maui view from Waillea with a view of Lanai in the distance

Maui 5-day Itinerary


A tropical mix of fun, exploration and dining on this stunning Hawaiian island

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IMPORTANT MAUI WILDFIRE INFORMATION: On August 8, 2023 West Maui experienced a catastrophic wildfire. The Hawaii Governor, Josh Green, is asking vacationers to return to the island to support the economy as the island recovers from this immense tragedy. Find the latest information at

Note that some of the restaurants in this itinerary are located in Lahaina. For now, I am leaving the story as it is. Once it’s clear which, if any, of these special places survived the wildfire, I will update the information. 

Hawaii is my favorite place for a tropical getaway and this Maui 5-day itinerary offers something for everyone – a mix of land adventures, ocean activities and world-class dining. All with time built in to relax on Maui’s stunning beaches. 

This itinerary is based on a 7-day vacation I took with my family in the spring of 2021. My boys were 17 and 20 at the time and we’d been to Hawaii before but this was our first visit to Maui. We all loved this special island and I would return in a heartbeat. I liked it just as much as Kauai (separate article coming soon). 

We stayed in West Maui, in Kaanapali, so this itinerary is based on that as our home base. I am also including a few suggestions for people staying in South Maui/Wailea. 

Susan Heinrich sits on a palm tree on a beach vacation in Maui
Susan Heinrich sits on a palm tree on a beach vacation in Maui

What to Expect in Maui (updated late 2023)

On March 26, 2022 all restrictions related to Covid were lifted. No requirement for pre-departure testing or uploading of a vaccine card, and no filling out the SafeArrivals app. Things can always change and Hawaii was the most cautious state during the pandemic, so you can check for current information at the State of Hawaii Travel website.

A sea turtle swims past coral through the Hawaiian waters

Rising Prices and Saving Money on a Maui Vacation

Prices rose significantly during the pandemic for everything from hotels (up an estimated 40% in Maui, from 2019) to rental cars. Here are a few ideas for saving money on a Maui vacation:  

  • Consider traveling in the shoulder season.
  • If you want to stay at a large resort, compare the price of booking directly with the resort, with the price on the Redweek website (it’s a site for timeshare owners to sell their weeks, often at a discount.)
  • If possible, book accommodation with a kitchen or kitchenette; it will save you on dining out for every meal, which can be very costly in Maui. 
Susan Heinrich and her family at a table at Mama's Fish House

Dining in Maui

If you take one thing away from this story it’s to book your rental car and dining reservations WAY AHEAD of your trip (ok, that was two things). 

Many restaurants now use OpenTable for booking and managing reservations. (Note that we stayed in Kaanapali, so most of the dining suggestions are in West Maui. If you are staying in Wailea you will have lots of wonderful options – just make a point of reserving them ahead.)

I’ve written a Dining Guide to West Maui that might be helpful to you.  

In this itinerary, I’m including restaurant suggestions for each of the five days. Note that Luau reservations should be made two months in advance, especially if you are traveling to Maui over any holidays.

A boat sits under palm trees at Mama's Fish House in Maui

Book even further out if you decide to splurge on a meal at Mama’s Fish House (above photo), which was one of our favorite meals, anywhere, ever. (Open daily from 11-8:30; make reservations on OpenTable). $$$$$

With all of that in mind, here is a suggested itinerary for making the most of your vacation on the Hawaiian island of Maui.

Maui 5-day Itinerary

Gazebo Restaurant Maui


West Maui - Brunch, Blowhole and the Beach

Aloha and Welcome to Maui! This assumes you arrived yesterday, got settled, dipped your toes in the sand, perhaps even enjoyed your first Mai Tai. Today you are ready for some fun and exploration.

Start your day with brunch at the Gazebo Restaurant. It is very popular so go early or be ready to wait.  It’s located in Lahaina at 5315 Lower Honoapi’ilani Rd. which is a small condo/hotel where you’ll park. 

After brunch you’ll head to Napili Bay, just steps from the restaurant. This crescent shaped bay is small and charming and offers good snorkeling at the north end of the beach. Bring along your suits and snorkel gear or relax with a book and the sounds of the surf. 

After some beach fun, return to your car and continue north on highway 30. I enjoyed the pretty drive to The Nakalele Blowhole as much as the natural geyser, which pushes water up to 100 feet in the air.  You’ll pass through verdant tropical forest and enjoy wonderful views. Note, this stretch of highway is quite twisty.  

