A dream come true for couples around the world, deciding to host your wedding on one of the most beautiful islands in the world is a true gift to yourself and your guests! While getting Maui’d comes with its fair share of obvious perks, many couples underestimate the amount of work it takes, especially when planning from thousands of miles away. Photos from successful Maui weddings by Natalie Brown.
We’re not sure about you, but the Summer Olympics are one of our favorite things to watch! And as much as we support all of our U.S. teams and athletes, we can’t deny our excitement for the Aloha Olympics, open only to Hawaii residents.
This Aloha Olympics team sport begins with a qualifier round on flat ground to see who will be given the advantage of the higher elevation side of the net once the official games begin on the slopes of Haleakala Volcano. The two teams of 6 will be challenged not only by the intensely sloping ground, which must be played at elevation levels of no less than 8,000 feet, but the added challenges of occasional fly-by clouds or Nene goose visitors.
Captain Roger Gildersleeve gave me the support and confidence to live the life I lead. He was my first marketing client on Maui, where I help promote his beautiful vessel the Kai Kanani. He gave me a shot, and his confidence in me was priceless. I now have 70 clients, support a family of four, and am positively growing every day thanks to his inspiration.
His loss is being felt throughout the islands, but his absence is not what this article is about. It’s important we share what he left behind.
I’ll never forget my first meeting with Roger. He’d seemed to have figured things out. Having had been through a life threatening illness (physically evident from a scar on his head.) He admitted to looking at the future with a positive nature and love for life. He was taking advantage of the gift of second chance.
For those not on Maui, it would seem that running a successful luxury catamaran in paradise would leave very little room for negativity. Those that live on Maui know that life’s challenges follow anywhere you go. But for Roger, even during a particularly stressful time in his life, he remained positive, celebrating each small success he managed during the turmoil. At least to me, he always seemed to be living with that 2nd lease on life mentality. Each additional breath was a blessing. Can you imagine our world if we all had that gift?
Over the near decade that I’ve had the pleasure of knowing him, he’s increased his dependency on his Kai Kanani ohana. He treated his captains and crew like family–he’s given his trust to great people like Captains Cary and Anthony–in order to spend his valuable time doing what he loved (even more than being on the water): time with his kids and grand kids. He’d also spent countless patient hours taking the most beautiful photos of birds I’ve ever seen. He dove into photography like a boy in love. His passion was infectious. Read More
In the meantime, check out our aerial video of Maalaea Harbor.
“I was really excited to check out the webcam to see if there were any waves at Freight Trains or Buzz’s. Then I remembered that it only breaks once every 100 years. HAHA!”
Justin Cooper – Wailuku
“I look forward to checking the weather before we go on our boat trip out of Maalaea Harbor. We’re on the fence whether to do a sunset cruise or a luau. Now we can make that decision before driving down there!”
These scuba dive spots are just a few of the best in the world. Please add more suggestions in the comments below, and we’ll add them to the list.
Directions from Central & North MauiAreas: Kahului, Wailuku, Waikapu, Paia
Approximate Time: 20 minutes
From Central and North Maui, take Honoapi’ilani Highway (Hwy 30) and go south until you reach the stoplight near Carls Jr. and the Maui Ocean Center. Make a left and drive down into the parking area for the harbor.
Areas: Olowalu, Lahaina, Ka’anapali, Napili, Kapalua
Approximate Time: 30 minutes
From West Maui, take Honoapi’ilani Highway (Hwy 30) and go southeast. After passing through the tunnel, you’ll see a sign for Maalaea Harbor. Turn right at the sign near Buzz’s Wharf, and arrive at the parking area for the harbor.
Areas: Kihei, Wailea, Makena
Approximate Time: 15 minutes
From South Maui, take Pi’ilani Highway (Hwy 31) and go north. Alternately, you can also follow South Kihei Road to Hwy 31 until you get to the stoplight. Turn left towards Lahaina onto Honoapi’ilani Highway (Hwy 30), and make another left at the stoplight near Carls Jr. and the Maui Ocean Center.
