Travel Guide: Maui, Hawaii

Jenna Kutcher 

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February 22, 2016


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Oh man, where do I begin? I might have to break this up into five segments (only if you request more details!) but goodness, this trip was our favorite one yet (and we’ve been all over together!) Hawaii, we chose it because we felt like it was a destination that people always yearned to visit but never actually made it. Life is short, travel is fun, we figured we would make it happen and celebrate our fifth anniversary a little early! There are so many reasons we loved Hawaii: the sun, the water, the volcanoes, the beaches, the fact that it’s America, the whales… the list goes on and on (and on!) Today I am going to sum up our trip, the excursions we went on, where we stayed, and how much it all cost (because full disclosure is always important, am I right?) So let’s get down to the juicy details, you ready?

Where we stayed: The Westin Kaanapali Ocean Resort Villas 

We have always worked with a travel agent, I would give Mary an A++ for always getting it right for us. People always seem surprised when we say we have a travel agent (yes, they exist and they are wonderful!) Working with one always gets us the best prices, flight patterns that work, and she does all the research for us that saves us hours upon hours staring at a million internet tabs until our eyes glaze over. Mary will send us about 10 options, then we narrow it down to top three, and then we pick! We chose this place because it was 4+ stars, in the middle of the price options, and our unit had a kitchenette so we could cook our own meals on the island! We absolutely loved this place! It had a few restaurants, a convenience store, a gift store, and concierges at every corner! It had multiple pools, a waterslide, beautiful beach access and was located on Kaanapali Beach!

What we did: Haleakala for Sunrise 

Total Cost: $15 for Park Fee, $40 for breakfast 

One of the hardest things about Hawaii was that everyone had opinions on what we should and shouldn’t do, they always said crazy Hawaiian words that we didn’t understand, and it was so hard to visualize or prioritize our time on the island. Many people referred us to Haleakala and we got the advice to do it early in the trip before you had adjusted to the time change (because it’s an early, early morning!) Thankfully, we took that advice and set out on our second day to drive up the 10,000+ feet and watch the sunrise! One major tip: Google maps says it takes 4 hours to get from Kaanapali to the top of Haleakala – google maps lies, we left at 2AM to make sure we got there in time for the 6:45AM sunrise, turns out it only takes two hours to get to the summit so we slept in the car and waited until the sun started rising! You’ll want to bring warm clothes! Wait, what? In Hawaii? Yes, at the top of the volcano, it is usually 40 degrees or colder. We brought our hotel blanket and layered up! This trip was totally worth it, the sunrise was incredible and to see it above the clouds was once in a lifetime. There are different excursions that you can bike down the volcano but we wanted to be on our own time frame and I am thankful we just did it on our own (saved money) and were able to drive down the cold summit and enjoy some pancakes. Funny story: we crashed at 4PM and slept for a solid five hours waking up just in time to get dinner and then go back to bed, so you do spend a good chunk of your day driving/recovering/enjoying this endeavor!

What we did: Feast at Lele 

Total Cost: $350 

We were told we had to go to a luau while on the island so we did just that. I have mixed feelings on this one! There are luaus every night all over the island! There were definitely reasons we chose this one above others, instead of sitting at a long table with strangers and passing food, this one offered private tables, all you can drink beverages, and a waiter who was with you all night. We went with our friends, Mollie and Isaac and got there around 6! The whole luau was a few hours long, it was a four course meal with different food from different cultures! The boys were more adventurous with trying all of the food, us ladies stuck with the basics that we knew! The food was good, it was small portions which was nice and then between each round of food there were dancing performances from the cultures of: Hawaii, Aotearoa, Tahiti and Samoa! It was wonderful to experience but I don’t think I ate enough food to legitimize the cost! I definitely think everyone should enjoy a luau and choose one that suits what you’re hoping to see and experience! It was really fun, I don’t know if I would have to do it again if I went back!

What we did: The Road to Hana 

Total Cost: Gas and $100 for food for the day 

This was a fun little road trip! We wanted to go with Mollie and Isaac because we knew it was going to be a long day (and a long day it was!) We left the hotel around 8AM, fueled up at Starbucks and hit the road! The entire trip was over 12 hours from when we left to when we returned! We met some Minnesota friends on the beach who gave us a Road to Hana CD, while the lady was a bit annoying, she talked through different mile markers and let us know what we were coming up on and if we should stop or keep going. We honestly didn’t stop too much, just enjoyed the crazy ride (Drew was a driving champ!) There are a lot of twists and turns and tiny bridges but it was beautiful and fun! We stopped at the arboretum, a few waterfalls, a wonderful organic food stand with paninis and tea, and the sweetest Hawaiian woman who encouraged us to go the whole way around Hana. Most tourists go to the Seven Sacred Pools and then turn around but we went all the way around and we are so glad we do. People threaten that the roads get super rough and your rental car companies won’t cover if you go all the way around but we found the opposite true. The road is rough the whole trek so a few miles of bumpy roads isn’t all that hard to manage and the traffic was far more minimal because everyone else had turned back! There were beautiful cliffs, we saw cute little mountain goats, beautiful water views, and loved seeing the transition from rain forest to arid dry land!

