicle has to pay. Although it can get pretty warm on Maui, bring warm clothes if you plan a tour to the Haleakala. The volcano is very high, so it can get snowy there sometimes. But with a thick jacket, long pants, and ahead you will be fine.
Road to Hana
The Road to Hana is a route that should be on everyone’s bucket list when visiting Maui in a 5-day itinerary. Hana was once an important Hawaiian settlement and scene of bloody battles. In addition, Queen Ka’ahumanu, the favorite wife of Kamehameha I, was born there in 1768.
Today, Hana is a popular sleepy ranch town, which visitors from all over the world visit daily. I recommend booking a tour to experience nature at its finest. Otherwise, you will be too busy driving. Because the Road to Hana passes cascading waterfalls, breathtaking vistas and 59 bridges around 620 adventurous curves. Also, a part of the way is not allowed to be driven with a rented car (which car rentals don’t tell you). So it’s better to book a tour.
But one of the highlights was the Black Sand Beach. We had an hour to enjoy this beautiful beach with fascinating black sand. From there we drove straight to lunch. And after that, we visited the famous Kailua Falls and made our way back through the Kipahulu Valley. All in all, it was a great tour with an awesome tour driver who gave us inside stories about celebrities and the locals. So one thing is for sure: no visit to Maui would be completed without visiting the Road to Hana.
“Merciless sun” means the Hawaiian name of the ancient whaling and plantation town of Lahaina on the west coast. Merciless is also the tourist marketing of the town and the north adjacent city Ka’anapali Beach, where the large hotels string together. Nevertheless, the place has retained its charm. So you can find old wooden houses along the shopping mile “Front Street” and an always-bustling harbor. Especially if you see the sunset from the beach, the promenade or one of the restaurants, you will fall in love with this charming little town.
It was the sun and the beautiful location at the foot of the West Maui Mountains that once caused King Kamehameha I. to transfer his farm to Lahaina. Later, the city became the most important whaling port in the Pacific. After 1860, however, the whaling went back and Lahaina fell into a deep sleep, from which it was only the modern tourism that woke it up again.
Nowadays, you can visit the picturesque harbor, the Front Street, the Banyan Court, which is the oldest tree of Maui and the Kamehameha Ili Park where you can try your surfing skills as a beginner.
The best time to do whale watching is from November to March (peak season is February though), which is also the best travel time. During this period, the animals swim year after year from Alaska waters to the coast of Maui for their annual winter migration. That’s why you can watch so many of them in their natural environment. But don’t worry. The boats are not allowed to get closer than 100 yards unless the whales swim by themselves to the boat.
Do you want to know more about whales? Then I can recommend the website Maui Whale Watching. They provide you with all the details and can probably answer any questions you have about whales.
Snorkeling at Lana’i
One of the things you shouldn’t miss out when you’re on Maui is snorkeling. While the Molokini Crater is a popular snorkeling spot, I would rather recommend snorkeling at the neighbor island Lana’i. Unlike the Molokini Crater, you still find live corals and a variety of different fish species at Lana’i. Also, you avoid many tourist boats and hundreds of people snorkeling there, too.
And on our way back we even had the chance to watch the whales from near. They got so close that it was even better than on our whale watching tour. So if you want to save money, book the snorkeling tour at Lana’i. Then you get both snorkeling and whale watching, which is an amazing experience and which was one of our highlights on our Maui 5-day itinerary.
Oneloa Beach is much bigger than Ka’opala, but also not a tourist magnet. It’s close to the Honokahua Bay which is a popular spot for surfers. Here the waves can get really high. So due to the closeness to the Honokahua Bay, you will notice that the ocean is rough at Oneloa Beach as well. But still, it’s a wonderful beach where you can enjoy the waves or watching surfers. When we got there we were so lucky, because the beach was almost empty.
But besides the nice area, the beach also strikes with lava formations and a little hiking path from where you have a great view over the beach and the coastline. It might not be a good beach for families with children, but definitely worth a visit for travelers and backpackers.
Unfortunately, we hadn’t had much time to visit Makena Beach on our Maui 5-day itinerary, but I’ve heard and read so many good things about it. People say it’s one of the most beautiful beaches on Maui. So at least, I want to mention it here. It’s also called Big Beach and is located on the southwest coast of the island.
While the beaches around the city Kihei are narrow and crowded, the beaches further south offer fine sand and secluded wideness. Here you would probably find the peace you’re looking for. So if you have enough time, please go and check it out. I’m sure you won’t regret it!