Parking is available at a small lot just off of the highway. A word of caution: admire the blowhole from a distance; people have been swept away by the high waves  that crash up over the shore. Also, it’s most impressive at high tide. You can time your visit based on Tide Reports

Depending on your timing, and the tides, you could flip this day around and start with a visit to the blowhole, then do lunch and Napili Bay after. 

Hula Grill Restaurant Maui

Dinner: Monkeypod Kitchen – Locations in Kaanapali and Wailea

This popular Maui restaurant celebrates local cuisine and is beloved by locals and visitors. It might be the Mai Tai’s with liliokai (passionfruit) foam, or the delicious fish tacos; this menu is crafted to celebrate Hawaiian flavors. 

The restaurant is named for the tree native to the Hawaiian islands that spreads into a sprawling shady canopy while fertilizing the soil beneath it. The saying goes that “the grass is greener under the Monkeypod Kitchen tree.”

The rugged coast of Maui seen from helicopter tour


A Splurge Tour: Molokini Crater, Whale Watching or a Helicopter tour of Maui

I like to plan one really special excursion on each trip. If your group enjoys snorkeling, the Molokini Crater day trip is among the island’s most popular outings. We decided not to go because I was nervous about a group tour, due to Covid rates at the time. It was the right decision for us, but I really regret missing this, as my son and I love to snorkel and this is a highlight for many who visit Maui. 

If you are staying in Wailea and want a deluxe snorkel tour/catamaran experience, check out: Kaikanani Catamarans.

If swimming with the fishes isn’t for you and you are visiting Maui during whale watching season (mid-December to early April, with peak season in February), arrange a tour to see the Humpback whales. Over 10,000 make the annual migration to winter in the shallow tropical waters west of Maui. A whale watching tour recommended by locals is the Ultimate Whale Watch. Their rafts offer a more intimate experience than on a traditional boat.  Learn more and explore other tour options at Maui Whale Watching.

We were able to see whales from the beach so if you don’t go on an excursion, you’ll still have the thrill of admiring them from a distance.

For some, the ultimate special excursion is seeing the Valley Isle from the air. My friend and fellow blogger Becky raved about her helicopter tour of Maui. The Maui Dream with Maverick Helicopters takes you above the Hana Rainforest and West Maui mountains for  a 65-minute exploration. This is at the top of my bucket list for a future trip.  

Susan Heinrich and her son Nate eat at a picnic table in theHoopiilani Food Truck Park in Kaanapali Maui
Susan and her son Nate enjoy dinner at the Hoopiilani Food Truck Park in Kaanapali Maui

Dinner: Honoapiilani Food Truck Park, Kaanapali

Enjoy a casual dinner tonight at the Honoapiilani Food Truck Park. There’s something for everyone at this open air park lit with string lights. I really enjoyed my poke bowl and everyone in our group found something they enjoyed. If you are staying in Kaanapali as we were, this might even be within walking distance of your hotel. While not as inexpensive as food trucks on the mainland (average entree is $14-$18) it’s a fun experience with very good food. 

In Wailea, there are many good food trucks, but no food truck parks as far as I know. Ask locally for the best.

Underwater view a surfboard in the ocean off Kaanapali Beach Maui


Hiking Maui’s Highest Peak or Surf & Snorkel at Kaanapali Beach

For the early birds and hiking enthusiasts: a sunrise hike to Haleakala Summit in Haleakala National Park is said to be a bucket list Maui experience. Haleakala means “house of the sun” and the sunrises here are a trip highlight for many visitors.  You need a reservation to enter the park between 3 am and 7 am and can reserve up to 60 days ahead at Haleakala National Park Summit Sunrise Reservations.

Note that driving time to the Haleakala summit (10,000 feet elevation) is 3.5 hours from Lahaina and 3 hours from Wailea.  The roads are said to be windy and the last 30 minutes of driving will be inside of the park. 

If you can’t get a reservation you can always go for sunset, no reservation required. Or book an organized tour and leave to driving to someone else. Sunrise at Haleakala National Park Note this is a 9-hour tour including hotel pickups and drive times! (ADD IN AFFILIATE LINK

A man carries a surfboard on his head as he walks next to Kaanapali Beach Maui


My young adult kids didn’t want to get up at 3:00 am (neither did I, to be honest) so we passed on the sunrise hike. My husband and I went surfing that morning; Maui is a really great place to learn. You can book surf lessons with Maui Wave Riders in Kihei (south Maui) or Lahaina (west Maui). Or, if you’ve surfed before you can rent boards from one of the local shops such as Island Surfboards. They will bring them to you at your hotel, or meet you at a beach. They also rent life jackets. 

