For our 5th wedding anniversary, Chris and I decided that a trip to Hawaii would be the perfect getaway for us. Before I get into what all we actually did during our trip, I thought that I’d break down our Hawaiian Itinerary so you could see exactly how to spend 9 days exploring Maui and Kauai.

The Wandering Weekenders- How To Spend 9 Days Exploring Maui And Kauai

After we had decided that Hawaii was where we would be jetting off to, we needed to decide which island or islands we wanted to visit in 9 days. I had been to The Big Island and Maui before and thought that the activities that we did on Maui would be something that Chris and I would have a blast doing again together. So Maui was definitely on the itinerary. My parents had also just gotten back Kauai and could not stop talking about how amazing it was, so the decision to add Kauai as a destination was very easy. We did look into whether or not we could add a quick stop on Oahu, but unfortunately there just wasn’t enough time with only 9 days. So Maui and Kauai was our final decision!


Day 1- Arrival

Hawaii is a long way from most places in the continental United States, even from California it’s about 2500 miles, so be prepared for a long flight to get there no matter where you’re flying from. We spent a good chunk of our first vacation day flying from Houston to Maui, but it was totally worth it! We had a layover in LA before landing in Maui around 5:30 that afternoon.

Once we had grabbed our bags, taxied over to our hotel, and checked in, we were very exhausted and hungry too! We quickly freshened up before heading to grab dinner before heading to bed. When we walked out of our room we were greeted with the most beautiful sunset, and we knew that we were going to have the time of our life!

The Wandering Weekenders- How To Spend 9 Days Exploring Maui And Kauai

Tip: Unfortunately, you will spend at least two days of your trip traveling, but it’s all worth it to have an amazing trip. Don’t plan on doing much your first day, just check in and spend some time relaxing at your hotel. You’re in paradise so you should enjoy it!

Day 2- Haleakala

Because Hawaii is so far away from the continental United States, there’s also a very large time difference as well, (Hawaii is 4 hours later than Central time). Because you will probably still be on mainland time for the first day that you’re in Hawaii, I suggest waking up early for the sunrise on Haleakala on your very first day in Maui. It won’t even be that bad to wake up early because you’ll be waking up naturally at that point in time.

The Wandering Weekenders- How To Spend 9 Days Exploring Maui And Kauai

For the adventure lovers out there, definitely take this opportunity to bike down Haleakala after you view the spectacular sunrise! There are a lot of tours out there that will guide you down the mountain, or you can opt to go by yourself. Ashley from My Wanderlusty Life has a great guide for biking down the mountain by yourself. If you’re not the an adventure lover, there are also tour groups to drive you up to the top for the sunrise and then back down, or you can rent a car and drive up yourself.

The Wandering Weekenders- How To Spend 9 Days Exploring Maui And Kauai

Since you’ll be up at the crack of dawn, definitely make sure to spend the rest of the day napping and relaxing by the pool cocktail in hand. There won’t be a more beautiful view, I’m sure!

The Wandering Weekenders- How To Spend 9 Days Exploring Maui And Kauai

Day 3- Road to Hana

The Road To Hana is probably the most treacherous road in the United States, but it’s also filled with some of the most beautiful sites as well! Which is why it definitely needs to be on your Maui itinerary. Because there are many blind and hairpin turns, I suggest booking a tour for the Road to Hana. It’s an all day event, will take you completely around the island, and well worth the time and money!

The Wandering Weekenders- How To Spend 9 Days Exploring Maui And Kauai

The Wandering Weekenders- How To Spend 9 Days Exploring Maui And Kauai

The Wandering Weekenders- How To Spend 9 Days Exploring Maui And Kauai

The Wandering Weekenders- How To Spend 9 Days Exploring Maui And Kauai


Day 4- Arrival

Island hopping can get very time consuming, but with all the different things to do between all of the different islands and relatively cheap flights through Hawaiian Air, it can totally be worth it. On our fourth day, we woke up bright and early in Maui, packed our bags and headed to the airport to head to Kauai. Less than an hour flight later, we had landed in beautiful Kauai, and were headed to grab a quick lunch.

The Wandering Weekenders- How To Spend 9 Days Exploring Maui And Kauai

Rather than spending your time exploring the islands on your travel days, use that time to relax and get to know your resort. Besides adventuring around Hawaii, I’m sure that you’re also looking to relax on your vacation as well, so make sure to take the time to relax as much as possible!

