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Today was the perfect day to write this travel guide — there’s snow on the ground in Minnesota and we’re hovering around 27 degrees today, which has me dreaming about Hawaii. As of this writing, I have been to Hawaii twice – the first time, I went for a month, spending two weeks on each Oahu and Kauai, and more recently, we took a 10-day trip for our honeymoon (spending 4 days on Oahu and 6 on Maui).

Plan your trip to Hawaii 

Think about the vibe you’re going for – do you want to be near hustle and bustle every day or do you want to relax most of the time? Are you a combination of those two? 

How long will you vacation? A longer period of time means you might want to consider island hopping for some variety and a change of scenery. 

Is shopping important to you? Shopping is available on every island but there are a couple of key places with more shopping or additional retailers to consider. 

The answers to these questions will help you figure out which island or islands you’ll want to visit.

I’ve also compiled a Google Map with all the places listed in my travel guide for your use.

FOUR DAYS ON OAHU

I like Oahu because it contains some really important pieces of Hawaiian history and culture provides important global context. Oahu is BUSY and there is nothing like it on other islands. If you are traveling to Hawaii with someone who has never been, Oahu is a must. When we decided to take our honeymoon in Hawaii, my husband had never been. He is very into history and culture, so I knew that we had to do a stop there. We decided to spend just four days there, but packed it full of incredible experiences. 

Here is a look at our Oahu itinerary:

Day One – Travel from MSP > LAX > HNL (landed around 5 p.m. HST)

We rented a convertible from a company at HNL and drove with our luggage to the Airbnb that we rented. We knew that we would not be in Honolulu for long and wanted to make the most of the days, so we opted for a very affordable studio apartment on Kuhio Ave, which was in a great location for us and had nearby parking that we could access.

After checking into the Airbnb, we knew that we needed to stay up to acclimate to the five hour time difference and also needed to grab dinner.

Duke’s

The sun had not yet set, so we hurried to Duke’s on Waikiki for a delicious meal (around a 45 minute wait at that point) and to watch the sunset from our table, which was awesome. Duke’s is a must, especially if you have never been to the Waikiki area. We wrapped up the meal just after sunset and headed back to the Airbnb to get some sleep for the rest of our trip.

Day Two

Pearl Harbor 

Be sure to get tickets in advance and read up on policies, as they can and have changed! We got tickets for one of the earliest times in the day (ours were for the 7:30 a.m. tour), which gives you more time with fewer people at the memorial. In my opinion, you only need to do the Arizona memorial (which is free) and not the others. 

You learn about the history leading up to the December 7, 1941 attack on Pearl Harbor with a 25-minute video before boarding a Navy-captained boat to the memorial site, which sits atop the USS Arizona wreckage. You get a designated amount of time to spend in the memorial in the harbor, which is incredibly powerful, especially if it’s your first time. There are some additional places to read more about some of the survivors and their backgrounds, which brings the history into focus.

Nu’uanu Pali Lookout

The day we went to see the lookout, it was incredibly rainy and windy, so we didn’t get to see much of anything. Pro tip (not that I would know or anything), there is absolutely nowhere to go to the bathroom along the way up or down from the lookout, so plan ahead!

Had the weather been better, we would’ve been able to see so many sights from the lookout, as you can see on the sign. Make sure you go on a clear day for a great view!

Helena’s Hawaiian Food (must-go)

Helena’s is a James Beard Award-winning restaurant that serves authentic and unfussy Hawaiian fare. It is a MUST! As of now, they’re open Tuesday through Friday from 10 a.m. to 7:30 p.m. and since it is so popular, expect it to be busy. We went on a Wednesday at around 11:30 a.m. and it was busy already, but we only had to wait a few minutes for a table. Parking can also be tricky, as they have a small lot and the streets around the restaurant are very busy.

You can order items off the menu a la carte, or you can choose a combo with your choice of side. When Bob and I went, we got the combo of Kalua Pig, Lomi Salmon, and Pipikaula Short Ribs, and added a Poi for our side (Menu C). Poi is a thick paste made from Taro root, but is fairly tasteless – a bit sweet with a slight tang, but not an intense taste. We also got a couple of scoops of rice and received a side of Haupia (Hawaiian coconut milk pudding shaped like bars) since we ordered a meal.

Iolani Palace

As I mentioned, the weather was dreary and rainy that day, so after getting completely drenched at the lookout and then getting some food in us, we decided to tour Iolani Palace to get a deeper look into Hawaiian history, focused on the monarchy. I had been here before but it was such a unique experience that I did not mind coming back.

