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Roam 2 Ways / Maui, Hawaii

Roam 2 Ways / Maui, Hawaii

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GO: March - May, September & October

Maui is paradise all the time with average temps between 75-85 everyday, year-round. The rainy season tends to be January through March, Summer can be dry and hot, and the locals favor September and October. With these weather trends, and the more touristy Spring Break destinations on the mainland and in Mexico, Maui is the perfect place to escape the winter blues.

Many airlines offer non-stop flights direct into Kahului (OGG), which is the main airport on Maui, but you'll pay for the upgrade. You can also fly into Honolulu International Airport (HNL) on Oahu, before heading to Maui on a 30-minute flight. If you are visiting from the East Coast or the Midwest, you may want to consider a connecting flight through Seattle, LA or San Francisco, to stretch your legs and break up the two fairly lengthy flights. We often use Skyscanner price alert to notify us of low-priced airfares. You’ll want to rent a car on the island and Maui is pretty easy to get around. While the distance between towns is short, it can take you 20 minutes to go 5 miles due to the one lane highway. Plan accordingly and use your navigation to gauge timing.

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Toni DeBernardi, Bella Bloom Local

I grew up vacationing in Maui and it was always my dream to one day live here. I finally took the plunge, leaving corporate America in the dust, and I’ve been living in paradise now for four years. I am a florist and I stay pretty busy, because in Maui it’s always wedding season. Being in the hospitality industry my whole career, I have had the opportunity to connect with people from all over the world and I love sharing my local perspective. When I'm not working, I enjoy exploring all the island has to offer.


Although Hawaii is part of the US, it is important to remember that local people have a strong heritage and deserve respect from tourists. Please don't touch the turtles, clean up after yourself and respect the "Aina" (which means Land in Hawaiian). 


Relative to the size of the island it’s incredible how many places there are to stay in Maui. Whether you want a vacation rental or a 5 star hotel, here is a breakdown on a few of my favorites.

Andaz Maui / reservations

This property is super trendy and Eco-friendly so it’s favored by the young folks, however it’s a Hyatt property and it’s expansive so the appeal is wide ranging. Now by expansive I mean sprawling, with a 15,000 square foot spa, four pools, award winning restaurants and more. Fortunately they provide a guest host to help arrange everything for you and the property has access to anything you can imagine as far as activities.

Hotel Wailea / reservations

Perched on a cliff over looking the southern coastline, this property is high-end and adults only. It isn't on the water, but they offer beach service and stunning ocean views, under a canopy of mangoes and avocados. It’s super secluded, but not out of reach and there are plenty of on-site dining options.

Travassa / reservations

My favorite property on Maui is Travassa - located in Hana - this boutique hotel is super cool. While it’s a bit of a hike to get there, you are in the jungles of Maui so you are rewarded with its gorgeous location. Travassa makes is easy to disconnect, and while they offer all the expected amenities, they also offer more unique activities. You can take wellness and mixology classes, participate in local culture such as lei making, bamboo pole fishing, Hawaiian net throwing, as well as outdoor adventure activities like paddle boarding, horseback or bike riding. Each cottage comes with an ocean view terrace and a complimentary loaf of banana bread — adorable.


Hit the Beach

I always suggest people visit Big Beach / Little Beach just south of Wailea. Big beach (Makena Beach) speaks for itself in terms of beauty. Little beach is the nude beach next door if that’s your thing. On the opposite side of the island, on Maui’s north shore, is Ho'okipa Beach where you can catch crazy surfing action, big wave windsurfing (watching and doing!) as well as the snoozing Hawaiian turtles on the beach. A final beach I’d suggest is Kapalua Bay. I went only recently for the first time and the snorkeling was delighful. It’s right next to a restaurant called Merriman's whose happy hour is awesome — and their Mai Thai rivals my favorite (below in “Sip”). If you are just after the snorkeling, I’d steer you to Honolua Bay. It’s near Kapalua if you want to hit both on the same day. Keep in mind though it’s not a beach (mostly rocks), but it’s a majestic place with a magical Hawaiian energy. There is a small parking lot or you can park on the side of the road. There is a food truck parked with local/organic food - small bites like smoothies and sandwiches. Just be sure to bring your own snorkel equipment as there is no where to rent nearby.