Driving Around Maalaea:Although Maalaea is easily reached from almost any area of the island, why not get there in style! Rent an all new lifted 2018 Jeep Wrangler from Maui Lifted Jeep Rentals and rest assured you’re in the best vehicle possible to explore Maui’s most stunning areas. Crank the aloha tunes and enjoy views of Maalaea Harbor and nearby areas like Baby Beach, Haycraft Beach Park and Sugar Beach from the seat of your lifted Jeep at an excellent price.
Maalaea Harbor has a huge variety of ocean tours available, including snorkeling, scuba diving, SNUBA, bottom fishing, sailing and more. Slip numbers are listed on the piers. Even numbers are further out on the ocean side, while odd numbers are on the land side.
Slip #37: Aloha Blue Charters – Snorkeling, Whale Watching
Slip #42: Island Star Excursions – Snorkeling, Whale Watching, Sailing
Slip #44: Quicksilver – Snorkeling, Whale Watching, Sunset Dinner Cruising
Slip #47: Mahana Naia – Snorkeling
Slip #55: Maui Magic – Snorkeling, Whale Watching
Slip #55: Pacific Whale Foundation – Whale Watching
Slip #56: Alii Nui – Sunset Cocktail Cruising
Slip #62: Trilogy – Whale Watching
Slip #65: Maui Fun Charters – Bottom Fishing on the Pamela
Slip #68: Pride of Maui – Snorkeling, Scuba Diving, SNUBA, Whale Watching, Sunset Cocktail Cruising
Slip #68: Leilani – Snorkeling, Whale Watching, Sunset Cruising
Slip #68: Maalaea Sportfishing – Sportfishing
Slip #70: Shadowfax – Private Snorkeling, Whale Watching, SUP, Sunset, Live Aboard and Sailing Cruises
Slip #72: Paragon Sailing Charters – Snorkeling, Sailing
Slip #76: Lani Kai – Snorkeling, SNUBA, Whale Watching
Slip #80: Four Winds II – Snorkeling, Whale Watching
Slip #88: Malolo Charters – Snorkeling, Whale Watching
Slip #97: Maui Fun Charters – Bottom Fishing on the Marjorie Ann
Slip #99: Trilogy – Whale Watching
Book a snorkel trip to Molokini Crater or Coral Gardens!
For travelers and residents who would like to visit Maui’s neighbor islands of Lanai and Molokai, the only current departure sites for the respective ferries is from Lahaina Harbor, though Expeditions’ Maalaea to Lanai ferry is set to reopen sometime in 2016.
“We went to to Molokini for our anniversary. The snorkeling was superb and the crew really fun. We also did a sunset cruise, which turned into a whale watch! It was unreal! So many whales. February apparently is the best time to go. NOTE TO SELF.”
Frankie Smits – California
“We ate at Beach Bums as well as the Oceanside Restaurant. Beach Bums was fun and perfect for hanging with friends with beers. Oceanside was something completely different. Each dish was other worldly! We ate there 4 times in 6 days. SO GOOD!”
Jenny Henderson – Georgia
At the top of our list are luaus. Why? Attending a Maui luau gives you so much in one event: delicious Hawaiian food, graceful hula dancing, history and legend from the told in story by a local Hawaiian expert, beautiful island music while sipping on tropical drinks and watching sunset over the ocean. Not sure it gets better than that. But it does! The best luau shows have fire-knife dancers to finish things off. VERY IMPRESSIVE! (And on that note, we suggest only going to a show that offers firedancing.) It’s perfect for the newlywed couples as well as for family with kids. We personally go to 4-5 shows ever year, and we live here. That says something. 
Departing daily from Maalaea Harbor, snorkel boats are perfect for travelers looking to explore some of Maui’s best snorkeling and scuba diving destinations, including Molokini Crater and South Maui’s Turtle Town. Whether you want to snorkel, scuba dive or give SNUBA a try, they offer options for every preference. Their most popular morning tours usually include snorkeling at Molokini and Turtle Town (with optional scuba and snuba), all necessary gear, complimentary BBQ and lunch, fully stocked open bar, impeccable service, spacious boat decks, top safety standards and optional underwater photo and video services. Highly recommended for all ages!