We walked up to purchase tour tickets and had to wait about 30 minutes for a tour. We opted for the self-guided audio tour ($25/adult), but you can also take a tour led by a docent ($30/adult).

It’s important that you dress properly for the Palace, as it is considered sacred grounds. Beachwear and cover ups are not permitted, nor is clothing with profanity. You will also have to put shoe covers on before entering. Bags are not permitted either, but there are lockers that you can rent during your time at Iolani Palace. Be sure to read up on all you need to know before going.

You can take images and videos for personal use only, but out of respect for the Palace and that rule, I will not be posting any of my photos here. Trust me when I say it’s pretty incredible and helps you understand the history a bit better.

Missed opportunity: Leonard’s Bakery

Leonard’s Bakery is very famous for its malasadas, a sort of Portuguese donut without a hole. They offer many flavors from 5:30 a.m. to 7 p.m. daily and I regret not getting some at Leonard’s constantly. This would’ve been a great stop on the way back from Iolani Palace before reaching our Airbnb to freshen up for dinner. Don’t make my mistake!

International Market Place

International Market Place was an easy walk from our place and while it is a mall, there are so many other offerings inside the market place. We also saw a hula demonstration as we were walking around and taking it all in before our dinner reservation.

Eating House 1849 by Roy Yamaguchi (could skip)

We made a reservation at Eating House 1849 and while it wasn’t my favorite meal of the trip, it was fine. The restaurant incorporates Asian fusion into the options for a fun spin on some classics. You can get ramen, burgers, build your own catch of the day feature, and your own steak combo. The restaurant was very kind and provided us with a dessert because we noted that it was our anniversary when making the reservation.

 

Day Three

We were up early and heading out of the city because we had a lot to accomplish on day three.

Olive & Oliver (skip, unless you’re nearby or staying there)

I’d heard that there was a great, local coffee shop called Olive & Oliver at a nearby hotel, so we stopped there to grab a coffee to start the day. Parking near the shop was very difficult and we ended up having to feed a meter.

The coffee shop is located inside the Surfjack Hotel. It has a very cute curated boutique within it, so I was excited to peruse but was a bit let down at the small selection. There was a long line and the drinks are very well hand-crafted, delaying us a bit time-wise. The cups are hand drawn and adorable, so a good photo op for sure.

Skip: Dole Plantation

First on our attraction itinerary was the famed Dole Plantation and it takes about 45 minutes to an hour to get there. We got there right when it opened, as you cannot purchase tickets for tours ahead of time. Our tickets were for the train and garden, which showed you various crops (including pineapples) that are grown on the Dole property. The garden was pretty but was an unnecessary stop. The gift shop has a lot of great curated Hawaiian memorabilia and we purchased some gifts for family, as well as ornaments for our Christmas tree. That was truly the best part of the Dole Plantation experience. I would not recommend coming here, as it’s overcrowded, an unnecessary expense, and there is a better tour on Maui (if you decide to visit there).

Giovanni’s Shrimp Truck (must-go)

Giovanni’s Shrimp Truck is part of a group of famed food trucks in the North Shore city of Haleiwa. Each meal on their simple but perfect menu comes on a paper plate with two scoops of rice and a dozen shrimp — it’s a heck of a deal! Bob and I each ordered the famous Shrimp Scampi which is absolutely COATED in minced garlic, but it is the most delectable shrimp I think I’ve ever had. I STILL dream about it!

Missed Opportunity: North Shore Goodies

The best peanut butter I have ever had, hands down, comes from North Shore Goodies. While they do ship the peanut butter, it is costly to do this. I wish that we would have stopped here in person when we went to Giovanni’s, as it’s just down the road. Do not miss out on their famous coconut peanut butter! Absolutely delicious!

Polynesian Cultural Center

You’ve probably gathered that we are into learning about history and culture at this point, which is part of the reason we decided to go to the Polynesian Cultural Center for the rest of the day. The other reason we decided to go is that my aunts said it was a very memorable experience from their trip to Oahu 20+ years earlier. There are a variety of ticket packages, which can be purchased in advance online or walk-up on the day of.

We explored the Islands of Polynesia exhibits and activities from 12:30 to around 4:30, when it was time to head to get seated for the luau (included in our package). Bob had never been to a luau and getting to experience it through the PCC was extra special. After dinner and the luau presentation, we headed to the theater at the PCC for the show that we had tickets to as part of our package. The show was similar to Cirque and was an interesting story, but I do not think it is a must-see, especially if you have a long drive home (as we did).

 

Day Four

After the long day we had the day prior, we decided to stay a bit closer to our place and unwind on our last day in Honolulu.

