5 Days In Maui itinerary

Day 2: Iao Valley, Lahaina & Kaanapali Coast Beaches

We’ll slow things down on the second day of this Maui itinerary. We’ll start with a bit of nature, continue with some history, and wrap things up at West Maui beaches. Naturally, the results of the devastating Lahaina fires might affect sightseeing in the historic city until full recovery.

Kaanapali Beach - Maui - Hawaii - Panoramic View

Iao Valley State Monument

Iao Valley Needle - By Michael Oswald, Mikeo

This pristine part of Maui is the prime reason behind Maui’s nickname – “The Valley Isle”. The deeply eroded volcano that makes up West Maui has been carved up for millennia by the forces of water to create a series of deep emerald valleys. The area is often covered in clouds and is one of the wettest places on Earth, but if you visit in the early morning hours, you have a decent shot of catching a glimpse of the Iao Valley in all its glory.

The main reason for visiting Iao Valley State Monument is the “Iao Needle” – a 2250 ft (696m) pinnacle that has become the unofficial icon of Maui. You can get a quick dose of the needle from the bridge near the parking lot or devote more time to the park’s hiking trails running up the wet valley. Out-of-state visitors must pre-purchase tickets in advance to enter the park.

Late Breakfast in Ma’alaea

As you’re heading south from Wailuku and just before bending westbound on the south shore, make a late-breakfast pit stop at the Ma’alaea General Store. Set in a historic building, be prepared for awesome breakfasts and lunches, and the coffee is quite good, considering this is America, after all (no offense). This can also be a good place to start your day when exploring the beaches of East Maui’s south coast. The Ma’alaea Harbor, right across the street, is the departure point for dozens of boat tours to Molokini, whale watching, and more.

Pro Tip

The coastal road connecting Lahaina with Ma’alaea is very scenic on both sides but is unfortunately mostly (if not solely) with one lane in either direction. It is very accident prone. Drive with extra care: think three times before overtaking, keep an extra distance from the car in front of you, and be extra patient when turning against oncoming traffic.

Papawai Point

This is a proper scenic overlook on the road north towards Lahaina. It’s a prime spot for watching whales (in season) and during sunsets. From here, you can catch great views of East Maui’s coastline, the island of Lanai, and Kaho‘olawe – the tiny island once used as a training ground and bombing range by the U.S. military.

Papawai Point to Lahaina

Many small beaches are just a left turn away on this stretch of road. Some are nicer than others, but they are not spectacular by any means, though a lot more laid back than what lies further up the coast. I stopped here and there to stretch my legs and have a quick look. I mostly found locals and slightly larger crowds just before the sunset. What is stunning, though, is the almost guaranteed chance of seeing giant rainbows on the mountainside of the road. You’ll mainly see them in late afternoons when the clouds have just about had enough and need to release some steam.

Beach in West Maui - Hawaii
Rainbow in West Maui Hawaii


As far as “historic towns” in Hawaii go, Lahaina is probably one of the few that actually justifies its title. Thanks to its strategic harbor, Lahaina was the capital of the Kingdom of Hawaii under King Kamehameha – originally from Kona on the Big Island – until moving to its present-day location in Honolulu in 1845.

The seaside capital’s harbor was a favorite stop for ships carrying whalers in the first half of the 19th century, followed by ships carrying sugarcane. These days, the historic tourist town is crowded with tourists, probably thanks to its proximity to the plethora of resorts on the Kaanapali coast. Lahaina’s top sights are centered around a few street blocks, so park your car (this can be tricky) and go on a walking tour.

exclamation mark icon

In August 2023, Lahaina suffered extensive loss of life and devastating damage following unexpected and widespread fires. It will take some time to rebuild the town, and some sites might be permanently destroyed. Take this into account when planning a visit and show your support to the local community as best you can. If visiting Lahaina still isn’t a viable option, spend more time in Kaanapali Beach or book the highly-rated Haleakala sunset tour.

Lahaina Banyan Court

The historical town center is dominated by a massive banyan tree that has completely taken over. It was planted in the 19th century and hasn’t ceased providing shade ever since.

You may also like
Lahaina Banyan Court - Maui - Hawaii

Old Lahaina Courthouse

The Old Lahaina Courthouse is a museum and a collection of art galleries. It’s free to enter and quite interesting if you’re keen on learning about the town’s history and getting a short lesson in geology. If not, you might as well use the restrooms. As a history buff, I found this place quite interesting, especially the collection of old images of Lahaina. Head to the Baldwin Home Museum for an additional stroll down history lane.

Lahaina Harbor

Right behind the courthouse is the historic harbor. You won’t be able to escape the tour operator stands, but if you simply take a left, you can go for a pleasant stroll leading to the rocky harbor wall with sweeping views. Just beyond the old lighthouse is the Hauola Stone – an interesting chair-shaped semi-submerged rock with a nice story behind it.

Front St.

Front Street is Lahaina’s de facto “Main Street”. This busy street is all about souvenir shops, restaurants, and boutiques. Don’t forget to make the pilgrimage to Ululani’s Hawaiian Shave Ice!

Lahaina Main Street - Maui - Hawaii


The prettiest strip of golden sand on West Maui is, for better or worse, taken up by the Kaanapali resort area. With the first beach resort springing to life in 1963, Kaanapali is the first master-planned resort area in the U.S., and developers haven’t stopped since. A magnet for families, couples, honeymooners, and package holidaymakers, Kaanapali boasts over a dozen high-end resorts, a couple of golf courses, shopping complexes, and a few thousand beach chairs and cabanas. Love it or hate it, you be the judge but just in case, I’ll list two choices that cater to most tastes.

Kaanapali Beach

If your eyes can ignore the concrete, the three-mile-long Kaanapali Beach is one of the prettiest beaches in Maui. The bad news is that there will be many people here, including many children, tour operators trying to sell you stuff, hardly any (free) shade, and, in general, a deep sense of inauthenticity.

The good news is that the beach is so long that you can easily find your own space… that is if you can find a parking space. Parking for nonguests is extremely limited in signposted lots along Kaanapali Parkway. If you arrive in the afternoon, you might have to wait until somebody pulls out.   

Kaanapali Beach - Maui - Hawaii

Another big plus is Black Rock Beach (Pu’u Keka’a), reached by either marching on the soft golden sand or heading north along the paved Ka’anapali Beach Walk, which runs parallel to the beach. This is the most scenic section of Kaanapali Beach.

Black Rock Beach is the westernmost point in Maui, and its cliff is a sacred site for Hawaiians. You can snorkel off its base, practice your cliff-jumping skills, or simply climb for panoramic coastline views.  

Ka'anapali Beach - Maui Hawaii

Kahekili Beach Park

If you’re looking for a more laid-back experience in Kaanapali (and more accessible parking), head to the “other side” of the Pu’u Keka’a to Kahekili Beach Park. This is essentially an extension of Kaanapali Beach, but there are fewer people and concrete. The beach is popular with families, snorkelers, picnic-goers, and casual beach walkers, thanks to the long strand of golden sand running in either direction. This is also a good spot for sunset!

Kahekili Beach Park - Maui - Hawaii

Old Lahaina Luau

If you didn’t opt for the Haleakala sunset tour, freshen up and rest before the evening’s entertainment. The Old Lahaina Luau is regarded as the best luau show in Maui. Though it isn’t cheap, your ticket does include a buffet dinner and a spectacular Polynesian dance show. Advanced reservations are a must, as this show often sells out weeks in advance.