From December 15th to April 15th, Maui is one of the best places in the world to whale watch! Trilogy offers daily whale watching tours from Maalaea Harbor aboard their comfortable catamarans, offering perfect views for a fun day on the water with friends and family. Their staff of expert naturalists share valuable information about the most popular humpback whale behaviors, and even have hydrophones on board to allow guests to hear as the males sing underwater! Tours include breakfast and lunch, cocktails, sodas and water, and they limit tour sizes to only 40 people for better viewing purposes.
Shoot down Kuihelani highway to Kahului Airport for a unique opportunity to learn how to fly a plane in the skies above Maui. Fly Maui presents a chance for people of all ages to take their first lesson in flight school. Not only does Fly Maui’s Discovery Flight experience bring the joy of flying to just about anyone, but it also offers an unforgettable experience of exploring the captivating terrain of the Valley Isle from above. 
With a central meeting point only a few minutes’ drive from Maalaea Harbor, Rappel Maui offers a unique opportunity to boost your adrenaline along the famous Road to Hana. Choose from three available rappelling tours based on your level of previous experience – none required! – and head out for a full day of waterfall adventure on the Hana Highway. One of Maui’s most bold adventures, guests will be transported to a 30 acre botanical garden, where they will hike a short distance and receive full a briefing and demonstration from professional guides before attempting their first rappel down a 60 foot dry jungle wall. After honing their skills, guests will then rappel down 50 and 30 foot waterfalls, taking plenty of breaks for a swim and catered lunch in the garden. Guests must be at least 10 years old and weigh between 70 and 250 pounds to participate.
The largest and most prestigious aquarium in Hawaii, Maui Ocean Center is an excellent place to learn more about Hawaii’s variety of marine life, spend a rainy afternoon with the kids, attend a special talk from one of Hawaii’s marine specialists, or even scuba dive in the 750,000 gallon saltwater shark tank! Located in the heart of Maalaea, guests will enjoy seeing special exhibits like the Hawaiian Green Sea Turtle Lagoon, Hammerhead Harbor, Sea Jelly Gallery, Marine Mammal Discovery Center, The Tide Pool, Hawaiians & The Sea, and more. Keep an eye on their events calendar for unique opportunities and tours!
Like the idea of catching your own dinner, or interested in seeing what Maui’s marine life has to offer? Head out for a day on the water with the bottom fishing pros at Maui Fun Charters. The 4 hour morning tour aboard the Marjorie Ann or Pamela departs from Maalaea Harbor, and includes personal attention from the crew, as well as an opportunity to try a greater variety of fishing styles, thanks to the small group sizes on each tour. This makes for the perfect family activity, and the views can’t be beat! They also use the newest electronics and offer plenty of comfortable seating for all guests.
Visiting Maui is always memorable. But learning to swim like a mermaid will set this trip apart from the others with great memories and incredible photos. Spend 2 hours learning to swim with your tail as your instructor takes you through it step by step. You won’t regret it!
Located only a 5 to 10 minute drive from Maalaea Harbor, Maui Zipline is one of our favorite activities in central Maui. Hosting guests anywhere from 5 to 88 years of age, you’ll be treated to a 5-line zip tour over some of Maui’s prettiest, most stunning areas. Guides are all very patient and safety-conscious, and we especially love that each line is side-by-side, giving you the opportunity to ride alongside your friends and family! Check out the amazing views of the nearby West Maui Mountains and swaying palm trees, tropical grounds and a sparkling lagoon of Maui Tropical Plantation, as well as distant views of Maui’s Haleakala Volcano. Then continue exploring the property, home to The Mill House restaurant, Kumu Farms fruit stand, Tropical Tram Tour, shopping and more.
