When planning a trip to Hawaii, many will tell you not to island hop because there’s so much to do and see on each island and a few days isn’t nearly enough to see everything. And yes, there’s a lot of traveling, flights, rental cars, etc. But for us, going to Hawaii is not something we can just pick up and do every year. It’s very likely that we won’t be able to visit Hawaii 4 times in our lifetime. It’s really far, requires a lot of time off work and it’s not all that cheap. We’re ‘on the go’ type travelers anyway, so we went for it. We wanted to get a taste of everything and so now, when and if we do get a chance to go back to Hawaii, we can make a more informed decision on which island we want to go back to and what we want to do there. I realize this may not be the way to do it for everyone, but for us it was so worth it and I have no regrets! In this post, I’ll share our two-week Hawaii itinerary including tips, highlights, and things to do on each island. 

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Things to Know When Planning a Trip to Hawaii:

• Hawaii has summer (highs in the 80s), and winter (highs in the upper 70s). There’s barely any difference in temperature, but winter will have rougher seas and more rain than the summer. The rain was not really an issue. It was usually short and isolated, with a few exceptions…see the next tip.
• Different parts of different islands have drastically different climates. Hilo on the Big Island gets over 130 inches of rain per year, while Waikoloa on the same island gets 0-30. Places along the Road to Hana on Maui receive over 300 inches of rain per year, meanwhile Kihei gets 0-30. You get the idea, do your research on the climates of each island before decided where to stay. Typically the south and west sides of the islands are drier and have calmer seas. Also keep this in mind when packing, a raincoat is probably something you’ll want to pack if you plan on visiting any of the wet areas, regardless of the season.
• If you plan on going to higher elevations, like Mauna Kea, Mauna Loa, or Haleakala, make sure to pack some warmer layers, potentially as much as a down jacket, hat and gloves especially if planning to go for sunrise or sunset.
• During the winter, North Pacific Humpback Whales migrate to the Hawaiian waters, so if you want to see whales, go during winter. Maui offers some of the best whale watching in the country. As long as you get out on the water, you are almost guaranteed to see them and lots of them. Sometimes, you can even see them from the shore. And if you listen close while you’re snorkeling, you can actually hear the males singing!
• If you are island hopping, you can’t see everything on every island. Do your research and pick YOUR top experiences on each one. Each island has its own ‘personality’ and uniqueness and offers different types of experiences.
  • Maui is well known for beaches, snorkeling and whale watching. It’s very touristy and there’s a lot to do.
  • Oahu in known for its city vibe and nightlife in Waikiki, Honolulu. With that comes traffic and lots of people. For me, I go on vacation to escape this, so when I come back I’ll be sure to stay outside of Honolulu. 
  • Kauai is lush and beautiful with jaw-dropping landscapes, luxurious resorts and a ton of great hiking trails. This was our favorite island and one we’ll definitely be returning to.
  • The Big Island is all about volcanoes, adventure and diversity. White, black, green or red sand beaches, lava, rainforests, the Big Island has it all.
• There are a lot of reasons to visit Hawaii, but one of the main reasons is definitely the beaches. Whatever your plans are, make sure you leave time to relax and enjoy the beautiful beaches!

Our Hawaii Itinerary:

Oahu (Day 1-2, Ala Moana Hotel, Waikiki):

Day 1-2: We arrived in Oahu pretty late, so we really only had one full day. We started early with breakfast in Waikiki, then went to Pearl Harbor. We spent the afternoon doing a driving tour of Mount Tantalus and Round Top Drive with stops at Puu Ualakaa Park and the National Memorial Cemetery of the Pacific. If we had more time, we definitely would’ve done the hike to Diamond Head and explored other parts of Oahu. Check out Aloha with Love’s post on the hike to Diamond Head to make the most of your experience.  

Big Island (Days 3-5, based in Volcano Village):

*Note: As of 5/11/2018, the national park and some surrounding areas are closed until further notice due to seismic activity from Kilauea Volcano. Check conditions before you head over to this area of the island.*

Day 3: We flew into Kona early, rented a car, and drove to our cute Airbnb in Volcano Village. For the evening, we drove, biked and hiked to see the lava flow. The location and means  to get to the lava flow is constantly changing, so you’ll need to check the national park website for updates to decide on how you will do this one. For us, we rented bikes from Kalapana Cultural Tours, biked 4 miles, then hiked at least 2 to get to the actual lava flow. We went in the evening because we wanted to see the lava glowing at night. Timing was perfect as the sun started to set right as we found the lava. It was a little jarring at first seeing the red glow and feeling the heat under the rocks that you’re walking on. Also, I don’t know if it was dehydration or the sulfur gases, but once we arrived at the lava, I quickly started to feel a little woozy, so we didn’t stay too long. We got our pictures and started heading back to our bikes, now in the dark. I did not anticipate this being so difficult. To say this adventure was strenuous is an understatement. It was still a lot of fun and such a cool experience so it was definitely worth it!

