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Vacation to Hawaii: Advice From Our Experiences

Vacation to Hawaii
My wife on the beach in Maui.

We travel often throughout the world, and our trip to Maui was one of the best vacations of our lives. The ocean beaches and tropical hikes are minutes away from each other. The island feel and pace have an instant calming effect, and the ocean breeze whipping off the Pacific keeps you cool. 

There is plenty to do, and you need at least a week to do it right. 

How to Save

Traveling is a priority and ongoing savings goal for us. We do not borrow for vacations. 

We look forward to our Money Date, which is designated for deciding where we will travel next. We set aside cash windfalls (e.g., bonuses) for vacation in a high-yield savings account. 

We prefer using Raisin to find the highest-paying yields. Our account currently earns 5.5% APY. 

Learn more about using Raisin to save for your next vacation.



Vacation Packing Checklist


✔️ Water Shoes: I wore these nearly each day

✔️ Flip Flops

✔️ Tennis shoes

✔️ Tank tops: Active wear

✔️ Tops: Non-active wear

✔️ Shorts: Active wear

✔️ Underwear

✔️ Casual summer clothes/ resort wear

✔️ Shorts: Non-active wear

✔️ Summer dresses / Collared Summer Shirts

✔️ Hawaiian Shirts

✔️ Long pants for high altitude hikes

✔️ Sport socks

✔️ Sweater or hooded sweatshirt for evenings

✔️ Long sleeve sun shirt

✔️ Camera 

✔️ Optional: Drone

✔️ Optional: Hiking shoes

Beach Items

✔️ Bathing suits / Swimming trunks 

✔️ Sunglasses

✔️ Sunscreen 

✔️ Sun hat / Baseball cap

✔️ Bathing Suits

✔️ Reef-safe sunscreen

✔️ Refillable water bottle

✔️ Beach towels (can buy locally)

✔️ Snorkel Gear (can rent locally) or purchase at Wal-Mart when you arrive

✔️ Underwater camera

✔️ Puddle jumper/water wings or Life jacket: For kids

✔️ Waterproof phone case

Hiking Items

✔️ Backpack for Day trips & Hiking

✔️ Light rain jacket

✔️ Hiking boots or hiking shoes 

✔️ Day pack

✔️ Dry bag during the rainy season or for waterfall hikes

✔️ Sun protection (i.e wide-brimmed hat and reef-friendly sunscreen)

✔️ Refillable water bottle 

Items to Pack Last

✔️ Phone charger base

✔️ New water bottles

✔️ Sunscreen 

✔️ AirPods

✔️ Apple Watch 

✔️ Books

✔️ Phone

✔️ Wallet (Double check for the passport, identification, credit cards, and cash)

Prepare for Lost Luggage

The airline lost our luggage on our honeymoon. We learned from experience why you should include the essentials you need for your first couple of days in your carry-on luggage, including swim trunks/swimsuits.



Vacation Packing List Template

Vacation Packing List Template

We love Coexist for household management coordination between us, including the premade templates you can draw from, such as the vacation packing list template. 

Learn more about how Coexist can simplify your life.

What to Purchase in Advance

It goes without saying that you need to purchase airfare and lodging well in advance. We also suggest purchasing in advance the following:

✔️ Luau

✔️ Any tour packages (e.g., helicopter ride) 

✔️ Necessary clothing unique for the trip (e.g., water shoes) 

✔️ Hawaiian Lei Greeting at Airport 

Where to Stay

There is an abundance of VRBO and hotel options at wide price ranges. However, we hate the VRBO fees, and hotel rooms are too small for what we are looking for in a long vacation. 

I strongly recommend exploring renting a TimeShare. It’s no secret that folks get trapped in these contracts, and their desperation is reflected in the price of the rentals, which seems to be in line with the annual maintenance cost. 

Consider Red Week for your search. 

Activity Options

Vacation to Hawaii: Activity Options

Downloadable PDF with links to the details

Download PDF • 1.25MB

Food Options

Vacation to Hawaii: Food Options

Downloadable PDF with links to the details

Download PDF • 921KB

Our Trip Details



✈️ Arrived at 5pm

🥥 Dinner at Coconuts. They serve large portions so we suggest sharing. 

🌅 We walked across the street to the beach to watch the sunset. 


🦐 Hilton Beach and clubhouse for lunch. We highly recommend the coconut shrimp.

☕ Maui Coffee Roasters: Best coffee we found. We highly recommend the Kona pour over. 

🌊 Twin Falls Trail: Yes, that is me, cliff diving. 


🛌 Lazy morning.

🏊‍♂️ Hotel pool.

🍽️ Grand Wailea Luau: We highly recommend it. Arrange for a ride on the way home if you plan on taking advantage of the open bar. 


🛌 Lazy morning.

🚁 Helicopter tour with Sunshine Helicopters. We purchased the first class seats on site. We had the opportunity to do so at a reduced cost because we were the first to arrive. It was well worth the money.

🍔 South Maui Gardens: An array of excellent food truck options and live music! 

🌅 Sunset at Kalama Park.


🥾 Īao Valley State Monument Hike: Wear water shoes! 

☕ Wailuku Coffee for lunch.

🍧 Peace Love Shave Ice for dinner.


❌ Coffee shops closed on Sundays.

❌ Waihou Spring Trails: We do not recommend the hike because of the fire damage.


Related: Take advantage of our free Marriage Toolkit preview to start, strengthen, or rebuild your marriage.



🧳 Packed our luggage first thing so we could enjoy the day.

🌊 Clubhouse pool at the beach and lots of drinking.

Vacation to Hawaii



✈️ 10 am departure.

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