Last month, I got back from an absolutely stellar 10-day Hawaiian vacation on the islands of Oahu and Maui. My personal goal was simple: pack as many beaches and volcanoes as possible into the time allotted. My wife and I soaked it all in as we traversed two incredibly picturesque and bustling Hawaiian islands. We enjoyed top-shelf poke and snorkeled alongside the Hawaiian state fish: humuhumunukunukuapuaa. I clicked away with my Nikon every step of the way.
While the trip was one of a kind and every bit the breath of fresh air, it was also planned relatively last minute. By using a planning approach that valued quality of landscape over total convenience, we pieced together a rejuvenating trip to paradise for just under $2,500.
Let’s take a look at the steps I took, decisions made, and highlights enjoyed along the way.
Oahu and Maui
All of the Hawaiian islands are beautiful and unique. But how would we decide on which one(s) to visit? Maui has always been calling my name. Just saying its name improves your mood, regardless of context. Maui is home to some of the world’s best beaches which surround the island’s 10,000 foot volcano, Haleakala. It’s mix of volcanoes, multi-colored beaches and legendary vibe brought Maui to the top of the list.
We also hoped to explore the best snorkeling spots and stay with friends living on Oahu. This would all of course be accompanied by us eating as much raw tuna as possible. Flying to Honolulu is the way most people arrive to any of the islands. It’s also the cheapest. Located on the southeastern (sort of) shores of Oahu, Honolulu International Airport (HNL) serves as a veritable hub for beach lovers from across the world. As such, it’s also the cheapest.
I can fly to Honolulu from Portland International Airport (PDX) for under $350 at certain times of the year. Even though we would be missing the Spring Break crowd the week after our departure, I knew airfares would be higher than usual. Using Google Flights, I scanned a vast majority of the flight options out there. A direct, round trip flight to Honolulu was going to run us about $450. I figured adding a quick 30 minute regional flight from Honolulu, Oahu to Kahului, Maui wouldn’t add more than $150 for each of us. A small price to pay for unfettered access to postcard-perfect white sand beaches and endless Hawaiian aloha.
I snagged a pair of direct flights with Hawaiian Islands and we were set. Mostly.10 days in Oahu and Maui. That’s $1,200 for all flights to, in and around, and back from Hawaii. They serve legitimate meals with a complimentary glass of red or white.
We agreed 10 days sounded like a nice round number.
Airfare – $1,200
Rainforest Friends and Air BnB
Airfare is expensive. Let’s be real here. It’s far more expensive when you have to line up accommodations on two separate islands. I was fortunate that we have good friends living just a couple of miles outside of Honolulu. Well, two thousand feet of elevation and a couple of miles above Honolulu to be exact. Cliff and Allison were kind enough to let us stay in their beautiful home setting in the hills overlooking the city. We were surrounded by lush jungle, a chorus of singing birds, fresh fruit and the occasional morning shower.
Not only did we enjoy the company of our wonderful hosts, we saved at least $600 in hotel costs. HUGE win.
Maui would prove trickier. With remarkably different vibes on every corner of the island, Maui has a place for everyone. But what kind of vacation did we want? Instant access to the stunning yet packed beaches strung along the west coast, or the more relaxed north coast with fewer of other travelers seeking paradise. Or the mystical town of Hana, on the far east side. We opted for a small, quiet AirBnB rental in Haiku. Our ‘Ho’okipa Home’ sat just 20 minutes east from the airport in Kahului, where we’d be flying in. At a remarkable $100/night for total comfort with a private yard, screened-in porch space to sleep four. The price point suddenly made 5 nights on Maui a whole lot easier.
4 nights on Oahu – $0 (plus some goodies for the hosts)
5 nights on Maui – $550 (w/ tax)
Ride on a Dime
If you’re like me, you enjoy being on the move and visiting many different places while exploring a new region. Both Oahu and Maui have dozens of world-class beaches and phenomenal seafood. I wanted it all, so we needed a car…for both islands.
Normally, I would expect to pay an arm and a leg for 10 days while on vacation, let alone two! But surprise to me, we found two locally operated rental car companies with cars available for $25 a night, taxes and fees included. I was dubious, but optimistic. In the end, we ended up with a brand new compact to cruise around Honolulu, and a Honday CRV to take us up the 10,000 feet of windy road up to Haleakala National Park.
Being inclusive of all rental brands when researching rental options will give you access to great deals on most of the islands. When arriving at the airport, you may need a ride to some off-property rental companies
10 days of car rental – $250
Aloha. Want to Eat?
As an active fella, I have a tendency to inhale food. It gets expensive…but I can’t hold back on my Hawaiian vacation, right? To ensure we could enjoy as much local fare as we wanted without paying $40 or $50 for each meal, we planned ahead. We snagged groceries on Day 1 to cover breakfast, snacks on the go, and some lunches. This approach brought our daily food costs as low as $25 when a home cooked dinner was on the menu as well. This gave us more flexibility in mixing-in spontaneous runs for fish tacos, steaming bowls of curry and rice, and poke. My goodness, the poke. I stuffed my face with fish and chips where the mahi-mahi had been line caught just hours earlier, and stuffed my face with Maui Gold pineapples until my mouth could take no more.
In all, our food and drink bill came to just under $500
Once-in-a-Lifetime Hawaiian Adventure
With the logistics in-place, job #1 was for us to soak up sun, dip toes in the bluest waters, snorkel alongside stunning fish, watch the sunset from the top of the world on Haleakala, and straight up enjoy one of favorite places in the world. In moments like these I appreciate having access to a plethora of tools and resources that everyone can use to get the most for their money. It’s easier than ever to access flight options, hotel recommendations, travel itineraries, menus, local favorites and money-saving deals. Planning a dream vacation last minute doesn’t have to cost a fortune or cause unnecessary stress.
This is great news for working millenials who need serious R&R and have $3,000 saved up in the rainy day fund.
Planning & Resource Recommendations
Airfare – Google Flights & Hawaiian Airlines
Accommodations – Air BnB & VRBO
Restaurants – Baked on Maui, Paia Fish Market & Rumfire
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