Curated by: Lucas Santos & Ben Dumas
Travel Period: August 2014
Traveled With: Just Us
Typical Weather: Hot during the day with muggy afternoons, but cooler breeze nights
Getting There: NYC - LA - Kahului (approximately 5 hours each leg)
Getting Around: Rent a car to get from Kahului to all the other parts of the island

The magical island of Maui is one of our favorite vacation destinations in the United States. The island has several areas that are all special in their own way – Hana is the Eastern-most town on the island and is a lush tropical unspoiled paradise, Wailea is more beachy and touristy with some top notch luxury hotels, and then the West Coast of Maui (Kaanapali and Kapalua) has the best weather and best sunsets. We were in Maui for a wedding (Lucas’ sister), which took place in Hana. To see a couple sides of Maui, we split our time in Hana and then went to the West Coast. Both are incredible and we’d recommend doing the same to get a diverse taste of the island.

HANA

STAY

  • Travaasa - Higher end, more modern and updated hotel closer to Hana town center. Traavasa has a beautiful pool and expansive grass fields that run right all the way up to the beach/cliff. This hotel is known for its spa treatments so indulge.
  • Hana Kai Maui - More traditional hotel with less modern amenities a little before Hana town. Rooms open up right on to Waikaloa Beach. This is definitely one of the nicer, yet affordable options in Hana.

SEE & DO

  • Waianapanapa State Park – Surreal black sand beach, very unique and a must if you’re in Hana. Its a park so you drive in and explore the beach, the caves, and the natural pools in the area.
  • Hamoa Beach – This is the main beach for the locals. Great people and surfing watching beach. Sunsets along the cliffs overlooking Hamoa Beach is unbelievable.
  • Red Sand Beach – Located tucked away in Kaihalulu Bay. To get to this secluded beach, you have to walk/hike around some rocks for about 5-10 minutes. Also sometimes a nude beach.
  • Koki Beach – Nice beach with Alau Island perfectly centered out on the horizon. Worth a stroll on the sand, but not the nicest water.
  • 7 Sacred Pools at O’heo Gulch – Incredible natural pools 30 minutes past Hana town. These pools belong to the Haleakela National Park so it can and does get pretty busy during sunny days. This is a must see spot so plan to get there before noon to avoid any crowds.
  • Bamboo Forest Park – Massive bamboo forest close to the 7 Sacred Pools that everyone staying in Hana should go to as well. Wear your hiking shoes since it gets pretty hilly at times.
  • Waioka Pond aka “Venus Pools” – This is a local cliff jumping and swimming hot spot just outside of Hana town. The natural ocean “pool” is deep enough and protected from the ocean currents and waves so tourists and locals can enjoy jumping or swimming in the crystal clear blue water.
  • Kula Farms – Super cute scenic farm located high above the mountain along the route from Hana to Kaanapali. Their strawberries were some of the best we’ve ever tasted.
  • Haleakala National Park – If you have not already done this at some point in your life, you absolutely need to consider it. Plan to wake up really early one morning and get to the top of Maui’s active volcano to enjoy an epic sunrise above the clouds. Bundle up, because it can be 30 degrees colder up top.

EAT & DRINK

  • Hana Farms/Ono Farms - Lots of organic, locally grown items for sale along the road right before getting into Hana town center. You’ll find anything from fruits and banana bread, to salads and brick oven pizzas – things change daily.
  • Coconut Glen’s Ice Cream – Organic vegan ice cream stand on the Road to Hana. This is a must stop for anyone doing this drive. Their passion fruit and coconut flavors are hands down the best.
  • Thai Food by Pranee – ABSOLUTELY THE BEST Thai food we have ever had ever, and we eat lots of Thai. Literally my mouth is watering as I type this. Pranne and her whole family are amazing and will take care of you. Get the Crispy Opoka Salad and the Thai Curry.
  • Brudda Hutt's BBQ – Family run BBQ food truck a few minutes past main town center. They’ve grown into two trucks and have set up a bunch of picnic tables along the trucks to make it more of a stop and eat spot. Everything is so good!

WEST MAUI

STAY

  • Montage (Kapalua) - Super high-end modern luxury hotel in Kapalua Bay on the west coast of Maui. If you want a retreat and relaxing type of trip in Maui, we’d suggest staying here since they have so much around the property that you don’t really have to ever leave.
  • Westin (Kaanapali) – Located right in the middle of the hotel strip along the beautiful Kaanapali coast. This area in Maui is almost always guaranteed to have the best weather and the best sunsets. There is also way more restaurant and activity options around here since it caters so couples and families staying around the area.

SEE & DO

  • Sail & Snorkel – Maui has incredible snorkeling with very lush coral reefs everywhere around Kaanapali. It is definitely worth a half day sailing trip or if you’re not that into activities during the day, you can always do a boozy sunset sailing trip which is also really amazing.
  • Black Rock Jumping – At the end of Kaanapali beach there is a massive black rock (directly in front of the Sheraton resort). It was so fun bringing a snorkle and mask to the top of the rock and jumping off to explore the reef below. We swam alongside a massive sea turtle and saw so many type of fish. 
  • Helicopter Ride – Maui is so beautiful and has some incredible cliffs and coastlines so we highly suggest doing a Helicopter ride. There are multiple routes, but we would recommend one that gets you around the West Coast of Maui and Molokai. This small island just outside of Maui has some surreal waterfalls that are more than 1,500 feet high.

EAT & DRINK

  • Cane & Canoe (Kapalua) – Delicious fine dining modern Hawaiian & Asian fusion restaurant in the Montage property. This mostly outdoor dining experience allows you to enjoy the sunset views right from your table. 
  • Leilani’s On The Beach (Kaanapali) – Easy and delicious beachside casual seafood restaurant right on the boardwalk. We got the seared ahi tuna almost every time we went since it is all daily caught. 
  • Relish Oceanside (Kaanapali) – Delicious American/Seafood restaurant with a nice outdoor atmosphere. Great for a sunset cocktail and more fancy dinner. 
  • Hula Grill (Kaanapali) – Seafood and steak restaurant next to Leilani's. Also on the boardwalk, but a little nicer so we went here for dinner. They tables are set on actual beach sand so it feels like you're still at the beach.