Cheeseburger in Paradise (for breakfast – could skip)

Bob is a big breakfast person and wanted to get a big, sit down breakfast on our last day, so we walked a block onto the street that borders Waikiki Beach and stumbled upon one of the only full-service breakfast spots, which ironically, was Cheeseburger in Paradise. The food was fine – nothing excellent, but there was some great entertainment in the form of listening to the host tell tales about his previous night’s activities, breaking to cheerfully greet new customers. We still giggle thinking about listening to this!

Maguro Spot (must-go!)

On the corner near our place, we’d seen a poke restaurant and decided to try it. Restaurant is overstating what this place is a bit, it’s really a corner market that serves up poke bowls with tables outside on the sidewalk. I’ve since learned that “The Poke Spot” is called Maguro Spot and my husband mentions it frequently, even though it’s been a few years since we went. It’s unfussy, fresh, quick, and delicious! Do not skip this one.

Starbucks Reserve

I wanted to make a stop at the Starbucks Reserve that I’d seen a few times on our street. We took a short walk to the Reserve, since it offers different merchandise (I collect mugs from my travels) and beverages than your typical Starbucks.

I was able to get some unique Honolulu-specific cups to bring home and remember the trip by, as well as a really delicious iced dark chocolate drink that is unique to the Reserve store experience.

I actually loved that drink so much that I walked to the Reserve store before it closed again that evening to get another one and put it in the refrigerator for the drive to the airport in the morning.

Magic Island

Bob read that Magic Island is a place that few tourists go because it’s essentially at the far end of Waikiki Beach and runs perpendicular, but it takes a bit to get to the park to access the peninsula and lookout. The view from Magic Island did not disappoint and we were able to sit on the beach and enjoy the great weather for the rest of our last day on Oahu.

LuLu’s Waikiki

As we were flying out to Maui the next morning, we wanted something close to our place with some American food for dinner that isn’t a chain. We decided to try LuLu’s because it was close to Waikiki Beach and had good reviews. The food was above average bar food and had a relaxed atmosphere. As it was on the end of Waikiki closer to Honolulu Zoo, it was a bit less busy than some of the other restaurants closer to the end with a bunch of large resorts.

 

MAUI HONEYMOON EXPERIENCE

Here’s a look at our Maui Itinerary:

Day Five — travel day and more

We got up bright and early to return our rental car at HNL and ensure we were there with enough time (traffic on H1 can be insane!). We flew Hawaiian Airlines to Maui and the inter-island airport experience was pretty seamless, as it has its own terminal at HNL. The flight itself was very short and we had an incredible view of the islands as we jetted over to Maui.

Once we landed and collected our bags, we had to take a long walk to the rental car center, as the shuttle took quite a while. Hauling very heavy bags in the humidity wasn’t ideal, but we made it and were off to our hotel. We were lucky enough to get a room at the Marriott Maui Ocean Club (right on Kaanapali beach), as we know some Marriott Vacation Club members who gifted us the stay. We got a room in a newer tower that had a partial ocean view.

We decided to visit the original Maui Brewing Company location, since it was only a few minutes north of where we were staying. I am a fan of their delicious flavors, especially Pineapple Mana. Bob was able to get a root beer that they make right on site, too! While they have food, we had a reservation a bit later on up the road, so we held off on eating.

Sansei Seafood Restaurant & Sushi Bar

We’d had our fill of seafood already, but were craving some sushi and Sansei had killer reviews, so we made a reservation (it was a Saturday evening) and I am glad that we did. The menu overall was very expansive and lived up to the hype! It was so good, in fact, that I said we needed to come back before we left. I can’t even express how incredible the meal was – and there are options for everyone in your family.

 

Day Six

We started a bit slower on the morning of our first anniversary, enjoying the view from our room, which had cleared up significantly from the day before but was still a bit windy and dreary. We had planned to spend the day exploring the town of Paia before our dinner reservation. It was about an hour drive to Paia and we enjoyed the sights along the way. Once we got to Paia, we had to find a spot to park, which proved to be a bit difficult, as the main area of town had limited spaces.

Paia Fish Market

We decided to grab lunch at Paia Fish Market, which was an experience where you order at a counter and then find a spot to sit while you wait for your order to be called. It was smaller inside than expected, and as it was raining outside, it was very busy. I had the fish tacos and Bob had a fresh catch plate. We both loved our meals and vowed to go back to another location if we had time.

Shops in Paia

There are several shops lined along the couple of streets that comprise the town’s center and we did stop to look inside each shop, but since it was rainy, they were all very crowded and it made for an experience that would’ve been improved with nicer weather.