We went to Kaanapali Beach which offered gentle waves for beginner surfers and a nice sandy beach for access. Kaanapali Beach was ideal for us because one area has waves big enough for a surfer and a little ways down was calm enough in the morning for snorkeling. You don’t always find both at the same beach. 

Susan Heinrich snorkels near Kaanapali Beach Maui
Underwater view a surfboard in the ocean off Kaanapali Beach Maui


You can take a Learn to Snorkel lesson which comes with equipment, or rent your own for your stay, through one of the  Snorkel Bob’s locations. We brought our own from home. Safe bets for swimming and snorkeling are the sheltered bays such as Napili Bay in West Maui and Ulua beach in Wailea.

The best turtle spotting is apparently in the aptly named “Turtle Town”, the coastline between Nahuna Point and Black Sand Beach, most specifically Maluaka Beach, south of Wailea. Mornings are generally best for the calmest water and best visibility. I hope you see a sea turtle! You can sign up here for daily snorkel reports from the Snorkel Store.

If you are concerned about sharks, attacks are extremely rare in Maui and there are precautions you can and should take to limit the chance that you encounter a shark. Find tips and guidelines here: Shark Safety Tips Maui.

Time to refuel! Before or after your surfing/snorkel at Kaanapali  visit the Whaler’s Village for breakfast or lunch. You can also get your parking validated here (3 hours free with a $20 purchase) and Kaanapali beach is directly in front of Whaler’s Village.

The Choice Health Bar has fabulous smoothies and Acai bowls. My favorite was the KowaPunga which came with extra protein and lots of fruit. Whaler’s Village also has a food court on the lower level with pizza, tacos, sandwiches and ice cream. There are two others locations on Maui – in Lahaina and Paia town.


This is a good time to mention ocean safety and Maui beaches. There are dangerous rip currents in the ocean off of many Maui beaches. When in doubt, don’t go in. If you are nervous or unfamiliar with ocean swimming,  you can visit one of the beaches with lifeguards such as at the state parks: Kamaole Beach Park’s I II & II. Note that many beaches with lifeguards are not appropriate for swimming, such as Ho’okipa Beach. More information at: Hawaiian Islands Ocean. Safety and Maui Beach Safety

The exterior of Duke's restaurant on Kaanapali Beach in Maui. Tall palm trees are beyond the Polynesian-style restaurant lit with tiki torches.

Dinner: Duke’s on Kaanapali Beach (at the Honua Kai resort.)

Duke’s has a gorgeous beachfront setting, lit by the glow of tiki torches and the sound of the ocean. The restaurant pays tribute to Duke Kahanamoku, a Hawaiian Olympic swimmer who founded the sport of surfing. The menu is Hawaiian, and the Rib & Chicken plate is a tasty and classic choice. We also enjoyed sharing the Coconut Shrimp with Lilikoi (passionfruit) Chili Water were delish. The cocktails are great as well.

Waves crash on the shore and a windsurfer is in the distance at Ho‘okipa Beach in Maui
A windsurfer in the distance at Ho‘okipa Beach in Maui


North Maui & Paia Town

Relax poolside or visit another beach on your list this morning. 

Splurge on a lunch at Mama’s Fish House, one of my favorite meals anywhere ever. If you didn’t reserve ahead, you can sometimes get a walk-up spot at the bar. The food is incredibly fresh and the menu shares the location and fisherman who caught your catch. The location is beautiful – be sure to check out the beach before or after lunch. There are lots of casual restaurants in Paia Town for lunch. 

 After lunch, head to one of the North Shore beaches which have an entirely different feel than the west side. Here it’s wild and windy and a lot of fun to watch the local surfers and windsurfers and you’ll often see turtles resting on the sand (be sure to give them lots of space). We really liked Ho’okipa Beach and saw a sleeping seal and a large sea turtle amble back into the churning surf. 

Just west of Paia town, Baldwin Beach Park is also popular with north shore locals, so stop in there if you have time. 


