It’s no secret that Maui is by far one of the most beautiful and breathtaking islands on earth. From pristine, white sand beaches, exotic wildlife, jaw-dropping scenic hikes and more! This island truly has it all. I’ve had the wonderful opportunity to visit this one-of-a-kind island a few times in my life and each time a small piece of my heart gets left behind. Spending 5 days in Maui is not enough, but it is a good length for a first trip, to see the highlights.
In this guide, I’ve put together for you the perfect Maui 5 day itinerary to spend the most amazing 5 days in Maui. And the best part of it all you ask? There are an abundance of things to do in Maui, as it truly is a Hawaiian treasure of an island. You will most definitely never get bored, and you will see the most beautiful sights. I am Caresa Lamers, a full time traveler, and creator of This Spontaneous Life, and I have visited Maui a few times.
My Maui 5 day itinerary includes the best of Maui, and something for everyone in your travel group. We get out on the beach, drive along the coast, go under the sea, fly through forest, and get above the clouds. You are going to love it. In case you want to couple your 5 days in Maui with another island, we have a whole host of Hawaii activities to choose from. You’ll find a full list at the bottom of this page.
Our Maui 5 Day Itinerary-
- Day 1: Relax at Makena Beach in Wailea
- Day 2: Drive the Road to Hana
- Day 3: Snorkel at Molokini Crater
- Day 4: Zipline through the Forest
- Day 5: Sunrise at Haleakala
There is the short version. The longer version has all the details, how to fill the rest of your day, and where to have some amazing food along the route. If you are ready to start planning read on!
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The Perfect Maui 5 Day Itinerary
5 Days in Maui Day 1:
Spend your day relaxing at Makena Beach in Wailea
We all know how exhausting traveling can be. From long flights to possibly jet lag, it’s always essential to give your body the rest that it needs. Which is why on the first day of your Maui vacation I strongly recommend to spend your day on one of the most beautiful beaches in the world. (Yes, you heard that right. Makena Beach in Wailea has actually been named one of the most beautiful beaches in the world.) Truly doesn’t get much better than this.
Makena Beach is split into two absolutely breathtaking beaches – Big Beach and Little Beach.
With dazzling, blue waters, 1.5 miles of golden sand and the most gorgeous backdrop you can imagine. You absolutely can’t go wrong with spending your day at Big Beach. I’ve been to Maui two amazing times and each time I make it a point to spend at least a full day on this out-of-this-world beach.
But of course, nobody likes these nasty tan lines. A little secret not a lot of people know about, Big Beach has a little sister called Little Beach and unlike Big Beach, Little Beach is a clothing optional beach. The best part of it? You can switch off between both of these amazing beaches since they are only a short five minute hike away from each other.
Lunch at Monkeypod Kitchen
Of course, it wouldn’t be a Hawaiian vacation without trying some delicious, authentic Hawaiian food. With 4.5 stars Monkeypod Kitchen has made an amazing name for themselves and with good reason too – Their food is to die for! After spending your day under the sun, make sure to nourish your body with some of their amazing cuisine.
Rating: 4.5 stars
Address: 10 Wailea Gateway Place, Kihei, HI 96753
Phone Number: 808-891-2322
Check out The Shops at Wailea
With over 70 shops, restaurants and some of the best entertainment on the island, The Shops at Wailea is a must-add to your Maui 5 day itinerary. During my time on this incredible island, I noticed how unique and beautiful the Hawaiian style is. Grab yourself a few souvenirs for your friends and family back home as well as some fun outfits for the rest of your Maui vacation.
Dinner at Tommy Bahama Restaurant
After a fun day at the beach, it’s finally time to relax, grab yourself a few cocktails and a nice dinner for the evening. Tommy Bahama Restaurant is conveniently located inside The Shops at Wailea and has mouthwatering food. Treat yourself to a nice dinner at this wonderful restaurant.
Rating: 4.4 stars
Address: The Shops at Wailea 3750, Wailea Alanui Dr, Kihei, HI 96753
Phone Number: 808-875-9983
5 Days in Maui Day 2:
Take a drive on the road to Hana
If you’re looking for beautiful sights and views, the road to Hana is a MUST! But be prepared to dedicate a whole day of your Maui 5 day Itinerary to this activity as the ride can last anywhere from two to four hours depending how much you stop. And trust me, you will want to make at least a few stops so you can truly bask in all the beauty this amazing road has to offer.
