Aloha & Congratulation! I was born and raised on Maui and know the island like the back of my hand. I will share with you my local insider knowledge when it comes to food and off the beaten track adventures.

Although when it comes to food you are going to have to try a little pork, Kalua Pork is the most traditional food of the islands. I will build you a 10 day action packed plan but don’t worry I will carve out a good amount of relaxation and beach time as well. I also run a concierge business on Maui and know first hand which boat trips, ziplines, luaus and so forth are worth the money and which aren’t. I’m happy to help you book the winners so that you have more time while on Maui to just enjoy your honeymoon.

Aloha – Arrival Day

Welcome to Maui! I hope that by the time you leave my home you will know why we say “Maui No Ka Oi!”

As you read this guide be sure to check the links as I have included step by step driving directions via Google Maps as well as links to websites for most restaurants and attractins.

You will be arriving in the evening today. So I would suggest that if you are hungry you should stop for dinner right after you leave the airport at Da Kitchen. Da Kitchen is a quick 5 minute drive from the airport and is a popular local food spot. If you aren’t hungry yet it will be about a 45 minute drive to your hotel so prepare accordingly. If you would prefer to just hit the road towards the west side of the island don’t worry I will mention a few other dinner options along the way.

About half way to your hotel in the little village of Olowalu is Leoda’s. I mostly stop here to eat pie. In fact I find it hard to drive by Leoda’s and not stop. You will be passing here a few times on your vacation so if you want dinner here tonight than go for it, if not remember to stop for pie and coffee at least once!

Finally if you choose to check into your hotel before stopping for dinner to drop off your bags and freshen up than my finally dinner recommendation for you is walking distance from your hotel. Simply take the beach path down to Whaler’s Village and you will find Hula Grill. This oceanfront, open-air restaurants invites you to relax in the warm ambiance of a plantation era beach house while savoring Hawaii regional seafood.

The Early Bird Cathes The Worm

#haleakala #nationalpark #volcano Via @dare2dream_big . . 📸 @debiflue

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For your first day on the island I suggest you use the jet lag in your favor and drive to the summit of Haleakala. This drive should take you about 2 hours form your hotel and you want to get there while it is still dark to catch a glimpse of the Milky Way. Sunrise should be around 6:10am in October, so plan accordingly. This 10,000ft mountain is the 2nd largest dormant volcano in the world and its name translated from Hawaii means house of the sun. At the summit you will be above the clouds as the sunrises the colors reflect off the clouds as the crater below you illuminates. Nothing compares to this view.

*It is very cold before the sunrises so dress appropriately. I suggest even bringing your hotel blanket!

If you are feeling adventurous and want to start your trip off with an adrenaline rush than I my next stop for you is an early morning zipline through the forests of Haleakala. You will be passing the course about 1/2 an hour on your way down from the sunrise so this is a convenient and thrilling stop. If this interests you let me know and I will get you booked for this activity.

Regardless of whether our not you stop to zipline or next stop on today’s plan is the charming town of Makawao and Komoda’s Store and Bakery. This long time local favorite has been catering to the island’s sugar cravings since 1916. They are famous for the donuts on a stick!

For a more substantial breakfast I suggest you stop at Market Fresh Bistro. The people behind Market Fresh Bistro believe that eating well should not only be on a special occasion. They showcase Hawaii’s finest produce and products. Although the slow food style of the restaurant is European, what makes it Hawai?ian are their ingredients and Aloha Spirit.

Take some time to explore Makawao if you wish. This old cowboy town has lots of charm and some excellent shopping.

It has been a busy first morning so your next stop is pure relaxations. You will be visiting Baby Beach near the town of Paia. At Baby Beach There is an exposed stretch of reef connected to a rocky red-dirt point. This creates a calm lagoon protected from the ocean. This is a popular spot for local families with young kids, hence the name, but adults will enjoy this refuge from the North Shore waves as well. It is a great place to swim laps, explore, or just and hang out on the beach soaking in the scenery.

When you have had enough lounging and are felling like it is time for lunch it is time to head into Paia. If you want a sit down lunch I suggest Flatbread for pizza and salads featuring organic and local ingredients. If you are feeling like you would rather pick up a quick snack and eat at the beach than I suggest Mana Grocery store just up the road. They have an excellent deli counter and salad bar. This is also a great place to pick up some healthy snacks for the road trips and adventures ahead!

