When we were trying to decide where to go for TJ’s birthday, we threw out a few ideas. Cabo was on the top of it for a while, but we threw it out the window when we started to think about taking a baby down there. We eventually decided that a return trip to Hawaii would be the best option. The summer months had been busy, and we were looking for a place where we could disconnect, reconnect, and enjoy a little relaxation. Having been to Kauai at the beginning of the summer (recap here), and having rather inclement weather, we were hoping for sunny skies, lots of pool + ocean time, and mai tais at sunset. All of which we happily enjoyed.

What we weren’t expecting, was that little miss would have a harder time adjusting than the previous trip. The first morning was to be expected… and she greeted us at 4:30am, ready to conquer the day. We made light of the situation, and figured that, since we were up, we might as well catch a sunrise. Yet, as the days moved on we continued to have rough evenings. She was teething, not napping, and having difficulties sleeping at night. TJ and I had two options. We could be frustrated or roll with the situation  (we chose the latter)…

I’ve been asked so many times for travel advice when bringing a baby in tow. My biggest advice is to be flexible and adjust your expectations. If you can do those two things, you’ll have a great time. What do I mean? Well, before little miss started joining us on our adventures, TJ and I would do whatever we wanted… sleep in, go on long hikes, make late dinner reservations, stay up until whatever hour we wanted… you get the drift. We knew that when we started to bring Harper, that would all go out the window…. and we were okay with that. When we go on trips, we know that we will still be on a schedule, and that we will need to stick to her usual bedtime. So, instead, we opt for fun breakfasts + lunches, and focus much of our attention on daytime activities. Given that, I thought I would share some of the highlights from this trip, as well as some of my top tips for traveling with a little one (you can see my first travel advice post here).

1. Flexibility, Lower Expectations: Please, I beg you, do not go into the trip expecting to do everything that you want, when you want,  and seamlessly. You. Will. Be. Disappointed. Instead, try to be flexible. Example?  I am big on having Harper nap in her crib, yet, when I realized she was not having it, we decided to take a day trip to The North Shore. We knew she would sleep in the carseat, so it ended up being a spur of the moment win-win situation.

2. When The Baby Goes Down, Have Some Fun: One of the most frequently asked questions I receive is “What do you do when she goes down, where do you put her?” Well… where we put her depends on the floor plan of the room. If there isn’t a hallway where the pack and play can go while we are up, then we place her in the bathroom… it’s nice and dark for her, and we can keep a light on for us. Once she is down, we have fun! If we haven’t eaten yet, we get take out and eat it in the corner of the room… sometimes the lights are out, sometimes they are on (that all depends on where little miss is sleeping). We open a bottle of wine, and just enjoy ourselves. It’s not ideal, but we’ve come to look forward to this time of the night. It’s all about that flexibility and lowering expectations.

3. Traveling On The Plane: The last time I gave tips, Harper wasn’t mobile. She was perfectly content sitting on our laps. Not the case on our trips to Boston or Hawaii. Which makes the flight a little more complicated. The best thing we did was bring our baby carrier. When she started to get feisty, TJ would put it on and walk around with her… sometimes he ended up in the back of the plane chatting with the flight attendants (who graciously gave him a beer….). It seemed to calm her down, and often put her to sleep. If you have a mobile baby, don’t forget this!

4. Schedule: I’ve been asked if I follow Harper’s schedule on vacation. Once again, this comes back to point #1. I follow it, but I am flexible… I mean, who wants to sit in the room the entire vacation? I know that her afternoon nap is the most important, so we typically have her take the morning nap while we are out and about exploring. It’s worked for us on the past few trips, so I imagine we will continue if we go anywhere soon.

I hope these tips help! We have always loved traveling, and promised ourselves we wouldn’t stop when Harper was born. It’s not always easy (actually, it’s not easy), but it’s worth it…. Now onto the recap (you can find all outfit details at the end of this post)…

{We landed in enough time to enjoy a half day. Once we got situated, we headed down to the Moana Surfrider Banyan Bar (we stayed there). It is situated right on the water, and they have the best Mai Tais (no joke). After, we headed over to Rum Fire to watch the sunset, listen to some music, and eat an early dinner.}

{The morning Harper decided to wake us up at 4:30am was actually TJ’s birthday. So, we headed to Sandy Beach, located on the East side of the island, to catch the sunrise. It was absolutely spectacular. After, we headed to Arvo for some delicious toast. It’s the cutest spot, and a must see if you’re visiting.}

{After, we headed back to the hotel for some ocean and pool time with our little fish. Each evening we enjoyed what we playfully called Mai Tai Time (MTT)… which was around 5pm. We would watch the sunset, and stay a few minutes after before heading up to get Harper ready for bed. This night we enjoyed take out from Sansei Sushi (so so good).}

{The next morning we headed to Egghead Cafe. We walked there for our morning workout, and Harper napped on the walk back. This place has a robust menu… and we just had to order the pancake sampler. I mean, how do you not??}

{Most of our afternoons were spent in a little cabana we rented. It made having Harper at the pool with us easier. We didn’t have to worry about the sun, since it was shaded, and she was able to crawl around on the cushions… it was also an excellent spot for her to nap on my chest. We enjoyed most of our sunset views from this spot too.}

{After a particularly rough night of sleep (I believe we had an 11pm wake up with her screaming), we decided to grab an acai bowl at Diamond Head Cove Health Bar… and then made a spontaneous choice to head to North Shore for the day. We figured that Harper could sleep in the car, and we could enjoy seeing a different part of the island. The tacos + quesadilla at North Shore Tacos were delicious. If we had spent a little more time there, we would have checked out all the shrimp food trucks they have (#NextTime). This side of the island is absolutely gorgeous, and so different than Waikiki. We couldn’t have been happier we made this choice!}

{On our last full day, we headed to Heavenly for breakfast. We were looking for something a little healthier, and they had some good options. After, we parked ourselves in the little cabana, and stayed there until well after Mai Tai Time. After Harper went down for the evening, we enjoyed take out from the most delicious Thai spot- Siam Square.}

If you’re heading to Oahu baby-less, check out this post I did when TJ and I went several years ago.

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{Outfit Details || Charcoal Peplum Tank | Denim Shorts | Stripe Coverup | Slouchy Off The Shoulder Sweater | Tan + Black Straw Hat}