Go Upcountry

Yes, Maui has beautiful beaches but there is another world just 45 minutes up the hill near the Kula Forest Reserve where cooler weather and incredible vistas await you. Go in the morning with a cup of coffee to walk Thompson Road, one of the best spots on the island for a morning jog. You could also head up on a Saturday for the most incredible local farmer’s market and to enjoy a gourmet lunch and farm tour at O’o Farms, where they grow fresh ingredients exclusively for their Pacific’O Restaruant in Lahaina. This area is also home to the must see fragrant purple paradise, Ali’i Kula Lavender Farm, and Thompson Ranch, where you can horseback ride, post visit to the the spectacular Haleakala volcanic crater, nearby.

Haleakala Crater

The 10,023-foot summit of Haleakalā National Park is an hour-and-a-half drive from Wailea. It’s best to go for sunrise or sunset. Sunrise requires a reservation with the park service and an early wake up call. If you are coming to Maui from a far away land, do this early on your trip when you are still jet-lagged so getting up early isn't such a drag. If you are going for sunset, make sure you can see the crater (no cloud coverage) which makes for a good sunset — if you can't see the crater you most likely won't have a good sunset. Oh and its COLD - you will need a jacket and gloves no matter when you go. If you are going for sunrise you can grab coffee and a breakfast bagel afterwards at Grandma’s Coffee.

Rtip: Contributor Joanna Wagner also suggests the sunrise bike ride with Bike Maui.


There are so many hikes, depending on your ability and location, to get out there and breathe in the real Hawaii. First I’d highly recommend Waihee Ridge, a moderate 4-mile hike near the West Maui Forest Reserve, which offers rewarding scenic views and distant waterfalls. Another good interior hiking trip is in the Iao Valley State Park in Central Maui, where you can explore the fora and fauna of the rainforest. The .5 mile Iao Needle Trail is great for families and the park system offers access to waterfalls, swimming holes and picnic areas as well. If you want to venture along the ocean, I’d send you to the South end of the island and suggest The Hoapili and La Perouse Bay trails, which take you across lava fields along the water’s edge. Bring your swim and snorkel gear to break at tide pools and hidden beaches along the 3 mile round trip route. A final hike to consider, for those on the East end of the island, is the Pipiwai Trail.  This 1.8-mile route winds along a string of dramatic pools and waterfalls, past a giant Banyan tree, through dense bamboo forests and culminates at the spectacular 400-foot Waimoku Falls. This is a wonderful alternative to the over-crowded and touristy, Seven Sacred Pools in the same area.

Road to Hana

East Maui is where you’ll find a picturesque and iconic Hawaii. Life is low-key in the isolated town of Hana, where the rainforest trumps the beach with it’s untouched beauty. The Hana Highway is a 65 mile stretch of road which connects Kahului to the town of Hana. Its an entire day trek, but well worth it - waterfalls and beauty abounds. I do not recommend the drive for someone who gets car sick, and you loose cell service on the drive so make sure you track your route before you go to select the mile markers you want to stop at ahead of time. Wai’anapanapa State Park is a must hit landmark for its unique black-sand beach and freshwater caves. Other suggestions include, Twin Falls Farm Stand & Waterfall, Kaihalulu Beach (red sand beach), Hamoa Beach and the Bamboo Forrest. I also love Ke’anae Peninsula where you can stop at Aunty Sandy’s for her world famous banana bread. The Gypsy Guide App and the website linked above can help earmark the best places to stop based on your interests.

“Don’t do Hana on a whim, make a little game plan and accept that you can’t see everything in a day.”


