On our 10th wedding anniversary, I ran home from work to make peanut butter and jelly sandwiches before the kids’ evening activities. We were so busy with “life” we failed to prioritize living! Since that time, we have reprioritized and don’t let the big (or little) wins in life go uncelebrated. So, for our 20th anniversary we went big!
Before jumping into our epic Hawaiian anniversary itinerary, let me start by addressing the fact that we took our kids. We are big believers in investing in our marriage, including date nights and weekends away. But we wanted to experience this trip with our 13- and 15-year-old boys. We only have three years before our oldest is officially an adult and the time we have is limited. If you read my “Bucket List” post you know that for me travel is about much more than just seeing the sights. It is about getting away from the day-to-day and having experiences with those you love.
Choosing Islands to Visit
We chose the islands based on activities; Hawaii is so unique, we focused on what we could only do there. We planned for a mix of adventure and relaxing. If we just wanted to hang out at the beach, there are cheaper places to go! We planned around the activities of volcanos, scuba diving and Road to Hana. Based on that, we chose two islands for our trip: The Big Island and Maui. Hawaii is expensive; if you are trying to cut costs just pick one island, go at a non-peak time and don’t stay on the beach.
Big Island of Hawaii
We started our trip in Hilo on The Big Island. I considered cutting Hilo out when planning the trip, but I am glad I didn’t. We stayed in a house in a quiet neighborhood and experienced living like a local for a few days. Our Hilo VRBO had chickens in the backyard, orange, lemon, papaya, and banana trees. Hilo is on the leeward side of the island which has significant rainfall and is a lush tropical environment. We went to sleep to the sound of the frogs and woke up to the birds chirping and roosters crowing. The owners lived next door and gave us great recommendations for our entire trip.
My family has a few foodies in it, so I will give you all the details of our food adventures on this trip. The night of our arrival we started our Hawaiian adventure sharing some traditional Hawaiian food at Kuhio Grill (recommended by our VRBO owners). We were the only tourists in the restaurant! Our dinner included Moco Loco, Laulau and a traditional Hawaiian combo plate. It was all delicious, except for the poi, a traditional Hawaiian food made from tara root that must be an acquired taste.
Day 1: Hilo / Volcano National Park
Farmer’s Market & Waterfall
We spent our first morning exploring the farmer’s market. There were all kinds of exotic tropical fruit we don’t see at home and affordable souvenirs! We had breakfast at the farmer’s market including spam and poke.
Next stop, Rainbow Falls, a waterfall that almost always produces a rainbow. This was a quick stop about 5 minutes from downtown. In Hilo we could get everywhere we wanted to go in about 10 minutes. It had a small town feel and was the least touristy area we visited.
Beach Time
We decided to spend our afternoon exploring the water scene. We hit a few Hilo highlights including:
- Carlsmith Beach Park – known as a great snorkel spot and turtle hangout (although we didn’t see any). There were lots of large lava rocks making a protected area to snorkel and swim. The park and the water were beautiful, but the water was cold! There was a noticeable difference in water temperature between the east and the west side of the island. Hilo had the coldest water temperatures of our trip.
- Richardson Ocean Park – was our next stop just a few miles down the road to dip our toes in our first black sand beach. Again, the water was cold, but the beach and park were beautiful. There were lots of locals hanging out. We were able to watch some surfers from this spot.
- We decided to skip our third water stop, Coconut Island, to go enjoy some acai bowls from Kula Shave Ice before heading to Volcano National Park (VNP). These were the best (and cheapest) acai bowls we had all week.
Our original plan was to head up to Mauna Kea observatory. This is a world class observatory, but after further research and advice from locals we decided to go to VNP instead. We are from the midwest, we can drive to the country and see the Milky Way and all the constellations, but there is nowhere else we can see an active volcano! We will put the observatory on our list to do next time.