Located just a short drive from Ma’alaea, Maui’s new indoor trampoline park is the ultimate way to spend a rainy afternoon with the kiddos or fun weekend outing with friends. The 25,000 foot park is open to all ages, and is separated into zones by age and size for the safest jumping experience. Kama’aina discounts are available, and unlimited jump passes are available for only $25. Guests are encouraged to reserve their spot and fill out the waiver online, as there is a capacity limit. This new Wailuku attraction is popular for all members of the family, and an entertaining workout for everyone!
One of the newest entertainment crazes in the U.S., escape rooms have landed in Wailuku Town at Mystery Maui. Available for groups of 2 to 6 people, whether it be your coworkers on a special pau hana mission, a fun date night activity, family-friendly outing on a rainy day or thrilling girls night out, you’ll use your best detective skills to solve one of two challenging and entertaining mysteries, including the missing chef at The Ramen Shop and Stella Superstar’s private pop concert. With under 60 minutes to decode the given clues, you’ll work together, along with help from your game marshal, to see how far you can get and escape the room.
Combine two memorable Maui tour experiences by embarking on a sunrise mission atop the 10,000 foot summit of Haleakala Volcano, followed by a scenic, self-guided 23-mile downhill bike ride to the north shore town of Haiku. Available for guests 12 and over who are at least 4’10” tall, Bike Maui’s Sunrise Special tour embarks from Haiku at 3am, where you’ll hop into a tour van for an entertaining – albeit dark – guided drive up to the entrance and summit of Haleakala National Park in time for sunrise. Afterward, you’ll be driven back down to 6,500 feet for the second portion of the experience, a self-paced bike ride down the volcanic slopes through Upcountry’s most gorgeous areas. Stop for breakfast, and to browse galleries and take plenty of photos, and return with plenty of time left to enjoy a day of fun in the sun.
One of the best budget-friendly evening boat tours on Maui, Quicksilver offers a fun sunset and dinner cruise departing directly from Maalaea Harbor. Cruise along the Pali coast while enjoying spectacular sunset views, and enjoy live music entertainment and dancing aboard their spacious double-decker boat. Tours include table seating, full dinner, tropical cocktails, beer, wine, and epic sunset views, and whale watching during winter months! Children 6 and under are free, and service is always friendly and welcoming.
Head back to Kahului Airport to partake in one of Maui’s most popular, thrilling, and memorable adventures: a scenic helicopter flight. Go Fly Maui offers two unique opportunities to soar above the Valley Isle. Take a flight lesson with Go Fly Maui’s certified instructors and learn how to navigate the skies around Maui. Or, opt for a photography adventure flight in a doors-off chopper. Work with the Go Fly Maui crew to build your ideal flight map and they will help you capture stunning aerial images of Maui.
Relax on the sea with a sail aboard the 44-foot Shadowfax. Operating directly out of Ma’alaea Harbor, Shadowfax offers private sailing charters, whale watches, custom snorkeling tours, and overnight adventures for up to six guests. No matter what adventure you choose, you’ll sail with a seasoned crew, explore some of Maui’s most secret locales, and take in unique views of the stunning Valley Isle and neighbor islands. 
Each summer, the Maui Film Festival returns to celebrate filmmakers, original cinema, culinary arts, and the Maui community. Over the course of five days and nights, the Maui Film Festival hosts an array of original film screenings, premiers, foodie festivals, award ceremonies, and so much more! The events take place at several open-air locations around Maui, with a focus on Wailea, located only a short distance from Ma’alaea. The 2020 Maui Film Festival runs June 17-21, and you can still get tickets!
Also located conveniently in Maalaea, Maui Golf & Sports Park is a fun, kid-friendly place to test your adventurous side. Play a round of mini golf, or choose from one of their other onsite activities, including rock climbing, bumper boats and x-treme bungee trampoline. Open daily from 10am to 6pm, this makes for a great midday break (and workout).
“We stay on Maui for 2 months every winter. My family bought the annual passes because we end up going to the aquarium so much. What a great spot!”
