You really can’t go wrong with Hawaii! I have visited Maui, Oahu, Kauai, and “The Big Island” of Hawaii, and each island is amazing in it’s own special way. Each island has a different “vibe” unique to itself. I was extremely lucky as a child, as I had family that lived in Hawaii, and I was able to spend extended periods of time there each year. Staying with family, I got to feel as though I was living there while on these trips. I did keiki deep sea fishing tournaments, and spent so much time trolling in the ocean on my family’s boat in hunt of the big kahuna marlin. This is most definitely where my passion for deep sea fishing began!
Since my childhood, I have been visiting Hawaii in a much more touristy fashion. Staying in hotels, and doing as much touristy stuff as I could fit into my vacation has been the norm for me over the years. Although each and every trip has been absolutely amazing, I wanted to plan a trip that reminded me of the time I spent in Hawaii as a child. I wanted to experience feeling like I was living there as a local. To achieve this feeling, it had to be as long of a trip as I could make it. I decided on 7 weeks in summer while the kiddos were out of school. Now which island to choose? I am most partial to Kauai (North Shore) for how lush the landscape is. But for this long of a trip, I chose the island Maui. Maui has beautiful landscape, but it also has a bit of a livelier vibe compared to Kauai. I thought it would be a good mix of beauty and things to do. Let the planning begin!!
I get a lot of questions about how I’m able to take extended trips like this. My husband and I work from home, and can really work from anywhere in the world. These extended trips are obviously working vacations which add to the the feeling of actually living there instead of vacationing.
To stay 7 weeks, I wasn’t trying to stay at the super high end places in town. I needed something reasonable, but also large enough to accommodate my family of six, and a home office set up. I landed at the Sands of Kahana. What a perfect choice! We had a huge three bedroom condo on the beach with a pool, kids pool, mini golf, gym, community beach bbq’s, and a restaurant on the property in case we were feeling too lazy to cook. We also had so many walk-able dining options in the village of Kahana.
This little village of Kahana sits right in between Kaanapali and Kapalua. It is so much more reasonably priced than its neighbors, but still right in the heart of all the action. I highly recommend this area if you are on a budget. For the nights when you would like to put a huge dent in your bank account, you can just hop on over to your neighboring towns to get some fine dining, or an expensive round of golf. You are also just a short drive to Lahaina, where most of the island nightlife resides.
Next, I needed to get a rental car. Getting a rental car for seven weeks isn’t cheap. I found Kimo’s Rent A Car online. They have vehicles of all price points but the one I rented was basically less than a basic vehicle. They gave a great rate on monthly rentals and I spent around $1,000 for the entire 7 weeks. It really was exactly what we needed, and the price was right. I have spent $700 on a car for one week in Hawaii, so I was pretty excited about this deal.
Ok, so now what did we really do on this trip to make us feel less like tourists and more like locals? First off, I hit Costco and stocked up. We bbq’d and ate dinner on the beach about 70% of the time. There was no rush to do anything, and we snorkeled until the sunlight was gone while bbqing on the beach…..that was our evening schedule. I found a bunch of beach equipment on Craigslist for us. I bought boogie boards, ice chest, chairs, an umbrella, beach toys, and I paid $35 for everything. This is a great tip to check there for your stuff because buying these items brand new will be hundreds. When we didn’t feel like bbqing, we would get seafood off the food trucks. We would take our food and paper plate it to watch the sun go down, hike, or chill at a park.
Road to Hana
What did we do with our time outside of being beach bum bqqers? My favorite adventure as a temporary local was going camping for the weekend in Hana. The Road to Hana is so beautiful!! It has waterfalls around every twist and turn, and is the epitome of the “it isn’t about the destination, it’s the journey” quote. I have driven the Road to Hana many times, and have even driven around the entire island in one day. I LOVE IT….but it’s not for everyone. You are truly in the car all day, and the road is very curvy. People with weak stomachs may call it the road to hell. I have definitely learned over the years (having a large family of six) that not everyone likes what I like. And although, I can explore and drive from sun up to sun down, my family would be miserable. However, there was no way I was going to Maui for 7 weeks and not driving the Road to Hana. So I checked into camping. What an amazing experience! I rented all of our gear from Camp Maui which we picked up on the way out of town to Hana. Camp Maui stocked us. We had everything….tent, pads, pillows, sleeping bags (which weren’t necessary), stove, flashlights, propane, etc. It was so reasonable and I didn’t need to pack anything from home other than clothes. We camped at Waianapanapa State Park with hiking, black sand beaches, and water caves. You need to get a permit in advance to camp here so plan ahead. This place gets crazy busy in the day with tourists coming in by the bus loads. We were able to go explore the ins and outs of this park early in the morning and late at night, completely skipping all the crowds.
