My Travel Essentials + How We Got 3 Free Tickets to Hawaii

We just got back from our amazing vacation in Hawaii! For those of you who don’t know, I am from Hawaii and my mom still lives there. But it has been a while since we have been back because we bought a house and had a baby and before you know it, four years went by. There is something so rejuvenating about going home and I had missed the ocean and all the familiar places. We made it a priority to go back this year and I’m so glad that we did!

Now that I’ve had a chance to unpack, it has been interesting to see what I thought I needed and what I actually ended up using. Things I packed that I thought I would use: a hefty book, a journal, a magazine, and about 90% of the clothes in my suitcase. Apparently, I was packing for a getaway with my husband, not a trip with a toddler. None of those things got used! BUT, here are the things that I did reach for!

(this post contains affiliate links and as an Amazon Associate, I may earn from qualifying purchases)

Gibson Convertible Cozy Fleece Wrap Cardigan – Travel fashion is hard. It just is. I’m always overly ambitious in my head about wearing something really trendy and almost always I envision the outfit with heels. It all sounds like a good idea until I think through the logistics of travel…all the walking, all the sitting, all the swelling! So, then I reach for yoga pants and a sweat shirt because I just want to be comfortable! It is hard to find the balance between being fashionable and being comfortable! This cardigan is the best of both worlds. It is buttery soft and versatile in how you can wear it (open or I can snap it shut and twist it and wear it like a cowl neck).

Target Nylon Weekender Bag – I needed a carry on bag that would contain all the things…the toddler toys, diapers, goldfish, and anything that I thought would keep Caroline entertained! But I wanted it to look stylish at the same time. I found this at Target and the size is perfect. I also love that it is nylon because it just wipes clean. We took it on the flight, to the beach and its a bag that I will use again.

Super-Brella – This beach/sport umbrella was the MVP of the trip. I had it mailed to my mom’s address so it was waiting for us when we got there. The sun in Hawaii is deceptively delightful…so I knew that if we wanted to enjoy the beach for more than an hour, we needed to have shade. The umbrella is easy to open, has flaps on the side so it feels a little like a tent, and comes with stakes so that it can withstand the wind.

Treasure & Bond Burnout Boyfriend Tee – I packed a lot of clothes. I mean, a lot of clothes. But I ended up reaching for this tee the most. The cut of the shirt is flattering to all body types, and is not boxy or short in the torso. It doesn’t cling, but if I wanted to create more definition, the shirt has the room for me to knot it at the waist.

Bali Linen Trouser – These linen pants from Athleta are my absolute favorite. They are 100% linen, which is important in the heat, because the fabric breathes and keeps you cool even though you are wearing pants. I love the wide waistband and that the pockets are sewn to the pant which makes the pant leg smooth and streamlined. You just can’t go wrong with these pants.

And now for the really good stuff…the free tickets…this is the unbelievable part. I had heard about people strategically opening credit cards for the sign up bonus points/miles, but had always dismissed it because we have been die-hard Dave Ramsey types. No credit cards or debt for us! But, recently, we decided to make a little experiment of it and see if we could get it work in our favor. We needed three tickets to Hawaii and I need 135,000 credit card points/miles to get there.

Here is how we did it!

We first opened the Chase Sapphire Preferred card and once we spent $4,000 in the first three months, we got the signing bonus of 50,000 points.

Then we opened the Chase Freedom Unlimited card and once we spent $500 on in the first three months, we got the signing bonus of 15,000 points.

Then we opened the Chase United card and once we spent $4,000 in the first three months, we got the signing bonus of 60,000 miles.

This brings us to 133,500 points! Between our normal monthly spending (groceries, gas etc) and having work done to the house, we were able to bring it up to the 135K points that we needed to get our free tickets to Hawaii. All the Chase points transferred seamlessly and instantly to United and the only thing we had to pay for was extra baggage fees and economy plus seating (because we are so tall and need the extra leg room!).

It worked!! This approach might not be for everyone but it was pretty simple and straightforward for us! We are already strategizing about our next trip to Hawaii.

So, tell me what you love to wear when you are flying, and I would love for you to join me on Instagram where I am sharing the outfits I’m putting together from my simple closet!