Hey there, fellow travel enthusiasts! I’m so excited to share our incredible UnCruise adventure in Hawaii with you all. We had been dreaming about this trip for ages, and we finally made it happen – sailing from the Big Island to Molokai. Let me tell you, it was absolutely mind-blowing! I know that I’m extra enthusiastic as I write about doing UnCruise Hawaii, but it was truly unique and special for us.
Now, we’re no strangers to Hawaii, but traveling between the islands from this new perspective was a total game-changer. It gave us a whole new set of stories and experiences to share with everyone. I don’t want to just gush about how awesome the boat and crew were (though they were pretty amazing). Instead, I want to give the scoop on what made small ship sailing in Hawaii such a unique experience for both us adults and the kids. If you’re curious about sailing around Hawaii or wondering what the UnCruise experience is like for families, drop a comment or shoot us a message. I know planning a small ship sailing can be a big commitment (and it comes with a premium price tag), so don’t be shy – ask away, and we’ll help you figure it out!
Getting Ready for Our Hawaii UnCruise
Okay, I’ll admit it – I’m a total planning nerd. When you’re traveling thousands of miles for a special trip like this, you want to make sure you’ve got everything sorted out, right? That’s exactly what we did for our Hawaii UnCruise sailing, but here’s the tricky part: the only bit I could really plan for was our few days on the Big Island before we set sail. UnCruise keeps their itineraries pretty vague, and now I get why.
With UnCruise Adventures, a lot of your experience depends on the weather, wildlife, and the captain’s decisions. Now that I’ve been through it, I totally understand and appreciate this approach. But I’ll be honest – before we set sail, my Type A side was a little stressed about not having a clear plan for activities and onboard stuff. I should’ve known that having a premium travel experience like this would be handled well, and it really was.
What to Pack for an UnCruise Hawaii Sailing
Alright, here’s the scoop on packing. You could basically get away with just pajamas and swim shorts. No joke! But let me break it down for you a bit more so you can actually have clothes when you’re not in the water
For clothes, think casual and comfy:
- Swimwear (don’t forget those rash guards!)
- Casual outfits for shore excursions
- A couple of nice-ish outfits (nothing fancy, just a step up from beach bum)
- Shoes: flip flops for most stuff, but bring closed-toe shoes for hiking and biking
- Hats: both wide-brim and baseball cap style (trust me, you’ll want the sun protection)
Now, we’re travel junkies, so we’ve got some extra gear we always bring along:
- My special snorkel mask (gotta protect that sensitive face of mine)
- Camera gear (I’m a bit of a photography geek)
- Waterproof phone cases (perfect for underwater shots)
- Reef-safe sunscreen – this is provided onboard but if you’d like to bring your own, I recommend finding one you like in advance
- A small backpack or fanny pack
- Books, Kindles, and school work for the kids
- Our personal pillows (yeah, we’re those people, but hey – comfort is key!)
Pro tip: When you’re packing, try this little trick. Pack everything you think you need, then unpack and repack with fewer items, talking yourself out of at least one item from each clothing category. You’ll thank me later when you’re not lugging around a ton of stuff you never use!
UnCruise Safari Explorer Sailing Experience
Finally, the big day arrived! After a year of anticipation, we were ready to set sail. We checked in at the King Kamehameha Beach Resort near the Kailua-Kona pier, where the lovely staff tagged our luggage and gave us our name badges. We had a few hours to kill before boarding, so we hit up the beach for some snorkeling – perfect way to start the vacay vibes!
When it was time to board, we all gathered for quick intros and then headed to the ship. Captain Andy greeted us, we snapped a group photo on the pier (handy for remembering who’s who), and then we were shown to our cabins. The kids were thrilled to have their own space, and I finally felt like I could relax and enjoy the adventure ahead.
After the usual safety briefings (gotta keep it ship-shape, you know?), we met the rest of the crew and headed to the decks to wave goodbye to Kailua-Kona. Talk about a perfect start to our journey! Now, here’s the thing about UnCruise itineraries – they’re super flexible. Our trip was different from the ones before and after us, which is part of what makes it so special. We got to follow the good weather and wildlife, making each day a new adventure.
Exploring Hawaii’s Kona Coast
I’ve said it before, and I’ll say it again – the Big Island is my absolute fave. But seeing the Kona Coast from the Safari Explorer? Mind. Blown. The coastline is incredible, with lava cliffs, hidden bays, and sea caves. Plus, we were constantly surrounded by whales and dolphins. How cool is that?
Some highlights from our Kona Coast adventures:
- Whale watching (basically all day, every day)
- Hiking up the Hualalai Volcano
- Night snorkeling with manta rays (in a spot we’d never been to before!)
- Early morning visit to Kealakekua Bay (my favorite snorkeling spot on the Kona Coast)
The Safari Explorer could get super close to the cliffs and snorkeling spots, which made exploring the coast feel totally fresh and exciting.
Oh, and just a heads up – if any activity doesn’t sound like your cup of tea, you can always choose something else. For example, while we were hiking Hualalai, some folks opted for a chill beach day at Kaloko Honokohau National Historic Site to watch sea turtles.
After a few amazing days along the Kona Coast, we said goodbye to the Big Island and set off across the ‘Alenuihāhā Channel (one of the world’s most dangerous sea crossings) to Molokai. Don’t worry, though – we slept right through it!
Flexible Sailing Days
Remember that “Captain’s Choice” thing I mentioned? Well, it really paid off! We woke up one morning to the most incredible sight – the north side of Molokai, home to the world’s tallest sea cliffs. Picture this: 4,000-foot-high walls of green, dotted with waterfalls, surrounded by seabirds and whales. Talk about a wake-up call!
