5-Day Maui Itinerary: A Dream Vacation

Travel writer Michelle Joy quit her job at a magazine to start a blog and explore the world. Now, she helps other women to adventure independently and publishes detailed travel itineraries for destinations in the U.S. and Europe. Find out more

Known as the Garden Isle, Maui is every bit the Hawaiian dream. Beaches glisten gold in the sun, waterfalls gush in lush rainforests, and sunsets dazzle in pink and yellow hues. And while the beaches here are everything to write home about, there is so much to do beyond the sand, from snorkeling with sea turtles to summiting a volcanic crater.

Spending five days in Maui will give you enough time to relax by the waves and try out some one-of-a-kind experiences. And this 5-day Maui itinerary will show you what you can’t miss on your trip to this spectacular Hawaiian island.

Day 1: Beaches and snorkeling

Spend the first of your 5-day Maui itinerary in South Maui soaking up the sun at some of the island’s best beaches and snorkeling spots before indulging in a welcoming luau.

Hit the waves at Wailea Beach

One of the best beaches in Maui, Wailea Beach has soft, golden sand and views of offshore islands. Some of the island’s top resorts and golf courses are located here too. 

If you want to do more than sunbathe, you can rent water sports gear like paddle boards, surf boards and snorkel gear to hit the waves. This beach can get a little crowded during the high season, but there are lots of amenities nearby.

Visit the beach at Makena State Park

Hop over to nearby Makena State Park for a more rustic beach experience. This area south of Wailea is less commercially developed and has fewer amenities. Big Beach in the park is more than a mile long, and offers blue waters, emerald rainforests, and golden sands.

Snorkel at Molokini Crater

Snorkel at Molokini Crater

From some of the southern Maui beaches, you may notice a little crescent-shaped island out in the water. This is Molokini, a volcanic crater, Marine Life Conservation District, and prime snorkeling spot. Book a snorkeling tour to Molokini Crater for a chance to swim with hundreds of species of fish, eels, octopus, dolphins, and more.

Feast at a luau

Your first night in Maui is the perfect time for a welcome-to-the-island luau. The experience typically includes a lei greeting, cultural entertainment, and a huge Polynesian feast. It’s best to reserve a ticket ahead of time because the best luaus book up early.

Day 2 — The Road to Hana

Plan to spend your second day on the Road to Hana, a bucket-list excursion in remote eastern Maui.

Cruise the Hana Highway

Famous for its hairpin turns, high cliffs, and lush rainforests, the Road to Hana is one of the best things to do in Maui. You can drive it yourself or book a full-day guided excursion if you prefer to sit back and enjoy the scenery, plus the traffic can be heavy in peak season.

Some of the highlights along the way include waterfalls like Twin Falls and Waikani Falls, the botanical Garden of Eden, and the black sand beach at Wai’ānapanapa State Park.

Explore Hana Town and beaches

When you arrive in remote Hana at the eastern tip of Maui, visit the Hana Cultural Center to learn more about the traditional Hawaiian way of life, grab lunch from one of the local food trucks, or check out the surf at Koki Beach Park and Hana Bay Beach Park.

See the falls beyond Hana

View of the Wailua Falls

Some of the best waterfalls in the area are just past Hana Town. Stop at Wailua Falls for an 80-foot drop and swimming pond. Or head into the Kipahulu district of Haleakala National Park for the Seven Sacred Pools at Ohe’o. This series of small cascades and pools is the perfect place for a relaxing swim.

Day 3 — Kaanapali and Lahaina

Spend one of your 5 days in West Maui soaking up the history of Lahaina and the oceanfront in Kaanapali.

Visit Lahaina town

Visit Lahaina town and see its ancient trees

Lahaina is an old whaling village, and was once the capital of the Kingdom of Hawaii. The historic Front Street is now filled with shops, galleries and breezy restaurants – the perfect spot for a relaxed brunch before heading to the beach. Make sure to stop by the Lahaina Banyan Court, where a mass of limbs from a huge 1800s tree fill the square in front of the Old Lahaina Courthouse.

