*** Thanks, Mark, for taking the time out of your busy and adventurous life to write this travel guide to Hawaii! It has me dreaming of taking a trip there! ***
Hawaii is one of those places where you never want to leave; the sun seems to always be out or around the corner, there are beaches on every bend in the road, and there are beautiful mountains to be hiked. That is until you look at your bank statement and you realize how much money you have dropped on the trip, which is about the time you start thinking about how to make one of these dreamy islands your home or at least make the trip sustainable. Finally, you, like most other visitors, just have say “mahalo” and hop on the plane home. Aloha, and welcome to the 30 something, nature lovers, man’s travel guide to Hawaii.
Planning Your Trip:
The best way we found to plan your Hawaii trip is to only plan your first day or two before you leave for Hawaii. Then for the third day going forward, make a plan for the next day after the sun goes down and while you are waiting for dinner. It is hard to know in advance what you will be feeling like the next day, how the weather will be, and what sort of pace you will want to go at. So, ditch your planned activities (at least most of them) and go with the flow.
Before leaving, pick out a laundry list of wants to use as a guide but nothing more. We did big picture planning like what islands we wanted to go to, how many days on each, hotels, and a bunch of bookmarks on Google Maps. We also ended up bringing a guide book since it was loaned to us which actually came in handy. Remember that cell service can be spotty in the mountains and sometimes having a paper copy pays off.
The motto for the trip was to enjoy the moment, keep moving around, and realize you can do a lot in one day. It’s okay to be a little touristy and go to the beach, drink out of a coconut, eat pineapple, and go to a luau. However; do some snorkeling, hike some trails, jump off some cliffs (into water), and try some local food – you won’t regret being adventurous here. We took a ton of pictures but remembered to put down the camera and just enjoy without looking through a viewfinder.
Now, I know I said to go with the flow, but we booked a couple of things since some reservations are required.
What to Book Ahead:
(1) Book a Luau – We went to the Old Lahaina Luau in Maui and had a fantastic time. It was a little pricey, but all the luaus are pricey. So if you are going to go, plan for a good one. The OLL books up months in advance, so do your planning. There is never a bad night for a luau, and you get a history lesson while watching a show and eating a feast.
(2) Book a Helicopter Ride – We decided to go with Blue Hawaiian in Kauai and did not regret it. This was the most expensive part of the trip ($/hr), but it was worth every penny. If you have the budget, then do it. I was very skeptical and almost backed out but had an amazing time!
(3) Book your Hotels – Hotels are not really a last minute thing in Hawaii, especially in the busy season.
(4) Rent a Car – In both Maui and Kauai we rented a car. It was perfect for getting around and seeing parts of the islands that would have been hard to reach if we only used the hotel shuttles and local buses.
Picking your Travel Partner(s):
For Hawaii you basically have two options: the classic couples get-away or the wild guys trip. I opted for the couples trip, but we made sure to get a little wild, jump off some cliffs, hike through the mud, and check out the off-the-beaten-path locations. That being said, there were tons of groups of guys on the trails. If you can get 4-5 guys together, it would be perfect for car rentals and restaurants, and you can share snorkel gear or surf boards.
What to Bring:
This seems like a no-brainer, it’s Hawaii – Aloha Shirt and swim shorts. Well there is a good amount more you might want to consider, but not too much. I managed to use almost everything I packed and only missed a couple things. So here is what I think a man should bring to Hawaii to make from the beach to muddy rain forest trails to luaus to “Hawaii formal” dinners at five-star restaurants.
I basically lived in my Zion Stretch shorts for anything from dinners to hiking. To go to a nice dinner all you need to do is put on a white button down and changing from flops to Sanuks. Make sure everything you have dries fast since you might go to the beach, rinse off, get sweaty, or get caught in a downpour…all in the same day. When I was leaving, I was debating between what shoes to bring. I have never brought more than two pairs of shoes when traveling. Why would I ever need three or four pairs? But, since I couldn’t decide, I did what I normally regret and brought all four. I could have reduced the shoes to Chacos and Sanuks and been just fine if you want to go light, but everything I brought easily fit into a 30L backpack.
