Best Family Travel Moments of 2017

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This year is just about in the books, and if you are the kind of person who rolls their eyes a bit at an end of the year “best of” post, I feel ya. They aren’t always my favorite either, but as I look back through photos from this year I realize just how far our family has come from January to December, so I wanted to share some highlights of travels in large part to share the evolution from life traveling with a 7 and 1.5 year old to life with an 8 and 2.5 year old. When you have an infant and young toddler it at times feels like you are never going to be able to easily go anywhere ever again, and while life will never be the same as you add children to the mix, 2017 was a year of transition for us as we started the year barely able to travel without feeling like it was more trouble than enjoyment, and are ending the year on a very different high note.

First trip without the baby

In February, my oldest daughter and I took a ski trip to Park City that was a bunch of fun, but it was significant because it was the first time I had gone anywhere without my second daughter. While I was traveling without the first by the time she was 5 months old, my second daughter couldn’t easily be left as she wouldn’t take a bottle and I wasn’t going to stop nursing her because of travel. I regretted that decision with my first daughter, and so through the first 19 months of her life, I was never away for more than a few hours.

It was a real commitment and a huge life change, but it was temporary and worth it in the end. It was very, very hard for me to leave her the first time, but we did it and I got some much-needed one on one time with my oldest and a little bit of my freedom back.

Spring breaking in Maui

After a successful weekend ski trip away, when we started to worry about hauling our youngest that far for just a few nights and she ended up sick the day of our scheduled spring break trip to Maui, my parents offered to keep her and we accepted. I was hesitant to be gone for that long, but we did it and had a few days toddler-free in Hawaiian paradise.

We did “big kid” things with our seven-year-old like snorkel and boogie board and it turns out that some days in the Hawaiian sun spent using points at the Andaz Maui and Hyatt Regency Maui seemed to have done us all some good.

As you will notice, my first several favorite trips of 2017 were not ones that the whole family was present. After 19 months of taking our second daughter everywhere, she was finally old enough to stay with grandparents, and she was simultaneously in the “hardest age to travel” range where frankly trips were easier and more enjoyable without her. We could have made trips with her work, but I don’t regret for one minute having her happy with Grandma and Grandpa while we spread our wings again a bit.

Adult trip to Costa Rica

Josh and I met some friends in May of 2017 at the Andaz Papagayo Costa Rica, and it was the first trip we had gone on without either kid in a few years, so it was a fabulous change of pace to our normal daily grind. Hanging out with friends over long meals in a beautiful setting was a nice reset, and we enjoyed this 15,000 points per night resort so much that we look forward to bringing our daughters here in 2018 – in part because of the fantastic (free) onsite kid’s club we toured on our trip

Family reunion in Rhode Island

In June of 2017, we met Josh’s whole family in Rhode Island for a family reunion of sorts. We stayed in two cottages right next to each other and the cousins got to have long days of fun and togetherness. Thanks to a storm back home, we got to extend our trip and stay a few extra days since everyone was having so much fun being close, but not too close, thanks to the adjoining individual cottages.

This trip was also the first time that then 23-month-old Baby S transitioned from being a lap baby to earning miles and sitting in her own seat on the plane. She was coming out of the hardest age to travel and ready to earn her wings.

Fulfilling a lifelong dream at the Polynesian at Disney World

In July my mom and I took the girls to Disney World and stayed somewhere I have always wanted to stay, at the Polynesian right on the monorail. It was every bit as good as I hoped it would be…so good, that it may have spoiled us forever!

Despite the July heat, this trip was special for a number of reasons, but in part it was special because my seven-year-old and two-year-old both got to share in the Disney magic together. I don’t know if we will make it back to Disney before my oldest daughter doesn’t experience magic and princesses in quite the same way as she has on all of our Disney trips to date. Heck, I’m not sure if she will wear a princess dress at Disney again, but on this trip, they got to do that together.

In my mind, there’s no bad age for Disney, but a seven and two-year-old were pretty great as the oldest was into both the fast rides as well as the magic and the youngest was just started to love everything while still being free.

Flying in a private plane for free…three times

The most unexpected “best of” moment in 2017 was getting to fly in a private plane for free three times thanks to an insane Jetsmarter promo. While all three trips were 5 star, my favorite of the three was probably getting to take my oldest daughter to Jackson Hole on just 12 hours notice on an insane private jet.

The flight was free, we stayed at a great new property on points, and escaping the late summer Texas heat for a night in one of the most beautiful spots in the country was absolutely memorable for all the right reasons. While this wasn’t the first time I had traveled without my then two-year-old it was the first time since she was born that I said yes to a spontaneous adventure, and it felt great. 

Living it up in New York, New York

In May of 2017, Josh took a position that requires him to travel more than ever before. At times he was gone every other week, which was hard on all of us…though great for the miles and points account. A week before school started Little C and I joined him on one of his work trips for a couple nights in New York City.

