We took an extended week long trip to Hawaii – A Friday to the following Sunday. We spent half the time in Maui and half the time in Kauai. Here is our itinerary with all the highlights from our trip.

Maui

Travel Day:

Flew into Maui (OGG airport). We arrived late in the afternoon, rented a car and checked into our AirBnB to freshen up. We stayed near Paia so we could get an early start on the road to Hana the next morning. For dinner we ate at Mama’s Fish House – it was delicious, right on the ocean, and had a truly beautiful ambiance. Reservations to Mama’s get booked upwards of 5 months in advance so book early.

Day 1:

We got an early start on the road to Hana. We skipped some of the first few popular stops to get out in front of the crowds. Below are pictures from some of our favorite stops. Unfortunately, the road was closed a couple miles before Pipwai to Waimoku Falls which we really wanted to do. Check road closures before you go – It is common that they have to repair bridges which completely shuts down the road for a few days.

Aloha Surf Hostel

Upper Waikani Falls – This was one of my favorite stops. There was no other people. We parked a bit past the falls and trail-blazed our own off the beaten path to the base of the falls. We had our own private waterfall and swimming area.

Pua’a Ka’a Falls

Hana Farms for some fruit juice and a bathroom break.

Wai’anapanapa Beach – Must make a reservation for black sand beach in advance and then time your route accordingly. The actual beach was very small so we didn’t stay long just took a walk along the trail to the left of the beach.

Huli Huli Chicken for Lunch

Hamoa Beach– We loved this beach. It was a big cove with lots of space and not too overcrowded. Was a great stop along the route to get out of the car for a bit and lounge/ go in the ocean.

Since the road was closed we checked into our AirBnB in Hana and hiked to the secret red sand beach for sunset. It was secluded with only a handful of other people and a very easy hike although some reports say conditions can change on the trail drastically.

We had poke for dinner from the food trucks. Be ware if staying in Hana places close early so make sure to not wait around for dinner.

Day 2:

We had plans to complete the backside of the Road to Hana and cruise along the coast to Makena Beach with a few other stops as we made our way down to Lanai, but road closures had other plans. So we ventured up to Haleakala National Park. The volcano was pretty incredible and the views of Maui the whole drive up were splendid. We hiked sliding sands trail. It was an out and back, all down hill on the way in so go as far as you want to hike back out. It was a slightly deceiving climb on the way out.

We checked into our AirBnB in Lahaina which we really loved. It was a condo right on the ocean with a pool and somewhat private beach right outside. It was also walking distance to all the bars, shops and restaurants on Front Street.

Day 3:

We went Scuba diving at the Lanai Cathedrals with Maui Dive shop. The boat ride was half the fun and the cathedrals had some amazing swim throughs. We even saw a whale on the boat ride back. Everyone at Maui Dive shop was terrific and made for excellent vibes the whole day. We highly recommend planning a trip with them if you want to go diving.

We enjoyed the beach at our condo for a relaxing afternoon and wandered front street taking in all the beautiful art and stopping at fun bars. We had cocktails at Fleetwood’s on Front which did require a reservation. They also take rooftop reservations for sunset which would’ve been really nice. We ate dinner at Lahaina Grill. The food was incredible and the service was top notch!

Other things we considered doing near Lahaina was the Kapalua Coastal Trail with a stop at Dragon’s Point.

Kauai

Day 4:

We flew to Kauai (LIH), rented a car and headed straight to our accommodations in Waimea. We stayed at Waimea Plantation Cottages. They were quaint little cottages with a full kitchen, peaceful surroundings and a great location for adventures in Waimea Canyon.

We did a quick sunset hike in Waimea Canyon that was spectacular. The Kalepa Ridge Trail starts at Kalalau lookout. It is not a marked trail, but you can easily find it heading towards the left at the lookout you will see a trail that runs right past the metal fence. Follow the obvious trail and you will soon find yourself on a beautiful ridgeline out to the ocean. It was a short 1.9 mile out and back hike.

Day 5:

Another Scuba Morning and lunch meetup with friends who were also in town. We did two morning dives – one of which rewarded us with so many sea turtle sighting and swimthroughs. The boat ride again was part of the fun as we caught up with a pod of dolphins and took in beautiful coastline views from just offshore.

We went to Japanese Grandma’s Café in Hanapepe for Sushi, which was soooo good and had a great atmosphere on their back patio. Other dinner places we had considered were Eating House and Red Salt, but they were a bit further from our accommodations.

Day 6:

Happy Thanksgiving! We spent the morning exploring Waimea Canyon. We hiked Awaawapuhi Trail which was a 6 mile moderate out and back hike. The views were similar to that of Kalepa Ridge just had a much farther route to get to them and it was more crowded.

After the hike we enjoyed lunch at a private little pull out near Pu’u Hinahina Lookout. We found that the busy overlooks with guardrails were not for us, but with a little sense of adventure you could find your own spot with incredible views at some of the 1-2 car off road parking pull-outs.

After the Canyon we had thanksgiving with our very gracious friends who invited us to their family Thanksgiving. Thank you to the Howisey / Huerter crew for an amazing meal and great company!

Day 7:

We snagged Poke Bowls from Koloa Fish Market and enjoyed them on the beach in Poipu. Then we checked into our next accommodations – The Marriot Kauai Beach Club. It was our one resort type stay of the trip and a great way to end the week.

In the afternoon we took off on a private, doors-off helicopter tour – My favorite activity of the whole trip! The views blew my mind the entire time. We booked the Kauai Experience with Mauna Loa Helicopter tours because it was private and you could guarantee doors off. Our pilot was wonderful and told us all about the island on the breathtaking, hour long tour.

We enjoyed sunset on the resort beach, played some pickup sand volleyball and had dinner at one of the onsite restaurants.

Day 8:

We headed up to the North Shore, stopping at Java Kai for breakfast on the way (expect a long wait). We went to Tunnels beach where you could snorkel right from the beach with very little effort. This beach was picturesque Hawaii to me – I loved it! After the beach we drove through the cute town of North Shore, stopping at Wishing Well for Shaved Ice.

I loved the North shore area and would stay at least a couple nights there if we ever go back.

Last Day:

We purposefully stayed at the Marriot Kauai Beach Club because it was close to the airport and with a late red eye flight it was nice to have a home base the day of our departure. We enjoyed brunch on the water and rented surf boards from a beach front shop connected to the hotel. The break at this beach was perfect for beginners with long 3-4ft waves. Post surf session we enjoyed poolside fruity drinks until it was time to depart paradise!

Hawaii was amazing, spendy, but amazing! Drop a comment if you have a question about anything in this post!