Volcano National Park – Night Time
- The highlight of our trip! VNP was an easy 30 minute drive from Hilo. We arrived at 4 PM and got directions on where to see the active lava in Halemaʻumaʻu crater. Parking lots start filling up about 4:30 or 5:00, so we made a quick stop by the visitors center and headed to the designated lava viewing area. We hiked about a mile from the parking lot on a well-marked path to see the lava lake and the eruption. We arrived in the daylight and stayed until dark. When it was fully dark the whole lava lake glowed and reflected off the smoke and clouds. The whole sky lit up shades of red from the eruption. Incredibly amazing!
- If you plan to visit VNP I highly recommend staying on the Hilo side of the island for at least a night or two. It is a long drive from Kona that would be difficult at night.
- Not so prepared – we had planned to pick up bento boxes from Kawamoto’s in Hilo to eat as we watched the sunset and the transition from light to dark at the viewing site. This would have been a great plan, but we didn’t get to Kawamoto’s before they closed early afternoon. We tried to find a place to eat close to the park, but they were all full / reservations only. For future planning, there is a restaurant overlooking the crater called The Rim that would be a great place to get reservations! We ended up eating a late dinner back in Hilo at Café Pesto. We weren’t really thinking we wanted to eat Italian in Hawaii, but we highly recommend it, especially the calamari.
Before Sunset 
After Sunset 
Day 2: Hilo / Volcano National Park
Hilo Lava Tube
Kaumana Caves (Lava Tube) – This lava tube in Hilo was less than a 10 minute drive from where we were staying. For those that don’t know, a lava tube is essentially a cave that has been formed by lava flowing under the earth. We have been in a lot of caves in Missouri so I didn’t think we would be overly impressed with these tubes, but I was wrong! This was another highlight of our trip. We had our flashlights/headlamps and were able to explore deep into this lava tube. It was not an easy path and required quite a bit of maneuvering, but that is what made it so much fun. We went about ¼ mile each way from the starting point and could have gone further if we wanted to get in some narrower spaces.
We also explored Thurston Lava Tube in VNP later in the day. Thurston is a great option for those that need a smooth/lit path, but if you want to see a lava tube in raw nature with all the formations still intact it is worth the trip to go to Kaumana Caves!
Volcano National Park – Day Time
After exploring Kaumana we said goodbye to Hilo and started making our way across the island via VNP. We passed by the Mauna Loa macadamia nut visitors center which was unfortunately still closed due to COVID; another item for our “next time” list!
The Chain of Craters Road in VNP takes you on a driving tour through the history of several different eruptions and lava flows. We hiked a few trails along this drive to see the aftermath of previous eruptions up close. As you continue the drive, you see the path of lava flow down the mountains to the cliffs with waves crashing against them; very scenic. The Holei Sea Arch at the end of this drive is an arch that has been formed out of lava on the cliff.
We had so much fun exploring VNP that we spent more time there than planned. We had lunch at The Rim and enjoyed our last overlook of Halemaʻumaʻu crater before heading toward Kona. Even though we couldn’t get in the restaurant, we got a table in the bar area at 2 pm for our late lunch.
Drive to Kona
We finished our day driving to Kona. We stopped at Punalu’u bakery and picked up some pastries for our breakfast the next day. If you have extra time, Punalu’u black sand beach and Ka’u coffee farms are also on this drive to Kona.
Day 3: Kona / Coffee & Manta Rays
We stayed in a condo in Kailua-Kona across from Kahaluu Bay. This is a great area to snorkel, visit coffee plantations and is easy access to downtown Kona. Most of the resorts with sandy beaches are north of Kona. We were there for only two nights with two things on our agenda: coffee & manta rays, so Kailua-Kona was a perfect location for us!
Coffee Plantation
We visited Greenwell Farms Coffee Plantation for a free guided 45 minute tour and samples. We thought our boys would be bored, but we were wrong. Greenwell not only grows coffee, but they have a variety of crops and a processing facility that added interest. The highlight of the tour was getting to try fresh peppercorn straight from the vine. After our coffee tasting (and buying) we headed to the dive shop to get fitted for our gear for our evening dive. We ate lunch at Kona Inn Restaurant (downtown Kona) with an amazing view of the water.
