Hawaii Travel Guides, Land Activities

Staying on Maui’s South Side: A 7 Day Itinerary

Maui’s South Side includes the popular communities of Kihei and Wailea. It is known for its sunshine and tropical beaches and is home to a variety of great shops and restaurants.

If you’ve booked a stay on the beautiful South Side of Maui, then you’ve made an excellent choice. But how is Maui best experienced from the South Side?

With so much to see and do in Maui, we’ve put together a 7 day itinerary to help you best explore the Island from the South.

Day 1: Enjoy Kihei’s beaches

Sugar Beach, Kihei

If you’re heading to Maui’s South Side then we are guessing you like beautiful beaches and sunny weather?

On day 1, explore the local area of Kihei and get a feel for the place. Pack a picnic and head to one of the many sandy beaches. There are lots to choose from – we like Charley Young Beach Park which joins onto Kam I.

After a day in the sun, have dinner at one of Kihei’s restaurants. We highly recommend the blackened Ahi or grilled Maui Mahi at Paia Fish Market South Side.

Day 2: Snorkel at Molokini Crater

snorkel molokini

Molokini crater

There is a whole world under the ocean and snorkeling is a great way to see it. If you look out to sea from the South Side you’ll spot Molokini, a partially submerged crater which is a top spot for snorkeling.

Book yourself on a snorkeling cruise and you’ll be directed to the best spots for seeing fishes, turtles and other marine life. The experts on board will get you hooked up with gear, and beginners are always welcome. We recommend this snorkel trip with Redline rafting for visiting the Molokini crater, La Perouse and Turtle town.

After your trip, relax with a coffee at Akamai Coffee Co [1325 S Kihei Rd Suite 100].

Day 3: Sightsee in Lahaina

Boats of Lahaina Harbor

Lahaina Harbor

You’ll want to explore more than just the South side when you visit Maui. We love the historic whaling town of Lahaina on Maui’s West Side.

In the center of Lahaina you’ll find a beautiful old Banyan tree which is an amazing sight to see. Underneath its many trunks and branches, you’ll find stalls showcasing local made items for sale.

Front street in Lahaina is home to a variety of shops, art galleries and restaurants. There are also several fascinating museums such as the Baldwin Missionary House and the Wo Hing Museum.

Take a break from sightseeing by stopping for shave ice and enjoying it by the beautiful harbor. For the perfect end to the day, book yourself on the Old Lahaina Luau for an outstanding evening of hula and feasting.

Day 4: Take in the sunset from Mt Haleakala

Haleakala National Park

Haleakala Crater

Back on Maui’s South Side have a slower morning on day 4, making the most of your proximity to some of the world’s most enviable beaches.

Later on take a drive upcountry and stop in the town of Makawao for either lunch or a coffee and a wander around the cute boutique shops there.

Then drive on up from Makawao to Mount Haleakala in time to watch the sunset. You don’t need a reservation for this (unlike the sunrise) but we advise getting there in plenty of time so you can take in the views while it is still light. Then pick your spot before watching the sunset show and doing a spot of stargazing.

For the keen explorers, who want to see even more of Haleakala’s beauty, book yourself on a volcano hike. 

Day 5: Discover local lava fields and learn to surf

La Perouse is great for snorkeling around

La Perouse Bay

Take a surf or SUP lesson! While on Maui, it is an excellent opportunity to learn to surf, and it is also a lot of fun. If you head to Kalama Beach Park in Kihei you’ll find a number of surf schools who offer beginner surf lessons for both adults and kids. You can also save money by booking online.

After your surf lesson drive further down the South Side and enjoy the golden sands of Makena Beach aptly known as Big Beach, and then carry on South towards La Perouse. Park up and take a stunning walk through rugged black lava fields to La Perouse Bay.

Day 6: Tackle the Road to Hana

View from the Hana Highway

On day 6, tackle the infamous Road to Hana. This is a great way to glimpse the old Hawaii and see the natural beauty of the rainforest with its fruit trees and waterfalls. Go early and stop in the charming town of Paia for breakfast before carrying on along the Hana Highway. Read more tips on how to best enjoy a day on the Road to Hana here.

Don’t have your own transport? Book yourself on a road to Hana tour and let a professional navigate those winding roads whilst you enjoy the view!

Day 7: Relax in Wailea

Wailea Beach Walkway

We don’t recommend planning a lot after a day on the Road to Hana, as it can be pretty full on.

On day 7 go for a gentle stroll along the Wailea beach path and then head to the shops at Wailea to pick up some souvenirs from your vacation.

You can eat at one of the well reputed restaurants there or go to Maui Brewing Company in Kihei for Beer and a Pizza.


Hana Day Tour by Valley Isle

From: $159.95

Hike Maui Haleakala Crater Hiking Tour (7 Hours*)

From: $219.00

Kihei Surfing Lessons with Maui Beach Boys

From: $54.95

Molokini and Forbidden Coast Snorkel Tour with Redline Rafting

From: $132.95

Old Lahaina Luau

From: $125.00

Road to Hana Van Tour by Mahalo Tours

From: $127.95

Have you stayed on Maui’s South Side? Share with us your favorite things to do.

Check out our itinerary for staying on Maui’s West Side.

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