I’ve been excited about doing an UnCruise in Hawaii for a long time and we’ve finally completed our sailing from the Big Island to Molokai. It was incredible and I am excited to share just what made it so special and unique. We travel to Hawaii a lot (more frequently than we ever expected) so getting to see the Islands from a different perspective doing UnCruise Hawaii was awesome and gave us a completely new set of stories and experiences to share.
I don’t just want to gush about how wonderful the boat and crew were, but I want to share what made small ship sailing in Hawaii such an unusual experience, both for us adults and the kids. If you have any questions about what it’s like to sail around Hawaii or what the UnCruise experience is like for a family, please leave a comment or send us a note. Planning a small ship sailing is a special commitment and has a premium price, so ask away and we’ll help you sort it out!
UnCruise Hawaii Podcast Episode
Yes, us adults had an incredible time on the Safari Explorer as we island hopped around Hawaii, but the kids did too. They had a very different adventure, or at least a different point of view, than us parents did. Give a listen to our podcast episode where we chat it up hearing directly from the kids what they loved and learned during our UnCruise Hawaii sailing.
Prep for our Hawaii UnCruise
I am such a planner, and when you’re heading thousands of miles for a special sort of travel experience, you plan things and thoughtfully pack. That’s just what we did for our Hawaii UnCruise sailing, but what made it a little tricky was that the only part of the trip I could really plan/pack for was the few days on the Big Island of Hawaii before we set sail. The way UnCruise words their itineraries is a bit vague, and there’s a reason for it.
When you’re doing an UnCruise Adventure, there’s a fair amount of the experience that is left up to the weather, the wildlife and the captain. Now that I know what that means, not just on paper but in practice, I get it and appreciate it. Before we set sail though, I was a bit stressed about not having a clear plan for activities and anything on board. This is my Type A side shining through, but once onboard I chilled out.
Note: we now partner with UnCruise so may receive a commission at no cost to you if you choose to book and use our code, TWODADS500, when you book. 🙂
What to Pack for an UnCruise Hawaii Sailing
Pajamas and swim shorts.
I’m kidding, but I really actually could have only packed pajamas and swim wear and we would have been fine for our sailing. The UnCruise Hawaii itinerary has a combination of the following: snorkeling, hiking, on-land cultural immersion, kayaking, skiff tours, biking, swimming, and relaxation. So how do you pack for an itinerary like this? Well, the first thing to keep in mind is that this is UNCRUISE, not a mega ship sailing, so it’s very informal and intimate. It’s a casual setting with your friends, not a formal nightly dinner party.
So here is my UnCruise Hawaii packing list for CLOTHING:
- Swimwear – this may include swim shirts / rash guards – 3 per person
- Landwear – you’ll have three days with shore excursions plus embarkation/disembarkation – 4 or 5 mix-n-match sets of clothes
- Look-nice-wear – it’s always fun to make a little effort every now and then – 2 or 3 aloha shirts
- Shoes – flip flops for everything EXCEPT hiking / biking, for which you’ll need close-toed shoes (I’ve used THESE KEENS for four trips to Hawaii)
- Hats – a wide brim hat and a cap are both recommended due to the amount of sun time
Now, there are some other things that we also pack when we’re traveling that make everything even more delightful, and that includes when we’re doing an UnCruise sailing. We bring specific gear and activities that help our family during travel, and these things are VERY important to us because we do travel so much.
Our non-clothing packing list:
- Frameless snorkel mask – I always bring my special mask with a thick rubber seal because my face is sensitive
- Digital camera – I bring my DSLR (Canon Rebel T7i) with 600mm lens (I LOVE LOVE LOVE my Sigma 150-600mm)
- Waterproof phone case – this one is good for kayaking and surface snorkeling | for free diving look for 50 foot rating
- GoPro – sometimes we bring a GoPro 11 / 12, but we use our phones more
- Small backpack / fanny pack
- Reading book / Kindle paperwhite / school work
- Personal pillow – yes, we do actually bring our own pillows when we travel, and because we do pack light, we never don’t have space for them.
When you’re packing for an UnCruise Hawaii sailing, or any trip for that matter, it’s always good to pack and then unpack and repack with fewer items than the first round. Really, packing lighter than you think you should is recommended for warm weather destinations, particularly when you’ll be in a ship cabin for a week.
Embarking on the Safari Explorer from Kona
It’s really exciting when your sailing day finally arrives. We knew that we were doing the UnCruise Hawaii trip a year before we set foot onboard, so the anticipation and excitement also became a feeling of accomplishment, that our patience and planning finally paid off. We arrived at the King Kamehameha Beach Resort near the Kailua-Kona pier and immediately found our check in desk.