Day 5- Waimea Canyon & Zip lining

The Grand Canyon of The Pacific as it’s referred to by the Hawaiians, Waimea Canyon is not to be missed during your trip to Kauai. Wake up early one morning and drive to the canyon on your first day on the island. Not only will you get the chance to see this beautiful part of the island, you can also use this opportunity to get to know the island as well. You can spend a few hours exploring the canyon or hiking and then head out for some lunch before your afternoon activities!

The Wandering Weekenders- How To Spend 9 Days Exploring Maui And Kauai

The Wandering Weekenders- Which Hawaiian Islands Should You Visit?

Kauai definitely has a wide range of activities that you can do on the island, and if you can handle heights, one thing that you do not want to miss is the chance to zip line on this island. It’s a huge rush to sail over the trees on the island, and you also have the opportunity to see some of the beauty of the island itself.

The Wandering Weekenders- How To Spend 9 Days Exploring Maui And Kauai

Day 6- Helicopter Ride & Luau

The Na’Pali Coast in Kauai is arguably one of the most beautiful coasts in the world. The mountains that define the coast are extremely treacherous though, which is why there are no roads through the Na’Pali Coast, and also means that you can only see the Na’Pali Coast by foot, by sea, or by air. When in Kauai, do not miss the opportunity to view this beautiful coast from the air by taking a helicopter ride around the island. You will not only learn about the history of the island, but you’ll also get to see some beautiful places on the island that aren’t even accessible by foot!

The Wandering Weekenders- How To Spend 9 Days Exploring Maui And Kauai

The Wandering Weekenders- How To Spend 9 Days Exploring Maui And Kauai

Spend the rest of the day exploring the island, and then end it by attending a traditional Luau. Yes it might be a very touristy thing to do, but it’ll also give you the opportunity to try some traditional Hawaiian food and to check out some amazing dancers hula! Plus it’ll give you the opportunity to get “lei’d”!

The Wandering Weekenders- How To Spend 9 Days Exploring Maui And Kauai

Day 7- Kayaking

Kauai is an island, so one thing you do not want to miss is the opportunity to explore some of the island by boat. Kayaking is a great way to get out and explore the island while also getting a little bit of a workout in as well. Most of the kayaks are tandem, so just be prepared for maybe some arguing if you haven’t kayaked in a tandem before.

The Wandering Weekenders- How To Spend 9 Days Exploring Maui And Kauai

Most of the excursions will last until the mid afternoon, so spend the rest of your relaxing by the pool at your resort. After your kayak adventure, you’re definitely going to need it!

The Wandering Weekenders- How To Spend 9 Days Exploring Maui And Kauai

Day 8- Pool Day & Sunset Cruise

The past few days of your Hawaiian vacation have been extremely busy and full of lots of adventure, so spend your last full day of your trip relaxing by the pool or the beach at your resort. If you’re worried about not being able to relax, the resorts on the island offer lots of activities right outside of your hotel room, including snorkeling, boogie boarding, and surfing.

The Wandering Weekenders- How To Spend 9 Days Exploring Maui And Kauai

The Na’Pali Coast was beautiful by air, but you don’t want to miss the opportunity to see the Coast by sea as well, and there isn’t a better time than at sunset! Instead of going out to dinner on your last night, go on a sunset cruise to the Na’Pali Coast. Have your eyes peeled on your cruise though, you never know when you might see some dolphins, sea turtles, or even some whales!

The Wandering Weekenders- How To Spend 9 Days Exploring Maui And Kauai

The Wandering Weekenders- How To Spend 9 Days Exploring Maui And Kauai

Day 9- Departure

Your last day of your vacation can sometimes be stressful with trying to pack up and make it back to the airport, but if your flight is a little later in the day, try waking up a little early to either relax by the pool for a bit or to explore the island a little bit more. You definitely won’t regret soaking up your last little bit of paradise before heading back home!

The Wandering Weekenders- How To Spend 9 Days Exploring Maui And Kauai

And there you have it, a 9 day itinerary for exploring Maui and Kauai! I did a lot of research before our trip, and I really feel like this itinerary gives you the opportunity to see both of the islands, lots of chances for adventures, plus some time for relaxing as well. I’m linking up with these Wanderful Women from some Wanderful Wednesday- Lauren of Lauren on Location, Van of Snow in Tromso, Isabel of The Sunny Side of This and Marcella of What a Wonderful World!

Have you visited Maui or Kauai? Is there anything else that you would add to this itinerary?

Other Hawaii Posts

My First Trip To Hawaii- Maui
My First Trip To Hawaii- The Big Island
10 Things I Learned While Visiting Hawaii
Hawaii In Instagram Photos
Which Hawaiian Islands Should You Visit?

