Eight days on the west side

I wrote this for friends going to Maui for the first time, staying in Napili. Their names are out of it now, but nothing else has been changed to make it sound more universal than it is. This is a west side trip. If you are staying in Kihei or Wailea, the shape still works and the drives get longer.

Maui looks small. There is really only one main road around the island, so every plan you make is a plan about driving.

The biggest mistake I see people make here is spending the whole trip in the car. Eight days is enough to see a lot of the island, or it is enough to actually be somewhere. I would rather be somewhere.

Before you go

Two stops on the way from the airport save the whole week.

Costco for water, snacks, breakfast, and sandwich supplies. Then place a Walmart pickup order before you fly, so it is sitting there waiting rather than costing you an afternoon.

Make breakfast at home. Make most lunches at home. Then spend properly on dinner. People say Maui is expensive, and it is, but mostly it is expensive when you eat three meals a day out for eight days. There is a Hawaiian Sun pancake mix we get every trip.

Day one, arrival

Go straight from the airport to Tiffany's in Wailuku. It is my favorite first meal on the island and it is right there when you land tired.

It is Sheldon Simeon's, from Top Chef. You may see people on TikTok telling you to go to Tin Roof instead. Same chef. This is the better restaurant.

Then check in, and go sit at Napili Bay. That is the whole afternoon.

For dinner, Joey's Kitchen or Sansei. Napili Market is right there too, and the poke is genuinely good.

Day two, snorkeling

Go early. The water is calmest in the morning and it is not close.

Kapalua Bay if you are staying in Napili, since it is about a ten minute walk. Honolua Bay if you want to drive ten minutes for it.

On the way back, stop at the Nakalele Blowhole.

Lunch at Fish Market Maui for poke and fish tacos. Dinner at Japengo, and book it for sunset if you can.

Day three, the beach

Breakfast at The Gazebo, which is worth it if you are close enough to walk. If the line is long, do not stand in it. It is not a line worth an hour of a short trip.

Then the beach, all day.

Happy hour at Sea House, two o'clock to four forty five. The appetizers are the point and it is one of my favorite views on the island.

Dinner is a burger from Napili Market, which uses Maui grass fed beef, or the Honoapiilani food truck park.

Day four, surf

If you want a lesson, we have only ever done them in Kihei, which is about forty five minutes each way. That is a real chunk of a day, but it does get you a morning on the other side of the island.

Afternoon back in Napili doing nothing.

Dinner at Star Noodle. Garlic noodles and pork buns, and ask for a sunset reservation.

Day five, Haleakala at sunset

My hot take: skip the sunrise. The full argument is in the Haleakala guide, but the short version is that sunset is just as good and you do not have to wake up at two in the morning.

Give yourself half a day and make the drive part of it. Download the Shaka Guide. Lunch at Paia Fish Market. Walk around Makawao.

Bring a sweatshirt, the blankets from your room, and chairs.

If it is clear, stay after the sun goes down. The stargazing up there is the part people forget to plan for. If it is cloudy, do not wait it out. Head straight down the hill and have dinner at Marlow instead.

Day six, do nothing on purpose

Sleep in. This is the day that makes the trip feel like a trip.

Brunch at the Plantation House, or Aloha Mixed Plate, which I love.

Then treat yourselves. ResortPass gets you into a hotel pool for the day, a private cabana is worth it once, and we have had massages at the spa at the Resort at Kapalua Bay and then stayed in the pools for the rest of the afternoon. It was one of our favorite days on the island.

Dinner at Merriman's. It is the biggest splurge here and it is worth it.

Day seven, pick one

Book a snorkel tour, Turtle Town or Molokini. Or stay around Napili and do the beaches and the coastal trails. Or drive down to Kihei and Wailea for the day: breakfast at Kihei Caffe, the beach at Wailea, dinner at Dang Dang Noodle.

Wailea is beautiful. I still think the west side is better.

Day eight, do not squeeze

Do not try to fit in one more attraction on your last day.

Go back to whichever beach turned out to be your favorite. Shop at Whalers Village if you want to bring something home. Farewell dinner at Monkeypod, or honestly anything in Whalers Village.

The short version

Stay on your side of the island as much as you can. Make sunset dinner reservations wherever you can, and walk in everywhere else. Cook breakfast.

And do not spend your trip in the car.