My Bucket List Travel Plans for My 40th Birthday

My 40th birthday will take place on January 6, 2020, meaning I could feasibly book flights for this trip in a few short months. I have a pretty big stash of points and miles and my husband basically said I could go anywhere I want — even if it takes forever to get there. Since it’s my 40th birthday, I hope to do something a little more exciting and over-the-top than usual. I might even fly business class (gasp!).

I’m still slightly torn on where to go and exactly how to make the trip happen, especially since I’m not sure if we’ll bring the kids along. January 6th is toward the very end of their winter break from school, so I could feasibly make our winter break trip into my 40th birthday trip. Then again, we could probably plan something a little more exciting if we did a separate trip with my kids at the beginning of winter break and left them at home for my actual birthday trip.

Decisions, decisions. Either way, here are the two main options I’m considering right now:

Conrad Rangali Island, Maldives

I am currently sitting on a stash of over 700,000 Hilton Honors points, so paying for a stay at the Conrad Rangali Island property in the Maldives would be a breeze. A stay in an overwater villa is just 95,000 points per night, after all, and you get a 5th night free when you book with points.

Since I get Hilton Diamond status from my Hilton Aspire card, we are supposed to receive a breakfast benefit here as well as an afternoon tea and happy hour. I packed a box of wine in my luggage for our trip to Bora Bora so I would probably do something similar to save on alcohol here.

To pay for our flights, I would probably fork over 70,000 American AAdvantage miles each way to fly from Chicago to Male, Maldives in business class on Qatar Airlines. On top of that amount, there is a $500+ unavoidable sea plane ride to get to the hotel, but I would grin and bear it if it meant waking up on my 40th birthday in an overwater hotel room.


We’re also considering visiting Thailand for a sightseeing/ tropical beach vacation for my 40th birthday, and Hilton Honors points would help us go a long way. I wouldn’t mind cashing in 95,000 Hilton Honors points per night (and getting a 5th night free) at the Conrad Koh Samui or staying at the Waldorf Astoria Bangkok for 65,000 points per night. I think I would like the ornate shrines, temples, and big city wonder of Bangkok, but I would like to have a beach vacation in either Koh Samui, Phuket, or the Krabi region of Thailand as well.

I’m not exactly sure where I would fly into or out of, but I would probably cash in 75,000 American AAdvantage miles to fly round-trip in economy on American Airlines or a OneWorld partner. I might also cash in 140,000 American miles per person to fly round-trip business class on Malaysia Airlines since it looks like that’s my best option for availability out of Chicago.

I’ll definitely have to see what my best choices are once the flight calendar opens up around 11 months out.

The Bottom Line

I don’t have an unlimited number of points and miles, but my current stash of American miles (450,000) and Hilton Honors points (over 700,000) could help me plan a pretty epic 40th birthday trip. As a side note, I also have around 100,000 Chase Ultimate Rewards points and 130,000 Citi ThankYou points to burn. Due to our business spending, we are also earning Chase Ultimate Rewards points at a rate of about 45,000 points per month.

We’ll have to see what works best as time gets closer, even if I come up with other trip ideas to add to this list. No matter what, I want to check off my travel bucket list on my 40th birthday. It’s going to cost a lot of points and miles (and probably some cash), but it will be worth it!

Are you planning a big trip for a milestone birthday? Please share below.


[Image: Flickr/Will Clayton]

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