Book the King Kamehameha Beach Resort here!
We were greeted and our luggage was tagged and stored (still accessible to us for the few hours before boarding). We were given name badges and welcomed to relax in the staging area, head to the beach or walk around Kona. We love the small beach at the King Kamehameha Beach Resort and there is some good snorkeling, so we grabbed our gear and went off to relax. We also started to see others in the staging area who would be sailing with us, but without an official introduction yet, we kept to ourselves.
When it was time to board, we all came back together for simple introductions by our expedition leader and a quick go-around-the-room, and then it was off to the ship. The Safari Explorer was waiting for us with the crew, ready to go Hawaii island hopping! An introduction to Captain Andy, a quick photo on the pier so we had a guide to who we were sailing with, and then being shown to our cabins made for a smooth boarding process.
Our bags were already waiting for us in our cabins, so after our steward showed us the ins and outs of it, we checked on the kids (they had their own cabin) and found them settling in nicely. This was the point where our Hawaii UnCruise really was a reality and I personally was able to chill and just enjoy.
Because it is a ship, albeit not a mega cruise ship, there are the standard safety briefings for muster, PFDs and procedures, but that’s quick and easy. Meeting the rest of the crew was next and then it was off to the decks to wave goodbye to Kailua-Kona. It was the perfect start to our adventure.
Pre-Sailing Accommodations
We 100% recommend arriving at your departure port the day before (Friday), if not two days before (Thursday) your sailing. There are enough inconsistencies in flying these days that you don’t want to risk a big delay causing you to miss your Hawaii UnCruise (or Alaska or Baja…). For a Kona departure, there are lots of choices.
We really like the King Kamehameha Courtyard Marriott (where you check in for your sailing) and also the Club Wyndham Kona Hawaiian when we’re in Kailua-Kona, and have also stayed at the Royal Kona Resort and even the Holiday Inn Express Kailua-Kona. I would recommend a place that’s walking distance to the pier for departure, but also there are plenty of Ubers in Kona and it’s not difficult to get around.
If you’re doing the reverse sailing, you’re hotel options on Molokai are very limited. There is either the Hotel Molokai, which is cute and we do enjoy (clean, good pool, nice rooms) or you can rent a condo at Molokai Shores. The condo option is good if you’re arrive a few days early to have some extra time exploring Molokai on your own.
UnCruise Hawaii Sailing on the Safari Explorer – Itinerary
As I share what our itinerary and experiences were like for our UnCruise Hawaii sailing on the Safari Explorer, please keep in mind that the official itinerary from the company is rather vague and very flexible. There are several notations about “captain’s choice” and such, and that’s because one of the joys of UnCruise is getting to be flexible and follow the good weather and wildlife. So, our Hawaii sailing was different than the week’s sailing before ours or after ours. Each experience is unique! See the company site for their itinerary description.
When booking an UnCruise small ship sailing, mention our code (online or via phone) TWODADS500 to receive $500 discount towards your passage. Education and adventure await!
Exploring Hawaii’s Kona Coast with UnCruise
I will say it a million times, the Big Island of Hawaii is my favorite for lots of reasons. From Hawaii Volcanoes National Park to visiting Hilo, from scenic drives on the Big Island to unique beaches, every trip is so different. And now sailing along the Kona Coast on the Safari Explorer with UnCruise has changed my view of the Big Island forever. I love it even more.
The coastline on the western side of the Big Island is fascinating. It’s full of lava flow cliffs, small bays, shallow sea caves and some really cool beaches. Sailing along the coast you get to see it all from a new perspective, all while watching whales and dolphins around you. Highlights of the activities on the Kona Coast included:
- Wildlife watching ALL THE TIME
- Hiking up the Hualalai Volcano
- Night snorkeling with manta rays in a new spot to us
- Early morning visit to Kealakekua Bay – my favorite snorkeling spot on the Kona Coast
The Safari Explorer can get wonderfully close to the cliffs and snorkeling areas, either directly or with its skiffs, so exploring the coast of the Big Island felt fresh and new and beautiful.
Something to keep in mind if you’re thinking that any activity doesn’t sound right for you, when you’re doing the UnCruise Hawaii sailing you can choose to do different activities than the ones I’m sharing about. For example, while we were doing the hike up Hualalai, other people opted to have a beach day at Kaloko Honokohau National Historic Site to relax and watch the sea turtles (honu).