Manta Rays
We saw manta rays scuba diving on our honeymoon in Tahiti 20 years ago and we came to Kona to see them again. The manta rays around Kona average a 12 ft. wingspan. If you are in Kona this is a must-do activity! We went through Big Island Divers which also has a snorkel option to see the mantas. We did a two-tank dive so we could have a dive in the daylight before we went in for our night dive. Our boys just got scuba certified last summer (in a lake). Since this was their first ocean dive, we wanted to get everyone comfortable and orientated before it was dark! Our first dive we were able to see an eel garden, zebra eel and lots of fish/coral along the reef.
Night Dive
After a surface interval to watch the sunset, it was time for the main event. We each had our flashlight and jumped in the water. Our group sat in a large circle on the ocean floor (about 30 ft. deep) around a “campfire.” In the center of the campfire the dive masters put bright lights that attracted plankton. We sat and waited, after about 10 minutes we spotted our first manta. They came swooping in, mouths open somersaulting in front of us and over our heads. It was amazing!
When we saw the mantas in Tahiti 20 years ago we were in the middle of a plankton bed and couldn’t see them very clearly. This was a much different experience where we could clearly see them and just sit back and watch the show! Since we were only at 30 ft, we were able to have a bottom time of about 45 minutes.
We got the best pictures we could with our inexpensive underwater camera, but the pictures don’t do the experience justice.
Day 4: Exploring Kona / Travel to Maui
We explored downtown Kona before our evening flight to Maui (after our 18 hr. post dive surface time). Downtown is about a mile long stretch along Ali’I Drive with shops, restaurants and a little beach area. It is also the site of the annual Ironman World Championship. We did not get inspired to become triathletes, but continued our eating fest with some amazing sushi, shave ice and acai bowls.
We loved our time on the Big Island, but were looking forward to our adventures in Maui. As we arrived in Maui, we had a traditional lei greeting and picked up our Jeep rental. The area stayed was the Ka’anapali Beach area on the west coast of Maui with nice beaches and beautiful sunsets. We wanted a resort where we could have some relaxation time, be able to order some food and swim. Our family would not be sitting around the resort the whole time and didn’t want to spend our entire budget on lodging. We settled on Aston Maui Ka’anapali Villas. It had all the basics: beachfront, pool and restaurant. It also had larger suites with a living room and kitchenette for our family of four.
We could have stayed at a resort with more amenities for the same cost, but it would have been traditional hotel room. Traveling as a family of four it was nice to have the larger room!
Planning Note
I like to be prepared for travel by researching ahead of time and having (at least) a loose itinerary to avoid wasting time. Getting firsthand experience and itinerary suggestions from someone with similar interests (such as this blog) are a great resource. I also always like to check local resources. On the Big Island, our VRBO owner’s from Hilo were our go-to local resource. We also got a lot of good information from The Hawaii Vacation Guide YouTube channel. My main source of information for planning our time in Maui was the Aloha360 podcast. John and Leslie Caubble have a lot of detailed information about Road to Hana and Maui in general. We even ended up getting a Road to Hana audio guide, lei greeting and renting a Jeep from them for our stay on Maui. Nice to have some local connections when planning a trip!
Maui
Day 5: Maui Diving
Our first morning in Maui we went diving again. We went through Maui Dreams Dive Co. who I highly recommend. Our first dive was Molokini Crater, a protected area known for its visibility. There are also many snorkel charters that go to this area if you are not a diver. Whale season typically starts in December, but we got to see a whale tail fin and blow on our boat ride out to Molokini. Our second dive was closer to shore along the grasses where the turtles like to feed. Highlights of our dives include frogfish, trumpet fish, flounder, turtles, eels, sea slugs and an octopus! We were lucky enough to be paired with Dave, the dive shop’s social media photographer who took some great pictures of us and what we saw on our dive. Photo credits below to Dave!
