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 TravelingDad.com
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.
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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Dan Miller travels with his wife and 6 (SIX!) children. He loves to help families travel for free / cheap, especially larger families. If you are looking for help, drop him an email at 
My girlfriend and I just did 8 days in Peru. We started off doing two nights in Ollantaytambo, and did Machu Picchu right away. I think this is the best way to do it and to acclimate.
We then spent three days in Cusco, which was nice, but after having done the Sacred Valley the best part seemed like our stay at the JW Marriott. I would spend more time in the SV next time around and just to day trips from there.
We spent three days in Lima. You probably only need two there. Be sure to visit Barranco, Miraflores, and San Isidro (in that order). We also did a day trip to Punta Hermosa beach, but only because we had a Peruvian friend there. In all, it’s an awesome country. Be sure to try the churros and chocolate cake at Manolo in Lima.
Ric at Loyaltytraveler has recommended the Clarion Hotel Sign in Stockholm. We stayed there 6 nights a couple years ago. It is a fantastic place, and the breakfast is truly tremendous. Great location in Stockholm as well.
For Peru, the quickest way to do Machu Picchu is taking the train into and out off Machu Picchu Pueblo (the town under the ruins). It can be pretty expensive. The cheaper alternative is to take shuttle run by one of the tour companies from Cuzco to Hydroelectrica. From there, it’s a US$12 to get to Machu Picchu Pueblo or about a 3 hour walk on the tracks. When we went last year, we too the shuttle in and the train out, took about 2.5 days.
You can read about it in my trip report: http://travel2walk.com/2016/07/01/trip-report-cusco-region-in-peru-june-2016/#machu
There are a couple of towns in the sacred valley and a few ruins and are day trip, depends on what you want to see.
For housing in Cuzco, much cheaper to just book local hotel rooms. Runs about US$30 for a decent one. Also allows you to be much more flexible.
I went to the Chicago Seminar in October 2016 and got a lot of useful information from you and the other presenters. I am having trouble finding the dates of the Chicago Seminar 2017, which I see you are attending and where you will be presenting. Could you give me a contact (perhaps a website) where I can go to find out information on the Seminar this year.
I am already on your mailing list for the newsletter. Thanks.
Keith – you can check the link in the Chicago Seminars section in this very post. The main Flyertalk thread with all the information is also the 2nd result if you Google Chicago Seminars 2017
Hi Dan!
We just returned from Peru and the Tambo del Inka is a strong recommendation – beautiful place. Lots of day trips are available from here, and it’s a good home base. You can take a super-early train from the hotel’s train station to Aquas Calientes and back in the same day – no problem. You could also take a cab to Ollantaytambo (Ollanta) and catch a later train there. Then take the return back to the Tambo del Inka which is what we did.
Consider trips to Maras, Ollanta, and Moray from here as well. We booked through the hotel concierge (Venturia Tours) and the charges go to the hotel bill so you earn some points that way. Also, starting your trip in the valley is smart because of the high altitude in Cusco. We saved that for last and it was a smart plan.
Might I suggest staying at the Palacio del Inka in Cusco? Make that your home base for your Cusco activities. The price in points is the same and it’s an awesome hotel.
Enjoy your trip! I look forward to reading about it!
-C
We spent a day at MP. If you want to spend extra days, it will cost a new admission. Get a guide while you’re there. It’s cheap, and you’ll get the facts. Plenty of guides in the area.
Now here’s the most important tip that we received, and I’ll pass it along to you. Buy Deet and use it at MP. We saw plenty of people that had these big welts all over their exposed skin. Use deet and you’ll be ok. The people that didn’t use this never knew what hit them. The visual is unbelievable.
I agree about the JW in Cusco. Spectacular. We spent a day in town after arrival, before heading out.
Hi Dan, I am relatively new to the points world since I only started accumulating points just over a year ago, but am now in my “redeeming” mode and making up for lost time. So far this year I booked a 4 night stay in Cancun for my wife and me using my 2 free nights from my Hyatt card at the Hyatt Zilka and points for the other two nights. I was able to find inexpensive ($180) direct flights from Detroit so just paid cash. Next I planned a trip to New Oreleans for Mardi Gras using my Citi prestige for 4th night free and southwest companion fare for flights. Now I have 6 other trips in process: whole family (5 of us) are heading to Cuba for 10 days using jet blue points and low cost Airbnb stays; a graduation trip for my son and me to go on a diving trip to Puerto Rico using American points and Citi prestige for 4th night free; a three week trip to Australia/New Zealand/Tahiti using various airline/ hotel points, and Airbnb; a 4 week trip to Boston/Lisbon/Madrid/Barcelona/repositioning cruise to Florida/St Augustine/Hilton Head/Charleston using various airline/hotel points and Airbnb stays (and some out of pocket expense partially offset by credit card cash back); a 4 week trip to New York/Hong Kong/Singapore/Bali/Perth/Sydney/Frankfurt using airline points (first class on Cathay Pacific and managed to get Sing suites on return flight using airline points); and finally a 2 week trip to Oahu/Maui/Lanai using airline and hotel points! As you can see I have a lot of balls in the air right now (my wife thinks I’m a bit nuts). If you had asked me a 18 months ago whether booking this much travel was possible using mostly points, I would have said “no way”, but as you well know it is possible, but it does take a lot of time and effort. Thanks for all your great posts/ideas – I liked your post about Machu Pichu – maybe my 7th trip?