Renee Hopkins – North Carolina
“I’ve been to Molokini twice. I was really impressed with how good the snorkeling was at Coral Gardens too. Protected by the sea cliffs, this spot was teaming with turtles. So much fun.”
Mike Johnson – Victoria, Canada
Located at the eastern area of the harbor, this beach is protected from waves and boat hazards, making it perfect for small children or inexperienced swimmers staying nearby.
Just east of Maalaea Harbor, Maalaea Beach is ideal for sunset walks, shell collecting and relaxed days spent enjoying the sun in an uncrowded area of Maui.
Connecting Maalaea Beach and Sugar Beach, this County Beach Park is a great place to enjoy an afternoon picnic or take a peaceful walk.
Including Maalaea and Haycraft Beach Park, this is longest uninterrupted stretch of beach on Maui. Though swimming isn’t great here, it’s a perfect place to enjoy the views and natural surroundings in paradise.
“Living here, you get to know the beaches. Some of my favorite spots are near Maalaea. You can always find a beach to yourself!”
Jason Hacker – Maui
“My kids and I were on our way back from lunch, and we jumped in the ocean right off the road. It was nice to have a quick dip without much walking. No one at the beach too!”
Frankie Harper – Illinois
Located at the Maui Ocean Center, Seascape Maalaea offers scenic views of the harbor and southern shoreline, as well as a variety of fresh, delicious dishes, perfect for an afternoon lunch or dinner after exploring the aquarium. Service is friendly and welcoming, and we love the Mango-Hoisin baby back ribs, Local Boy Club Sandwich and Coconut Shrimp. They also have a great cocktail menu and selection of local beers!
For more information, please visit Seascape Restaurant, call 808.270.7068 or visit 192 Maalaea Rd., Maalaea.
For a slightly more relaxed meal, we recommend a trip to Maalaea General Store’s delicious deli and cafe. Choose from one of their breakfast menu items, including the Spicy Avocado Egg Toast or Acai Bowl, or go with their wide variety of lunch menu items like the Reuben Sandwich, General’s Chop Salad, Mahi Mahi Tacos, Jalapeño Jack Burger or Kalua Pork Tacos. Large portions, and perfect for a laid-back meal in paradise.
For more information, please visit Maalaea General Store, call 808.242.8900 or visit 132 Maalaea Rd., Maalaea.
Open daily for breakfast, lunch and dinner, Beach Bums is a great place to kick back and enjoy a cold beverage, mingle and listen to live music. Try the Portuguese Sausage Eggs Benedict and Bloody Mary for breakfast, or the Prime Rib and Blackened Fish Tacos for lunch and dinner. Happy Hour is daily from 3pm to 6pm, with live music from 5pm to 8pm.
For more information, please visit Beach Bums, call 808.243.2286 or visit 300 Maalaea Rd. #1M, Maalaea.
Located in the heart of the gorgeous Maui Tropical Plantation only a few minutes from Maalaea Harbor, The Mill House is one of the most respected restaurants on The Valley Isle. Executive Chef Taylor Ponte creates innovative menus focusing on local, organic and sustainable ingredients, and the views from the dining area can’t be beat. Open daily for lunch and dinner, we recommend the House Pickles, Cubano Pork, Beef Ragu Gnocchi, Pizzeta Harissa and Cioppino, though the menu changes regularly depending on what’s in season. Don’t miss the cocktail menu, and catch Happy Hour daily from 3 to 5pm!
For more information, please visit The Mill House, call 808.270.0333 or visit 1670 Honoapiilani Hwy., Waikapu.
“We ended up at Beach Bums after a snorkel trip and had a blast. Delicious BBQ and great beers.”
Taj Billings – Vancouver, Canada
“After a long day traveling the Road to Hana, we stopped in Maalaea on the way home to our rental in Ka’anapali. We heard Oceanside was great. We were far from disappointed. Every dish was exceptional. We ended up traveling back to Maalaea just to have another meal. UNREAL!”