Mama’s Fish House
Mama’s Fish House was the one restaurant recommendation we got over and over before our trip. Being Thanksgiving week, it booked up months ahead of time. We got our reservation three months ahead of time and the only time slot we could get was Wednesday at lunch. Not ideal rolling into our nicest meal of the week straight from a dive boat, but Hawaii is casual!
Mama’s Fish House did not disappoint. We had an amazing meal, but also our most expensive meal of the week. Between the four of us we tried Antarctic Toothfish, Fish Curry and Mahi-Mahi. Seriously good food. Mama’s Fish House had an anniversary card for us and complimentary dessert just for saying we were celebrating an anniversary when we booked through Open Table. The view from our table was beautiful with the open air out to the palm trees and water. Mama’s Fish House is on the north shore right next to Ho’okipa State Park where you can watch big wave surfing. This is worth the stop to watch before/after you eat at Mama’s Fish House.
Day 6: Thanksgiving Day Surfing Lessons and & Luau
Surfing
My 15 yr. old was interested in surfing, so the two of us took a morning surfing lesson on Ka’anapali beach with Ka’anapali Surf Club. I recommend trying it, but we were disappointed we didn’t do better; we want a redo! We had an unusually calm day with minimal waves. A group lesson with minimal waves meant we only got to try to ride a handful of waves. We both had a few good runs, but we had a lot of sitting in the water waiting for waves and our turn! I will probably try it again some time and see if I can stand all the way up! My son got to full standing position, but I only made it to toes and fingertips!
Cayman standing! 
About as good as it got for me!
Luau
We chose to go on vacation Thanksgiving week when the kids were out of school and we didn’t have to take as much time off work. Not ideal going at a peak time, but for our season of life that is when we could go! We decided to book a Hawaiian luau on Thanksgiving Day as our own holiday celebration. After airline tickets, lodging and car rentals, the luau was the next thing we booked about six months ahead of time to get Thanksgiving Day seats (we should have also booked Mama’s Fish House six months out)!
There are several Luau options in Maui, but we looked at two in Lahaina close to our resort. We chose to go to The Feast of Lele because it was smaller and had private tables with table service vs. buffet (COVID consideration). We also liked The Feast of Lele variety of cuisine/dance from different islands. Old Lahaina Luau doesn’t have fire dancers as it is not a traditional Hawaiian dance. Here is a great article comparing The Feast of Lele with Old Lahaina Luau. I don’t think you can go wrong between these two; just depends on what you are looking for. These Luaus are expensive, but it was worth the experience at least once! Side note – do not tell your children their meal comes with unlimited free non-alcoholic frozen drinks. My boys were full of frozen drinks before the third of five courses!
Day 7: Road to Hana
I was so excited for our Road to Hana day. Ka’anapali Beach area is nice, but I wanted to break out of the resort/touristy areas and see the real Maui. I had been listening to the Road to Hana Audio Guide and the Aloha 360 podcast for months to plan all of our stops. This is our detailed itinerary and what worked/didn’t work for our day. I would have liked to make more stops, but I also knew we had to pace ourselves. I had to keep our family moving and turn around by 2 pm or so to get back to our resort area before we hit a wall!
Swimming at Secret Falls 
Rainbow Eucalyptus Tree at Garden of Eden
Garden of Eden, Ke’anae Peninsula, Secret Falls
- 6:30 AM left Ka’anapali Beach area to head to Paia. We wanted to beat the crowds on the Road to Hana so we started early. Keep in mind Hawaii is 4 hours behind my time zone (central), so early mornings didn’t feel too early! We stopped at Costco (right off the road) to fill up with the cheapest gas on the island and picked up breakfast sandwiches and coffee from Paia Bay Coffee https://www.paiabaycoffee.com/ . Our strategy was to start early and skip the early stops (Ho’okipa State Park and Twin Falls) to get past the crowds.