Your final stop before heading back to Ka’anapali is Ho’okepia Beach Park. This beach is famous for its waves that attract both surfers and windsurfers the real draw for you though are the Sea Turtles that you can often find sunning themselves on the beach.

Please be respectful of these animals! Keep a distance! No touching! These are endangered animals!

Looking at the ocean walk to the right side end of the beach. Notice all the giant rocks. Look carefully more often than not you will find a handful of sunbathing turtles here! Like I said before keep a distance or you will be reprimanded by the locals.

West Side Relaxation

Just a couple of beach bums…🏄🏼‍♂️#hawaii #dadlife

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Today you will be sticking close to home and focusing on rest and relaxation. For both today and your 5th day on the island I will have you staying on the West Side. So these two day’s itineraries can easily by flip flopped as you see fit.

Spend your morning enjoying breakfast on your hotel grounds than it is time to soak up the sun either at the pool or on Ka’anapali Beach. Perhaps it is time to enjoy a Mai Tai or Lava Flow. It’s your vacation enjoy it!

If you are looking for some adventure for this afternoon and you didn’t go with the zipline option on Haleakala there is a fun tour on the mountain side of Lahaina that offers a zip and dip option. Not only are you ziplining but you also get to drop off the lines into a pool as well as the opportunity to try stand up paddle boarding. Adrenaline rush + water activities = WIN in my book. Another option for adrenaline rush is an ATV and water slide tour that is offered in the same area. If either sounds tempting let me know and I will give you more details and help you book.

If this doesn’t float your boat you could also spend the afternoon strolling the streets of Lahaina and Front Street. Go check out the Banyan Tree as well as the old sailor prison made out of coral. Lahaina is an old whaling town and has quite the rowdy past. If you head this way I suggest you stop at Fleetwood’s on Front Street for sunset cocktails. Every night they put on a sunset ceremony with a Hawaiian Chant and Blessing as well as a Bagpipe show. It is an eclectic mix but it works!

For dinner I suggest you head up to Star Noodle. This hip noodle shop is one of the best restaurants on the West Side as well as a hidden gem. It can be hard to find and filled with locals but it is worth the efforts. It became well known nationally when the former chef was on Top Chef and became a fan favorite. Even though Sheldon has left Star noodle remains as tasty as ever. The food is Asian in culture but has a lot of local flavor added! I think you two will love this spot.

The Road to Hana

Today is going to be another long and busy day. Once again while your clock hasn’t completely set itself to island time it is time to get an early start and hit The Road To Hana!

Hana is an all day adventure and while it is tempting to make every stop along the road for me the real charm of Hana is actually being in Hana, if you don’t make any stops it should take about 2 1/2 hours from your hotel to Hana town so plan accordingly, remember that as you are tempted to pull over at every tempting vista and look out on the way out there.

I recently went to Hana using the Road To Hana CD guide and found it really useful. Even with growing up on Maui I learned a bit of interesting history about the drive as well as some interesting new stops. This guide is worth checking out.

Pack a few snacks and drinks for the drive and make sure to fill your tank up in Paia as this is the last big stop for gas. I also suggest that you do the full circle drive. Your car rental company and lots of people will say not to do this but in my opinion the drive out of Hana the back way is the most gorgeous drive on the island.

Tips: Forget your mainland road manners. Practice aloha. Give way at one-lane bridges, wave at oncoming motorists, and let the big guys in 4*4s have the right of way. If the guy behind you blinks his lights, let him pass. They know the road better than you and trust me you don’t want them behind you for long.

Here’s some items you may want to bring:

Hiking shoes
Mosquito repellant
Bathing suit
Cash for food & park fees
Remedy for car sickness
Sweatshirt (if you will be driving back at night with the top down)

My Highlighted Stops:

1. Waikamoi Ridge Trail: This easy loop hike is filled with ferns, tropical flowers, tall trees and scenic overlooks. There are two hiking options; the long route and the short. I suggest the short .75 mile loop as it is just the right amount of time to stretch your legs and be ready to get back in the car and head to Hana.

