four day travel guide

what to do on a long weekend in maui

A four day travel guide

If you have a long weekend (especially if you live on the West Coast), why not take the 5.5 hour flight to Maui? I recently did this trip with a friend, after taking advantage of a sale from Southwest, and here’s what we were able to do in only four days. Enjoy!

Day 1

3am - 7am: Watch the sunrise at Haleakala National Park. This is a must-do, and I’m glad we did it on Day 1 so that the time difference (and jet lag) was on our side.

Tip: Reserve a spot about 2 months in advance if you can. This allows you to enter the park and drive to the summit. It costs $1 to reserve.

Once you get to the park itself, it will cost $25 per car to enter.
Upon entering the park, make sure to account for an extra 20 minutes / 11 miles to drive all the way to the summit for the best view. This matters if you’re trying to catch the sunrise and/or sunset at a specific time.

8am - 9am: After getting up early for the sunrise, we were starving, so we grabbed breakfast at Kula Lodge & Restaurant. I ordered the breakfast burrito and coffee. Very lovely view and you can walk around the gardens. Also, the smell of the flowers is incredible.

9am - 10am: Stopped by the Lavender Farm. It hadn’t opened for the day when we got there, but the drive was actually quite beautiful and rustic, so I’m glad we did it.

11am - 4pm: Drove back to the Westin and spent the afternoon sitting by the pool. Later, I did some exploring and walked down the Kaanapali Beach just a mile or so to Black Rock (near the Sheraton).

6pm - 8pm: Dinner at Merriman’s at Kapalua; This was probably the best food we had on the whole trip and the restaurant had a great view and live music. The only thing I didn’t like was the stuffy vibe - more upscale clientele.

Day 2

9am - 11am: Drove to Ioa Valley and spent the morning walking around the lush landscape and taking photos. It’s not really a hike - you just take a short walk to the top and see the mountains, and then you can also walk further down to the river and swim. It only costs $5 to park, and it’s well worth it.

On the way back, we drove by Maui Plantation. We didn’t stop in then (but we did go back for dinner another night)--- I highly regret it. I wish I had checked it out during the day! Apparently they have an ice cream shop and zip-lining, and a really cool view of the mountains.

12pm - 1pm: Drove down to Weila and got Mai Tais and lunch at MonkeyPod. This spot is great! But, I actually recommend eating at the MonkeyPod location in Kaanapali. It has a better view.

1pm - 3pm: Went to the Four Seasons to sit by their pool and enjoy their beach without paying $750 a night to stay there! Life hack: hotels in Hawaii don’t seem to care if you use their amenities if you’re not a guest there, so take advantage of it. Plus, the bathrooms at 5-star resorts are to die for.

3pm - 4pm: Quick stop at Leoda’s Kitchen and Pie Shop! Got the Coconut Cream pie.

3pm - 9pm: Drove back to Kaanapali, got dinner at MonkeyPod (yes, we ate their twice in one day), checked out the view and pool from the Sheraton, and then walked around Whalers Village (cute shopping there with some local vendors). The live music here was amazing -- way better than Merriman’s, and for a lot cheaper. ;-)

Day 3

9am - 3pm: A whole day of Road to Hana - below are the stops we made:

TIP: Download the Shaka Guide app and pay $10 for the tour. Download it when you have wifi and it works offline.

Paia Town - the first stop! We grabbed coffee at a local coffee shop, and took some photos at a surfboard fence before getting on the road. You could do a few more shops on the way back if you have time.
Stop at the smoothie and fruit stands along the way and get banana bread.
Stop at the Peninsula and see the church, get banana bread (again), and take photos by the pools and black rocks.
Stop at the free Arboretum. They have beautiful rainbow eucalyptus trees and other plants that are fun to see.
Stop at Ching’s Pond and at least one waterfall (there are at least 4)

4pm - 6pm: Dinner at Mama’s Fish House - everyone says you MUST go. It’s a little pricey, but the view is worth it! The inside of the restaurant is really pretty, too.

Stopping in Paia Town on the Road to Hana

DAY 4

10am - 2pm: Snorkeling at Kapalua Bay.

You can rent snorkel gear at Boss Frog’s for like $10 and return it to any location within 24 hours. I got to see a lot of beautiful fish right there in Kapalua Bay, and didn’t have to take a boat tour out to another location. If you’re trying to save money, it’s a good option.

I also bought an underwater case for my iPhone, but it didn’t really work. I’d recommend investing in a real underwater camera if you want cool photos of turtles and fish.

2pm - 4pm: Walked around Front Street, Lahaina and got lunch at Paia Fish Market. I didn’t think I would like this part of town as much as I did - but it’s super cute and definitely recommend it for a few hours of souvenir shopping and eating. Get shaved ice!

6pm - 8pm: Dinner at The Mill House at Maui Tropical Plantation. This was my favorite dinner spot of the whole trip. The location is super beautiful, and the food and service was really great. Can not recommend this place more!

My first trip to Hawaii was magical, and I’m so happy I got to experience it. If you want more details (or photos) on anything I did, please let me know.

–– Natasha