Susan Heinrich enjoys a shave ice at Ululanis in Maui

On your way back through Paia town, it’s the perfect chance to stop at Ululani’s for a Hawaiian shave Ice. (Ululani’s Hawaiian Shave Ice, 115 Hana Hwy #D) It’s a must for every visitor to Maui and tastes unlike shaved ice you’ve had before. It’s somehow creamy and you choose from a huge array of flavors including wonderful tropical flavors such as passionfruit, mango and coconut.

Dinner:  Tonight you could splurge on Mama’s Fish House if you didn’t go for lunch or have a lovely dinner at Paia Fish Market Restaurant which also serves incredibly fresh fish and several alternatives for those who don’t like fish. Again, book this ahead. For casual dining, there are lots of choices including Café Mambo and Flatbread Company for pizza.

Scenery on the road to Hana on Maui


Road to Hana (or maybe halfway to Hana)

On our last day in Maui we set out on the island’s most famous drive, the “Road to Hana”. We were flying out that evening so thought we had enough time to take the scenic trip of 4-5 hours.

Hana is a small town on the southern coast of Maui and the Hana Highway that takes you there has 620 curves and 59 bridges. I can’t say how many curves we had travelled when I suggested we go “halfway to Hana”. I was a bit queasy and the map was telling me that the Aunt Sandy’s Banana Bread stand was located at the halfway point. 

So that’s what we did. The drive through the coastal rainforest was gorgeous, and the banana bread was delicious. We watched the waves crash into the shore’s black volcanic rock; it felt wild and rugged, very different from the Kaanapali coast where we had stayed the week. On the way back, we stopped at Twin Falls. Twin Falls is located on private land, and the owners generously allow public access to it, via their property. There are two waterfalls to explore. Afterwards you can treat yourself to a pineapple smoothie at the farm stand. 

If you do go only halfway to Hana, and haven’t yet been to Paia town, this is a nice chance to stop in there.

Dinner: will depend on your schedule today, and where you are after your long drive. There’s a a food truck park near the airport, off of Keolani Place, between the Costco and Courtyard by Marriott. You could also stop in Paia town and have dinner there. There are several casual restaurants you could walk in to. 

Or, if you haven;t been to one on the list, like Duke’s or Monkeypod Kitchen, go as early as possible and put your name in. I saw several parties who were able to get in that way, on the night we went.

The view of the beach and ocean in Waianapapa State Park Maui
Waianapapa State Park Maui, accessed on the Road to Hana

I can only half check the “Road to Hana” off my list, but I was happy to travel a few less curves and have more time to enjoy them. It’s what I would also recommend – leave enough time to just relax and be on vacation. It’s impossible to do it all in 5 days, or a week. And I’ve realized we shouldn’t try. I would rather do a little less, and have time to really enjoy my vacation than try to pack everything in.  


Where to Stay in Maui

Susan Heinrich walks toward the beach at the Westin Nanea Ocean Villas in Maui
Susan Heinrich walks toward the beach at the Westin Nanea Ocean Villas in Maui

We stayed in the Kaanapali area of West Maui, at the Westin Nanea Ocean Villas. I’ve written a  Review of the Westin Nanea Ocean Villas Kaanapali where I go into much detail about the pros and cons.

Most visitors either stay in West Maui or Wailea. We chose the former because there was more villa-style accommodation, which is what we wanted, traveling with young adult kids. I would love to try Wailea on our next visit. 

Bottom line: we really enjoyed the Westin Nanea and I would recommend it if you are traveling with kids. If you are looking for a  serene environment it’s probably not the best option. 

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It’s been fun reliving one of our favorite family holidays by sharing this Maui 5-day itinerary! You’ll find more planning ideas in Tips for a Hawaii Vacation.

Writing this has me dreaming of another trip to Hawaii. I’d have to decide between the two islands I’ve visited and loved, Maui and Kauai, and the one still on my bucket list — the Big Island!

If you’ve been to Maui and have additional suggestions or updates, please share them in the comments below. Aloha and happy travels! 🌺

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About - Midlife Globetrotter

Hey there,

I’m glad you’re here. Can we talk about midlife? I reached my late 40’s, realized my kids were growing up, and adventure began calling in a new way: big travel adventures as well as everyday ones. I want Midlife Globetrotter to be a place where we explore how to add a sense of fun, freedom and meaning to these precious years. Let’s celebrate how far we’ve come, and all that’s ahead.




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