Because of our “big kid” agenda, the quick duration of the trip, and the fact that she could no longer fly for free, the youngest again didn’t join, but the oldest had a blast swimming with cousins at the Park Hyatt New York, climbing rocks in Central Park, and taking in her first Broadway show. I love seeing her just as comfortable on the streets of NYC as she is in our own suburban neighborhood at home.

Beach getaway at the Grand Hyatt Baha Mar

Our school district just introduced a fall break this year, so we put it to use by heading with Grandma to the new Grand Hyatt Baha Mar in the Bahamas. The hotel is gorgeous, the pools are top-notch, and the club lounges is one of the best Hyatt has to offer. However, my favorite part was watching the sisters play and experience travel together. This wasn’t the first time this happened, but it was awesome to watch none the less. Because of their 5.5 year age gap, I wasn’t sure how much they would actually play together, but when we travel you can see them really turn to each other for company and support. That was one of my favorite things to watch as 2017 progressed, and while we see it happen at home, it shines on the road.

To grandmother’s house we go

November brought with it a trip to see Josh’s parents in Kansas, and my first flight with the two girls and no other adults around for support. I didn’t intentionally wait this long to fly with both girls by myself, but because they were both pretty comfortable in the air by this point, it was mostly smooth sailing. 

It’s a pretty great feeling to know that you can work together to get where you want or need to be without anyone else’s helping hands. I’m also glad that even as our travel horizons begin to expand again, we continue to use miles to stay connected with family near and far.

Rounding out 2017 in snowy Whistler

Our final 2017 is unquestionably one of the best. We flew into Seattle and then took a road trip up to Whistler in Canada for days of sledding, skiing, and enjoying a week in another climate. This trip is a serious best of for many reasons. The snow is top notch, all four of us made the journey, it is the longest we have (ever?) been in any one place on a trip, and at the risk of jinxing something before we get home…it is “easy”. While the logistics of getting here weren’t necessarily easy, travel with our now 2.5 and 8 year olds is, well, kinda easy when all cylinders are firing.

Everyone now piles in the beds and mostly sleeps well for naps and at night (and that was not at all the case in 2016), and being able to sleep makes everything easier. We took a five-hour road trip from Seattle to Whistler and not one kid cried or whined the entire way, again something that would have been 100% impossible in 2015 or 2016. Heck, I wouldn’t have even attempted it outside of an emergency situation as my youngest daughter hated car rides with a passion.

On the five-hour evening flight from Houston to Seattle, I simply told my two-year-old about halfway through when it was time to sleep, handed her a blanket, and that was it. Seriously. I don’t say that to brag, but to give you hope if you are still in the throes of the “hardest age to travel”. We left her out of many family trips for a few months and waited until she cleared that phase to start up her journeys again and the payoff has been fantastic flights (when she isn’t getting motion sickness, but that is a post for another day).

2017 wasn’t all sunshine and roses, but no year ever is. I hope to do a 2017 “travel mishaps” post too to share some of the travel times that weren’t as sunny, but on the whole, this year of transition took us out of the dark days of feeling isolated and a bit trapped with an infant and young toddler and into a phase that is looking bright with some happy travel-loving kids and a mama that is thrilled to again be exploring and enjoying.

While we went some great places in 2017, in retrospect it wasn’t about where we were, it was more about who we were with on the journey and what we were taking with us from the experience. Miles and points played a huge role in each and every one of these adventures, so here’s to another great year of earning, exploring, and sharing.

What were some of your 2017 best of travel memories?

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  1. I love your comment about handing your youngest a blanket and telling her it’s nap time. My (now 4 year old) thinks when ever they dim the cabin lights and the flight attendant makes an announcement, she is telling us it’s nap time. Out comes his pillow and blanket and I get at least an hour of peace! So nice not to fight with them about it.

  2. Great post!

    Heading up to Whistler in a couple of weeks.

    Any tips on ski deals or where you stayed (there will be myself and two 15 year olds)

  3. I think it’s so great that you’re able to share with us, but also document history for your own family. Priceless. They grow so fast.

    • So true. Certainly a motivator for some posts for sure. So much of this stuff I would forget if it wasn’t written down. Thank you for stopping by!

  4. Great post! My girls are 8 and 4, and travel is definitely getting easier as the younger one has transitioned from being a toddler to being a preschooler. We had kind of a rough trip to Disney World in 2015, when they were 6 & 2, so this year we went back for a “do-over” and it went MUCH better. This year we’re planning trips to Washington, DC and California and I’m excited to be able to expand our travel radius as my kids get older.

    • Fantastic! I think I wrote a post somewhere about the magic of being “3 and potty trained” and what an awesome transition that is when you enter the preschool realm. Have a great 2018 of “easier” adventures!

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