The best part about this camping trip? We got to explore Seven Sacred Pools for the entire day. This place is gorgeous, and could be my favorite place on all of Maui. It is so far to get here if you are driving in for the day, so most tourists only get a short visit as they have to get back on the road for the very long drive home. Not us! We stayed all day swimming and rock jumping and then drove 15 mins back to our camp for a bbq. This mini vacay was beyond amazing and pretty eye opening for me. I was so happy that my family didn’t want to drive to Hana for the day because it forced me to find a way to achieve exploring this side of the island along with keeping everyone happy. There is more than one way to skin a cat! Ps- I really hate that saying…who came up with that anyway?? Skinning a cat is just wrong. Plus, I love cats.
Back at home in our little village of Kahana we began to make friends with a lot of locals who lived there. I think Kahana is popular with the locals because its cheaper but still so central. When you eat and drink at the same places quite often you begin to run into the same people. We met a local who took us all surfing for a private lesson for next to nothing. No waivers or contracts…just a local teaching us how to ride the waves. This local became our friend, and he spent an entire second day with us taking us to a private property to go fishing.
Best Date Nights/Days
Before arriving on this trip, I found a babysitter to come on a schedule to give my husband and I some adult time. With the grandmas back on the main land, this was an absolute must. I hired a nursing student who was training in Labor and Delivery at the Maui General Hospital. Can you get a better resume for a sitter? She also had nursing student friends to replace her when she was busy.
For most of our dates, we would pack an ice chest, and hang out at the beach all night. But my favorite date night was attending a Reggae Concert at the Maui Tropical Plantation. Maxi Priest and Big Mountain were the big headliners, and it was probably one of the best concerts I have ever seen. Super fun, and definitely something I wouldn’t have squeezed in on a one week vacation. We also spent several nights partying in downtown Lahaina. Fleetwoods was my favorite place to get a drink and listen to live music.
My favorite Day Date was snorkeling at Honolua Bay. It is untapped serenity…so beautiful, and so peaceful. We loved it so much that we planned a second day here to bring back the kids to enjoy with them.
Favorite Touristy Things to do
We didn’t book many tours on this trip, but one that we did do was a snorkeling cruise to Molokini Crater. The snorkeling there is awesome! We saw dolphins along the way and snorkeled with a ton of beautiful fish. The kids loved this cruise! One of them actually started crying when we had to leave the crater. LOL.
One of the seven weeks we had Grandma and Grandpa visit, and we did zip lining and parasailing. I mean you have to get high at least once in Hawaii, right? The kids absolutely loved both these days. This was definitely the one week where we packed in a lot of touristy adventures. After parasailing off of Kaanapali Beach, we ended our day at my favorite happy hour spot on the beach….Hula Grill. You can sip Mai Tais with your feet in the sand while listening to live music. Heaven!
To finish up our one “touristy” packed week we ended it with a traditional Luau. There are so many great Luau’s on Maui. They are no doubt pricey! I chose Royal Lahaina Luau for the simple reason that for every paying adult, you get one child for free. It worked out pretty well with four adults and four kids. This was a perfect way to end our week spent with my parents!
You can stay anywhere on Maui and will be happy with your choice, but the majority of people choose the west or south shore. I’m more partial to the west shore since it is so close to Lahaina, and is a bit more lush. But the south side is beautiful too. So beautiful it is in fact my favorite beach on Maui…Makena Beach. Makena Beach is split into Big Beach and Little Beach with Little Beach being bathing suit optional. From our village in Kahana, it was about a 45 minute drive to get there but so worth it. Stay the entire day!