It’s no secret Mama’s Fish House is the place to go for the best food on the island. The overall experience is amazing and the cocktails are top notch. They use local sustainable ingredients, all the fish is caught in Hawaii and the menu even indicates who caught it and in what area. They serve a full menu starting at 11 so if you don’t have a reservation, lunchtime is a good time to check it out. In that case, I suggest a local "plate lunch."


Everyone has opinion for where to get the best fish tacos in Maui and my vote is goes to Coconuts Fish Cafe. Their lightly battered tacos are piled with 17 toppings including mango salsa and a super tasty coconut-milk coleslaw. It’s counter service and appropriately sized portions are the perfect lunch break from a sandy, hot day at the beach.


Tucked away on Maui’s peaceful North Shore, this cozy sushi spot is perfect —and as a bonus they serve some killer craft cocktails. They offer a ton of small plate options and unique specialty rolls, but very little parking and no reservations. Make sure you try the “Haiku” and Haleakala rolls as well as the black sesame ice cream.

Cafe Des Amis

Located in the low-key, colorful surf town of Paia this Mediterranean restaurant is one of my favorites. The simple Indian menu includes specialty crepes, vegetable curry and an amazing hummus platter. Stretch out on the benches and linger through happy hour until the live music begins (many nights a week) at 6:30.


Save room for pie! This is the best brunch spot on the island, known for its homemade biscuits and fresh-squeezed juices, but it’s the sweet and savory pies that get me excited. Thermal tote bags are available for purchase in case you want to take one back to your hotel.


As far as alcohol goes, there is no need to drink anything from the mainland with all the local distilleries on Maui. The organic, Ocean Vodka is distilled on the island from ocean water and sugar cane. Hali’imaile Distillery also calls Maui home and in addition to vodka makes a yummy rum and a solid whiskey. The island even has a winery and a microbrewery, Maui Brew Co. If you want to check out their beer do it at their Kihei location instead of the Lahaina location. I’m partial to the Bikini Blonde Lager, wink wink. For coffee I like, Akamai Coffee and Sip Me. And for the best Mai Thai on the island go to Monkeypod.


If you are going hiking you’ll need real shoes, not flip flops. Tennis shoes will do, but walking shoes are better. I like the brand Chaco - they are a hiking sandal - durable enough to go on a hike, but can also be used as a water shoe. Maui is super laid back, so no need to get fancy. A couple swimsuits and a lux coverup and you’re all set. And don’t forget the sunscreen, but not the spray kind because it kills the coral.

The Hauenstein Family Tourists

The Hauenstein Family lives in a suburb of Minneapolis. Mom, Kristi is a coffee drinker, runner and yoga enthusiast. She’s also a self described beach lover and cookbook hoarder. When she is not Ubering kids to sports she likes to spend time cooking and sharing time with friends and family at the cabin. She plans the family vacations for her engineer husband Kelly and their 3 kiddos, Reese, Riley and Avery. Every year they take a warm weather getaway around Spring Break and a big ski vacation out west.


Most larger resorts are located in Kaanapali and Wailea on the island’s West Peninsula. We narrowed in on staying central to Kaanapali's North Beach and we considered the following two properties.

The Honua Kai / reservations

We stayed at the Honua Kai and loved it. It is more or less a condo complex with the amenities of a traditional resort. For our family of five, a two-bedroom condo gave us the space we needed while still giving us access to all the amenities we are used to on vacation. Duke’s restaurant is on site, they have several pools, waterfalls and a lovely spa. They offer direct beach access where you can walk as far as you like, and there is plenty of un-crowded room to bring your beach chairs and boogie boards to camp out all day. The surf right in front of the resort can be a little rough, so walk a few yards down and you’ll find that it's quiet and calm.