Clothes:
– PrAna Zion Stretch Shorts
– Swim Suit or Board Shorts
– White Linen button down
– Light button down or Aloha shirt
– T-shirts (at least one dry fit) (3)
– Tank top (dry fit)
– Long sleeve T (dry fit)
– Pairs of socks (2) – Low cut hikers
– Pairs of underwear (4) – ExOfficio boxers work for me
– Hoodie – it does get chilling on top of mountains and at night
– PrAna Zion Stretch Pants (Not really needed)
Shoes:
– Flip flops – Cheap-O flops or your favorites
– Hiking shoes – Scarpa Zens
– Hiking sandals – I brought my Chacos Z1s
– Closed Toed “shoes” – Sanuk Sidewalk Surfers
Other:
– Sunglasses
– Drawstring backpack – essential hiking/beach go bag
– Water-proof watch – G-Shock Classic in White
– Camera – Sony a6300
– Dopp Kit – deodorant, nail clippers, toothbrush, etc.
– Patagonia Black Hole 30L Backpack – Main bag
– Headlamp – Did not use but might have come in handy
– Stuff sacks (2-3)
– Rope – 550 paracord – to use as a clothesline or one of the other many uses
– Dry bag – Did not use but might have come in handy
Itinerary Breakdown:
Day One
Where: Maui
Stay: Wailea Area
Activities: Check out beaches in Wailea | Relax at the hotel pools | Watch the sunset | Dinner at Sansei Sushi
Protip: Go straight to the beach, drop the jet lag and your worries in the ocean
———
Day Two
Where: Maui
Stay: Wailea Area
Activities: Road to Hana (Waianapanapa SP, Pools at Ohe’o, and so much more) | Eat at vendors on the road including fish tacos, banana bread, and fruits
Protip: Skip twin falls all together and pack some snacks
———
Day Three
Where: Maui
Stay: Ka’anapa
Activities: Snorkel in Wailea | Look for sea turtles | Outrigger canoe trip | Beaches & Overlooks | Kona Coffee | Live music
Protip: Get Ululani’s Hawaiian Shaved Ice. It is worth it. Coconut/Lichee/Mango with a snow cap and mochi if they have it for the win!
———
Day Four
Where: Maui
Stay: Ka’anapa
Activities: Snorkeling in Ka’anapa, Cliff jumping, The blow hole, and The Old Lahaina Luau
Protip: If the locals are jumping, you know it will be fun!
———
Day Five
Where: Maui to Kauai
Activities: Lahaina shops | Banyan tree | Travel to Kauai | Drive through the tunnel of trees | Set up at Poipu
Protip: Watch out for the cruise ship masses if you want a peaceful time in Lahaina.
Bonus Protip: Don’t worry if everyone is 50+ with gold clubs on your flight to Kauai. It is rugged, wild, and fun for all ages.
———
Day Six
Where: Kauai
Stay: Poipu
Activities: Waimea Canyon State Park drive | Hike the Awa’awapuhi Trail | Check out the overlooks | Enjoy a relaxing evening
Protip: Go to the overlooks in the morning to avoid clouds. If you don’t like the clouds, just wait a bit and they will change.
———
Day Seven
Where: Kauai Eastside
Stay: Poipu
Activities: Drive to Wailua Falls and hike down to the base | Passion Bakery Cafe for brunch | Check out series of nice beaches (Lydgate beach, Donkey Beach, Kilauea Lighthouse) | Break open a coconut | Finish the day at Secret Beach | Eat Kilauea Bakery & Pau Hana Pizza for dinner.
Protip: Beaches are not quite the same as Maui, but they don’t have the crowd.
———
Day Eight
Where: Kauai Northside
Stay: Poipu
Activities: Wake up early and drove to the north side | Take a break at small town coffee (huge line!) | Hike to Hono’Onapali Beach (we wanted to go further but rain was coming in) | If it rains like it did for us, come back later for a midnight stroll on the beach.
Protip: Stay on the Northside for a day or two if you can. It looks like it is close, but it turns out to be a bit of a drive.
———
Day Nine
Where: Kauai Southside
Stay: Poipu
Activities: Kalaheo Cafe & Coffee Company for breakfast | Go to Aloha Exchange for souvenirs | Check out glass beach | Chill out in Waimea | Go to the sprouting horn | Visit baby beach.
Protip: When you’re in Hawaii, relax.
——
Day Ten
Day Ten: Kauai
Stay: Poipu
Activities: Nounou-East Trail | Stop at a couple beach |Opaeka’a Falls | Take a helicopter ride with Blue Hawaiian | Hike Makauwahi Cave trail | Watch the sunset at Shipwreck beach on the rock
Protip: If you are on the fence for a helicopter ride, just say yes.
———
Day Eleven
Where: Kauai to Chicago
Stay: Home
Activities: Kalaheo Cafe & Coffee Company again for breakfast | Souvenir shopping (we did a lot of our shopping at Safeway) | Final stop in Hawaii | Ahukini Recreation Pier State Park | Fly Home
Protip: Hawaiian Host are half the price at Safeway and taste the same.
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