Aloha! I finally made it to Hawaii. Hawaii has been one of my top destinations I’ve wanted to visit for a long while now. Its kind of ironic how it happened for my family so of course I will give you all the details! Last year, Southwest Air announced that they would be opening up flights to Hawaii. I then began to use my credit card and rack up points. At one point I had over 80k points and was selfishly thinking flights would be so expensive I would just go on a solo trip. Well, March 4th (the day before my birthday) I happened to randomly open Facebook and someone had posted that the SW schedule for Hawaii had opened up! I logged on immediately and booked the first flights for June that I could find. My daughter and I are off all summer but my husbands tight vacation schedule didn’t allow for much wiggle room. I couldn’t believe my eyes but I was able to book $49 flights from OAK to HNL! I also was able to book $92 flights from my home base to SFO which is just over the bridge and will allow us to be able to sight see San Francisco while we are there. Mostly, I used points to book as $49 was equivalent to about 2300 points and $92 is about 5300 points. Basically our flights totaled about $400 each if we had used cash.
IND>SFO $92, OAK>HNL $49, HNL>OAK $189 and SFO>IND $92
Lodging: This was a task all in itself! Nice hotels we’re running $250/night +tax +resort fees which was about $2k for the 5 nights we planned to stay! After lots of research I thought maybe we should view a timeshare & get some overhead knocked off! As usual everything worked out & we stayed at the beautiful Marriott Ko Olina Beach Club which is just one hotel lot away from the Disney Aulani. It was also in a much better area than Waikiki Beach! We snagged the room for $599 which was inclusive of tax & the resort fees were waived. We were more than comfortable in the 1 bedroom with full kitchen/dining & living room space with two balconies. The resort included a water slide, lanai & multiple pools with multiple activities including bingo, water slide races, water aerobics, dive in movie nights, hula lessons & so much more!
Another way we were able to keep cost down was to make a quick Target run & pick up lots of snacks & groceries so we could take advantage of the grills a couple of days & nights for lunch and/or dinner.
View our room tour HERE
Things to know: purchase sunscreen on the island, they have a specific kind that is reef friendly! Also BYOB (bags) grocery & shopping bags of any sort are not complimentary.
Sights to see:
Makapu’u Point
Hoomula Botanical Garden
Koko Crater Hike
Tantalus Lookout (At night)
Dukes on Waikiki Beach
NorthShore: Giovanni’s Shrimp Truck
Matsumoto’s shaved ice
Day 1: San Fran- we had lunch at Franciscian Crab House down at Pier 39, we walked, drive sightseeing & visited the Golden Gate Bridge. I was born in Fairfield, CA so my Godmother took me to see the apartments we use to live in, the hospital I was born in and some of the areas my parents use to hang out at!
Day 2: Aloha!! As soon as we touched down we connected with our Turo driver Chad, HERE (for $25 off your first ride), had breakfast, visited Pearl Harbor & then to the resort for pool, beach, food & drinks! We also made our Target run.
Day 3: North Shore!! This is a must do! We visited Wamiea Beach & cliff jumped, Wameia Falls & Swam in the Waterfall and ate at Giovanni’s Shrimp Truck. HERE (for cliff jumping videos)
Day 4: We ventured down to Waikiki Beach & took surf lessons. This also is a must do, especially if you want to see how in or out of shape you are! While down in Oahu we had breakfast & lunch, and did some shopping on the strip! HERE for surfing footage!!
Day 5: Diamond Head & the Swap Meet at Aloha Stadium which allows you to get all your souvenirs & locally made items at an awesome price! Oh & of course a Luau at Paradise Cove (HERE for Luau video)
Day 6: Spent the day relaxing by the pool! Taylen met a friend & went back & Firth between the 3 pools & beach. We took advantage of all the resort had to offer doing all their activities for the day. Last, we had to view the time share presentation.
Day 7: Mahalo KoOlina! We left Hawaii at 9:30a & landed in Oakland at 5:40p, we got dinner & headed back to my God moms to stay the evening for dinner and a few hands of spades.
Day 8: Today we decided to sleep in and enjoy spending time with my God parents before our evening flight heading home to Indy!
In all it wasn’t as expensive as we thought & we had the most amazing time & I can’t wait to catch another deal so I can visit Maui!
As always, thanks for traveling along! 💋

Great info. I guess I should have read your amazing, very informative blog before I asked you all of those questions about this trip because you clearly stated everything I wanted to know on your post. I will start reading before I hound you with travel questions. LOL
Hawaii looked like an amazing time for the entire family. You all were glowing!! After seeing your trip I am now planning a trip for my family and I.