Maui 5-Days Travel Itinerary

Last December we vacationed in Maui, Hawaii. With reliably good weather throughout, it’s one of the most sought-after destinations for beach lovers any time of year. Maui has varied landscapes from mountains, rainforests, beaches, cliffs to volcanoes. Maui has the perfect balance of laid back remoteness and commercial enough for entertainment.

Here’s our 5-days Itinerary of Maui.
Day 1 >  Explore Kaanapali/Black Rock beach
Day 2 > Mt. Haleakala and Lahaina
Day 3 > Paia and Road to Hana
Day 4 > Iao Needle and explore South Maui
Day 5 > Explore West Maui


We stayed at the Sheraton Black Rock Hotel and Spa in Kaanapali, West Maui. The west of Maui with mountain ranges in the backdrop is very lush and exotic. Being close to nature and entertainment, pristine beaches, restaurants, shopping, and nightlife of Lahaina, it’s the perfect area to stay in Maui

Please note, most of the resorts are located in West and South Maui, which is far from main attractions like Hana and Haleakala. Every day we drove 50 – 60 miles to explore other areas. Hence, renting a car in Maui is an absolute necessity to explore the island. My recommendation is to rent from the airport for easy pick-up and drop-off. Tip: For stay, I would suggest the best way is to make Paia the base for at least 1 night to experience the beauty of Hana thoroughly and then relocate to west/south for the rest of the days to explore other parts of the island. This will save a lot of driving time.

Mountains west

Mystical west mountains

Day 1 – Exploring Kaanapali and Black Rock Beach

Geste's Shrimp TruckFrom the airport, we headed straight to the famous Geste’s Shrimp Truck at Kahului Harbor for a lunch pickup. It’s a short drive and this place is NOT to be missed, definitely one of the best meals in Maui! Our culinary experience started here. Huge garlic cajun shrimps served with potato salad on the side, I still dream of it.

Day 1 we spent exploring the beautiful Sheraton Maui Resort and the beach. The hotel is truly a tropical paradise tugged in the Black Rock Cliff at the far north point of Kaanapali beach. Every evening at sunset (around 6 PM) Sheraton hosts an elaborate cliff diving ceremony followed by live music and Hula dance. The ceremony starts with the call of a conch shell, torch lighting then followed by cliff diving. Tip: The best location to enjoy the ceremony is from the hotel’s Cliff Dive Bar as you sip delicious Mai Tais and watch the sun go down.

One of the best snorkeling spots in Hawaii is right here at the Black Rock. This cove is amazing for turtle-spotting, swimming, snorkeling, and cliff-jumping due to abundant bright colorful tropical fishes and sea turtles. We spotted a Honu turtle and chased the most colorful fishes on the cliff side. Tip: Sheraton has a rental store by the cliff to rent snorkeling gear for $30 all day. 

Kaanapali resort area is lined with tiki-torch laden restaurants, shops at the Whalers Village mall, condominiums and resorts, connected by paved beach walk. The scene in the evenings is very lively. We had a relaxing day 1 ending with a great dinner at Leilani’s. Don’t miss the famous Hula Pie here!

The list below is the best places to eat and drink around Kaanapali.

  • Gazebo for brunch, one of the BEST on the island!
  • Leilani’s OR Hula Grill, Whalers Village – Both these places offer great outdoor atmosphere. Leilani’s MUST TRY – Ono fish taco and Hula Pie. Hula Grill is packed in the evenings, has great cocktails and local bands playing.
  • Miso Phat, hands down my favorite sushi place. A MUST! This place was on the TV show Diners Drive-Ins and Dives and hey, Guy Fierri was here.
  • Duke’s Beach House has Mai Tai which wins the top honors. Duke’s has good HH from 3-5pm daily and best live entertainment.
  • Japengo in Hyatt is a classy combo of upscale and casual. The best place to enjoy the sunset with ocean view and drinks, local beers on tap, live music and hand-rolled sushi at the bar.

Day 2 – Visit Mt. Haleakala and Lahaina

We kicked off our day at 8 AM to visit Mt. Haleakala, world’s largest dormant volcano. Most people leave as early as 3 AM to watch the stunning sunrise, which is like no other as the drama unfolds in the sky. But we decided to skip the sunrise rush and instead made a day trip. On our way, we stopped at Leoda’s Pie Shop for a quick breakfast. Ohh, this place has the BEST PIE in the entire freaking world! MUST TRY – coconut cream pie and banana cream pie. Don’t leave Maui without trying here.

The road to Mt. Haleakala is long and winding. It took us 2 hours to reach the peak. The park is open 24 hours, 7 days a week. Entrance is $15 per vehicle. At 10,000ft high, you feel like you’re on the top of the world! However, it is cold and extremely windy. Be prepared with warm clothing. Located immediately below the summit is the visitor center from where you see the most magnificent landscape – Haleakala crater. The colors of this landscape are like a painting unfolding. There are hiking trails that go to the crater. It was interesting to see the endangered silversword plant, which is found only at Mt. Haleakala summit in the entire planet! While driving back we stopped at Kula Bistro for lunch, a popular brunch/lunch stop for visitors on way to Haleakala.