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Planning a trip to Hawaii can be overwhelming, but here's the perfect itinerary to spend 9 days exploring Maui and Kauai during your Hawaiian vacation!

  • Alexandra Moresco

    Your photos are GORGEOUS! Looks like such a nice relaxing time!!

  • I can never get over how gorgeous everything is– and how different parts of the island(s) look so different! From everything I’ve read I think Maui would be the island I’d choose to visit if I ever get to go. I love that picture of you guys on the bike!

    • I know! It really is amazing how different each island is from one another, but also how different parts of the islands are. Maui was exceptionally different, which I really loved. I hope that you do get to visit Maui one day because I think that you’d love it!

  • Living on Cloud Nine

    These were my moms two most favorite of the islands. This is so informative for when Mr. Nine and I finally go someday. Such beautiful nature and true beauty!!

    • After finally getting to visit Kauai, I totally understand why it’s included in your mom’s favorites! I hope that you and Mr. Nine get to visit soon because it’s amazing to see the beauty of the islands in real life!

  • I’ve never been all that interested in visiting Hawaii, but if I did Kauai would be the island I’d most want to visit! It looks gorgeous!

    • Kauai was by far our favorite, and I would go back in a heartbeat! It’s beautiful and still feels untouched by tourism.

  • Christina Sotherden

    You guys have got it down! You saw so much and I must say you two are so adventurous! Maui was our favorite when we went.

    • I’m definitely not one that can just sit at the beach all day, which is why we tried to plan quite a few different activities. Although the time that we did spend at the beach and the pool were very nice and relaxing!

  • These photos are so gorgeous and I am sure they do not even to begin to do it justice! I have never been and it is on my list, one day! Y’all really crammed so much in. Ah zip lining is the best!

    • Zip lining really is so much fun and exhilarating! It’s amazing how much you can see too! I hope that you get to visit one day because it really is even more beautiful than pictures show!

  • My husband and daughter desperately want to go to Hawaii and when we finally make it, this will come in so handy!

  • That looks like the perfect itinerary! I love how you suggest using the time change to your advantage and see the sunrise – that’s a fantastic idea! I love seeing sunrises while traveling. It’s such a beautiful, calm part of the day.

    • Sunrises and sunsets are always so beautiful, and while we don’t usually see sunrises that often on our trips because we’re not usually up that early, we couldn’t miss seeing the sunrise over Haleakala. It wasn’t that big of a time change, but it was definitely the best way to take advantage of jet lag.

  • Jen

    Kauai is definitely on my list of places that I want to visit! We actually had the opportunity to move to Hawaii with the military but we ended up turning it down, I’m up for visiting just not living there haha.

    • We were actually just talking about that last night, that the cost of living is just so high because you’re living on an island. But if you do end up getting stationed there at some point, at least you know that you’d probably have a lot of friends that would come and visit you! I think that’s how our friends feel now that they’re in Italy, everybody now wants to come and visit them!

  • That’s certainly a sunrise worth getting up early for! My boyfriend would love to go zip-lining – no chance I’d ever do that though, I think I’d much prefer a cruise 🙂

    • Haha if you’re scared of heights, zip lining is definitely not for you, but the sunset cruise is definitely something that everybody can get behind! It was amazing to see the coast from the boat, and of course the amazing sunset!

  • Is this the perfect wedding anniversary getaway or what? Love your pictures and perfect itinerary!!

  • Nadine

    Every picture I see from HI is just so amazing and gorgeous! I would love to go someday. It sounds like you guys got to make the most of your trip! How fun!

    • I really did try to make sure that we utilized our time in the best possible ways because it was so expensive to get over there. Hawaii is so incredibly beautiful, and definitely worth a trip!

  • Ahhh your Kauai pictures take me down memory lane! I was there back in uh… 2002? I’d love to go back! #WanderfulWednesday

    • I hope that you do get to go back! The beauty never ceases to amaze me either, and I’m already dreaming about another trip back too!

  • That sunrise! Those sunsets! Just so incredibly beautiful! Y’all did so much on your trip! 🙂 The Road to Hana was one of my favorite things ever. PS-Been thinking of you all week. Hope you’re doing OK. <3

    • Thank you Olya! Things have been going better over here, especially since Dart is starting to feel better. I know that we did the Road To Hana when we went to Hawaii the first time, but I don’t really remember it, so I was really glad that we were able to do it this time around. We tried as hard as possible to see the sunset every night, and it really was one of my favorite parts of the day!

  • Wow, gorgeous sites and scenes in Hawaii! I’ve always wanted to visit but thought of it as more of a relaxing tropical vacation. You just opened my eyes to so much more! So lucky you guys got to experience all that Maui and Kauai have to offer!

