Over the past six years, I’ve helped a lot of people book their dream vacations on points and miles. Whether it was readers, friends or family members, I’ve offered advice and booking strategies to anyone who’s asked. The one person who hasn’t benefited from all of this, but who absolutely deserves it? My older sister. She hasn’t been able to join us on any of our family trips for one reason or another. She’s traveled with her family to places like Hawaii and Mexico but she has yet to really go “abroad” (sorry Mexico, you’re too close to home for me to consider you “abroad”).
I’ve decided to just ignore her excuses and force her to go on our next family vacation. She’s currently in the midst of a demanding coding bootcamp, she works as a loan officer part time, and takes care of three kids under the age of 6. She does all of this without losing her mind or burning the house down, which makes her Superwoman in my eyes. At some point (preferably December), I want to reward her for her efforts with an over-the-top vacation. Before you think I’m ruining the surprise – she already knows I’m planning something. She just doesn’t know where we’re going or when. In fact, I don’t really know 100% either.
The idea for this trip is to visit 2-3 somewhat kid-friendly destinations over at least two weeks and to fly in business class. My nieces are 3 and 5 years old while my nephew is turning 1 this year. The plan is for all of them to come along, plus my parents and siblings. Will the kids be flying in business class? I don’t know how realistic that is but if they end up flying in coach, I’ll let the adults sit up front while my younger sister and I babysit the kiddos in the back of the plane.
So now it’s really down to destination. I don’t know where to go. Ever since I mentioned Singapore to my 5 year-old niece (her response, “What’s that? Does it have a Starbucks?”), she’s always talking about it. Singapore is a very kid-friendly city and one that adults can enjoy as well. So I’d like to work that in. But now I’m stuck – I don’t want to repeat 2015 and go to Hong Kong and Bali. My parents have this aversion to visiting the same place twice. “There’s so much to see in the world. Why go back to someplace you’ve already been?” That’s what my dad always says. So I need some ideas. We don’t have to stay in the immediate area – we can go to the Middle East to change things up.
The bottom line is I need ideas for destinations that are kid-friendly, somewhat easy to get to (i.e. no seaplane transfers), and where the dollar goes further than, say, the Maldives. This trip is all about my sister, who is one of the kindest, most compassionate, and selfless people you’ll ever meet. I want her to have an amazing time and see the incredible experiences that points and miles can bring about.
So if I can get some solid ideas from readers, especially those who have some understanding of the challenges involved in traveling with kids, I’d greatly appreciate it.
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