Paia Bay Coffee

I’d heard about Paia Bay Coffee, which is a cute coffee shop that was hidden behind some shops on the main street. After walking through a shop and trying to find the entrance (per my Google Maps) and asking someone, they pointed me to the correct entrance. I got a delicious iced macadamia milk latte and sipped it while being sheltered from the rain for a little pick me up.

We drove along the Hana Highway as we waited for the rain to clear a little bit and we also had time to kill. As the rain cleared, we made our way back west (closer to Paia) to see some amazing sights.

Ho’okipa Beach Park (must-go)

If you want to see turtles, THIS is the place to do it! It’s very, very busy and difficult to find parking on weekends and in afternoons because it’s a popular spot to surf and also watch the Honu (turtles).

Here is what the park looks like from a distance (it’s on the left, where the building and people are).

If you glance at the photo of the beach, you may only see dark rocks, but look closer – so, so many honu! Hawaiians believe very strongly in taking care of the environment and preserving nature. You should never go close enough to bother the turtles, as they are seen as sacred in Hawaiian culture. You can photograph them from a distance, as we did, though!

Around the corner from the park itself, there is a lookout where you can venture out onto some rocks to get photos like this. There are signs warning you about the dangers of the uneven ground and rocks, which I was a little unsure about, but this VIEW!

Mama’s Fish House (must-go)

We’d heard so much about Mama’s Fish House and knew that our first anniversary dinner needed to be here. I made reservations at least six months in advance, when they opened, to ensure we could eat here on the day that we wanted to. I also put notes in my reservation requesting a table where you could view the water if possible, and it was accommodated (hooray!) Note that reservations are required and can be made through OpenTable. Even with a reservation, it did take a bit to get seated, but it was worth it.

I had the bouillabaisse and Bob had the macadamia crusted fish. Both were EXCELLENT!

 

Day Seven

We started slow with a coffee and some time on our lanai at the hotel before heading into Lahaina, which is a short drive from Kaanapali. We found parking in the public parking area (which is JAM PACKED, by the way!) and I’m so glad that we went there very early so we had plenty of time to eat lunch before we had to check in for our whale watch tour. People were downright savage in the parking area, so be prepared. I think it took us over a half hour to park the car, when all was said and done.

Down The Hatch

This Diners, Drive Ins & Dives-featured restaurant is in the heart of Lahaina’s main street and has an expansive and delicious menu. We couldn’t get enough fish, so I opted for the local fish tacos and Bob had the Captain’s Catch. Down The Hatch has a full bar that you can also order food from or you can opt to order in line and eat in a food court style table setting. We opted for the latter and it was a casual and fun experience for a quick early lunch.

Shops in Lahaina

There were several shops along a main street in Lahaina and a few on side streets, as well. We perused the shops but they were very similar to what we saw in Paia, so we did not spend much time here. If this is one of your only stops, you’ll have plenty to look at. Be sure to stop at the giant old banyon tree in the middle of it all, too! It is one of the largest banyon trees in the United States.

Whale Watching in Lahaina (highly recommend)

If you are visiting during whale watching season, you HAVE to do a tour! If nothing else, for the amazing views from the ocean.

Here is a resource for the whale watching companies that have tours leaving Lahaina Harbor (days/offerings vary). We personally booked the Whale Explorer – Lahaina Harbor tour and had a wonderful time!

During the two hour tour, we saw so many whales! The tour guides were very knowledgeable and provided us with tons of opportunity to see them and safely capture the sightings.

Leilani’s on the Beach (must-go)

We opted to do a dinner pretty close to our hotel around sunset. Leilani’s is known for its delicious food (of course) but also its wonderful open air dining room right on Kaanapali Beach. We booked a reservation for the restaurant very early on OpenTable to ensure we got the time we wanted, as the wait is usually VERY long. There is only a five minute grace period for reservations due to the long waiting list, so be sure that you show up on time, if not early.

The view from our table was amazing, especially as the sun was setting. We got more seafood (surprise!) and ordered the very famous Hula Pie to take back to the hotel for dessert later. Hula Pie is made with ice cream, but because we were so close to the hotel and also had a freezer in our room, we were able to enjoy it once we had some extra room in our stomachs after our feast.

 

Day Eight

This day started off with an idea that I don’t recommend anyone else execute. If you look at a map of Maui, you’ll see that to get from the airport to Kaanapali (where we stayed), it takes you south and then northwest in the shape of a U. My darling husband wondered why we didn’t just take a road north and then west, kind of like an upside down U, so he wanted to explore it.