After a few days sailing along the Kona Coast on the Safari Explorer, we said goodbye to the Big Island and did an overnight crossing of the strait between Hawaii and Maui, the ‘Alenuihāhā Channel, we woke up on the north shore of Molokai. This is one of the most dangerous sea crossings in the world and we got to enjoy sleeping through it!
Flexible Sailing Days on the Safari Explorer
“Captain’s Choice” strikes again! But in the best way. That whole UnCruise flexibility piece really does set you up for an unusual and amazing trip. Flexible sailing days on the UnCruise Hawaii itinerary allowed us to have a very special experience: sailing along the north side of Molokai. Here you’ll find the tallest sea cliffs in the world, at a towering 4000 feet high. We woke up to a gentle announcement from our captain to look out the port side and wow. Cliffs, green walls, waterfalls, albatross and tropics birds, whales… What a way to wake up!
Other highlights of our flexible sailing on the UnCruise Hawaii itinerary brought us to sea caves for kayaking, trawling around following humpback whales (proper distances), and getting to watch the sunset over Maui.
Something I found surprisingly pleasant about the sailing days was the amount of downtime for straight up relaxing or doing school work. Traveling on UnCruise with kids meant that there would be homework to complete, and when we would sail between destinations/activities, this was the perfect time for the kids to catch up on reading or worksheets. I also used this time for writing and chatting it up with other passengers.
Visiting Lanai for UnCruise Hawaii
Lanai is one of the least visited islands in Hawaii. It’s known as the Pineapple Island, as at one point 90% of the pineapple consumed in the USA came from this one island. Almost the whole thing was farmland, which wasn’t smart. Farming all but ended and now it’s a quiet island with few residents, a small town (Lanai City), only a few options for places to stay and not much else. But there are lots of hiking spots and biking trails, and our kids’ favorite thing ever: the Lanai Cat Sanctuary.
Off shore we enjoyed kayaking to the sea caves and swimming just a bit from the cliffs of Lanai, and did some incredible snorkeling at an area called Shark Fin. On land our family split up to what each of us wanted (that’s the cool thing about the flexibility of the Hawaii UnCruise itinerary). Chris and the kids joined a few other guests and went in a van (transportation provided) to the Lanai Cat Sanctuary. They loved it and got to spend hours hanging out with kitties.
I joined some other guests from the Safari Explorer and went for an ATV ride with a hike. We went from the Lanai Adventure Center, where other guests headed out on E-bikes, and headed up the mountain in the middle of the island in a Polaris (like a hunting ATV), and then continued on over the hills to an epic view of Molokai and Maui. Here I just took in the view and actually photographed breaching humpback whales from afar. We all enjoyed our time on Lanai very much.
Exploring and Learning on Molokai
I honestly knew nothing about Molokai before we visited during our UnCruise Hawaii sailing. All I knew was that there was a leprosy story, perhaps a leper colony, on the island and that’s it. Well, Molokai is much more than that, although that’s an important part of the island’s modern history.
When the 1946 tsunami hit Hawaii, it didn’t just crash into Hilo. When it got to Molokai it swept up into the Halawa Valley on the North Shore and wiped out the whole village and farm system in the valley. Today this valley is a place to learn about Hawaiian culture, the history of the people who lived here and farmed the Halawa Valley dating back 1500 years, and see how the current residents live with their farm and off-the-grid lifestyle. As a part of the UnCruise Hawaii itinerary you get to visit.
The drive to the Halawa Valley is beautiful and when you get to the valley itself it’s amazing. We opted for the 3.4 mile round trip waterfall hike when we arrived, but due to rain and the rising river we didn’t get to complete it. Instead we got to spend time with Greg, whose father lived in the valley when the tsunami hit, and we got to tour the taro farm and learn a bunch about Hawaiian customs. We finished with a visit to the cove at Halawa Beach Park.
We finished our visit to Molokai with a special dinner (pā’ina), hosted by aunties and uncles, with live music, local Hawaiian dishes and spending one last evening with our UnCruise friend we’d made. The pā’ina was the perfect end to our amazing week aboard the Safari Explorer.
Wildlife on our Hawaii UnCruise
When you’re visiting Hawaii with kids, it’s difficult to pinpoint what they really take in and enjoy, but our small ship sailing experience with UnCruise left us with no question about what they loved the most: the ABUNDANCE of wildlife. There was rarely a moment in our 8 days, 7 nights on the Safari Explorer that we didn’t have a whale in view or dolphins at the bow of the ship.
We estimated our humpback whale sighting count at over 170. When it comes to dolphins, we saw three different types: bottlenose, pan-tropical spotted and Hawaiian spinner dolphins. There were Hawaiian monk seals in several places, and so many cool birds. My favorite experience though is always being in the water for snorkeling and seeing underwater life.
