Shapin Up | Maui Travel Guide: How to Spend a Weekend on the Island

Maui Travel Guide

When MM and I moved to the west coast a few years ago (first living in SF), Hawaii was high on our travel list. The flight from the west coast is about 5-6 hours. Yes, that’s kind of a long flight. But when you compare it to the 10+ hours it would take you from the east coast, it seems so close! We had both been to Hawaii, though many years ago, so it remained high on our list. It slipped through our fingers while we lived in SF and we never made the hop over there, so when we moved back to the west coast (now in Portland), we were determined to make it happen.

We decided to plan a babymoon and Hawaii was the only place we considered. Hawaii is an ideal location for a babymoon (it’s tropical, has no Zika and is not a crazy long flight). It’s also perfect for honeymoons or just a long weekend getaway. Really, any excuse you can make to get over to Hawaii is a good one.

There are lots of islands to choose from. We picked Maui and loved our experience. If you’re thinking of a trip to Maui, read on for all the details.

Maui Travel Guide

Where to stay

The Andaz Maui Wailea: After multiple people recommended this hotel, we couldn’t pass it up. And it completely lived up to the hype. The Andaz is on the pricier side but is perfect if you’re headed to Hawaii for a special occasion and want to splurge. We covered most of our stay with credit card points. It wiped out a big portion of my points and it was worth it. The hotel has multiple pools and restaurants, is right on the beach and offers a great breakfast buffet. The staff is incredibly attentive and it’s the type of hotel where you feel very well taken care of. And if you happen to be on your babymoon, make sure to sign up for the babymoon package and enjoy the delicious mocktails. If you’re flying out late on your last day, the hotel offers lockers, showers and changing rooms so you can enjoy the full day and freshen up before your flight. We took a red eye home and took advantage of this much appreciated amenity. Splurge-woth for sure!

What to do:

The Road to Hana: This is a must-do activities while on Maui. Be warned, if you want to do it right, it’s going to take up a full day and will be exhausting. We spent about 9 hours doing the drive through windy roads and beautiful scenery to the town of Hana. The actual town isn’t much to see, it’s all about the trip there. There are waterfalls, hikes, and beaches along the way; you can make the day as long or as short as you’d like. I highly recommend downloading a guide app before you go so you know what you’re seeing and where to stop. Without an app, it would be very overwhelming and would be hard to know what is worth stopping for. We used GyPSy Guide and it was perfect. Make sure to stop at Aunty Sandy’s for fresh banana bread. Also there’s a cool food stand area for lunch (it’s mentioned in the guide). I will note that our app said when you get to Hana you should turn around and drive back the same way but we decided to just keep driving to do the full loop and I’m glad we did. It wasn’t as treacherous as they described and was new scenery. The Road to Hana can be full of adventure and long hikes, or you can keep it tame and view most things from your car. It’s a great choose-your-own-adventure type outing.

Haleakala Sunrise: After Hana, this was the second most recommended activity on Maui. In order to see this epic sunrise above the clouds, you’ll have to make a reservation in advance (details here). Also expect to wake up super early as you need to leave your hotel around 3 or 4am. I’m told it’s only worth it if the weather will be clear so make sure to check that the night before. We decided against this activity as our vacation was short and sleeping in sounded more appealing since we were already doing The Road to Hana. Next time I’d make this a priority.

Wailea Beach Path: If you’re staying at one of the Wailea hotels there is a great path along the beach that connects all the hotels. This is perfect for a morning or evening stroll at sunset.

Lahaina: Spend some time wandering around the town of Lahiana, full of cute shops, restaurants and beach-side views. Make sure to pop into the Maui Pineapple Store, so cute!

*Note, our trip was very short and it rained for a lot of it, so our list of activities is pretty short. No complaints, it was a very relaxing time.

Where to Eat

Paia Fish Market: Great place for a low-key meal. Head here for fresh fish at a reasonable price. It’s a casual order-at-the-counter type joint so don’t expect anything fancy.

Monkey Pod Kitchen: Another solid dinner option. Reservations recommended.

Choice Health Food Bar: A tasty place to stop for an acai bowl or avocado toast at the starting town (Paia) for the Road to Hana.

Ululani’s Shave Ice: A delicious treat! Tons of flavors to choose from and I recommend the “snow cap” (sweetened condensed milk mixture) coating on top. Multiple locations on the island.

Places we didn’t go but people recommended: Mama’s Fish House (one of the places everyone raves about. Expensive, but really good food/views. Reservations required), Coconut’s Fish Cafe, Kihei Cafe, South Maui Fish Company, Nalu’s South Shore Grill, Maui Brewing Company

Travel Tips:

Rent a car: The island isn’t enormous but if you want to explore beyond your hotel, a car is necessary. We rented a Wrangler and it seemed like 90% of visitors do the same. This was a good car choice for The Road to Hana.
Drink up: On your flight over, order a cup of half guava juice and half seltzer. The perfect (& free!) mocktail to get you in the island spirit.
Plan around the sunset: The sunsets on Maui are epic. Check the sunset timing each day and make sure you’re in a prime spot to enjoy it. We were at our hotel for sunset each night and it was perfect.
Make sure to relax: There are lots of activities to be done, but make sure you take some time to unwind and just enjoy the beauty that is around you. Usually we are go-go-go on trips and want to see as much as possible. For this one though, we slowed down and only chose a few activities, leaving plenty of time for laying at the pool or walking along the beach.