Charles Dory – Florida
Maalaea BanyansIt’s hard to beat 1 and 2 bedroom condos only steps from the ocean at affordable rates.
This property is popular for many reasons, including the oceanfront heated swimming pool, jacuzzi, picnic area and gas BBQ grills. You can enter the water from the property, and there’s also a beautiful white sand beach only a few minute walk down the street. With free parking and wifi, having your own kitchen also makes these units some of the best prices you’ll find on the Valley Isle.
For more information, please visit Maalaea Banyan Condos at 222 Hauoli Street, Maalaea.
Milowai Condominium ResortAlso located in the heart of Maalaea, Milowai Condos offer an inviting, relaxing escape in central Maui, perfect for couples or solo travelers.
With an assortment of 1 bedroom condos for rent, Milowai offers panoramic ocean views from every room, as well as a washer and dryer, fully-equipped kitchen, onsite restaurant, heated pool, elevator, BBQ grills, picnic area, tropical garden, cable TV and more.
For more information, please call 323.942.9725 or visit 50 Hauoli Street, Maalaea.
Maui Island Sands ResortA short walk from Maui Ocean Center and Maalaea Harbor, Maui Islands Sands Resort features 1 and 2 bedroom condos in the heart of central Maui.
Every unit includes sweeping ocean views, as well as a private lanai, A/C, washer and dryer, cable TV, DVD, telephone, and fully-equipped kitchen. Visitors can enjoy the tropically landscaped grounds, oceanfront swimming pool and BBQ facilities, or take a quick walk to one of the surrounding restaurants.
For more information, please call 1.888.977.2637 or visit 150 Hauoli Street, Maalaea.
Located on the serene sands of Sugar Beach, Kealia Resort is a secluded escape, ideal for travelers seeking a convenient location without sacrificing peace and quiet.
Choose from a Studio or 1 Bedroom Suite with a Partial Ocean View, 1 Bedroom Ocean View, 1 Bedroom Oceanfront, or 2 Bedroom Oceanfront room, all of which include beachfront access, private lanai, washer and dryer, full kitchen, A/C, cable TV, and telephone. Complex amenities include an oceanside pool, BBQ grills, lawn lounge chairs, and weekly pupu party.
For more information, please call 1.800.265.0686 or visit 191 North Kihei Rd., Kihei.
Located on five acres of tropical gardens and fronting a stretch of uncrowded beach, Maalaea Surf Resort offers spacious 1 and 2 bedroom oceanfront condos.
Each unit features a full kitchen, private lanai overlooking Maalaea Bay, wifi, maid service, complimentary amenities, TV, DVD player and A/C, while the resort itself also includes 2 swimming pools, 2 tennis courts, BBQ grills, and a shuffleboard court. Guests can enjoy scenic sunset views all year long, and whale watching during winter months at this conveniently-located Maalaea accommodation option.
For more information, please call 1.800.423.7953 or visit 12 South Kihei Rd., Kihei.
The Penthouse MauiLocated only a short 10-minute drive from Ma’alaea, The Penthouse Maui overlooks one of South Maui’s most pristine beaches. Guests will enjoy The Penthouse Maui’s tastefully styled interior as well as striking sunset and ocean views from the open-air lanai. With an unparalleled beachfront location in sunny South Kihei, guests will find easy access to a handful of nearby amenities and activities.
The Penthouse Maui is also in close proximity to Ma’alaea Harbor- the nucleus for snorkel tours and whale watch excursions. The Penthouse Maui’s spacious design can sleep groups of up to ten.
For more information, please call 1.808.283.8265 or visit 2480 South Kihei Rd., Kihei.
“I loved staying at the Maalaea Kai. Everything is so close! We could walk to dinner and to boat trips. Walk to the beach. We loved the Maui Ocean Center too.”
“I think we’ll stay at Maalaea again since it’s so central. Traveling around to explore Maui was so easy since it’s smack dab in the middle of the island.”