Go on a whale- and dolphin-watching excursion

From Lahaina Harbor, head off on a wildlife-watching excursion for a chance to spot sea turtles, dolphins and whales. Half-day snorkeling trips or sightseeing boat rides head toward the island of Lanai and typically include a picnic lunch onboard. While whale season is only in winter, you’ll always be able to spot vibrant marine life under the waves as your guide leads you to vibrant coral reefs.

Stroll the Kaanapali Beachwalk

View of the Kaanapali Beachwalk

Less than five miles north of Lahaina, Kaanapali Beach has a hub of oceanfront resorts and breezy restaurants to explore. You can spend some time on the sand at Hanakaoo Park before strolling the Kaanapali Beachwalk around sunset. The paved path stretches for over a mile and connects to Whalers Village, an open-air shopping and dining destination. 

Make sure you try a slice of hula pie with dinner — the famous macadamia ice cream and cookie crust dish originated at a seafood restaurant in Lahaina, but you can find it on most dessert menus around the island.

Day 4 — Maui sunrise to sunset

Start day four with an epic island sunrise and end it with a sunset sail.

Watch the sunrise from the Haleakala summit

A spectacular sunrise

No 5-day Maui itinerary would be complete without watching the sunrise from the 10,023-foot high summit of Haleakala is one of the best experiences you can enjoy in Maui. If you arrive early enough, you’ll be able to see a night sky full of stars before it begins to brighten.

The drive can be over an hour from the nearest resort hubs and takes you through winding mountain roads in the dark. Stay safe and enjoy the expertise of the local guides by booking a sunrise and breakfast tour that includes transportation, warm jackets to borrow (the summit is often freezing around sunset), and a hearty meal after dawn. 

If you’re traveling without booking a tour, you’ll need to make reservations through the National Park Service to visit, and aim to arrive at least an hour before sunrise.

Hike in Haleakala National Park

If you want to spend a little more time in the Maui mountains, the Summit District of Haleakala National Park has over 30 miles of hiking trails. Start with a visit to the Haleakala Visitor Center, which is perched on the edge of a crater. Be sure to check out the exhibits and grab a trail map.

Sightsee in Upcountry Maui

The Upcountry Maui area sits in the hills of Haleakala and is home to several celebrity estates and historic villages. Some of the best places to explore in this area include a lavender farm and botanical garden in Kula and old-timey Makawao, a cowboy village turned arts district with galleries and shops.

Set sail on a sunset dinner cruise

Sunsets along the west coast of Maui dazzle in pinks and oranges, and an evening cruise makes the experience extra magical. From the deck of a catamaran you can toast the twilight on a romantic sunset sailing with drinks trip, or go for a full-on Maui dinner cruise with live music.

Day 5 of your Maui itinerary — from coast to sky

The final day of your 5-day Maui itinerary should be spent enjoying your vacation favorites all over again, whether that’s basking under the sun or heading off on an adventure.

Head back to the beach

You’ll want to say a proper goodbye to the beautiful beaches of Maui before leaving the island. If you’re still on the hunt for your favorite spot, use today to check out Kanaha Beach Park near Kahului, a popular windsurfing spot. Alternatively, head to Kapalua for rocky cliffs and sandy coves, or the beaches in Kīhei Park for their beautiful golden sand.

Hike in the Iao Valley

Hike for the best views

Iao Valley State Monument is set out over 4,000 acres in the West Maui mountains. Follow the 0.6 mile Iao Needle Lookout Trail here to see an ethnobotanical garden and the famous Kuka’emoku, an eroded peak that juts 1,200 feet from out of the valley.

Soar above the island

A helicopter tour above Maui is the best way to see parts of the island that aren’t easily accessible. Plus, it makes the perfect send-off on your final day. Flights will take you above the Haleakalā crater, through the Iao Valley, along shoreside cliffs, and to hidden waterfalls.

Travel writer Michelle Joy quit her job at a magazine to start a blog and explore the world. Now, she helps other women to adventure independently and publishes detailed travel itineraries for destinations in the U.S. and Europe. You can read her Maui guides on her website HarborsandHavens.com.

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