The Road to Hana is known for it’s amazing sights and intense turns. With over 620 turns and 59 bridges, it’s definitely not for the queasy. Make sure to pack lots of nausea medication as you will most definitely need it. As well as an immensely scenic drive, there are some amazing hikes on the way to Hana, including the Bamboo Forest, The Seven Sacred Pools and more! A little glimpse of the Seven Sacred Pools is on the story cover photo.
PRO TIP: Unless you’re planning on staying in Hana, make sure to leave at least a few hours before nighttime. With many one lane roads, it can get pretty dangerous at night.
Lunch at Hana Ranch Restaurant
After such a long drive, grab some delicious American cuisine at Hana Ranch Restaurant. With a laid back atmosphere and some breathtaking ocean views, you will truly be in heaven while pleasing your taste buds with their wonderful food.
Rating: 3.9 stars
Address: 5031 Hana Hwy, Hana, HI 96713
Phone Number: 808-248-8211
Visit Kaihalulu red sand beach
During your visit in Hana, make sure to check out one its most iconic beaches, Kaihalulu red sand beach. Beaches are already gorgeous and located all throughout the world, but not many of them have red sand which makes it all the more special. The rocky outcrops break the surf so the waters are calm.
Dinner at Thai Food by Pranee
No need to eat a fancy restaurant to enjoy some great food. Food trucks are known around the world for having some of the best food, sometimes even better than the most famous restaurants out there. While Thai Food by Pranee is surely no gourmet restaurant, but it is authentic and delicious and will exceed your expectations beyond all levels. Grab a bit to eat and enjoy the outdoor seating before heading back to town. The Drunken Noodles is a crowd favorite.
Rating: 4.7 stars
Address: 5050 Uakea Rd Hana Hwy, Hana, HI, 96713
Phone Number: 808-264-9942
5 Days in Maui Day 3:
Take a snorkeling tour
Another all day activity and one that you should absolutely include during your 5 days in Maui, is a snorkeling tour to Molokini Crater. Molokini Crater is known for it’s crystal clear water and amazing snorkeling spots. Spend your day with the aquatic wildlife by taking a snorkeling tour. I went to Molokini Crater twice and had the opportunity to swim with turtles and some of the most beautiful fish I’ve ever seen.
I went through Quick Silver Tours and they surely did not disappoint. After a 90 minute boat ride to Molokini Crater, we got to enjoy our time in the water with some of the best and most amazing staff. On the way back, they also served low priced beers and cocktails as well as lunch!
Check out Kihea
We previously recommended one of Maui’s most famous towns is Lahaina. Sadly, much of the town was destroyed during the wildfires of 2023. So for now, we are opting for a quieter option, but one still filled with things to do. You might try a hike to the north of town at Kealia Pond National Wildlife Refuge, operated by the US Fish and Wildlife Service. The boardwalk trail goes through a marshlands different than anything we have experienced on Maui so far, and its brilliant pink pond. You will also find plenty of shopping and market options in Kihea, as well as waterfront parks and beaches.
Dinner at Paia Fish Market
With a couple of locations across the island, Paia Fish Market is a local favorite, and hands down some of the best fish I’ve ever had. This casual gem is an indoor/outdoor restaurant featuring a variety of “burgers” and other delicious food. Along with their amazing service, they also offer live music. End your active day with a happy stomach by grabbing dinner at Paia before heading back to your hotel.
Rating: 4.6 stars
Address: 1913 South Kihei Road
Phone Number: 808-874-8888
5 Days in Maui Day 4:
Go zip lining
As I’ve mentioned before, Maui is known for its breathtaking views. And what better way to enjoy those views than gliding through the air on a zipline? Skyline Eco-Adventures offers some of the best zip lining tours on the island. Located in Kula, HI, you will be taken on multiple zip lines with the most jaw dropping views. It may be one of the most exciting things to do in Maui!