Several times we boarded our skiffs to head to awesome snorkeling spots. Getting to snorkel with monk seals, Hawaiian green sea turtles (honu), octopus and manta rays was such a treat. Adding another layer of cool to the experience, almost every time we got in the water we could hear humpback whales singing! We also used a hydrophone when out on the water to hear the whale songs even better, and it was downright astounding.
“You didn’t go ashore on Maui?”
That’s correct. During our UnCruise Hawaii sailing we didn’t have the normal port visit to Maui. Following the raging fires of 2023 that burned Lahaina to the ground, the visit ashore was removed from our Safari Explorer itinerary. That’s okay though, because we did have a special day of snorkeling at our favorite spot on Maui, Olowalu Beach. Snorkeling here is one of the best things to do on Maui, so although we didn’t get to make port here, we still had a fantastic experience underwater.
Tip: you can always book a few days on Maui for after your sailing if you want time on the island. There are lots of flights to the mainland from Maui (OGG) so it’s an easy way to end your trip to the Islands.
Disembarking from UnCruise Hawaii
It may sound cheesy but disembarking from the Safari Exploring for the last time was sad. We said goodbyes to the passengers and crew that we got to know. The kids hugged their new buddies. We waved as we got in the van to Hotel Molokai to kill time before our departing flight. Thankfully we had a lovely place to spend a few more hours with some of those we had met. We had a dip in the pool, watched more whales breaching between Molokai and Lanai, and enjoyed lunch as we quietly watched the water.
Spending a week on the water in close quarters with everyone was a wonderful experience. If you haven’t read our article about what to expect on an UnCruise, and about the community we found on board, be sure to give it a read and listen to our podcast episode about it. Sailing on the Safari Explorer around Hawaii was one of the best travel experiences I’ve ever had. Ever.
Continuing Hawaii Visit Options
If you’re like us, making the journey all the way to the middle of the Pacific Ocean means that you want to maximize your time there. Please take a look at our Hawaii Island Hopping article for ideas for how to spend a few extra days or to dig further into Hawaiian culture and nature.
The long and short of it though, from Molokai you can fly on Mokulele Airlines (very small planes) to either Honolulu (Oahu – HNL) or Kahului (Maui – OGG), and then from there it’s easy to get to either the Big Island of Hawaii or Kauai.
If you haven’t gotten to spend a lot of time on the Big Island, that would be my first pick. Waterfalls, volcanoes, unique beaches and fascinating historic/cultural sites make it easy to spend 3-10 days on the Big Island. You can do a few days on the Kona side and then the Hilo side for two very different experiences from what you have done and seen on the UnCruise Hawaii itinerary. Check out our One Week Big Island Itinerary.
The second choice to visit, in my not so humble opinion, is Kauai. I do love Kauai and we’ve enjoyed many days of hiking and sightseeing here. The Garden Island is more mellow than Oahu and again, you can easily spend a few days of a whole week on Kauai. Check out our 5 Day Kauai Itinerary.
Oahu is my next pick (yes, more so than Maui) because it’s got great beaches, tons of hiking, and awesome food. Oahu is more than Honolulu, so spending a few days enjoying beaches and exploring the North Shore of Oahu and the sights all around the island is very much worth your time.
Maui is my last pick for additional time in Hawaii. Yes, Maui is beautiful and there are lots of things to do, but I just prefer the other islands more. The highlight of visiting Maui is spending time in Haleakala National Park. It’s incredible and I’ve never seen any other place like it. This is YOUR time, so you choose the sort of experience you want!
Planning our Next UnCruise – Alaska!
While you’re onboard, you actually have an option to book or put a deposit down on another UnCruise, which also gives you a big discount for the next one you do. And if you’ve done multiple, the discount increases with each cruise you’ve done. Want to head to Alaska? Great. Think it would be amazing to sail around Baja California? Awesome. You can put down a deposit and then book something within the next three years. We already had our next sailing booked, so we didn’t do the deal, but others in our group did.
Where else are we exploring with UnCruise? I’m so glad you asked!! Next up: Alaska on the Frontier Legacy! It’s going to be amazing, in particular because we’re doing the Kids in Nature itinerary, so there will be more families than our Hawaiian Seascapes sailing.
If you have any questions either about our Hawaii UnCruise itinerary or our overall experience sailing with the company, please leave a comment or send us a note. We’re happy to share more about it all! Also, we get to spend a lot of time in Hawaii so have lots of recommendations and advice if you need it, so reach out if you do!