Day 4: Our main plan for this day was to see the sunset and stargaze at Mauna Kea. Our tour departed in the late afternoon and we had an hours drive to get there, so we had some time to kill in the morning. We decided to do Chain of Craters Road in Hawaii Volcanoes National Park and we were able to fit in some short hikes, including the lava tube, before needing to head to Mauna Kea. On the way to Mauna Kea, we made a quick stop in Hilo to see Rainbow Falls. We did our sunset and stargazing tour with Mauna Kea Summit Adventures and were very happy with it. In hindsight, we probably could’ve done the drive on our own, but the road conditions are unpredictable and we didn’t know what to expect. Plus, we wouldn’t have been able to look through the telescopes and learn as much as we did on the tour. It was definitely worth it and one of the highlights of our whole trip, so I’d definitely recommend it!

Day 5: Our last day on the Big Island, we decided to go back to Hawaii Volcanoes National Park to finish the Crater Rim Drive and we also hiked the 4-mile Kilauea Iki Trail through the bottom of the crater. Our flight to Kauai was later in the evening, so after our morning drive and hike, we decided to take the scenic route back to Kona and go to Punalu’u Black Sand Beach. We contemplated going to the green and red sand beaches, but it was too difficult to get to those and we didn’t have the time. Punalu’u Beach was amazing and I’m so glad we made the stop. We saw a TON of sea turtles (it’s illegal to touch them so keep your distance)! The beach was beautiful and it was much needed relaxation after all the hiking we did the last two days. We ended our day with a nice ocean-front dinner in Kona before our flight to Kauai.

Kauai (days 6-8,  Marriott’s Kauai Beach Club, on Kalapaki Beach in Lihue):

Day 6: Our first full day in Kauai, we rented a car, which was available at our resort (so convenient). We drove through Waimea Canyon all the way to Pu’u O Kila Lookout in Koke’e State Park. Along the way, we hiked the 6 mile Awa’awapuhi Trail. The trail itself was just okay, but the views at the end were incredible! I would definitely recommend the hike! One our way back to our resort, we stopped at the Kauai Coffee Estate, drank a lot of really good coffee, which was just we needed after that hike, and went on a free walking tour around the plantation. And of course we came home with Kauai Coffee, but we ate all the chocolate covered coffee beans before we even left!

Day 7: We spent the morning relaxing on the beach at our resort. I know that Kauai has so much to offer and I want to see all of it, but this resort was also so amazing and we really needed to have some beach time, so we didn’t go all out in Kauai. I have no regrets but I’m pretty sure we’ll be coming back to Kauai! Our afternoon was set for the Napali Coast Sunset Sail with Captain Andy’s. This was one of the things I was looking forward to the most. And of course, the rough seas meant that we couldn’t go out to the Napali Coast. We could’ve tried again the next day, but I just didn’t have high hopes that the surf would be any better. We still went out on the sail, but we had to stick to the south and east shores. As disappointed as I was about not being able to see the Napali Coast, the sail was still really nice. We saw whales and sea turtles and the dinner was incredible. If we weren’t sold on coming back to Kauai already, not being able to see the Napali Coast made this a necessity.

Day 8: We had no plans for this day. And we decided to keep it that way. We had been pretty much on the go the whole trip, so we decided to hang out at the resort. There were surfing lessons offered at the resort by the Kauai Beach Boys, and at the last minute we decided we wanted to try surfing! (If you haven’t caught on, Chris and I are not very good at just relaxing). We were the only ones who signed up so we ended up getting our own private lesson! Be warned, if you try surfing, you may have ridiculously sore ribs for days!  Chris was able to catch his last wave of the day. I was always too scared to let go of the board with my hands, so I usually just squatted low, holding onto the sides of my board and when I got too nervous I would just slam my body back down on the board to avoid falling (hence the sore ribs, I guess?). It was such a fun experience, and our instructor, Marlo, really helped make it so memorable!

