If you’re looking for a romantic trip for a honeymoon or anniversary, we have the perfect 5 Day Maui Itinerary! We stayed on West Maui and explored the island for our anniversary, and it was great mix of adventure and relaxation.
The goal of our 5 Day Maui Itinerary was to maximize our time on the island. We researched the best places and planned out a few full days of exploring. Then, we also included more relaxing, private days to spend at the beautiful beaches and nice adult pool at our hotel, the Fairmont Kea Lani.
Was 5 days enough time for the trip?
We worried 5 days wouldn’t be enough time, but it actually ended up being the perfect time! By staying less time, we were able to spend more on a 5-star hotel and activities while we were there. It was a great trip!
We also were able to upgrade our seats for the long flight! If you can, start saving up your points or money now! Business class was well worth it!
See how we planned out the Maui itinerary to make the next 5 days super memorable!
Where to Stay in Maui
Since we wanted a romantic spot, we chose Wailea. It’s a bit cooler and offers more lush views. With that said, we went all over the island while we were there.
If you want the maximum amount of sunshine and don’t mind the heat, Kihei and Lahaina are great. Both towns are also more developed for families and friends versus a honeymoon-vibe.
We stayed at The Fairmont Kea Lani, and we’d highly recommend it again!
They had access to a private beach, great food on-site, and the adult-only pool was really nice as well. Everyone was super friendly and helpful, too. They also had a pretty big parking lot which was nice with a rental car.
They also had some of the most beautiful sunsets on site! Which – I know, it’s Hawaii, hello!- but the Fairmont purposely set up their resort to have a spot to take in the sunset each day. I really appreciate that.
Our 2nd choice when we were researching where to stay in Wailea was Grand Wailea Resort.
We didn’t choose it because some reviews mentioned it wasn’t as clean as they would have liked, and they didn’t have an adult-only area.
Do you need a rental car for this 5 day itinerary?
Yes, we used a rental car every single day on the trip.
Whether it was just up the road to Monkeypod for happy hour or a scenic drive, we really used our rental.
We chose a convertible, and it was so nice! A Jeep would also be a great choice.
Our Maui Itinerary at a Glance
- We arrived Saturday afternoon and left Friday in the evening.
- Stayed in Wailea
- Mixed adventure, food, and relaxation into the plan
- If you want to go to a luau, buy tickets to the Old Lahaina Luau before your trip.
- Mama’s Fish House requires reservations weeks in advance.
- Book your sunrise reservation at Haleakalฤ National Park 60 days in advance!
- If you want to snorkel or go on a private charter, we recommend booking it in advance.
Arrival Day
We arrived in the afternoon and found our convertible rental car. We checked into the hotel and explored everything on site. (They gave us each a lai upon arriving!)
We ended the night overlooking the ocean from our hotel.
Day 1
On your first day, we recommend a couples massage, relaxing at the ocean, or renting a cabana at the pool in the morning.
It helped us set the tone for the trip.
Before going to explore Lahaina town, we stopped at Leoda’s Kitchen and Pie Shop for a sweet treat. It was recommended to us by a local, and it was so delicious!
From there we went to Lahaina to take in the shopping and sights.
The Lahaina Banyan tree was breathtaking, and the shops and restaurants were a good mix. Some things were super touristy, but there were also several cool spots.
Other historical sites in Lahaina:
- Lahaina Banyon Tree: The largest Banyan tree in Hawaii stands in Lahaina.
- The Wo Hing Society Hall
- Baldwin Home Museum (oldest home)
Our main activity for the night was the Old Lahaina Luau.
The food, drinks, and experience were all well worth it. We really enjoyed the Hawaiian culture and history from the luau as well.
If you don’t have a reservation for the luau, we also like Lahaina Fish Co for dinner.
The Dirty Monkey was suppose to be a cool spot to go to after, but it was a little underwhelming.
Day 2
Take in one of the most beautiful sites on Day 2 at the Haleakalฤ National Park. The park offers sunrise reservations where you can enter between 3AM and 7AM.
If you’re an early riser, this is definitely worth it. You can also see a great sunset up there, and you don’t need a reservation.
We chose the sunrise though, and then ate in Kula. There are several places to choose from. La Provence and Kula Lodge Restaurant have great views, but you can find several cool spots there.