Montage Kapalua / reservations

Located in picturesque Kapalua Bay we also considered, Preferred Property’s, Montage Kapalua. It’s a fairly ritzy, suites-only property but it comes highly recommended. It’s great for families and groups because of it’s larger accommodations, each with a full kitchen, albeit a bit pricier for the same reason.

Rtip: If you want to be on Maui’s North Shore, central to some amazing dining, and you prefer a smaller property, consider the quaint Paia Inn, which also has an incredible spa (available for non-guests of the property as well).


Our resort was located in Kaanapali, and we found that the southern end of that area tended to be busier with the larger resorts and whalers village shopping area. With that said, there is a walking path that connects you to the shopping area, restaurants and beach. We liked staying on the northern end of Kaanapali beach to avoid the crowds. We spent a lot of time in Kapalua, Lahina, and Paia as well.

“Keep your eyes open! With an array of breathtaking sights to see in Maui, many are simply right in front of you.”

Whale Watching

While we were able to see whales from our Lanai each day, they were from a distance. If you want to get up close and personal, I recommend doing a whale watching tour. We did our tour in the morning when the whales are active and the waters are a little calmer. There are sunset tours as well, however waters in the afternoon can be rough. We were on the tail end of whale watching season (winter) so we were lucky to see them. We used Trilolgy Excursions for this experience and they were great. They have smaller Catamaran's so your not fighting for a spot to sit and watch. They offer light appetizers, drinks and have a professional photographer on board so you can just sit back and enjoy.

Off-shore Snorkeling

Without a doubt, snorkeling should be on your list of must do's. Maui's close to Molokini crater which is a small crescent-shaped island just a few miles off the coast. Molokini is beautiful without getting below the surface, but if you’re ocean enthusiasts like we are, snorkeling here is a real treat. You will most likely see the famous green sea turtles but there is also a spectacular reef where you'll find hundreds of tropical fish. I should note, that you can kayak here if snorkeling isn't your thing. Another island to consider snorkeling is Lanai. Its very different then Maui and way less populated. There is a beautiful area called Manele Bay where you can snorkel, or you can rent a jeep for the day and just cruise around. The ferry leaves from Lahaina harbor and it takes 45 minutes. Both can be arranged through Trilogy, which we used for our whale watching tour.

A Lanai day trip is a great way to island hop without getting on a plane.


If you are looking for something new and a little bit humbling, try a surf lesson. My advice would be too stay away from crowded beaches if you are just learning. Instead look for private or semi private lessons that offer secluded beaches and wide breaks. One company to consider is Rivers to the Sea. They offer a range of lessons that are taught by local surfing enthusiasts. Plus, they take pictures of your lesson if you want to see yourself hang 10!

Cliff Jumping

Black Rock Beach in Kaanapali (an easy walk down from our resort) is a pretty stretch of sand near the famous Black Rock (a stone jetty and Hawaiian sacred cultural heritage site) most known for its cliff jumping. Not for the faint of heart, the jump is farther than you think and the swim back to the rock requires you to be a decent swimmer and climber. If you are daring enough, this is a fun adventure and easy to get to during a day at the beach. It is located right in front of the Sheraton Hotel.


No trip to Hawaii is complete without a Luau, especially if you’ve never done one – the ultimate Hawaiian experience! We chose Feast at Lele, as it was a sit down meal vs. buffet style. You'll enjoy watching talented Hawaiian dancers with out-of-this-world belly shaking moves, and more drinks and food than you know what to do with. All the tables are directly on the beach and the setting is perfect for a few photos to document your trip. Two others that have been recommended are Royal Lahaina and Old Lahaina.

Visit Paia

We did this on the last day of our trip on the way to the airport. We had the whole day before a long flight, so we were able to spend quite a bit of time here. Many people just pass through on the "Road to Hana". Whether its on your way to Hana or a deliberate stop you will find Paia to be a quaint, quirky, boho town, with a mix of locals and tourists. The town has interesting shops, colorful art museums and affordable small restaurants, including an awesome fish market. The whole area is an escape from the overpriced resort restaurants.


