Spectacular 2-Week Hawaii Itinerary with Family

We visited Hawaii and chose the incredible islands of Maui, Kauai, and the Big Island for our family vacation. Each island is distinct in its terrain and vibe. We had a wonderful time and hope our 2-week Hawaii Itinerary with Family will inspire you to visit these amazing islands.

2-week Hawaii itinerary

2-Week Hawaii Itinerary

Day 1: Arrive in Maui
Day 2: Maui: Paia and North Shore
Day 3: Maui: Road to Hana
Day 4: Maui: Hotel pool and Haleakala Sunset
Day 5: Fly to Kauai
Day 6: Kauai: Helicopter Tour and Luau
Day 7: Kauai: Hanapepe and Sprouting Horn
Day 8: Anini Beach
Day 9: Fly to the Big Island
Day 10: Big Island: Hotel pool
Day 11: Big Island: Hawaii Volcano National Park & Black Sand Beach
Day 12: Big Island: Horseback Riding
Day 13: Big Island: Hotel pool
Day 14: Fly back home

Maui (Days 1-4)

In Maui we rented a car and ventured the Road to Hana, experienced the sunset over the clouds, and had some great poke. There is so much to see and do in Maui that we could have easily stayed a whole week.

Paia and the North Shore

On our first day in Maui, we decided to take it easy and go to Paia to walk around, do some shopping, and to have lunch.

Many sites recommended Paia Fish Market or Mama’s Fish House for lunch, but we decided to go to Tobi’s Shaved Ice instead.

The name is deceiving as they also have great Poke. It was so good that we compared any other Poke we had for the rest of the trip against it. Tobi’s always won.

The shaved ice was pretty good as well. We walked through the streets and did our obligatory souvenir shopping. There is a good mix of local shops, art galleries, and touristy souvenir shops.

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We kept on walking past the stores to Lower Pāʻia Park where the kids were able to run around and play for a little bit. We wanted to go to Baldwin beach, but it proved too far of a walk so we headed back to the car and drove there. Once we were at Baldwin beach, although picturesque and amazing, it was also extremely windy. So we decided to get back in the car and drive back to the hotel.

Road to Hana

The Road to Hana is a famous drive in Maui. There are waterfalls, hikes, food stalls, and other sites throughout the drive.

We saw a black lava beach, walked inside a lava tube, and hiked the Pipiwai Trail. We ate great banana bread and pineapple.

For more information and tips, see my posted about the Road to Hana.

Ho’okipa Beach Park

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When researching where to go in Maui, one site stated that Ho’okipa Beach Park was a great place to see the sunset and “where you’ll find an insane population of sea turtles splashing around and hanging out ashore.” Although we didn’t get to experience the sea turtles, I did get to see part of the sunset. It’s a local beach with lots of surfers, reportedly some of the “best surfing in Maui.”

Since we arrived in the evening, the surfers were mostly on the water hanging out on their boards watching the sunset. There were plenty of other people on the shore waiting for the sun to go down. Beach chairs were lined up waiting for their owners to sit down and witness the spectacular event. Unfortunately, we didn’t have a lot of time. My daughter had fallen asleep in the car (after the long road to Hana) and my husband was stuck in the car with her. But, for a few minutes my son and I experienced something truly memorable.

Haleakala National Park Sunset or Sunrise

A very popular activity in Maui is watching the sunrise at Haleakala National Park (the crater side). You can do a tour or reserve ahead of time and do it on your own.

We opted for watching the sunset instead. The idea of waking up in the middle of the night and navigating the road in the dark was not appealing to us. So, instead, we drove up in the afternoon and waited for the sunset, which was around 7pm.

But, it was very cold, and my daughter and I could not stay outside for very long, so we watched it from the car. Remember, we’re from Miami, so anything below 70 degrees is cold for us! My husband and son would go back and forth between watching it from outside and warming up inside the car.


Take warm clothes: whether or not you do the sunrise or sunset, it is much colder at the top then it is at sea level. A sweater, rain jacket, and long pants are likely enough (unless you are cold-averse).

