Haleakala National Park

Haleakala is an immovable and unmistakable presence on Maui and a drive to the top of the Island is a must. You start at the beach, low and hot in the desert and make your way through the eucalyptus forests of Upcountry to the winding roads and rolling emerald hills dotted with cattle. You eventually rise above the cloud line and see the top of this beautiful volcano, and you can feel why Hawaiians named it the House of the Sun. Remember to bring warm layers, you just climbed almost 10,000 feet in elevation.

Early birds will love the sunrise on Haleakala. Make sure you get a permit. And if you’re not a morning person, you can plan a road trip on your own time to see the sunset. Either way, on the trip up or down, pull over for pictures or to visit that cute shop. Since it’s a road trip, bring lots of snacks! I like the poke from Foodland with taro or Maui onion chips. I use the chips as edible spoons. Another good stopping spot for snacks is Mana Foods in Paia Town. I like their deli counter and fruit selection.

For the more adventurous: Consider biking down Haleakala. A van takes you to the start of the park and you’re off! There’s barely any pedaling needed since it’s almost all downhill, and it's especially exhilarating to bike through the cloud layer. Stop often for pictures, and especially make a pit stop in Makawao for lunch and some shopping. I like the seafood enchiladas at Polli’s Mexican. Just make sure to stay on the side of the road while biking. You don’t want to be a nuisance for the locals driving about their day.

Water Activities

Hawaii is a swimmer’s paradise. If you’re comfortable swimming in the ocean, keep a swimsuit in your car along with renting snorkeling gear. It allows spontaneous beach moments - which, you will probably be tempted a lot by on Maui. You may be lucky enough to see dolphins or the beloved Honu, the green sea turtle and if you’re visiting during whale season keep your ears pricked for whale-song! Craving a deeper snorkeling or scuba experience? A guided snorkeling tour of Molokini Crater is a must do.

Maui is a fantastic place to try canoeing, kayaking, paddle boarding and surfing too. There are lots of options, like sunrise canoes and all-female owned and operated surfing schools. There are also numerous leisure cruises available if you'd like to prioritize R&R on your vacation. Sunset cocktail cruises and whale-sighting cruises are the most popular.
Some of my favorite beaches are Makena, Baldwin and Ka'anapali.

If ocean activities are not your speed, there are a plethora of relaxing resort pools throughout the island with poolside service that cater to both adult and family friendly tilts.

Hike Town and Talk Story

Maui has a lot of cute walkable towns with interesting history related to the industries of the Island. Explore outside the resort or hotel and take a stroll through a few!

Makawao is a Paniolo Town, which means it's a cowboy town! Located Upcountry, Makawao is an icon of Upcountry Plantation architecture and has a reputation for being an artists’ destination. This is a great place to spend a morning or afternoon perusing art galleries and snacking while enjoying the pristine Upcountry climate. The cream puffs from Komoda are legendary. Makawao is a great stop on the way up or down from Haleakala. In fact, it’s hard NOT to stop in Makawao while Upcountry. If you’re visiting over the Fourth of July weekend, the Makawao Rodeo is a must do and a big event for the whole island.

Lahaina on East Maui is another town with distinctive style and plenty to see. Lahaina is an old whaling village and the former capital of the Hawaiian Kingdom. Its Front Street runs parallel to the ocean and is host to numerous boutiques, restaurants and bars, so makes for a fantastic stroll. It’s easy to spend an entire day here window shopping, picking out flip flops and noshing place to place. The most notable attraction is the Banyan Tree Court and the site of the old palace, known as The Brick Palace. The Banyan Tree is a wonderful place to enjoy an ice cream or shave ice and watch the world go by.

Paia Town on the North Shore is also known as The Last Town Before Hana. Paia town was originally home to the employees of the shuttered Paia Sugar Mill, and now hosts a variety of locals and transplants, many being descendents of 60’s and 70’s hippies and/or avid wind-surfers. Nearby Ho’okipa Beach is considered one of the best windsurfing destinations in the world, if not the best. If you’re visiting Paia it’s worth it to pop into this beach and watch the pros practice. Paia currently hosts several boutiques and many delicious restaurants, notably the original Paia Fish Market (there are locations in Lahaina and Kihei too). I recommend the tacos. If you’re making the drive out to Hana, Paia is a more than worthwhile rest stop, and at the very least you should stock up on snacks at Mana Foods.