My favorite beaches on our side of the island were Napili Bay Beach and Kaanapali Beach. Napili Bay Beach is literally the most fun beach I have ever been to with kids. The rolling waves are like an ongoing roller coaster and you can hear the screams of excitement and laughter from the road as you park your car. Boogie boards and floaties make this day an absolute blast. Be careful of the waves wiping out your entire beach set up. It happened to us! Try to sit as far back as possible on the beach away from the water.
Kannapali Beach is home to the famous Black Rock. It is a very popular beach. The snorkeling is awesome and you can jump of the rocks at Black Rock. Super fun!
Favorite Land Activity
You really can’t go to Maui without being blasted with marketing materials everywhere in your face about bike riding down the Haleakala Crater. I have done this ride several times but unfortunately it wasn’t in the cards for us on this trip as our littlest kids weren’t big enough for a ride like this. I have to include a little write up though because it is truly such an experience. You need to get up early for this at 3:00am and take the two hour drive up the crater. It’s cold when you get up there so bundle up! You watch what is hopefully the most beautiful sunrise you have ever seen in your life. Once the sun is up, you begin the bike ride down the crater. There are a million tours going down where you all follow each other in one line all the way down the crater. Not for me!! I’m not big on group activities with strangers. I have always found a company who drove me to the top of the crater, handed me my bike to ride down alone and at my own pace, and then met me at the end of the day to pick me up. Most tours end at the bottom of the crater but I like to continue the bike ride to the Maui Pineapple Winery. The extra ride is rolling hills closer and closer to the coast. It is a beautiful ride! The bonus is you get to end the 18 mile ride with some wine tasting and a picnic.
What To Do When It Rains
Maui isn’t as beautiful as it is without getting rain. My favorite “ohana” day spent during the rain was the aquarium. The Maui Ocean Center is one of the coolest aquariums that I have ever been to. We learned so much and got to see so many fish that are in the Hawaiian ocean waters.
Favorite Family Friendly Hike
As I said, this was a working vacation. I had to keep the kids busy on many days when my husband was holed up in the condo working. My favorite day I spent with them was a very moderate but beautiful hike to the Iao Needle. It was really pretty, and we learned so much history on the battles fought in this area back in the old days.
Well it wouldn’t be a good blog if I didn’t write a bit about food. There are endless amazing dining options on Maui. My all time favorite is Mama’s Fish House. Bring your camera because the location is right on the beach and is quite the photo op. This is definitely an expensive dinner but worth the splurge! And you simply can not visit the island of Maui without going to the famous Cheeseburgers In Paradise. The cheeseburgers are delicious, the cocktails are tasty, the view of the ocean is to die for, the live music is a blast, and the location in downtown Lahaina makes it easy to bar hop around after dinner. Lastly my favorite “cheap eat” on Maui is Ohana Tacos. Seriously…if I didn’t watch my weight, I would live a fulfilled life having Ohana Tacos for every meal! It is the bomb.com! It’s pretty much fast food so perfect to take on the go while adventuring.
So after spending six weeks on Maui we started to get panicky that we only had one week left. We had zero island fever. We really didn’t want to go home. Our time here really allowed us to enjoy everything at our own pace and we truly felt like we were living there. Mission accomplished!!
In our last week we had two back-to-back hurricanes hit. If this had been our only week of vacation, it would have been a huge disappointment! But we felt really lucky to experience it. It was very cool to watch Mother Nature do her thing and once they passed we were left with the calmest ocean and most beautiful sunset of the entire trip. It was quite a farewell.
How to vacation more like a local and not like a tourist in a short vacation
My all time favorite read prior to visiting Hawaii is the Maui Revealed book. The authors have a book for every island and I have purchased the newest edition for every single trip I have taken to the Hawaiian Islands. It gives you hidden secrets that you would never find without it. I’m talking directions like “Hit the 42 mile marker, hike a quarter mile to the left, enter the broken chain link fence, go through the bamboo forest, hike a quarter more mile through the dirt steps and you will find a huge lagoon with a rope swing to spend the day at”. Haha. I have led the way with directions from this book on so many adventures with people I am on vacation with. Believe me I have gotten the stink eye from people traveling with me as they follow me to these secret places. But once there, everyone has always thanked me for such a special experience. Buy the book before going! It is truly the best vacation guide I have ever read!!