Kauai (Days 5-8)

From Maui we took a flight to Kauai on Hawaiian Airlines. Kauai, the oldest of the Hawaiian islands, is lush and beautiful. We did a helicopter tour, went to the beach and a small town, and experienced a luau during our 4 nights in this laid back island and weren’t able to experience it all.

Helicopter Tour

We wanted to do a helicopter tour and there are so many options, but I decided to go with Island Helicopters. They have good reviews, closed door helicopters, and good safety ratings. I picked the tour that takes you to “Jurassic” falls.

And, it did not disappoint. It was an amazing experience. My 10 year old was nervous about it, but she ended up loving it and it was a highlight of our trip. The pilot took us around the island to the Napali Coast and Waimea Canyon and gave us background on Kauai. We landed near the waterfall where the original Jurassic park was filmed. It was truly incredible.

Hanapepe and Spouting Horn

For a more relaxed outing, we went to the town of Hanapepe to see the swinging bridge and explore. When we arrived, the restaurant we wanted to eat at and most of the shops and other restaurants were closed. However, we found a couple of stores that were open and the proprietors were very friendly. They explained that apparently it’s a very typical day in Hanapepe; things might be open or closed.

Luckily, we found an open restaurant, Japanese Grandma’s Cafe, with courtyard seating. It has great sushi and bento and poke bowls.

From there we headed for a quick stop to Spouting Horn, which is a blowhole on the coast. The day we went the water wasn’t spouting very high, but it was gratifying to watch the water come in and blow up the spout.

Anini Beach

We rented snorkel gear and a cooler and took a picnic and spent the day at Anini Beach in the northern part of Kauai. It was recommended as a calm spot for kids. There were sea turtles and some marine life, but not a lot. Even though the snorkeling wasn’t great, it was a relaxing day at the beach. There is a lot of shade, calm waters, and a nice breeze.


When looking for a Luau, I wanted something authenticate with good food, and not very expensive. Tall order! I decided on the Smith Family Garden Luau. You can walk through their beautiful gardens, view the removal of one of the pigs that they started cooking early in the day for the meal, eat a traditional Hawaiian buffet dinner, learn how to hula, and then watch a spectacular show afterwards. (There is also the option of skipping dinner and just watching the show.)

The Big Island (Days 9-14)

The Island of Hawaii, also known as the Big Island, has an abundance of outdoor activities, such as hiking and horseback riding. We flew into Kona and stayed on the West side of the island, which is drier. But, we also visited the Northern and Eastern side of the island, which is more lush with vegetation.

Hawaii Volcano National Park

The only active volcanoes in Hawaii are in Hawaii Volcano National Park on the Big Island. There are two eruption sites, Mauna Loa and Kilauea. When we went Kilauea had just stopped flowing, so we didn’t get to experience the lava flow, however, it was still impressive to see the crater. We also saw the petroglyphs, steam vents, and Sulphur banks. For more information and tips, see my post about the Big Island.

Punalu’u Black Sand Beach

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On our way back to Kona from Hawaii Volcano National Park we stopped at Punalu’u Black Sand Beach. We didn’t stay long, but there were lots of people swimming in the water, laying on the sand, and taking pictures.

Horseback Riding

Looking for another activity in the Big Island, we considered a few options and decided on horseback riding that included a swim at a waterfall with Wailea Horseback Adventure. The staff and horses were friendly and informative. They taught us about each of the horses and how to ride them. The ride to and from the waterfall had amazing views. At the waterfall we were able to, not only swim, but also kayak and paddle board.

Car Rental

Discount Hawaii Car Rental has deals on all the major car rental companies but at a very reduced rate than what you’ll find going directly through those companies.

In Maui, a car is a necessity if you want to get around on your own without having to hire a tour guide. We found a local company, Makoa Rental Car Company, that was very easy to work with. They have older cars, but they are in very good working condition. The company leaves the car at the airport for you and gives you instructions on how to pick it up and drop it off. You can even rent beach chairs and coolers through them and they will leave them in the car!

We experienced the beauty and wonder of this amazing state and we’ll have lots of stories to last us a lifetime. I hope this 2-week Hawaii itinerary will inspire your travel to this beautiful island chain.

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