2. Keanae Peninsula: The old Hawaiian village of Keanae stands out against the Pacific like a place time forgot. Here, on an old lava flow graced by an 1860 stone church and swaying palms, is one of the last coastal enclaves of native Hawaiians. They still grow taro in patches and pound it into poi, the staple of the old Hawaiian diet. And they still pluck opihi from tide pools along the jagged coast and cast throw nets at schools of fish.The turnoff to the Keanae Peninsula is on the left, just after the arboretum. The road passes by farms as it hugs the peninsula. Where the road bends, there’s a small beach where fishermen gather to catch dinner. A 1/4 mile farther is the Keanae Congregational Church, built in 1860 of lava rocks and coral mortar, standing in stark contrast to the green fields surrounding it. To experience untouched Hawaii, follow the road until it ends. Park at the end get out to stretch the legs, take photos and if you are feeling peckish this is a great place for a picnic.

3. Keanae Lookout: Just past mile marker 17 is a wide spot on the ocean side of the road, where you can see the entire Keanae Peninsula’s checkerboard pattern of green taro fields and its ocean boundary etched in black lava. This look out gives you a great perspective on the little village you just visited. Also a great place to picnic.

4. Nahiku Marketplace: At Mile Marker 28.8, is a Hana shopping center, which consists of a tiny handful of Hawaiian product shops. There are lots of handicrafts as well as snacks. This is a fun eclectic stop along the road.

5. Waianapanapa Black Sand Beach: The Waianapanapa Black Sand Beach, Mile Marker 32.2, for many is their favorite stop in along the Road to Hana.
was my favorite stop along the Road to Hana. A short, yet steep, path leads to the shiny black sand beach. Waianapanapa Beach appears like a vivid dream, with bright-green jungle foliage on three sides and cobalt-blue water lapping at its feet. Don’t miss this one. Do the swim in the caves, it is a bit cold but an unique experience. The 120-acre park on an ancient lava flow includes sea cliffs, lava tubes, arches, and the beach, plus 12 cabins, tent camping, picnic pavilions, restrooms, showers, drinking water, and hiking trails.

6. Hana Town: Now after all that driving you might wonder if it was all worth it once you reach Hana town. Town itself is nothing much but the drive and having some time to relax in the area is what it is all about. SLOW DOWN and let yourself fall into Hawaiian Time. If you want to grab lunch in town I suggest either Thai Food by Pranee. This little stand in the driveway of the Hana Ball Park reminds me of being in Thailand. Sketchy ambiance and killer food! In my opinion this is the best Thai Food on the island! If you are feeling like BBQ than I suggest Bruddah Hut’s roadside (literally someone’s front yard) BBQ, which is just past Hasegawa Store and the gas station on the far side of Hana Town. This place serves seriously big portions of grilled meat with your choice of sides. Also while in Hana you should stop at Hasegawa’s. This is a good place to get staples (water, snacks, etc) you may want for the rest of your drive. Hasegawa is a Hana institution; a cluttered old-time General Store and worth a stop to check out this funky stores charm and eclectic offerings.

7. Hamoa & Koki Beach: Shortly after passing the town of Hana, you will notice a turn to the left hand side of the road to both of these beaches. Take this small detour. Both beaches are extremely picturesque but if you want to swim and sunbath go to Hamoa. The waves at Koki are often big and the undertow is strong, this beach is not for the novice swimmer. When I go to Hana I spend hours at Hamoa as this is one of my favorite beaches on the island.

8. Ohe’o Gulch – Seven Sacred Pools: When I was young you were often able to visit Ohe’o Gulch and have it all to yourself. Sadly those days are gone as this stop is a main highlight on the Road To Hana adventure. It is definitely worth the stop for a few pictures. These days for me the highlight of the area is the Pipiwai Trail to the Waimoku Falls that are opposite the 7 Sacred Pools. The 4 mile round trip to the falls and back takes in several great waterfalls before reaching the spectacular Waimoku Falls, and a boardwalk journey through dense, dark bamboo forest that you’re unlikely to forget. In my opinion this is one of the best easiest hikes on the island!

Bonus. Fruit and Flower Stands: Around mile marker 18, the road widens; you’ll start to see numerous small stands selling fruit or flowers. Many of these stands work on the honor system: You leave your money in the basket and select your purchase.