Don’t forget! Book your sunrise reservation at Haleakalฤ National Park 60 days in advance!
Since the day started so early, it’s a great to take the time to relax after.
You could stay in upcountry Maui or visit Wailea or Makena Beach to the Ali’i Kula Lavender Farm in Kula, or visit Wailea Beach or Makena Beach.
We enjoyed the beautiful beaches and the time to just be together, but if you wanted an activity up-country Maui has a lot to offer.
You may like Aliโi Lavender Farm, MauiWine, or the Maui Pineapple Tour.
Kihei in the Evening
We did quite a bit of driving today (and tomorrow is Hana), but we took a 20 minute drive from Makena to explore Kihei.
We ate at Da Kitchen, a local favorite.
A lot of the items had sold out, but what we got was still delicious.
After we went to Three’s Bar & Grill for their “Happier Hour” from 9-10PM. They made a great Mai Tai, and we got some wings to split.
RIP Charley’s in Maui
Day 3
We got an early start so that we could do the Road to Hana!
While you can go on a guided tour on a van or bus, we chose to do the Road to Hana on our own.
We liked having the flexibility to pick and choose where we wanted to stop, and we also got to spend more time at our favorite places.
The road is really narrow and has some one lane bridges — so just prepare yourself whether you go with a tour group or on your own.
Out of all 5 days, this was the biggest (and longest) day on our Maui itinerary.
We started our early morning in Paia at Charley’s. Sadly, it has since permanently closed.
An alternative would be to pick up something at Kลซสปau Store or try out Paia Bowls in Paia before starting the Road to Hana.
Luckily, there are all kinds of foods to enjoy on the road to Mile Marker Zero!
What to Pack for the Road to Hana
- Drinking water
- Snacks
- Sunscreen
- Swimwear
- Towel
- Clothing & shoes that you can get dirty
- Shoes with good traction
- Change of clothing
- Optional: Mosquito repellant
- Optional: Hiking gear for longer hikes
3 Pro Tips for Hana
- Get gas in Paia
- Plan your day so you get back before dark. The Hana Highway has no lights, and it’s narrow!
- Use an audio guide to learn about each stop.
We downloaded the the Gypsy Guide Road to Hana app and listened to the audio tour from our car.
The app connects to your location so the guide will tell you all about the area you’re driving through. It was super cool and under $10 to download.
Stops on the Road to Hana
The Road to Hana guide will tell you spots to stop at, but here are a few we stopped at and what we thought!
Twin Falls (Mile Marker 2)
We stopped here, and we were disappointed. It was so crowded. The waterfalls were pretty, but not worth the crowd and walk in our opinion.
Rainbow Eucalyptus Trees (Mile Marker 6.7)
The trees are gorgeous and flew by. I was thankful we got to see them again at the next stop, Waikamoi Ridge Trail.
Waikamoi Ridge Trail and Falls (Mile Marker 9.5 and 10)
This trail was worth the stop compared to Twin Falls. It was already quiet, and I could see the eucalyptus tress up close. The trail is a short short hike at .8 miles if you do the loop or a 1.5 miles if you do the extension.
Garden of Eden (Mile Marker 10.5)
The Garden of Eden’s botanical garden felt a bit like a tourist trap, and you have to pay to get in. With that said, we were glad we stopped. They had a bathroom and some amazing pineapple juice — along with some great views!
Keanae Peninsula and Arboretum (Mile Marker 16.5)
Keanae is a MUST-DO! We almost skipped it because the audio guide just barely mentioned it. But it was our favorite spot out of the whole day trip!
As you venture down the road, you’ll find Aunt Sandy’s banana bread, and you have to try it! (It closes most days around 2). If you miss it, you can try our copycat Aunt Sandy’s banana bread.
After you grab a bite of bread, keep going until you come up on the black rock beach.
The waves and water were so gorgeous, and the beach was lined with a few coconut trees and 2 local old men watching the waves.
We couldn’t have asked for more. It was one of the best spots of our whole trip.
Due to time, we skipped Upper Waikani Falls, Puaa Kaa State Wayside Park, and Kahanu Garden and Piilanihale Heiau, and Kaeleku Caverns. They were on mile marker 19.5 – 31.
Nahiku Marketplace (Mile Marker 28.8)
If it’s not too late in the day, you’ll have a variety of different options to enjoy at this daily market!
