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I like to travel and since I found out the tricks to using miles and points a few years ago, our family has definitely been traveling a LOT more.   Just in the past year, all or part of our family has been to New York City, Texas, California, Seattle, Disney World and much more.  I was in the middle of doing some points bookings and realized that I had 5 different vacations going.  I wrote a post about it over at

Afterwards, I realized that I had actually forgotten one trip and it’s SIX vacations that are in various stages of preparation, so I thought I would revisit it here, as well as mention some miles and points details that regular travelers probably don’t care about as much.

Here are my 6 upcoming trips

1. Disney World – April

Our family is heading back to Disney World in April as part of the Traveling Mom / Traveling Dad retreat.  Since this trip is coming up (soon!), we have most of these details ironed out.  We’re driving down so no flights to worry about, though we are getting a hitch put on our new van (to carry more luggage!)


SEE ALSO: Disney World Hacks to Keep Costs Down

We have one hotel room nailed down as part of the conference, but that won’t fit our family of 8.  Because the conference hotel is sold out (not to mention super expensive due to being on property), we ended up using 30,000 Hilton points to book a 1BR suite for 3 nights (90,000 Hilton points total).  Then with me being Diamond at Hilton, I called up the hotel and they upgraded us to a 2BR

The Homewood Suites is off property, but one nice thing we’ll have going for us is that in addition to free breakfast each day for the 8 of us, we’ll get one night of free dinner on Thursday night

[Which hotels give free dinner?]

We also used 20,000 Hyatt points to get 2 rooms on each of 2 different nights for our drive down to Orlando.  Both hotels are Category 1 Hyatt points (5000 points / night), or we could pay over $200 / night instead


Guess it pays to know the difference between cash points and “points” points huh?

2. Peru – May

My wife and I are also planning on heading to Peru in May.  We have the skeleton of this trip already planned in that we have someone(s) watching the kids, and we have our flights booked for Peru.

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We also have the basic itinerary planned out and I know which hotels I want to stay at, but we don’t yet have our reservations booked.

When I last looked for advice on hotels while we’re in Peru, we got some pretty overwhelming advice to stay at the Tambo del Inka, so that’s our plan.  It’s 12,000 points / night, with the 5th night free, but I’m having trouble figuring out the best way to fit in everything I want to do in Lima, Cusco, Machu Picchu and the Sacred Valley.  We have 6.5 days so suggestions are welcome! 🙂

3. Scotland – August

Now we get to the first of our trips for someone else.  I was working with my mom to surprise my stepdad with a trip to Scotland this summer.  He is very in to his Scottish heritage and in fact owns a kilt :-).  She ended up telling him about the trip (so they could coordinate) but they are still very much looking forward to it.

I’ve been periodically checking flight award availability and am waiting on the right flights to book it with miles.  The plan is to use 57,500 United miles * 2 for one way, then maybe another 57,500 on the way back or possibly use Alaska or American miles if we can find good availability.  The good news about this trip is that once I get the tickets then I am off the hook for the rest of the planning 🙂

4. Sweden – Summer

Each year, my wife and I try to go on long-distance “dates” with each of our 6 children.  She takes 3 and I take 3 and the kids are the ones who are more or less in charge of the destinations.  I’ve written before about my trips with my son to Texas or my daughter to New York.

This year, one of my sons wants to go to Sweden, so he and I are planning on taking a few days there.  We just sent off for his passport, but planning is still in the early stages

Miles plan there would be possible WOW or Norwegian flight out of BWI (then using cheap CVG-BWI on Southwest) and maybe miles back.  Still need to figure out hotels while there as well – maybe Choice hotels (SEE ALSO: 4 best uses of Choice points)

5. New York City – New Year’s Eve

The next trip is paying back my friend who bartered babysitting with me for a trip for her and her family.  It’s been a long time, and we’ve tried a few times to get her trip going but haven’t been able to make it happen.

They are planning to be in New York City for New Year’s Eve and I finally was able to book things.

  • Flights we used 7500 Avios * 4 people * 2 directions for a total of 60,000 Avios (plus a bunch of $5.60s).  Can we get a giant BOOOOO for no more 4500 Avios flights in the US – would have saved me 24,000 Ultimate Rewards points!
  • We booked 5 nights at the Sheraton Times Square in New York City.  Over New Year’s Eve the cash prices were INSANE (see below), but with miles and points it was just 48,000 SPG points total (5th night free)


That’s a value of 6.35 cents / SPG points!  Not too shabby…

6. Chicago Seminars – October

This is the trip I forgot about for my original post – I am also speaking at the Chicago Seminars 2017 in October.

Even though my flight is covered as a speaker (up to a certain amount), I’m having trouble just booking something because it’s not the “best” deal and I keep wondering if the prices will come down or not.  I know I should just book something…

I enjoy traveling and I enjoy planning but I have to say this is getting a bit ridiculous!

Readers – now it’s your turn.  Where are you headed?  How many trips are you trying to juggle?

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