    • I’m definitely not one for just sitting on the beach or at the pool on a vacation because I feel like I get too bored so I definitely tried to make sure that we had an even amount of doing and relaxing on this trip. I would go back and visit again in a heartbeat!

  • This has to be one of the best anniversaries ever! I am glad you posted your itinerary since I love to learn from what other have experienced in certain destinations. I have not been to Maui or Kauai, so, this looks perfect to me. Hawaii is great! #WanderfulWednesday

    • It really was an amazing anniversary, and one that I don’t think that we’ll ever forget! We started planning for it a year or two in advance, and I think that it totally paid off. Maui and Kauai are absolutely stunning, and worth every penny it takes to get there!

  • What a spectacular anniversary trip..! This is a great itinerary and I’m so in love with the landscape!!

    • Thank you! It still amazes me to this day how strikingly different some parts of the islands are from other parts of the island. It just makes it that much more beautiful!

  • So many ppl told me not to do the luau and I’m so glad I didn’t listen to them! It’s a must-do at least once! I love it!! Thanks for sharing your itinerary with us!

    • I totally agree! My parents had been once before they had kids, so they didn’t take us to a luau when I went in high school. Even though it’s touristy, I signed us up for a luau, and I’m really glad that we went because it was so much fun!

  • Rebecca

    Looks superb though I’d be terrified to do a zip line across the island!!

    • Zip lining was so much fun, but if you’re scared of heights, I don’t think that it’ll be for you. But there’s a lot of other things to still do on the islands!

  • Rachel

    You guys did so much stuff in 9 days! When we were in Maui, I don’t remember us doing that much except relaxing haha but, I was in kindergarten so I could be forgetting things! If we ever go back, I definitely want to do more exploring. I don’t think zip lining is in my future though, my palms started to get sweaty just looking at your pictures haha! Such a great 5th anniversary trip though!

    xo, Rachel
    A Blonde’s Moment

    • It really was such a great anniversary, and one that we’ll not forget for a very long time! I’m not one that likes to sit by the pool or at the beach for a whole vacation because I get bored and can’t sit still, which is why we tried to include some fun activities as well. Zip lining is definitely not for everyone, even my mom that loves roller coasters almost started crying when she zip lined while they were there.

  • David E

    This looks amazing. I have thought about planning a trip to Hawaii with my daughter as my brother went with his family this last December. I will have to remember this.

    • It’s definitely a fun place to go with family too! I went with my my parents and sister when we were in high school, and I still remember how much fun we had and how beautiful it was!

  • I visited Hawaii back in high school and it was so beautiful!! I can not wait to go back one day. It looks like y’all had a blast!

    • We really did have so much fun, and it’s an amazing place to visit with family or with a significant other. I visited in high school with my parents and sister, and have some of the best memories! I hope that you get to go back soon!

  • oh man, SIGN ME UP. I loved the information but just looking at these pictures was enough. So stunningly gorgeous. Man, jonesing to go!

    • I hope that y’all get to visit soon! I’m so jealous that it’s a little bit easier for y’all to get there since you’re on the west coast! One of my favorite parts about writing posts about past vacations is that I get to go back and look at all of our pictures because I forget about some of the little details.

  • Ahila Thillainathan

    Happy anniversary! Hawai’i is a beautiful place to go to for your celebration. I must visit Kauai, when I revisit Oahu.

    • Thank you! It really was the perfect place to visit for our anniversary, and I loved both of the islands that we visited! Kauai is just so beautiful!

  • WOW! This sounds like an incredible 9 days!! I love how many adventurous and outdoorsy things you guys do when you travel! I still want to go Kayaking!! So badly. So far our upcoming trips are NOLA and NYC… and I can’t see that fitting in super well on either of those trips. hehe Xo – Alexandra

    Simply Alexandra: My Favorite Things

    • Haha I think that means that you need to try and find a place that you can do kayaking at! I think that my goal for our Hawaii trip was that I didn’t just want to sit at the beach or by the pool because we were in Hawaii, so I tried to plan a lot of different activities. Overall, I thought that we had the perfect amount of doing and relaxing!

  • Leigh

    Action-packed itinerary! I am visiting Maui for the first time later this year. Island hopping is tempting, but I think I want to really explore each island on it’s own trip.

    • I definitely think that you could spend a whole trip on each island because they have so many different things to offer. You’re going to have so much fun in Maui, and I hope that you’ll do the sunrise at Haleakala! It was one of my favorite moments of the whole trip!