Day trips

• Roadtrip to the top of Haleakala.

• Roadtrip to Hana.

Breakfast

Leoda’s Kitchen and Pie Shop (Lahaina) - This scrumptious pie shop is slinging some serious classic breakfast and clean American fare. It’s truly a great place for both breakfast and lunch, and their Olowalu Lime Pie is not to be missed (it’s so good it was the dessert at my wedding.)

Baked on Maui (Upcountry) - Baked on Maui is serving “fresh baked aloha." This casual Upcountry eatery serves eggs and other breakfast proteins with fresh bread, pastries and granola packed with coconut. The granola makes for a great gift or an edible memento.

Akami Coffee (Kahalui, Kihei and Wailea) - For the coffee lovers: This roastery has award-winning beans and the staff knows how to show it off. This top tier coffee shop also has delicious nosh like avocado toast and belgian waffles.

Ka’ana Kitchen (Wailea) - This restaurant in the Andaz Wailea is the only restaurant in a hotel that makes my list because they make the most beautiful breakfast buffet I have ever seen. Fill your plate with a bounty of fresh fruit and a variety of breakfast proteins and pastries. They have a fresh juicing station, cinnamon roll pancakes and kimchi pancakes, but the jewel in the crown is their mochi waffles. Perfectly bouncy and chewy, it’s hard to have just one.

Lunch

O’o Farms (Upcountry) - This is an experience as much as a meal. Enjoy an open air lunch cooked over an open flame after you take a tour of the organic garden hosted by one of the gardeners. Pick your own salad greens, then relax and enjoy the bounty and the view. You can bring your own wine too.

Paia Fish Market (various locations) - No frills counter service. They have daily catch options and you pick your fish, its preparation, then what format you would like your fish in. I usually get Cajun style ono tacos and my partner loves the quesadillas. Pastas, salads and burgers available as well.

Cafe o Lei at the Mill House (Wailuku) - I love coming to this restaurant for lunch because I think this is the best way to enjoy its gorgeous garden setting. Cafe o Lei is located on the 60 acre Maui Tropical Plantation and serves elevated Hawaiian classics. This is a very romantic place for dinner, especially during sunset.

Polli’s Mexican (Makawao) - This mainstay has been serving solid Mexican food since 1981. Polli’s is a laid back local favorite with great margaritas and better vibes. I recommend the seafood enchiladas.

Maui Brewing Company (Kihei and Lahaina) - For the beer lovers: Maui Brewing Company is the largest craft brewery in the state and one of the few solar powered breweries in the US. Their commitment to sustainability makes the beer taste even better, if possible. The Pineapple Mana Wheat Ale is brewed with fresh Hawaiian pineapple juice that is crisp and perfect on a warm vacation day. Food is as expected from a brewpub, with Hawaiian twists like pulled pork sliders with guava jelly, and edamame offered alongside typical fries.

Dinner

Mama’s Fish House (North Shore) - At first glance, Mama’s seems like a tourist trap but don’t let that deter you. This upscale restaurant has some of the best seafood in all of Maui thanks to their longstanding partnership with local fishermen. Mama’s is fantastic for a romantic night - they have great ocean views and open air seating. If it’s a special night, request a special table and they’ll do their best to accommodate. Reservations highly recommended.

Monkeypod Kitchen (Wailea and Ka’anapali) - This spirits forward restaurant has some of the best mai tais on the island. Their lilikoi foam is amazing. They serve various appetizers like lobster deviled eggs, as well as pizzas, salads and burgers. Monkeypod is an especially great place for happy hour.

Star Noodle (Lahaina) - A delicious oceanfront Asian fusion restaurant serving delectable salads, steam buns, and yes - noodles. You really can’t go wrong with any dish here, but I recommend the Hapa Ramen, which marries the richness of traditional Japanese Tonkatsu with Hawaiian kalua pork. Reservations are highly recommended.

Marlow (Makawao) - This newer addition to the Makawao scene is giving modern minimal decor and delicious Napolean style pizza. The owners are passionate about growing and sourcing their ingredients, which translates beautifully into their pies. Try the wood fired octopus.

Milagro’s Mexican (Paia) - Another great local favorite. Milagro’s is the perfect place to meet new friends and talk story. This breezy restaurant serves delicious Tex-Mex options, and was voted Maui’s best margarita. Their extensive drink lists makes for a fabulous happy hour (everyday 3pm-6pm).