In the evening we headed to Lahaina where we strolled through its touristy shops,  boutiques, galleries, and eateries. The 400 years old banyan tree in the middle of the town is the highlight! This tree covers the largest area of any tree I have ever seen, spreading over a block wide. It’s magical to walk under its vast aerial branches shooting to the ground that looks like a connected chain of trees.

Our favorite eateries in Lahaina not to miss are listed below.

  • Aloha Mixed Plate offers authentic Hawaiian fare at a reasonable price and a perfect sunset view. MUST TRY – Ono Kau Kau spam musubi and Loco Moco
  • Honu Seafood and Pizza
  • Star Noodle 
  • Ululani’s or Local Boys West has the best fluffy shaved ice. Try the Haleakala made with coconut, leche and topped with sweetened condensed milk.
  • Maui Brewing Company for drinks. Try the Hawaiian pineapple wine.

Day 3 – Paia and Road to Hana

Day 3 we set out to Paia early to explore the hipster town and then head to Road to Hana. Paia’s Baldwin Avenue is lined with art galleries and eclectic boutiques, good for some shopping. We had our coffee and packed some lunch for our way.

Paia surfboard

Vibrant Paia


Honu n me

Best beaches around Paia are – Baldwin beach with tide pools and Ho’okipa Beach.  If you are looking to see the Hawaiian green turtles and some top-level surfers, Ho’okipa Beach is THE place. Go up the cliff to get the best view of the windsurfers from the lookout above.

Below is the list of best restaurants in Paia.

  • Mama’s Fish House ($$$) listed in the top 25 Best Restaurants in U.S. Arrive for sunset to stroll the palm grove and hidden cove. Note: Reservation must be made at least a month in advance.
  • Café des Amis for excellent sweet and savory crepes
  • Flatbread Pizza
  • Paia Fish Market
  • Ono Gelato Company – Don’t miss a scoop of homemade gelato here.
  • Charley’s – a popular local hangout for food and drinks.

Road to Hana

The road to Hana is in the list of the most beautiful drives in the world. The drive is quite an adventure through lush rainforest with ferns and tropical flowers, waterfalls, never-ending hairpin switchbacks and many one-lane bridges, and out of this world ocean cliff views along the way.

Few things to note before starting the road to Hana:

  • Highly recommend getting the GyPSy app for $10 or the Maui Revealed app! This app was so useful that I can’t stress enough! It was like a guided tour of our entire trip. It tells what the next highlight is based on your GPS location, where to park the car at each attraction, its history, and importance.
  • Start early and return early.  It will take the full day. We targetted to leave from Paia at around 8 AM for the road. We also ensured to leave the last stop (Oheo Gulch) around 4.30 PM to return safely before dark.
  • It could be a great option to stay the night here before or after the Hana drive to save time in driving and also to enjoy the laidback remoteness of this place.
  • If you have just 1 day, plan carefully on which stops to see. 2 full days is good to cover all properly.
  • Fill up the gas and pack some lunch and water at Paia, the last gas station before the drive.
  • Have cash on hand since most places accepted only cash.
  • Wear good hiking shoes and keep extra pairs of flip-flops. It rains on and off, so the trails very muddy.
  •  MUST TRY – banana breadcoconut chips and fresh fruit smoothies on the way!

We stopped at the below Marker Mile (MM) points. Note: (*) based on the level of recommendation, ( ***) being MUST SEE steps.

** MM # 2, Twin Falls – It’s an easy short walk through a slippery but beautiful trail to the falls. Sadly couldn’t take a dip as the falls water was at the high-risk level. In return, we grabbed some fresh sugarcane juice and locally grown fruit at the farm stand.

* MM #4.5, Huelo Lookout – This is a quick stop as nothing noteworthy to see. You may skip or stop at the fruit stand to pick up a banana bliss smoothie out of freshest fruits.

Huleo Lookout

Fresh smoothie at Huelo lookout fruit stand

** Between MM #6 and #7, Painted Grove – Look to the left to not miss the grove. These eucalyptus trees appear to have brushstrokes in shades of red, purple and green, caused by bark peeling over the years.

* MM #9.5Waikamoi Nature Trail – We took the short 15 minutes nature trail (a mile approx) for a warm up. The trail passes through beautiful trees, ferns, and an overlook.

** MM #17Keane Peninsula. It’s a short detour which is completely worth. The rocky black volcanic coastline against the stark blue ocean is otherworldly!

Keane Peninsula

*** MM #17 1/3, Halfway to Hana – A quick MUST stop for the freshly baked banana bread! We got back some for friends and family too, they loved it.

*** MM #28.8, Nahiku Roadside Marketplace – Here you will find some Hawaiian local products. MUST TRY the coconut candy chips from Willie for $6. Ohh! these chips are so good. Nahiku Marketplace also has ‘the best fish tacos’ in Maui. Quick stop.

hana banana chips

Best coconut chips at Willie’s

*** MM #32.2, Waianapanapa Park – Black Sand Beach is a MUST STOP! A short steep trail down takes to the beach with caves to explore. It’s my 1st time at a black sand beach, I was thrilled at the sheer uniqueness and rarity that’s not found many places on earth. Tip: Check the weather before your visit as it’s closed during rough weather.