Other cool stuff we did on our flexible sailing days:
- Kayaking to sea caves
- Following humpback whales (at a safe distance, of course)
- Watching the sunset from zodiacs on the water
- BBQ pizza night on deck and live music night
I was surprised by how much downtime we had for relaxing or, in the kids’ case, doing schoolwork. It was actually pretty nice to have some chill time between all the adventures. Even during downtime, it’s nonstop wildlife watching.
Visiting Lanai from our Hawaii UnCruise
Lanai is like the hidden gem of Hawaii. It’s super quiet, with just a small town and not much else – but that’s what makes it so special. We split up to do different activities here:
- Chris and the kids went to the Lanai Cat Sanctuary (a huge hit with our little animal lovers)
- I joined an ATV ride and hike, getting some incredible views of Molokai and Maui (and even spotted some breaching whales in the distance!)
We also did some awesome kayaking and snorkeling around the island. The spot called Shark Fin was especially amazing for underwater exploration. I have never seen so many pyramid butterfly fish as we did here. Lanai is really pretty and getting to stop here during our Hawaii UnCruise was a great surprise to us.
Exploring Molokai
I’ll be honest – I knew next to nothing about Molokai before this trip. But wow, what an incredible place! We learned so much about Hawaiian culture and history here.
The highlight was definitely our visit to Halawa Valley. This place has an incredible history, dating back 1,500 years. We hiked towards a waterfall (though we didn’t make it all the way due to rain), toured a taro farm, and learned tons about Hawaiian customs from our guide, Greg.
We wrapped up our Molokai visit with a special dinner (pā’ina) hosted by local aunties and uncles. There was live music, delicious Hawaiian dishes, and one last evening with our new UnCruise friends. It was the perfect way to end our week on the Safari Explorer.
Watching for Wildlife with UnCruise
Let me tell you, the wildlife on this trip was absolutely insane. We saw over 170 humpback whales (yes, we counted!), three types of dolphins, Hawaiian monk seals, and so many cool birds. But the real magic happened underwater.
We went snorkeling in some incredible spots, swimming with monk seals, sea turtles, octopus, and manta rays. And get this – we could hear whale songs underwater! It was like being in a nature documentary.
What About Maui?
You might be wondering why we didn’t stop on Maui. Well, due to the tragic fires in Lahaina in 2023, our itinerary was adjusted. But we still got to snorkel at Olowalu Beach, which is one of the best spots on Maui, and so much of our time was spent in the waters around Maui whale watching that it was basically what we do when we stay on Maui anyways.
If you really want to spend time on Maui, you can always book a few extra days there after your cruise, including more Maui whale watching if you didn’t get enough. Places like Haleakala National Park, the Road to Hana and all the beautiful sights are worth the visit. And you can plan to stop at Iao Valley State Park and the Maui Ocean Center too! There’s a lot that you’ll love here, so set some extra time aside if you can.
Ending our Hawaii UnCruise
I won’t lie – leaving the Safari Explorer was tough. We’d made such great friends with both passengers and crew. The kids were hugging their new buddies, and we all felt a little emotional as we waved goodbye.
We spent our last few hours on Molokai at Hotel Molokai, taking one last dip in the pool and watching whales breach in the distance. It was a bittersweet end to an incredible week.
What to Add onto a Hawaii UnCruise Trip
If you’re thinking of extending your Hawaii trip (and honestly, why wouldn’t you?), here are some ideas to add anywhere from 2-6 days in the Islands:
- Explore more of the Big Island – volcanoes, waterfalls, and unique beaches galore!
- Check out Kauai – the Garden Island is perfect for hiking and relaxation.
- Visit Oahu – there’s way more to it than just Honolulu.
- Spend some time on Maui – Haleakala National Park is a must-see
- Add another day or two on Molokai – there’s more to see that you get to experience with UnCruise
As for us? We’ve since enjoyed another UnCruise adventure – Alaska on the Frontier Legacy! We did the Kids in Nature itinerary, and it was another fantastic family experience. You can read all about it on our Alaska travel site, MyAlaskaTrip.com.
Booking an UnCruise Hawaii Adventure
So how do you actually book an UnCruise Adventure in Hawaii? You can do it online or call them, and then a specialist will follow up with you to confirm all the details, from your flights to specifications for your travelers. Like with other major travel decisions, you can book this pretty far in advance if you want to. The cost is more than $5k per person, but when you consider the costs of this level of experience, it’s not terribly different from manual island hopping.
If you’re trying to plan 8 days of island hopping in Hawaii, here’s the budget breakdown for what that may cost, as it too can be a costly trip (we’ve done it!). My prices noted in the below budget table are based on our costs from a November trip to the Big Island, Kauai and Maui and are per person for 8 days/7 nights.
| Base Fare | Hotel | Dining | Rental Car | Flights | Activities | Total | |
| Island Hopping | 1400 | 1120 | 455 | 240 | 900 | 4115 | |
| UnCruise | 5310 | 0 | 0 | 0 | 0 | 0 | 5310 |
When booking an UnCruise Adventure, mention our code (online or via phone) TWODADS500 to receive $500 discount towards your passage. Education and adventure await!
Well, that’s the scoop on our amazing Hawaii UnCruise adventure. If you’ve got any questions about our trip or Hawaii in general, don’t hesitate to ask. We’re always happy to share our experiences and help fellow travelers out. Please leave a comment or send us a note so we can follow up with you. Aloha and happy travels!
