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The Ultimate Hawaii Travel Guide: Where to Stay and What to Do

Aloha!! After years of traveling to Hawaii, I am here to give a quick recap of our most recent trip! 

This trip was so different for me as this time I wasn’t traveling somewhere for work. I didn’t have a speaking engagement to attend or an important meeting to go to, it was just about getting away for some much-needed R&R with Justin and the kids. 

Before I dive into the details of the trip I want to be transparent about partnerships and if this trip was in fact sponsored or not! Technically this trip was NOT sponsored but we did have one partnership while we were away with Discount Hawaii Car Rental. I’ll get into the specifics of this partnership a little later!

This industry can get somewhat complicated and there is not always an easy yes or no answer when it comes to sponsorships. For example, a big pharmacy usually buys items in bulk and because of that, they get many if not all of their products at a discounted rate! In the media industry, while we may not buy things in bulk we are often given media rates for things such as hotel stays. While we didn’t have a contractual agreement with The Fairmont on this trip, we did receive a media rate during our stay. Also, due to our long-standing partnership with The Fairmont, we had a built-up credit that we used towards our vacation.

If you have ANY questions about sponsorships, media rates, or about gifted items please feel free to ask! I will always be open and honest about whether something was gifted or if I have a partnership with a specific company! The answer may not always be simple, but I will always explain it as best I can.

Now that that is settled, let’s dive into the similarities and the difference between The Fairmont Kea Lani and The Fairmont Orchid

Fairmont Kea Lani View

Ok so most of you know that I have been traveling to Maui for years, it’s one of my favourite places! This was my 3rd time staying at The Fairmont Kea Lani and Justin’s 2nd. It’s really difficult to compare the two islands but I will separate them so you can determine which would be best for you.

But, if you are planning a vacation, I do recommend that you visit both Maui and the “Big Island”, they are both so different and unique. That’s actually why during the 12 Days of Christmas we did a combination giveaway, for the winner to receive a stay at both accommodations that I LOVE so much in Hawaii!

The Fairmont Kea Lani

When we arrived at The Fairmont Kea Lani, I was still in work mode (usually it takes me a couple of days to completely transition and relax). Since I travel so much I had some work that needed to get done while we were away. There was a lot of stuff going on for JHD that needed my attention; new employees onboarding, contractual agreements that needed my approval, finalizing details at Team Jilly HQ and so on, which was making it very difficult to unplug and just be present. Justin was soo patient with me and for the first few days, he would take the kids and give me a couple of hours to work. By the third day, I was able to completely unplug and just be with my family. 

At The Fairmont Kea Lani, we usually like to stay in the Villas. The villas are our favourite; they are perfect for a family or large group of people to stay in. The villas are so big that you could quite literally go with three families and split the costs! They are the perfect size for us as Leo and Annie’s schedules don’t always align, but the villas make it perfect to put Annie down for a nap and to still play with Leo in the private pool. 

In Maui, our days were filled with LOTS of swimming, spending time with the kids and Justin was able to play a couple of rounds of golf (which he loved!). We didn’t leave the resort much but we did meet up with … drumroll, please … a realtor to help us start looking for another condo in Maui!!! Some of you may know I used to have a property in Maui but ended up selling it. I would love nothing more than to own another place here to be able to rent out and also have a place to bring Leo and Annie for our family vacations! Don’t worry, we will be posting more about our Maui condo search soon!

Flytographer Maui Shot

Reasons why I LOVE Maui and The Fairmont Kea Lani

  • The villas are great for a family or a large group! 
  • The villas with a private pool feel like your own little tropical oasis. 
  • Old Lahaina Luau while it isn’t located at The Fairmont but one of the many reasons that I LOVE Maui. It is a great experience for the entire family. Great food, delicious drinks and a slice of the Hawaiian culture!
  • Maui is not as bustling as O’ahu but there is still plenty to do. There are lots of adorable local shops and amazing restaurants.
  • There is so much variety on the island and the scenery options are endless. There is a wonderful variety of sandy beaches and greenery!
  • The Fairmont Kea Lani has the most AMAZING gift shop. The products in this shop are perfectly curated, they have amazing bathing suits and great finds for the kids.
  • The Fairmont brunch is one of my FAVS (tofu scramble is my go-to, while Leo likes to stack his plate with fruit loops and sweets!). There is seriously something for everyone. Here are some more of my FAV restaurants in Maui! 