Hana Black Sand Beach

*** Hamoa Beach – It’s a crescent beach surrounded by trees and one of the most beautiful beaches I’ve ever seen. It feels like a jungle beach, a half-moon beach surrounded by trees, relaxed vibe, perfect waves for swimming or surfing, the water is incredibly clear. Wish I could spend more time there. It’s listed as one of the best beaches in America! One of the highlights and hidden gems of Maui.

*** MM #42, Seven Sacred Pools and Pipiwai Bamboo Trail – The most awaited stop on the road to Hana is at the very end. We reached Oheo Gulch around 3 PM and immediately headed to the Pipiwai trail. It is 4 miles round trip and takes about 2 hours. On the way, there is a huge banyan tree and Waimoku waterfalls. The bamboo trail is such a magical place! After Pipiwai trail, we did the quick 1/2 mile Kuloa loop to see the Sacred pools which take 15 minutes. The 7 cascading pools are quite a  wonder of nature.

bamboo trail

Pipiwai Bamboo Trail

seven sacred pools

Seven Sacred Pools

Since the road further through the backside is pretty rough and not advisable during the late hours,  we decided to come back through the same route as going. It took about 2 1/2 hours from the Seven Pools back to Paia. Note: car rentals don’t cover insurance in that area of Maui.

Day 4 – Iao Needle and explore South Maui

Day 4 we set off to see the Iao Needle, the iconic natural rock formation protruding from the midst of lush green. This was on my list but unfortunately, the park was closed due to heavy flooding. So instead we explored the Southern coastline – the beaches of Kihei, Wailea, Makena followed by dinner at Miso Phat, the best sushi in town.

The 1st town to come across is Kihei. Kamaʻole Beach, located in Kihei is divided into three distinct beach areas (Park l, ll & lll) which has beautiful reefs for snorkeling and boardwalks through the dunes to the beach. Kamaole I is the nicest beach of the three with fine white sand and great swimming conditions.

Keawakapu beach is my personal favorite local beach. A short hike from here is the Kihei boat landing, my secret little spot in Maui to watch the sunset.

Keawakapu Beach

Kihei boat landing

Kihei boat landing

In the next town, Makena Cove Beach aka Big Beach is one of the prettiest beaches on Maui!! It also gets great views of Molokini and Kahoolawe.

Hiking up the hill from the Big Beach is the Little beach. This beach is a clothing optional/nude beach. However, it’s only after dark that little Beach comes to life with real spectacle. After dusk, the free-spirited hippies play drums and dance with fire. This event is an off-beat adventure, held every Sundays and full moons. Note: Bring a flashlight to hike back over the cliff at night.

Just past the third parking lot at Big Beach, hidden behind a tall lava rock wall is the Secret Beach aka Pakao Cove. This tiny, yet most romantic beach in Maui is the #1 beach for weddings and photo shoots in all of Hawaiʻi, for its incredible beauty. The sunsets are spectacular with the island of Kahoolawe and Molokini Crater offshore and turtles basking on the lava rocks.


Maui Sunset

For dinner, we headed to the famous sushi restaurant Miso Phat from the famed TV show Diners Drive-Ins and Dives. I would highly recommend this restaurant to all sushi lovers out there.

Miso Phat

Miso Phat

Below is the list of best local restaurants in South Maui.

  • Sansei Sushi has the best sushi in Maui!
  • Coconut’s Fish Cafe for fish tacos. Listed in CNN top 10 must-try in the United States!!!
  • Eskimo Candy Deli for excellent poke bowls
  • Da Kitchen and Cafe O’Lei for simple casual dining
  • Monkeypod Kitchen in Wailea has one of the best lunch menus

Day 5 – Exploring West Maui and Honolua Bay

We spent the last day exploring north of Maui, driving up to Honolua Bay. We started off with a hearty brunch at the Gazebo, known for big breakfasts. Fluffy macadamia pancakes, tastiest and huge portion of Hawaiian fried rice, sweeping ocean view – Gazebo’s breakfast is legendary, not to be missed!! Be prepared to stand in line for at least 30 minutes in wait. Walk off breakfast on the spectacular gem – the Napili Bay beach. This is a prime location to spot turtles and great for snorkeling, especially at the very left by the big black rocks.


Post lunch, we drove up to Honolua Bay for snorkeling. It’s a short walk to the bay through the lush beautiful jungle. This is one of the prime spots for snorkeling and spotting honu turtles. However, the shore is all rocks only and the water was murky on the day we went.

 honolua bay lookout

Another spot not to miss is the Nakalele Blowhole and its picturesque heart-shaped rock that we have seen in so many pictures of Maui.

I feel obligated to acquaint you with the highlights of the culinary delicacies of the island with a summarizing picture. So memorable!

Maui cuisine

Having devoured the sights and sounds of Maui it was time to wind down. My memories of Maui is etched forever as the adventurer’s ultimate paradise, the land of macadamia nuts and the best Mai Tai in the world. Mahalo for reading!


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