What we did: Blue Hawaiian Helicopter Tours

Total Cost: $280 per person 

This was a highlight for all of us! The four of us had an early morning! We were told to take the earliest helicopter tour and it was so worth it! The air is less rough in the morning and the cloud coverage is minimal, so morning it was! We chose to go big (and not go home) so we did the complete island option which was about 65 minutes in total. I had never been in a helicopter before but it was so incredible, Drew and I were in the front seat with the captain. We all had headphones and microphones and I pretended I was on a date from The Bachelor (since they always seem to end up in helicopters!) We took so crazy turns, massive dips, and my stomach dropped more than once but our pilot was hilarious, put up with the boy’s humor, and told us what we were seeing! One of the coolest parts was watching the whales from overhead, he circled a few pods of whales and it was so neat to watch them swim, jump, and play below us! The time flew (pun intended) and we loved this experience. If you can swing it, just do it because it’s such a cool way to see and experience the island, especially since we had just driven across it on the Road the Hana the day before!

What we did: Captain Steve’s Whale Watching Tour

Total Cost: $48 per person 

This was the last excursion we went on and it was so fun! We were also advised to go early in the morning because the waters less rough! The tour was about two hours long and we were told to choose Captain Steve because he’s a whale whisperer of sorts! The boat was more like a raft boat and not a catamaran, which most said brings the whales closer. We got to watch a few different pods of whales around the boat, saw a handful of dolphins, a few full breeches, and enjoy time on the water! It was super fun, really relaxed, and such an amazing thing to see while visiting. While we could see whales jumping around and swimming from our hotel beach, this was a way closer and more intimate look accompanied with education! It was also so nice because we were done by 10AM and had the rest of the day to beach it and enjoy!

Why Hawaii was our favorite: 

We’ve been all over, Costa Rica, St. Lucia, Jamaica, the Dominican Republic, and more but this was our favorite. Why? It felt good to still be in the U.S.A! Nothing felt unsafe the entire time, island life was relaxed, there wasn’t a language barrier. We were surprised that we enjoyed the non-all inclusive aspect as much as we did. We felt like we didn’t stuff our faces each meal, didn’t drink ourselves to oblivion, and enjoyed leaving the resort to see more places. There was so much to do, but don’t let our list fool you, we got in plenty of beach time and even snorkeled and saw some sea turtles! Hawaii life was so convincing, Drew tried to tell me we should move (don’t worry, we aren’t.) While the prices were steep and it was hard to swallow spending $20 for a breakfast of an egg and toast, we were lucky and resourceful to have a kitchen to make snacks and breakfast in! What we think? If you’re going to go, just do it all. Soak it in! You’ve already spent a lot to get there so enjoy each moment of it! The travel days are long, bring lots of books and buy a sweet neck pillow at the airport but you’ll be there in no time!


Hotel, Flights, Rental Car: $5400 

Excursions: $1000 

Food and Drink: $1000 

Total Hawaii Vacation Budget: $7500

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  1. Kim says:

    Your vacation looked amazing! Loved that you are so adventurous and your country side images speak a thousand words. I’m trying to plan a 15 year anniversary trip to Hawaii yet this year and this helps out tremendously. Thank you!

  2. Kurt Hanson says:

    Dana shared this with me (her Dad). We just got here on the 22nd, when you posted your comments. Very helpful, thank you.

  3. April Allard says:

    Wish we did the helicopter tour…we did a very scary small engine plane tour…yikes!! We were there 10 years ago for our wedding and honeymoon and I loved reliving it all through your post.

  4. Kate Shelerud says:

    this is amazing !!!! all these pics– wowowowowowow

  5. Ali Acker says:

    Thanks for sharing your in depth view on your trip to Maui last year, Jenna! My husband and I are going in the beginning of June to celebrate our five year anniversary a couple of months early! If you have any other tips or must see places, please let me know. We are looking for a photographer to an anniversary session while we are there…to bad you are traveling to Hawaii now and not in a few months!

  6. I am so glad I stumbled upon this!! We are planning our 5 year anniversary trip to Maui this September! Thanks for the tips. 🙂

  7. Emily Hines says:

    The helicopter tour was the only thing I didn’t do when I lived in Maui! Next time 🙂

  8. Ketan says:

    I liked your blog on maui visit. I and my wife are planning a trip to Maui. If it’s possible would you please provide me your travel agent contact details that will be helpful to us.

  9. Lise says:

    I really enjoy reading your blog. Your pictures are amazing and I love how you break down the prices. .
    I am fortunate enough to live on this beautiful island and always recommend people drive the back side when doing the road to Hana. It has such amazing views to offer that a lot of people don’t get to see. From your pictures it looks like you experienced that first hand.
    My husband and I own a grocery delivery service here on Maui and have also stayed at the Westin in the past. One way you can elevate your next vacation here is to use our grocery delivery service. Next time you find yourself back on the valley isle let us know and we would love to get your vacation rental set up with some groceries so you can arrive to your rental to a stocked kitchen. Please check out our website and feel free to contact us with any questions!
    Mahalo nui loa!

  10. Alex Cortez says:

    Wow, you had a great visit!!! If you visit again, I would strongly suggest staying on the South side, as each micro-climate presents a very different perspective of life on the island. As you stayed in the West side (kaanapali), now you could experience Maui in a different light.

  11. Lisa says:

    We just came back from Maui. I love your photos and the insight that you shared. Thanks!

  12. Great experience you have shared of Hawaii Visit.
    I want to go Hawaiian Islands.

  13. Very nice blog, Thanks for guide us with this amazing stuff.

  14. Very beautiful photographs, I love Hawaii, this is a truly magical place, with its special air, charm, beauty …
    we went to Honolulu, it was excellent, as for the prices, I did it the same way, only for 1 night less


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A small town Minnesota photographer, podcaster, educator and puppy rescuer, my happiest days are spent behind my computer screen sharing my secrets with the world. I'm glad you're here.

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