Waianapanapa State Park (Mile Marker 32)
We stopped here to see the black sand beaches and lava tubes! It was really cool and different.
Hana Town (Mile Marker 34)
The locals don’t want you exactly hanging out, but there are a few little tourist-type shops and foods to pick from.
Other Spots on the Road to Hana We Skipped
- Food: Past Hana is Braddah Hutts BBQ Grill
- Food: Huli Huli Chicken is before Hamoa Beach as well.
- Hamoa Beach (Mile Marker 51)
- Wailua Falls (Mile Marker 44.8)
- Venus Pools Mile Marker 48
3 More Notes Note:
We also skipped Kaihalulu Beach.
While the photos of the pink sand and blue waters are gorgeous, the Red Sand Beach is technically on private property. It’s also a pretty dangerous trail to get to it, too.
The Seven Sacred Pools used to be a popular spot, but they are permanently closed as of 2022.
Ho’okipa Beach Park is a great beach as well, and a lot of the time you can see sea turtles there!
We stopped at Ho’okipa Beach Park on our way back to Paia.
Dinner
After the long day and long drive, we personally wanted something easy and close by to eat. We grabbed a pizza and mai tai at Monkeypod because it was by our hotel. That mai tai was a thing of wonders. YUM!
If you are wanting something nicer though, check out Mama’s Fish House!
It’s locally owned and serves locally caught seafood. Decorated in old-Polynesian style, it’s been a staple since 1973. It’s pricey, but it’s a very well known spot, too.
Day 4
We loved the idea of getting out on the water! You can either snorkel at Molokini Crater, and home of Pacific green sea turtles, Turtle Arches or rent a private charter.
Out of the companies we researched our Maui itinerary, we liked Aqua Adventures the best.
The snorkeling trip is about 5 hours, and you can customize the private charter option.
Needless to say, this was our main activity for the day.
Dinner was Miso Phat Sushi.
There was a wait, but man, it was so worth it! It’s a tiny place with big personality and great sushi!
Day 5
If you’re not departing on day 5 or have some extra time, you could do a couple of different things!
For us – we were departing, so we rented a private cabana at the pool until it was time for our flight.
The Fairmont Kea Lani stored our luggage and even had a room we could shower in after checking out!
5 More Ideas for Your Maui Itinerary
1. If you’re wanting to see more and are up for another adventure — jump on a ferry to Lanai!
It’s a great day trip, and the Four Seasons there is breathtaking. They have restaurants on site, and you could just grab a drink and enjoy the beach. (There is a bus shuttle to take you).
2. You could also go to the Organic Ocean Vodka Distillery Tour or MauiWine.
You could technically do both if you wanted! They are about a 30 minute card ride from one another.
3. The Surfing Goat Diary offers tours.
If you love cheese and enjoy tours, this could be a great option as well.
4. Love Food Trucks?
Have a great time trying several different food trucks’ offerings at the Honoapiilani Food Truck Park.
Make sure to get in banana bread, poi, hula pie, shaved ice, poke, roasted pig, fresh fish, and pineapple while you’re on the island.
5. Whale Watching
If you’re in Maui between November and April, you may have the chance to see whales! You can check out Pacific Whale for more info on tours and pricing.
We hope this 5 Day Maui Itinerary helps you plan the perfect trip for you and your special someone! We definitely had the best time!
A few other places you may like not on the Maui Itinerary:
- Stillwell’s Bakery & Cafe – Wailuku
- Honu or Mala (right beside each other) – Lahaina
- Leilani’s on the Beach – Lahaina
- Sea House (Happy Hour) – Lahaina
- Fleetwoods on Front street – Lahaina
- Ululanis Hawaiian Shave Ice – Kihei
Stillwell’s Bakery
Final Tip
Our first full day, we made the mistake of going to Costco in the morning. We had heard it was great for sunscreen and snacks. Let this be your warning — Whatever you do, do not go to Costco on a weekend in Maui. It was a nightmare! It was so packed. Just go to Target or Walmart.
We can’t wait to visit Maui again!
While Kim has been to a few of the Hawaiian Islands, I’ve only been to the one. Next up on my bucket list is the Big Island!
Save these ideas on Pinterest for later!
Let us know how you like our Maui Itinerary in the comments below!
Get More Simple Life Hacks on Our Podcast!
