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Maui & Oahu - October 2018


The sunny islands of Hawaii, here we come! This was a very exciting trip for us. Especially for Milan because of a bucket list adventure.

We visited the islands of Maui and Oahu.

DAY 1:

Our first day in Hawaii! Our first destination was a beautiful 5 days in Maui. Our flight landed at Kahului Airport late in the evening so our first day was limited. We picked up our rental car and made our way to our AirBnB in Kihei. We choose this location because it allowed us a central location on the island. We grabbed dinner and settled in for the night.

DAY 2:

A simple day. We grabbed breakfast then made our way to the beach to start our day off right. After some R&R. We made our way back to our AirBnB to get cleaned up to make our way to our first destination, Haleakala National Park. Many people visit here to view a sunrise above the clouds. We opted for the sunset view.

TIP: If you decided to visit Haleakala National Park for sunrise, you need to purchase and reserve entrance tickets well in advanced. This is a very popular location so expect a large crowd. If you decide to go for sunset, entrance is free and the crowd is smaller.

Because we had our own rental car, we drove up the mountain. This was a beautiful drive. We stopped every 5 minutes to take in the view. The elevation gain is pretty dramatic and the temperature change can be felt. Crazy to think you will need a jacket in Hawaii, but make sure to bring warm clothes if you venture to the summit. Also, the mountain is used as open pasture for animals. Make sure to drive safely around ever corner. We had a few close encounters with cattle. Fortunately, no animals where harmed in the making of this post.

We had packed a picnic to enjoy with our sunset. Make sure you arrive early enough to get a good spot to see one of the most beautiful sunsets you will ever see!

TIP: If you enjoy astronomy or star gazing, hang back for awhile after sunset! You will see the night sky light up like nothing you’ve seen before. Because your are well above the cloud lines, there are no distractions or light pollution to distort your view. We met a lot of Astrophotographers and astronomy enthusiast with impressive telescope setups.

We journeyed back to our AirBnB to end the night.


Today, we planned a trip to Western Maui. We started on the southern Highway 30 to travel around the West Maui Mountains. We stopped in multiple beach towns along the way. One of the most famous spots was Lahaina Beach Town and Kaanapali Beach.

As we made our way to the northern side of the mountains, the view became endlessly beautiful. We entered Iao State Park. The drive through this park is beyond words! A beautiful coastline to a left and soaring mountain peaks to our right. It was hard to believe a place like this existed. The roads on this side of the island are windy. Parts of them are not fully paved and single lanes. You have to have a level of confidence and patience if you are to venture out to this part of the island. I can promise you, you will not be disappointed.

We took the whole day exploring around western Maui. We grabbed dinner along the way and soon we were back to our AirBnB and off to bed.

DAY 4: One of the most iconic/must do activities in Maui is the famous Road to Hana. Your journey starts from Pa’ia. You take highway 360, a windy, narrow, and at times, a primitive road to the town of Hana. This road trip is famous for scenic drives, hidden waterfalls, lush rainforest, and famous black and red sand beaches. The final town of Hana is still small with local residents. You won’t find large hotels or many activities in the town itself. This road has over 600 turnsalong the way! If you easily get car sick, you may want to reconsider this drive. At the least, stop frequently to save your lunch. We downloaded an App called Shaka Guide: Maui Road to Hana. I highly recommend it! It uses your GPS location as you drive along Hana Highway and provides information for stopover locations, interesting facts, history of Hawaii, and island music. It was entertaining and a perfect in car guide.

Along the Road to Hana, we had ample opportunities to hike for hidden waterfalls, explore bamboo forest and endless beaches. I recommend you start your journey early in the morning if you plan to stop frequently. Especially if you will be driving back the same night. TIP: If you can, we recommend you stay in Hana for the night, and do the drive back the next day. We felt rushed to finished the Road to Hana because of the return journey. We made it back before sunset but just barely. Remember, those +600 turns to Hana, you have to repeat them on the way back. We did not plan for this but in hindsight, it would have been beneficial.

A lot of tourist will be doing this drive so you will see the same faces at many of the stops. Also remember that locals drive this road daily. They will be more aggressive drivers because they are use to the conditions. Kindly pull to the side and let them pass so you can leisurely enjoy your journey. The Road to Hana is a great driver’s journey, but personally, Heerali and I enjoyed the drive around West Maui Mountains better. The view is less hindered because you are not driving through a rainforest. Also you can enjoy the drive in peace because less tourist venture out this way. Still, highly recommend the Road to Hana to see some of the iconic landmarks of Maui.

DAY 5: Our last day in Maui. We came to learn of a “Back Road to Hana”. So of course we had to explore this opportunity. This route takes you from the southern coast of Maui to the east towards Hana. This journey started from the town of Ulupalakuato Kaupoand continues on to Hana. Again another beautiful and picturesque coastline drive on the island of Maui. We past windmill farms, pastures, fields of wild flowers and dynamic coast. Absolutely beautiful! Our journey was to the bamboo forest and the seven pools waterfall near Hana.