Once we determine where we’re going on vacation, the next step is planning where we will eat! Thankfully, there are many places to indulge in great food in Maui and a few notable places stand out as our favorites.

Slappy Cakes

If you are looking for a hands-on way to start your day, Slappy Cakes in Kaanapali is a fun place to visit. The center of your table is a griddle where you have the option to make your own pancakes with an endless variety of batters and add-ins. If pancakes aren't your thing, there are many other breakfast plates to choose from. They don't take reservations and the wait can be long so get a Maui Grown coffee or craft cocktail inside at the bar while you wait.

Rtip: Contributor Joanna Wagner also suggests Gazebo Restaurant for the best macadamia-nut pancake breakfast.

Mama’s Fish House

If I were to choose a meal to repeat again and again, it would be at Mama's fish house on Maui's North Shore just past Paia. Although you can eat here for lunch, I would choose this for a special dinner, the atmosphere and grounds are gorgeous at night — lush tropical flowers, tiki torches and ocean views. Order the Bouillabaisse, it is seafood magic in a dish! And top it off with the outstanding Creme Brûlée. It is on the pricier side but worth it and reservations are a must.

Rtip: Contributor Mallory Barr suggests getting the Hamachi Kama if they have it and the curry special for an incredible meal.

Paia Fish Market

I recommend the Mahi Fish Taco's! We had a lot of fish tacos throughout our stay and these were by far my favorite. They are terrific on their own, but the tarter sauce makes the dish. If you plan to drive the Road to Hana, you will pass through Paia and you should plan your day to stop for lunch at the Fish Market. If you don't make it all the way to Paia during your stay they have a location in Lahaina. This location is small with communal tables, so be on the lookout for a table before you order!

Aloha Mixed Plate

For the best local’s breakfast and insane views Aloha Mixed Plate is a solid recommendation. Contributor Mallary Barr suggests you try the Chinese chicken salad for a refreshing change from a daily diet of fish tacos.


Mala’s Ocean Tavern

Make sure to take time to head to Mala's Ocean Tavern in Lahina for a drink if not dinner. Mala's is a casual spot right on the ocean — you can literally hear and (almost) touch the waves from your table, and the incredible views can't be beat. A great spot for sipping a Mai Tai or one of their craft cocktails at sunset.

Breakwall Shave Ice

If your looking for an unforgettable experience in Hawaiian Shaved Ice, head to Breakwall in Lahaina. They have every topping and flavor you can think of, including alcohol to make your own "adult" beverage. While you’re there, check out Down the Hatch for inventive appetizers at happy hour.


I am a dedicated Aviator sunglasses fan and I actually prefer Maui Jim's. They are light to wear all day and polarized for the best clarity and color, especially when you want to see across water. We travel to the beach regularly, so rash guards are essential for all our warm weather vacations — not only do they protect you from the sun, but also from contact when using a body board, surf board, or a long day of snorkeling. Inevitably you will want to grab a cocktail or a bite to eat after a day in the sun so bring a great dress that packs well, doesn’t wrinkle, and is easy to throw on and dress up or down. Finally, I want to suggest day-pack large enough to fit a couple beach towels, water bottles and all your gear for the day.

Rtip: If you are going to pack a towel to take with you on a beach vacation, consider the extra long, quick-drying microfiber towels that are normally used for women’s hair. They dry easy and pack small.


As an avid coffee drinker, I always bring some home from vacation (our favorite was Maui Grown Coffee). Another obvious souvenir is Macadamia nuts. You will find every variety you can imagine, many you simply can’t buy at home. I love to cook, so I bought Hawaiian cooking salts to remind me of our trip. If cooking isn’t your thing, freshwater pearl jewelry is another option.


Click our link here to see everywhere we recommend you visit in Maui

What are we missing? Tell us your aloha options in the comments below.

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