Maui (days 9-12,  Kohea Kai in Kihei):

Day 9: We departed Kauai early to head to Maui. Our schedule excursion for the day was whale watching in Lahaina, and we were staying in Kihei for most of our time in Maui. We decided we would just go straight to Kaanapali Beach and Lahaina for the day and not check into our room until that night. We saw plenty of whales on our whale watching trip, but by we actually saw just as many, if not more, on our snorkeling excursion later in the trip. We realized that the whale watching probably wasn’t necessary, but hindsight is 20/20. The plus side of the whale watching tour was that the nature guide really taught us a lot and put a speaker in the ocean so we could hear the whales singing (it’s actually even cooler to hear them singing when you’re snorkeling though…). We had a great dinner in Lahaina at Down the Hatch (and ate shave ice)!

Day 10: We woke up extremely early to start the 1.5 hour drive to the summit of Haleakala for sunrise. It was cloudy, but it didn’t even matter because we were above the clouds. It feels like you’re on a different planet. Definitely a must-do if you’re visiting Maui! We spent the rest of our day relaxing on the beach at Makena State Park.

Day 11: We had another early morning start for our snorkel and snuba dive excursion. We actually booked this at the last minute because we realized a trip to Hawaii, especially Maui, wasn’t complete with a snorkeling experience and once we heard about snuba diving, we were sold! Snuba is a mix between snorkeling and scuba diving. You don’t have to be a certified diver to snuba dive so it’s a great experience for someone who’s never dived before. Your air tank floats on a raft above you, so you don’t need to know how to operate it or carry the 40 pounds on your back which is a huge plus! The tank is connected to you by a 15-foot hose, so you can dive as deep as about 15 feet without having to come up for air! We went with Aqua Adventures and had a seriously amazing time. The boat serves breakfast and lunch, and goes to two locations, the Molokini Crater and Turtle Town off the Makena Coast. We paid for snuba up front, which covers one snuba experience. The guide goes down with you and shows you all the different kinds of fish (using a magnetic slate underwater communication device). You can pay extra if you want to do snuba again at the second location, which we did because once you snuba, you don’t want to snorkel! They also have an underwater professional photographer on the boat, from whom you can pay a reasonable price to receive all the pictures they take on your excursion! On this one snorkel/snuba trip, we saw breaching whales, heard their songs, swam with giant sea turtles, and held an octopus. This was one of the best experiences I’ve had on all my vacations. I couldn’t recommend it enough.  

Day 12: Road to Hana. Some major points of attraction on this day were Keanae Peninsula, Wailua Iki Falls and hike, and Waianapanapa State Park. In my opinion, it’s a little overrated. BUT I will recommend the Road to Hana for a few reasons.

1. If you are like me and you don’t do it, you’ll be left wondering what all the hype is about. Everyone will tell you the road to Hana is a must-do when you visit Maui, so go for it and experience it for yourself.

2. It’s really the only reliable way to get to the coastal region of Haleakala National Park, which is home to the seven sacred pools and the Pipiwai Trail which is  a must (see more on the next day)! Also, the banana bread you probably have already read about really is as amazing as everyone makes it out to be.

A few things I will say:

• As I already mentioned, places along the road to Hana get over 300 inches of rain per year. It is not uncommon, no matter what month, for it to be cloudy and rainy on your drive to Hana, which for us, had a huge impact on how much we could enjoy it.
• If you are doing the road to Hana, I HIGHLY recommend spending the night in Hana (we stayed at Hana Kai Maui, which was a nice ocean front condo and not overly expensive). We did this and I’m so happy that we did because if we had to make that drive back in the same day, Chris and I both would have NOT been happy campers. We were already pretty grumpy by the time we made it to Hana. All that gloomy weather will do that to you I guess.
• And last, make sure you do some research and know which places are worth stopping for and which ones you’ll want to spend some extra time at. See my post on the Road to Hana for more detailed information and worthy stops!

Day 13: Quite a few of the worthy spots on the road to Hana are actually past Hana. Our destination for the day though was Kipahulu District of Haleakala National Park. Here, you will find the 4-mile Pipiwai Trail that takes you past waterfalls, a banyan tree, through a bamboo forest to the amazing 400-foot Waimoku Falls! You can also do a short loop to see the Seven Sacred Pools at Ohe’o. For our drive back, we went back and forth on continuing the drive and finishing the loop, or driving back along the road to Hana. Because it had been raining so much, we thought the road would be too muddy and didn’t want to risk getting stuck especially since we had a flight to catch that night. If road conditions are likely to be good and dry, we would have went for it so we didn’t have to drive back on the road to Hana.

To see more pictures from Hawaii, click here.

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