As our family has grown over the years, we like to just stay at the resort and not venture too far. The amenities and offerings are endless at The Fairmont Kea Lani, there is really no need to leave the resort for anything as they have something for everyone! 

The Fairmont Orchid View

The Fairmont Orchid

We wanted to spend a couple of days on the “Big Island” during this trip! I stayed at The Fairmont Orchid during my Bachelor days and I have also visited with Justin, but the kids have never been. 

Our routine consisted of spending a lot of time by the beach, making sandcastles all day long and just soaking up some much-needed vitamin D. The kids were in bed by 7:30 pm at the very latest and didn’t wake up until 8 am the following day. Hellloooooo … talk about a vacation!! LOL!

I only attempted to leave the resort once … if you follow me on Instagram, you’ll know that it was a complete disaster. I was so excited to head to Target and indulge in a mini Target haul. The kids were fast asleep in the car having a little afternoon nap, as soon as we got there we strolled up and down every aisle. After filling up an entire cart of snacks, toys, clothing, etc (nothing we REALLY needed) I headed to checkout … only to discover that I left my wallet at the hotel. I tried to pay with apple pay but since I was out of the country I had a limit of $100 to spend. I really didn’t want to dig through the cart and pick the items that I wanted to keep so we quickly abandoned that mission. By the end, the kids were hungry and crying and all I wanted to do was be back at the hotel by the beach. Someone, please remind me to not leave the resort next time LOL! 

On our final day at The Fairmont Orchid, we got to switch rooms and stay in the presidential suite. It has been a dream of mine to stay in this suite with my family since I stayed here during my days on The Bachelor. I had inquired about it when we were planning our trip, but it was completely booked up. Luckily on the very last day, we were notified that the suite was vacant and we could switch rooms and stay in the suite!! It was seriously a dream come true, I don’t think we left the room once. It was STUNNING and better than I even remembered. 

The Fairmont Orchid Presidential Suite

Reasons why I LOVE The Fairmont Orchid

  • I love the buzz of the “big island” there is no shortage of things to do and local places to shop.
  • The Orchid has an amazing swimming cove and a swim club for the kids! 
  • The Spa Without Walls is INCREDIBLE. All of their spa services are done right on the beach in private little tiki huts … how RELAXING is that!?
  • Justin played a few rounds of golf and just LOVED the Mauna Lina Golf Course!
  • The food at the hotel was incredible, it was so fresh, flavourful, and there are so many vegetarian and vegan options.

There is really no reason to leave the resort, but if it is your first time experiencing the island it is nice to venture off. The Hawaiian culture is truly so unique, the scenery is breathtaking and everyone is so kind and compassionate. 

Making Sandcastles in Maui

Which resort would I recommend?

Now it’s time to answer the question you all have been so curious about, which hotel is better, The Fairmont Kea Lani or The Fairmont Orchid? The truth is … they are both SO unique and we love visiting each one for different reasons, you just can’t compare the two! 

The Fairmont Kea Lani Beach The Fairmont Kea Lani Beachfront The Fairmont Kea Lani Maui

Photo credit Flytographer

Discount Hawaii Car Rental

As I mentioned at the beginning of the post, we did have one project/ partnership while we were in Hawaii, with Discount Hawaii Car Rental. They provided us with both car rentals on each island. We have been renting cars from Discount Hawaii Car Rental for the last six years. We started out renting a two-door jeep for Justin and I. Then when Leo came along we had to upgrade to a four-door Jeep. Now with the four of us, and all of our stuff we had to upgrade to the biggest vehicle that they offer, the GMC Denali … extended cab!! LOL! Oh, how our car rental has evolved over the years! 😂

Discount Car Rental Hawaii GMC Denali

Well, there you have it! A very detailed recap of our most recent trip to Hawaii! Is there anything I missed that you want to know? Let me know in the comments below. 



Leave a Reply

  1. Have been to the islands several times. This is my opinion:
    BIG ISLAND – like landing on the moon – all that black lava
    OAHU – like Toronto with a beach
    MAUI – like NIAGARA on the Lake with a beach
    KAUI – how I expected Hawaii would be – lush & tropical, u til last time there, saw a Costco.
    Still worth a visit!

  2. Thank you so much for the feedback, Jillian!
    My spouse and I are headed to Maui for the first time for a couple weeks this coming Feb, 2022. I noticed you had a discount code last(?) year for the Fairmont. Is there a chance you’ll be doing the same any time soon?
    Thank you,
    Candice 🤍

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