Hawaii on the Fly

Why Hawaii? Sometimes you just need a vacation. After three months with kids on summer break that can hit hard. No amount of camps, community activities and babysitters can quite take up the slack that a summer without school leaves. I love my kids, but sometimes even I need a bit of a break. So, I set my searches far and wide, looking for something that would fill every need for an escape from New England, and not quite bankrupt me.

Hawaii

That probably sounds a little extravagant, but it all comes down to who you do business with. I spent several years flying back and forth to Alaska for work. Most of the time, I made sure to book Alaska Air for the comfort, low number of connections, and my ability to make MVP status quickly and be able to get upgrades. I built up quite a few miles that way, but sadly, Alaska doesn’t fly to many places from Boston. In truth, I would have to start off any trip with a flight all the way to the West Coast before being able to go anywhere else. So, Hawaii wasn’t that unreasonable. And, after transferring a few miles between accounts, two fully funded milage tickets (that even included a First Class leg) took the problem of airfare right off the table.

AirBnB vs Hotel

This made a huge difference. I was able to find an AirBnB for roughly $125 a night, including all fees. It was located on the scenic North Shore. An easy walk to beaches, close to a few towns worth seeing, and had a full modern kitchen which eliminated the need to eat out almost completely. I know, you’re on vacation, you want to go out and have a good time. Easily done, but when the Poké at the local Food Lion blows the doors off anything that you’ve had stateside, you might not need to spend as much as you think. And seriously, I didn’t go all the way to Hawaii to sit at a hotel and sip pineapple juice, I went to hike gorgeous tropical mountains, eat fish, and sit on the beach. Dali was a great host, and I highly recommend her cottage to anyone planning a stay on the North Shore.

Food in Paradise – Go Small and outside

That being said, we did eat out a few times in Haleiwa, and once in Waikiki. Generally decent, but nothing worth planning your trip around. But the food trucks. For truly local fare it is almost always your best bet to eat street food wherever your travel. Oahu was no exception. Shrimp, fish and sandwich trucks are scattered all over the North Shore, often in fields converted to parking areas. And the food they serve is among the best on the island. It was a simple thing to walk up from the beach for a pile of shrimp or fish served steaming hot on a roll that would have you raving to your friends. And for post hiking or early morning grabs Açai bowls were a great discovery. The Banzai Bowl near Sunset Beach was an easy walk from our AirBnB, and easily served the best bowl I had on the island. Full of fresh fruit, granola and berry goodness, the small was easily twice the size of any other I saw, and very reasonably priced.

Hike, Swim, Snorkel

For the most part, these are free activities. We had to pay a nominal fee to go up Diamond Head, which was an incredible view, but also terribly crowded.

A few North Shore hikes near Waialua were free, picturesque, and we saw less than a dozen people all day. We entered via the Mokulēʻia Trail, which was mostly paved and clear, though quite steep in places. A pretty realistic family hike, or intro to the area. Other than a few trail runners it was surprisingly empty. This trail then feeds into the Mokulēʻia Forest Reserve, and several of the other trails in the area. With more time to explore I think we could have kept busy up there for days.

I was pumped to dive and snorkel, but that was not to be. The winter weather leads to pretty choppy water, and sadly the visibility was less than 15 feet the entire time we were there. I spent a fair amount of time in the water, body surfed, watched the real surfers, but had very little time under it (I did see one Green Turtle swim by in the murk, so not a total bust).

It really was the perfect vacation. 8 days in Hawaii with no agenda. And the trip cost less than $2000 for two people, including airfare, lodging, rental car, and food for the week. We even went out to dinner a few times. For the full cost breakdown and details, click here. And, amazingly, we got more work done plugging at computers for a few hours each morning (never past lunch) than we had in weeks trying to fit it in between life with the kids at home.