Lunch at Kula Lodge
At an elevation of 3200 feet, you are in for a treat by treating yourself to lunch at Kula Lodge. Located a few miles away from Skyline Eco-Adventures, Kula Lodge is an exceptional restaurant with some of the best food on the island. And the best part of it, if you choose outdoor seating you will have a gorgeous, panoramic view of the island as well as the ocean.
Rating: 4.2 stars
Address: 15200 Haleakala Hwy, Kula, HI 96790
Phone Number: 808-878-1535
Visit a Luau
End your night by attending one of the most famous things to do in Maui – A luau. A luau is a traditional Hawaiian party which has everything from a wonderful show, food and drinks! While it’s not the cheapest thing to do, dinner and drinks come included with your ticket and the entertainment is truly a once-in-a-lifetime experience. During your 5 days in Maui, I strongly recommend to include a luau at some point.
5 Days in Maui Day 5:
Sunrise at Haleakala
End your wonderful vacation by witnessing one of the most beautiful sights on earth, the sunrise at Haleakala National Park. Unique to Maui, I can’t imagine a Maui 5 day itinerary, or any Maui itinerary for that matter, that did not include this spectacular experience. At over 10,000 feet above sea level, this view will take your breath away. Make sure to arrive about an hour before the sunrise to find parking and get yourself situated in a great spot to watch the sunrise.
PRO TIP: Make sure to pack sweaters and blankets on your excursion as it gets pretty cold up there due to the high elevation.
If driving to Haleakela makes you a bit nervous, don’t miss out! You can still have an amazing sunrise experience with a group tour! You get the added benefit of a guide who shares all of the legends and ancient myths about the volcano, and you don’t have to drive. You can make your reservation right now!
Breakfast at Kula Bistro
You know what they say, breakfast is the most important meal of the day. Get some fuel in your body after watching the sunrise to get yourself ready for the rest of your day. Kula Bistro is a wonderful, family owned restaurant which serves nothing but excellent food and offers exceptional customer service.
Rating: 4.7 stars
Address: 4566 Lower Kula Rd, Kula, HI 96790
Phone Number: 808-871-2960
Have some fun in the sun at Ka’anapali Beach
After an amazing 5 days in Maui, spend your last day spending some much needed down time on one of the best beaches in Maui – Ka’anapali Beach. Along with a vast array of shops and restaurants, you can also find quite a few ocean activities on Ka’anapali Beach. Including stand up paddle boarding, parasailing, boogie boarding, surfing and more.
Lunch at Leilani’s on the Beach
After spending some time on the beach, you will find yourself quite famished. Get a few drinks and some of the freshest seafood on the island by dining at Leilani’s on the Beach. With a gorgeous view of the crystal clear, blue ocean ahead, it will make your experience that much more memorable.
Rating: 4.4 stars
Address: 2435 Kaanapali Pkwy, Lahaina, HI, 96761
Phone Number: 808-661-4495
Take a sunset dinner cruise
What better way to end your day than by taking a sunset dinner cruise through the waters? Maui has a vast variety of different sunset cruises and they are a must-add to your Maui 5 day itinerary. You will sail through the ocean as you get to enjoy a wonderfully cooked dinner as you sip on a drink while watching the sun go down and make way for the new day. There is truly no better way to end your 5 days in Maui vacation than with a sunset cruise.
Ready to plan your own Maui 5 day itinerary?
I hope this Maui 5 day itinerary has enticed you with the variety of things to do in Maui, the drop dead gorgeous sights, and the delicious food choices. There is so much more to see and do on this amazing island if you want to spend more time. These highlights can easily be added to, but they also showcase some of the best experiences, if you want a quick visit before heading to other destinations. A trip to Maui is one you will never forget!
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If you are thinking of other Hawaiian destinations, check out our other articles:
Oahu One Week Itinerary
20 Things to do in Oahu North Shore
The Oahu Budget Guide
The Big Island Budget Guide
A Big Island 5 Day Itinerary
A Big Island Road Trip
Views of Waimea Canyon, Kauai
NaPali Coast Boat Tour, Kauai
Cruising Kauai
About the Author
Caresa Lamers is an average girl who has dreams, a passion and a heart full of wanderlust. One day she decided to sell everything she owns to be able to travel the world without being tied to any materialistic things. Read more about her adventures and travel tips at This Spontaneous Life. You can also find her on Pinterest.
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