For many Ohe’o Gulch will be the turn around point but keep driving the way you came. You will heading home on the back road, as we locals call it. The road is fine! In fact when I go to Hana I use this route for both ways. Many locals byppass the Road To Hana and instead take this route to avoid the tourists and all the single lane bridges. You will end up back in upcountry around sunset. Where ever you might be pull over and watch the sunset! This is probably be your only oportunity to see it from above sea leavel.

Another Lazy West Side Day

After your full day in Hana we are keeping things relaxed today. This morning you will simply be walking out to Ka’anapali Beach where there will be convenient beach loading onto your snorkeling tour boat. This half-day ocean adventure gets you to some of Maui’s best dive sites quickly for snorkeling, swimming, and discovering SNUBA. With spectacular views of Moloka‘i and Lana‘i and the majestic West Maui Mountains as a backdrop, this tour is a photographer’s dream. From the pristine waters of Honolua Bay to the protected shallows of Olowalu, the west coast of Maui offers some of Hawaii’s most unspoiled coral reef ecosystems known for their abundance of honu (the Hawaiian green sea turtle). Breakfast and lunch are served on the boat. This trip is truly a sailor’s delight with steady tradewinds, warm tropical seas, and a semi-protected coastline with the added bonus of being close to home!

The rest of the day upon retuning to the hotel is open for you to decide what you want to do. Maybe it involves nothing more than a movie and room service night in the hotel room or maybe you feel like tacos. If it is tacos you are craving than I suggest Sangrita Grill and Cantina, only a 12 minute walk from your hotel. This new Mexican restaurant and tequila bar in West Maui is serving inspired versions of authentic Mexican soul food and offers the island’s largest selection of artisanal tequila and mezcal.

South Side Day Trip

Start your morning off with a light breakfast of Acai bowls at Choice Health Bar before heading to the South Side for a beach filled day. There is no need to rush this morning, operate on ‘Island Time’ and let the day take you where it will.

As you head to the South Side, Kihei & Wailea, you have the option of stopping in Ma’alaea General Store or the Aquarium if you choose. The next stop for picking up a picnic for the beach is Cafe Carmen. This hidden gem in Kihei is run by the wife of The Four Seasons Head Chef. So you know that they pay great to the ingredients and technique here. This is a spot that you would never find on your own! Just stop somewhere and pick up some snacks and drinks for the beach.

You will be heading to Makena Beach Park, or as the locals call it Big Beach. This gorgeous long white sand beach is the real show stopper when it comes to beaches on Maui. It is so stunning. There are a few food trucks on your way to the beach if you want to pick up a coconut, smoothie or fish taco. Find a cozy spot in the sand and let the suntanning commence!

* Be careful here if the waves are big. They break directly on the shore and can cause quite the headache if you get caught in them. As always respect the ocean.

After you have had enough lounging in the sun it is time to hop back in the car and continue down the road to Ahihi Bay for some snorkeling. Ahihi Bay is just a few minute drive past Makena and you will easily spot a few cars parked on the side of the narrow road and people in the water. At some point in your trip I recommend renting your own set of snorkel and fins for a few days. The ocean is filled with life and even right out of your hotel or at Black Rock you should be able to see plenty of fish.

When you are done snorkeling I recommend you continue down the road till it ends. The real highlight here is driving through the old lava fields. The landscape is one you don’t find in most places.

Now if you are easy going I recommend taking a quick shower at the Polo Beach Park and changing into some clothes for exploring the Wailea food scene.

The new Andaz Hotel has some of my favorite cocktails on the island. Sit at the poolside bar and enjoy a few libations.

For dinner I recommend you dine at Capische at the Hotel Wailea. The fare is Italian but the ingredients are as the chef says ‘brought to you from seed to saute.’ If they don’t grow the ingredients themselves than the product is sourced from the island. Every bit is delicious and well thought out. Reservations are reccomended.

