5-Day Maui Itinerary: Easy Adventures for Families and Couples

Planning a trip that will appeal to everyone in your group can be a daunting exercise, especially if you’ve never been to the location before.

Maybe you’re traveling with your family and need easy adventures kiddos will enjoy. Or perhaps you’re on a couple’s getaway and want to fill your days with exciting activities that don’t require too much prep.

Regardless of what you’re looking for, this 5-day Maui itinerary has you covered with easy adventures everyone will love. Check it out below and start counting down to your Hawaiian getaway!

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Day 1: Relaxing South Maui Beach Day

You didn’t come all the way to the Island of Maui to miss its incredible beaches. Ease into day one of your vacation with some time spent on the warm sandy shores.

Morning at Wailea Beach

• Begin your day enjoying the calm waters and easy beach parking at Wailea Beach. Perfect for families, this crescent-shaped beach is in a resort community near golf courses and plenty of entertainment. Bring your boogie boards and body surf on the gentle waves as you soak up the Hawaiian sunshine.

Afternoon Snorkeling at Turtle Town

• Minutes from Wailea, Turtle Town is one of South Maui’s top snorkeling spots. Here, you’ll have an excellent chance of encountering the magnificent Hawaiian Green Sea Turtle in its natural habitat. Just remember – no touching or disturbing marine life! You can either bring your own snorkel gear, rent from a nearby shop, or take a guided snorkeling tour where gear is provided. Don’t forget your reef-safe sunscreen!

Evening Dinner at Mama’s Fish House

• Mama’s Fish House is a staple on Maui. Enjoy beautiful ocean views and insanely fresh seafood when you dine with them. Given how popular this restaurant is, making your reservation well in advance is advised.

Day 2: Explore Haleakala National Park

See one of the most famous views on the island and spend some time in the great outdoors.

Sunrise Views

• Seeing the sunrise from Haleakala National Park is life-changing, so, naturally, we had to include it in our 5-day Maui itinerary. You’ll need to get an early start for this activity, but we promise it’s worth it. Make the one-hour drive from South Maui to the park and greet the day atop the “house of the sun.” Revered in Polynesian folklore as the place where the demigod Maui lassoed the sun, it’s full of stunning views and rich history. Remember, reservations are required for visits between 3 and 7 AM and can be made up to 60 days in advance.

Late Morning Hiking

• After watching the sunrise, take some time to hike the nearby trails like Pa Ka’oao or Hosmer Grove. You should wear light layers when you visit the park. The temps at sunrise will be much colder than down near the beach, and you’ll likely get warm as you hike, so having the ability to adjust throughout the day will be key.

Afternoon Sights in Upcountry Maui

• Once you’ve worked up an appetite, visit nearby Kula, thirty minutes past the park, for a bite to eat and some fun upcountry sightseeing. Maui Wine winery, La Provence restaurant, and O’o Farm are notable places to check out.

Dinner at Your I Go Maui Vacation Rental

• After this busy day, why not stay in for the night? Your I Go Maui vacation rental comes with a fully equipped kitchen, excellent amenities, and fantastic views, so you can cook a delicious dinner and relax as a family while you talk about your favorite parts of the day.

Day 3: Molokini Crater and More Beach Fun

More ocean fun awaits with day three’s adventures!

Morning Snorkel Tour

• Book a half-day snorkeling adventure to Molokini Crater and enjoy swimming in the crystal clear waters as you try to spot as many different marine species as you can. Blue tangs, rays, octopi, and sea stars are just a few of the incredible things you may see.

Afternoon at Family-Friendly Kamaole Beaches

• The Kamaole Beach Parks are popular for their on-site facilities and family-friendly vibes, with Kamaole III being the most popular. Here, you’ll find a playground, parking, lifeguards, and convenient bathrooms. However, it gets very busy on weekends and holidays, so keep that in mind when you visit.

Evening Shopping in Wailea

• The Shops at Wailea boasts more than 70 global retail brands, including luxury and lifestyle stores. With delicious restaurants and tons to see and do, this is a great spot to finish day three of your 5-day Maui itinerary. Let the little ones take a lei-making or coconut frond weaving class, or catch the Tuesday Polynesian Show from 5:30 – 6:30 PM.

Day 4: Road to Hana (Partial Route)

Take it easy on day four with a casual drive and good food along the way.

Morning Partial Route Drive

• Hop in your rental car for a thrilling half-day road trip along the famous Road to Hana. While this drive can typically take 12-14 hours, this route will let you see some top sites and have you home in time for dinner. Drive as far as Twin Falls or Garden of Eden Arboretum and take in views of cascading waterfalls, beautiful tropical flowers, and unbeatable ocean views. You can even stop at Twin Falls and enjoy some easy hikes as a way to stretch your legs.

Afternoon Exploring

• Wander past colorful old buildings and enjoy this quaint town known as the hub of the North Shore. You can shop for a perfect souvenir, grab a bite at Paia Fish Market, and even get a pick-me-up at Paia Bay Coffee & Bar. With the main drag clocking in at just a half mile, it’s easy to experience a lot of unique culture with this stopover.

Kihei or Wailea Dinner

• Head to delicious Three’s Bar and Grill for dinner in Kihei. This popular spot is owned by three friends who each specialize in a different cuisine. The product is a menu that perfectly highlights Hawaiian, Southwestern, and Pacific Rim dishes made with local ingredients. As an island staple for 15 years, they’ve more than earned their stripes in the Maui food scene. Don’t forget to grab a happy hour Mai Tai from 3 – 6 PM.

Day 5: West Maui Day Trip

For your last day in paradise, we’re heading to the West Shore.

Morning in Lahaina

• After the 2023 fires, Lahaina and the Maui community have been busy rebuilding and restoring this precious part of the island. While there is still much to be done, many businesses have reopened. Head to this historic area and visit the shops at Lahaina Cannery or Whalers Village. Both offer on-site events, restaurants, and activities beyond shopping that will keep everyone entertained.

Afternoon Swim at Ka’anapali Beach

• Make sure you either come prepared to get in the water or be sure to grab a new swimsuit on your shopping spree because, for our last afternoon on Maui, we’re heading to the Ka’anapali beaches for their beautiful views, excellent snorkeling at Black Rock and nearby cliff-diving opportunities! If you’re here from November to April, you're in for an even bigger treat! That's peak whale-watching season on Maui, and this location is a great spot to look for distant breaching humpbacks.

Evening Sunset Cruise

• There’s no better way to end a 5-day Maui itinerary than with a sunset cruise. There are many tour companies to choose from, but we love the offerings from PacWhale. When in season, their sunset whale-watching cruises are incredible. Year-round, though, you can choose from sunset dinner cruises, cocktail sunset sails, or even private boat charters.

Optional Add-On: Black Sand Beach Day Trip

If you're in town for more than five days, consider a slightly longer adventure: a day trip to Waiʻānapanapa State Park to explore the striking black sand beach, sea caves, and lava arches. It’s a unique experience that everyone from adults and adventurous children will love.

Tips for Your Maui Vacation:

• Reserve your rental car early: Secure the best rates and ensure you have the right vehicle for your trip.
• Check daily weather forecasts: Weather can vary greatly across Maui, so plan accordingly each morning.
• Pack essentials for comfort: Always carry reef-safe sunscreen, water, snacks, beach gear, and comfortable walking shoes.
• Get an early start: Beat the crowds and fully enjoy popular spots by starting your days early.

Secure Your Maui Vacation When You Book Direct

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Now that you have some excellent ideas for your 5-day Maui itinerary, the only thing you need to do is book your vacation accommodations! That’s where I Go Maui comes in.

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