- Stop 1, Mile Marker 10, Garden of Eden Arboretum – This stop was a paid admission to see all the rainforest highlights in one stop. This can be a quick stop to see eucalyptus rainbow trees, bamboo forest, mango trees, banana patch, scenic overlooks of waterfalls, gardens and the opening scene of Jurassic Park. They also have exotic birds wandering around. This is a great stop for those that want to see a lot without having to hike. We had a lot more planned for the day, so we only spent about 40 minutes here. https://mauigardenofeden.com/
- Stop 2, Mile Marker 16, Ke’anae Peninsula – This was my favorite stop. This was one that you could miss if you don’t have the audio guide. This stop is where you can pick up warm banana bread (or chocolate chip cookie) from Auntie Sandy’s and sit on the lava rock with the waves crashing behind you. It was beautiful! This was about a 10-15 minute stop to get a snack and walk along the rock to see the amazing views, but well worth the stop.
- Stop 3, Mile Marker 22.6, Secret Falls at Pua’a Ka’a Park – This waterfall was right off the road with zero hiking and was one place you could swim in a waterfall! My boys braved the cold water for this amazing experience.
Wai’anapanapa State Park, Hana
- Stop 4, Mile Marker 32, Wai’anapanapa State Park – This park required a reservation. This started during COVID, but I wouldn’t be surprised if they continued this to limit the crowds. I wasn’t sure what time we would arrive, so I reserved two sets of vouchers: 10 am-12:30 pm and 12:30 -3 pm. We ended up arriving about 11:45 am and leaving about 12:45 pm, so we needed both sets of vouchers to be there.
- The black sand beach is the draw at Wai’anapanapa State Park. It was beautiful, but we chose not to swim. We did hike down to the beach and around to a blow hole. We thoroughly enjoyed the stop and the scenery even without swimming. If we had more time, I would have loved to jump in, but again doing Road to Hana in one day (from the west side of Maui) we had to keep moving.
- It was lunch time when we arrived in Hana town. We wanted to stop at a place called Braddah Huts to get some traditional Hawaiian lunch plates, but they were closed the day after Thanksgiving. We ended up stopping at a food truck court which was very crowded as it was one of the only places open.
- I wanted to go beyond Hana (another 30 minutes) to Waimoku Falls and The Seven Pools at Haleakala National Park, but we knew if we didn’t turn around at Hana it would be too much. Even without doing that last stop, we had a 12 hour day; so, I am glad we turned around when we did. If I were to do it again, I would plan to spend a night (or more) in Hana town so we wouldn’t be so rushed.
- When planning your trip, you do NOT want to be on the road in the dark. Although we thoroughly enjoyed the Road to Hana, it is not for everyone. If you don’t handle driving on curvy, mountainous roads, you will not enjoy it. There is a reason they sell “I survived the Road to Hana” t-shirts complete with the stats of 620 curves and 59 bridges. We did buy one for my husband who chauffeured us for the day!
- The Road to Hana guide and Aloha360 podcast does promote driving on the back side of Hana (i.e. driving around Haleakala National Park vs. going back to Paia). We considered this, but we also had lunch with someone who had just gotten in a wreck coming from that direction. There was also road construction going on and some closures. For us it wasn’t worth it, but if you consider it make sure your car rental company allows it and check on current conditions and closures.
- Turning around in Hana town when we did gave us some time to make some stops on the way back. We decided to stop at Twin Falls, mile marker #2, on the way back with no crowd and make one more pass by Ho’okipa State Park to see the big waves and surfers on the way back to Lahaina.
Day 8: Relaxation
I had made reservations for us to go see the sunrise at Haleakala National Park on our last full day in Maui. After 12 hours in the car for the Road to Hana the day before, my family was not going to get in the car for another long drive. We spent a much-needed day at the pool/beach and relaxing after breakfast at a kids’ favorite restaurant, Slappy Cakes. Our final evening, we had an amazing dinner at Duke’s on the beach. This was a short walk from our resort with our best sunset all week and the famous Hula Pie dessert!
Sunset at Duke’s 
Last night’s dinner at Duke’s
What an amazing trip!! I
Loved reading about your adventure and all that your family did! Next time we start planning a trip to Hawaii, this will be my first stop to help plan!! Great job detailing your trip!