Island Hopping to Lanai

From your hotel you will see two islands off in the distance. The one on the right is Molokai and the one on your right is Lanai. Both of these islands have a very small population and only a few places for tourists to spend the night. Molokai in my opinion deserves a long weekend visit while Lanai is easily accessible and best visited on a day trip. There is only one boat company that is allowed to visit Lanai and to visit the beach on the island so this trip is exclusive and does book out fast so if you are interested in this options lets discuss it. It is a full day trip that includes breakfast, a light snack and a full BBQ lunch with you returning right around sunset. Often you see dolphins on the ride over to Lanai as they like to stay in the less populated water. Once you arrive on Lanai you have the option to take a mini van tour of Lanai City before you spend the day on the beach snorkeling and Snuba diving.

West Side Drive

#napilibay #maui #hawaii🌴 #husbandcrush 😍😍😍

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Start your morning off by heading to The Gazebo for breakfast at Napili Bay. This place is always busy so expect a wait but the food is great and so is the view! Take your time and enjoy your morning. I will be giving you a few options for your day so decide ahead of time what interest you most and plan accordingly.

You will be continuing your drive around the West Maui Mountains today. You have the option of doing the full circle or turning around at whatever point you decide. In my opinion this drive is just as gorgeous as the Road To Hana and even a bit more thrilling at points. Once again yield to oncoming traffic. You will be on the mountain side and not the cliff side so let those people coming at you have the right away. This is a “Maui Road Rule” that you should follow.

After leaving The Gazebo head Honolua Bay to watch the surf after this quick stop get back in the car and continue on until you see a stand on the left side of the road where a local man is carving tiki’s. Stop here and take your snorkeling gear down the path. The trees are giant and covered in vines than shade the path. It is something out of a tropical dream. The bay you will get to is often calm and a great spot for easy snorkeling. Just steps into the water and you will be surrounded by fish.

When finished here hop back in the car and continue driving. You will be entering an area we called Hobbit Land when I was young. There will be a few places with cars parked and each of these is worth a visit. First is the Nakalele Blowhole and second is Olivine Pools.

This is a good place to turn around if you are tired. The road narrows as you continue but if you are feeling adventerous keep going.Continue your drive to the little village of Kahakuloa. There are a few stands to stop and get drinks and banana bread if you so choose.

If you continue you can get to Mendes Ranch where you have the opportunity to go Horseback Riding in the afternoon. Your notes mentioned mule ride but the place that everyone talks about going mule riding in Hawaii is actually on Molokai. So this is your best option if you want something similar. You would have to be there by noon to check in though so plan accordingly.

The other option for you if you continue this way is to hike the Waihee Ridge Trail. This trail takes me on average 3 hours, 2 hours up and 1 down. I’m not the fastest hiker in the world and take multiple breaks up the path to give you an idea.

Tonight would be the night I think you should go to a Luau. There are two good options on the West Side, for a more traditional atmosphere go to The Old Lahaina Luau if you are looking for something classier go to Feast at Lele.

Aloha Friday

Your last full day on Maui should be enjoyed however you see fit. Relax and soak in as much Maui Magic as you can before you head home. The only thing I have scheduled for you is one final trip out on the water. End your vacation with this special Hawaiian-style sail: Music, Appetizers, and open bar!

In Hawaii, “Aloha Friday” refers to a feeling of laid-back happiness and leisure in anticipation to the weekend. In your case use this time to reflect on this special time in your life. Unwind from the day and enjoy an authentic Aloha Friday you sail along the West Maui coastline surrounding Ka’anapali. Live “local-jams” by ukulele enthusiasts will serenade your minds into deep relaxation. With Maui’s legendary makani (wind) we hoist the sails and enjoy the panoramic views as we glide through the seas. Aloha Friday — the perfect way to say goodbye to Maui.

Time to say Aloha

Spend your morning getting some last minute sun before you need to check out of the hotel.


Black Rock When facing the water from your hotel look right and notice the point of lava rock. This is Black Rock and you will often find local kids and a few brave tourists making the cliff jump. You should try it!

Waihee Ridge Trail This 4.5 mile round-trip hike in West Maui Forest Reserve promises lush scenery, great valley views and some dramatic ridge-line hiking. There is a 1500ft elevation climb on this hike but the trail is well marked and easily traversed. This is one of my favorite hikes in Maui.

Spam Musubi At almost every gas station you will find this iconic snack food of Hawaii. It is basically our version of sushi and should be tried at least once while in Hawaii.

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