Kahekili Highway (do not recommend!!!)

Just don’t do it, okay? People talk about how scary the Road to Hana is (because it’s narrow, winding, etc.) but I’ve read that this journey is worse. We spent more than an hour in the car through twists and turns on a steep, narrow, rough terrain laden, one-lane highway. I was so scared at times that my Apple Watch thought I was working out and claimed I’d had more than 30 minutes of exercise while a passenger in the car. There is nowhere to go to the bathroom, stop, etc.

Wailuku

The Kahekili Highway ends in Wailuku and I’d read that there was a gorgeous mural painted on the side of a Texaco station, which was perfect because I needed to go to the bathroom and we needed to fill up the car after that insane ride.

Foodland Wailuku

During trip planning, we’d read that some of the best poke you can get on the island comes from Foodland, a local supermarket. Sure enough, in the back of the store sits a counter where you can order various kinds of incredibly fresh poke at a very reasonable cost. We decided to try it out and ate a quick lunch of our Foodland poke in the car — it lived up to the hype!

Maui Tropical Plantation

With a disappointing Dole experience behind us, we decided to try a plantation tour at Maui Tropical Plantation; a smaller, locally-owned business. We did the tropical express loop but if you’re adventurous, they also have zipline courses on the property that you can book. During the tour, they show you how to husk a coconut, which is really cool! After the tour is over, you get your own dish of delicious pineapple and can hang out in the gift shop or head out on another adventure.

Skip: Monkeypod Kitchen by Merriman

We’d seen great things about Monkeypod Kitchen so we decided to make a reservation. It’s right next to Leilani’s (where we’d had an incredible meal the night before, so we knew that it would be a similar vibe with the open air dining near the beach. What we didn’t know is that the food would underwhelm us and we’d be seated next to the (very loud) live music, making it impossible to have a conversation. It took forever to get food and soured the experience a bit more. I’d recommend skipping this one — we had pizza, which you can get anywhere. There are much better options.

 

Day Nine

We took this day to unwind and have lunch poolside and dinner at one of the resort’s restaurants. We hung out by one of the pools at the resort all day as we hadn’t had a chance to slow down. Highly recommend one day of rest if you’re on a big Hawaiian adventure, like we were.

 

Day Ten

Our last day! We booked a coconut farm tour when we were sitting at the pool on the previous day because it sounded like a unique thing to do and because our flight left in the evening, we’d have all day to do something else.

Punakea Palms (HIGHLY recommend!)

Punakea Palms hasn’t been around all that long (est. 2005) and it’s a very small farm that offers tours to bring the revenue in to help their business grow and expand. They take a small group of around 10 people through the growth cycles of palm trees and coconuts, walking a short distance into the forest of palm trees on the grounds.

Your guide will be incredibly knowledgeable and show you how to spot coconuts at different stages, when they’re ready to harvest for a particular need (coconut water, coconut flesh, etc.), and HOW to husk a coconut. We’d seen how to husk a coconut during our visit at Maui Tropical Plantation, but that was in a much larger setting.

Your guide will help you husk a coconut so that you can make your very own coconut milk on site at Punakea Palms! You walk away with a mason jar of your own handmade coconut milk from the coconuts at the farm and it is the best tasting stuff EVER! I was really sad it was our last day and we couldn’t take it home with us so you bet I went to Starbucks at our hotel and got some shots of espresso so I could make my own iced latte with my coconut milk.

After our tour was over, we grabbed a quick lunch at Paia Fish Market in downtown Lahaina, as it was a short drive from the hotel. We then went back to the hotel to relax on the grounds for a bit before our dinner reservation (early reservation at Sansei — yes, the Sansei from the first evening on Maui! I told you we loved it!)

Traveling home

After Sansei, we drove back to the airport to drop off our rental car (which is off site) and be sure that we had enough time to go through the security at OGG in Kahului. When traveling back to the mainland U.S. from Hawaii, your baggage must go through a USDA inspection to ensure that you are not transporting restricted or prohibited plant materials out of the state. This adds an extra layer (read: line) of complexity at the airport, so leave plenty of time to get through it all.

We went from OGG to SEA to MSP and I don’t know that I would take that route again, due to the plane size and lack of comfort for a red eye. I would consider going from OGG to HNL to MSP next time. This way, you have a shorter flight to hop on a larger plane that’s nonstop for nearly the entire duration of travel and allowing you to be a bit more comfortable and get some additional sleep.

Whew — that was a LOT! I hope that my recommendations and links have been helpful. Let me know what questions you have down in the comments.