Where to eat on Maui
Since we ate most of the time in Lahaina and Kahana, I can only give you recommendations in these two cities. If you stay in Kahana, you should check out the Maui Brewing Co. It’s Hawaii’s largest craft brewery and serves delicious food – including vegetarian and even vegan dishes.
In Lahaina, we enjoyed a great burger and sunset at Cheeseburger in Paradise. It’s an oceanfront restaurant with great burgers and a beautiful view of the ocean. Other restaurants I can recommend are Surfside Pizza Maui, where you get oven-fresh pizza as you like it, and the Cool Cat Café, where you also can enjoy delicious burgers.
And if you’re just looking for a little dessert after dinner or a good refreshment, go to Banyan Treats. They are located in the heart of Lahaina and have ice cream to die for. Also, try the ice cream sandwiches. They were voted Best Dessert at Lahaina’s Plantation Days. Locally produced and 28 tropical flavors – what else can I say, except yummy!
Last but not least: banana bread. It’s very popular on Maui, so you won’t have a hard time finding it. We loved it and bought a whole bread, which didn’t last long!
Where to stay on Maui
I must say, finding cheap accommodation wasn’t that easy at all. Maybe it was so expensive because I searched for it for only 2 months in advance. But I guess Hawaii is just expensive. Luckily, I found a nice resort for my boyfriend and me for a reasonable price. The Kahana Falls Resort is situated 20 minutes north of Lahaina by car and has a little pool and a waterfall, a small fitness room, and a 24-hour-reception. Tours can be easily booked by the Island Activities desk. The woman there also gave us great tips about the area and food recommendations. Moreover, they have a welcome get-together for new hotel guests on several days.
The rooms were more like apartments with a little kitchen area. That made it possible to store some food in the fridge and cook something (although we always went out for dinner). The Kahana Falls Resort also has a barbecue area, where you can grill. So no matter how hungry you are, I think you won’t starve at all.
The total price of the trip
As you might have noticed, Hawaii is pretty expensive and not a good destination for backpackers. But still, it’s so diverse in nature, that I can only recommend to everyone to go there and experience it yourself. But let’s get to the most important part: how much did we pay for the whole trip, Maui in a 5-day itinerary?
Our flight from San Diego to Kahului and back costs $300 per person. As I wrote earlier, it’s cheaper to fly into Honolulu first. But we wanted it more convenient and looked for a direct flight.
The Kahana Falls Resort was about $960 for the two of us for 5 nights. It was one of the cheapest hotels we could find. But we were quite happy with our choice because we had everything we needed. For the clean-up, we had to pay an extra fee, which wasn’t included in the price we already paid. So all in all, it was about $1.020.
For Uber drives, we paid around $100. We drove with Uber from the airport to our hotel and two times from our resort to Lahaina and back.
The tours were a bit pricey. The Road to Hana tour costs us $180 per person. The snorkeling adventure around the island Lana’i was about $120 per person. And the private tour to the Haleakala volcano was $200 for the two of us plus the entrance fee of $25 for the vehicle. So for all of our tours, we paid about $825 for both of us.
In addition, we went surfing in Lahaina. We brought our wetsuits so we just had to pay for the board. We only rented one and shared it, which costs us $30 per day.
That’s it pretty much. As you can see, it was quite an expensive vacation with a total of $2.575 for two people. So if you plan your trip to one of the beautiful islands of Hawaii, make sure you saved enough money.
Download my Maui 5-day itinerary checklist
If you would like to have all the information about this post summed up, simply download my free accessible checklist here. You will find on it the best things to see and do, food recommendations and where to sleep – all on one sheet. So you can easily print it and take it with you on your big trip to Maui.
Also, I hope you enjoyed my Maui 5-day itinerary and you could get helpful information for your next vacation. Let me know in the comments below if you have any further questions or if you have already been to Maui. I would love to hear about your experiences.
I just wanted to let you know that this page contains affiliate links. If you decide to buy something using one of these links, I will earn a small commission. Don’t worry that’s at no extra cost to you, but it does help to fund my travels and keep the website running. Thank you!
im going in july!! this is so helpful :)!! cant wait
Postcards from V
Cool, have fun Kathleen! 🙂
Great itinerary! Doing the road to Hana was one of my favorite parts of visiting Maui. I didn’t get to Haleakala, so I’ll have to do that next time- looked awesome!
Postcards from V
Oh then you should go again. From the Haleakala you have an amazing view over the island!
I was in Maui last year and absolutely loved it! This is a great post with beautiful pictures and I’ll be sure to reference it when I go back!
Postcards from V
Thank you Marisa, if you need more tips, let me know!