A word of caution. Majority of the road is new, smooth and easy drive. But as you get further out, paved roads turn to gravel, single landed, steep and at times dangerous due to rough coastlines. Driving all the way to Hana should be taken with caution.

We made our way back and got cleaned up. Our night ended with a Luau, amazing food and drinks. An amazing end to Maui.

DAY 6:

A simple day. We started the day lazy, relaxed at the beach in the morning then packed for the next part of our journey. We made our way to the Kahului Airport and took a short, 1 hour flight to the island of Oahu. We flew into Kalaeloa Airport, picked up our rental car and settled into our local AirBnB and called it a night.

DAY 7:

Total beach bum day. We have been running around so much that this was an intentional lazy day. Nothing more to say here.

DAY 8:

We wanted to travel to the eastern part of the island. He got onto the H3 and drove along the coast and around as we made our way to Diamond Head Monument. We stopped at Lanikai Beach, we walked the coast and watched surfers. Close by, there is the famous Pillbox Hike. We passed on this hike but it is highly recommended if you have the time. We are not ones to pass up on hikes but we had upcoming plans and didn’t want to expend too much energy of be sore later on.

We continued southbound, making many stops just to take in the views. Makapu’u Lookout, Lighthouse and Point are well known in this area but again a long hike that we passed on at this time.

We continued along and made our way to Diamond Head. We got luck with parking, given the fact we got here fairly late. It was well past noon by the time we arrived. We hiked to the summit and enjoyed the view over Waikiki. This hike is pretty steep and portions are long stairways. Overall not too hard but there is limited cover. Recommend having a hat, water and sunscreen for your way up. We ended our day at the famous Kahanamoku Beach. The iconic view of towering hotels along the coast and Diamond Head Monument in the backdrop. Just image the view before all the hotels and development!

DAY 9:

Today we headed to the Norther shores of Oahu. We took the coastal way up Highway 83and just enjoyed the cruise. No worries, no rush to get anywhere. We passed Kuala Ranch which is famously known for the movie set of Jurassic Park. We did not get to do the set tour, unfortunately it was booked out well in advance.

At the northern tip of Oahu sits Kawela Bay and the Turtle Bay Resort. This resort was the location for the movie Forgetting Sarah Marshall (one of our favorite rom-coms!). We walked around the hotel just to explore and continues on our way

Further along the way, we passed endless beaches. One of the most famous is the Banzai Pipeline. Known for some of the biggest waves, only the most experienced surfers venture out. We relaxed on the beach in amazement as the surfers commanded the waves with such ease.

We had plans to visit the Dole Pineapple Plantation, but it was already pretty late in the day. We grabbed some food from some food trucks and watched the sunset at Sunset Beach. We made our way back to our AirBnB and got to bed early. We had a big day planned for tomorrow.

DAY 10: Talk about saving the best for last! Heerali and I really enjoy hiking/trekking. Every vacation we have been on, we have done some sort of adventurous, off the beaten path hike. For Hawaii, it’s the famous Haiku Stairs, more commonly known as Stairway to Heaven. The historic stairs to the top of the World War II radio tower is considered illegal to climb as you trespass private property. If you get caught, the fines are very high and a mandatory court appearance is required, meaning you have to travel back to Oahu just to be seen in front of a judge. That is a whole lot of extra expense we were not willing to risk. To avoid getting caught, we took the back trail up to the top of the Haiku Stairs. The trail you will take is known as Kaulana’ahane Trail. has a great post that can answer a lot of questions. Youtube has a lot of video of this trail, so you can know what to expect. This hike is long and moderately difficult. Round trip, the trek was 9.1 miles. You will travel through the jungle, cross rivers, walk across mountain ridges, and climb rock wall.

TIP: Kaulana’ahane Trail is not well marked and you could easily get turned around and lost. We hired a guide. You can contact our guide Mike Karas on his Instagram page at mike.karas . He was absolutely excellent, and professional. We felt safe the entire journey and would highly recommend him. He does this trail almost weekly, so he is very familiar with the journey.

Also pack as light as possible and bring as much water and snacks as you can. Trust me, you will need it!

From the top you have an amazing panoramic view of the island. We ventured down the stairs a bit and basked in the accomplishment. Sadly we soon had to leave to make the trek back down. But we left with smiles, and crossed the Stairway to Heaven off from our bucket list!

DAY 11:

Our last day in Oahu, our last day in Hawaii. Not surprisingly, we slept in after yesterdays trek. Our flight was later at night so we had some time to kill before heading to the airport. We planned a last minute open door Helicopter Tour which flew us around the entire island. It was a cool experience having the doors off and perfect for photo ops. They couldn’t/wouldn’t hover the helicopter in one spot so you had to get the shot quick as you flew by, cool experience none the less.

After, we made our way to Kalaeloa Airport for our journey back home.



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