How We Pick Our Travel Destinations

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School is now wrapping up for the year, and that means a few months of summer freedom are upon us. Of course for working parents (and perhaps all parents), summer freedom is met at least with an equal mix of excitement and dread since trying to fill the kids’ days with activities consisting more than using an iPad or eating crackers in the backyard without going broke in the process can be a challenge. Still, the upside of summer is that you can travel whenever you want for several months without being restricted by a school schedule. Being on the threshold of that ‘freedom’, now seems like a good time to talk about how we pick our travel destinations.


In my view, your ability to get a big return for your miles and points depends very heavily on how you pick your travel destinations and plan your trips. In other words, how you approach this topic is crucial to your miles and points strategy.

1. Chase the Fare, Not the Destination

I didn’t come up with this phrase, but I very much adhere to this strategy as much as possible for our leisure travel. You will do much better with travel deals and stretching your miles and points if you follow where the deals are instead of trying to force deals to fit a very fixed schedule and destination.

For example, you may know you want to take the family to Paris at some point. However, if instead of being set on only flying into Paris, you keep your options open to deals across Europe, then you may be able to hop on a $400 round trip deal to Madrid instead of paying $1,000 to fly to Paris. Of course, that doesn’t mean you can’t travel to Paris on that trip as well, it just means that the more you keep your options open for the order, timing, and exact location of your trips, the more likely you will be to score great deals. If you are tied to a set destination on set dates your chance of getting a really good deal goes down, which is okay in some situations, but I prefer to spend less on any one trip in order to have more funds for more trips.

We booked a trip to Spain in part because of a great fare deal!

2. Go Where the Awards Are

Similar to going somewhere because the fare is good, we also choose our travel destinations in part based on where the awards can be found. There are dozens, if not hundreds, of place I want to visit, so the order of those visits isn’t all that important to me much of the time. If I am craving a beach trip and can get award flights and/or award rooms in Grand Cayman instead of Puerto Vallarta, then that is the clear destination winner that time around. I’ll make it back to Mexico on another adventure. The beauty of traveling with miles and points is that no one trip has to be the end all and be all and there can always be another trip, so I’m okay letting award availability dictate a bit of where and when we go somewhere.

This can also play out if we are considering a longer haul journey and we want to fly in business class. For example, if we are heading to Asia and can only find premium award availability to Singapore instead of Tokyo then we will work with that even if Tokyo was our intended target. In that case we would likely fly to Singapore and potentially spend a day or two there and then continue on to Tokyo. In some ways it can be fun letting factors beyond your control play a hand in planning your travels, but to make that happen you have to be looking at a wider range of dates and locations than just X city on X date.

3. Use the Award Chart Sweet Spots

Some places and routes are just too of a good deal on miles or points to not to use at some point. A perfect example of giving preference to an award chart sweet spot occurred on our recent trip to the Andaz Papagayo in Costa Rica. This resort is a Hyatt Category 4 that goes for 15,000 points per night, or you can even use the Hyatt Category 1-4 awards for your stay. Paid room rates are easily $300 – $400 and up per night at this property, so it is an award chart sweet spot at just 15,000 Hyatt points.

To give some perspective to those not super familiar with the Hyatt chart, the Andaz Maui is 25,000 Hyatt points per night, and the new Andaz Mayakoba in Mexico is 20,000 Hyatt points per night. No award chart sweet spot sticks around forever, so we wanted to be sure to visit the resort sooner rather than later to get advantage of getting that great value from our Hyatt points.

Another good example of following the trail of tremendous point value is the Park Hyatt Maldives that is 25,000 Hyatt points per night, but would have been astronomically out of our price range if we had to pay with cash. While 25,000 points is still a sizable number of points, it made an otherwise out of range experience doable for us and worth the trek around the globe.

Points and award chart sweet spots have also helped us decide where to go skiing as there are some award sweet spots to be had at ski resorts. As an example, while paid rates during holiday weeks can approach $1,000 per night, we booked the Westin Whistler on a holiday week for just 9,600 SPG points per night with the fifth night free. There are lots of places I would have been happy to ski, but following the award chart sweet spots makes sense.

4. Go Where the Freebies Are

All things being equal, we also give preference to places where we can put our elite status perks into play to give us a more comfortable and more affordable stay. The perks (aka freebies) can impact not only where we go, but also the timing of when we go in the event we have elite status perks to use one year, but don’t think that we will re-qualify in a subsequent year. Whether it is heading to a resort in Hawaii where your perks will get your lounge access, a suite, and/or free breakfast, or taking a long haul flight when you have confirmable airline upgrades to use, it can make sense to time your trips with when and where your perks will really help you out.

100 Euro breakfast “for free”

5. Where Will the Kids Have Easy Access to Fun

Assuming we are planning a trip that includes the kids, we like to go to places where there is easy access to kid-friendly fun. For example, if we are going to a beach resort I want to actually be on the beach so we can go out to the ocean and then retreat back to the hotel without dealing with packing up a car, car seats, bathroom breaks, etc. Even better yet is when there is a top notch on-site pool complex with slides and a shallow end for the toddler. Pools and beach trips may not be as culturally stimulating as a walk through a European museum, but a happy kid means a happy parent, so the museums can wait a few more years.

Hyatt Regency Maui

We also enjoy places that have high qualify kid’s clubs….and free ones like at the Hyatt Ziva Cancun, Hyatt Ziva Rose Hall, Andaz Maui, Andaz Papagayo, St. Regis Punta Mita, etc. hold an especially top spot in our planning book.

Hyatt Ziva Cancun Kid’s Club

6. Follow Your Heart

Last, but absolutely not least, don’t only follow 1-5, but also go where your heart says you should go even if it otherwise doesn’t make sense. Alternatively, don’t go somewhere just because it is a great deal on paper if it isn’t of any interest or is potentially an unsafe destination. I am not a slave to elite perks and award availability, and if my family wants to get together in XYZ location on ABC date, then we will find a way to make it happen. Or if you have your heart 100% set on a trip to the North Shore Kauai over spring break and nothing else will substitute, then that’s okay to go with that even if the awards aren’t lining up perfectly to make it a killer redemption on paper.

This is where your fixed value point rewards programs can come into play so that you can go where your heart wants even when the saver awards aren’t popping up. Along those lines, if you find yourself frequently traveling without much date or destination flexibility then you will probably want to give preference to programs that let you use your points for any award at any time rather than a traditional award program that may not have what you want when you need it. You probably won’t get as high of a return that way, but you will get where you want to be.

Some of our upcoming trips we have targeted using these decision making points include Whistler, The Bahamas, Grand Cayman, Mexico, Vienna, and a summer beach house in Rhode Island that was a total wash on points, but it was where our family wanted us to be, so it was a great destination for us.

How does your family decide where to go? Do you pick a destination and make the awards fit, or do you let deals and awards somewhat be your guide in travel planning?

Editorial Note: The opinions expressed here are mine and not provided, reviewed, by any bank, card issuer, or other company unless otherwise stated.

The responses below are not provided or commissioned by the bank advertiser. Responses have not been reviewed, approved or otherwise endorsed by the bank advertiser. It is not the bank advertiser's responsibility to ensure all posts and/or questions are answered.


  1. Thank you for the list Mommy Points. Many of my vacations start out as PointBreaks locations, the 5000-point hotel deals that IHG announces every couple of months. They are an excellent way to enjoy unusual destinations, places you would not normally select for a vacation…or maybe you would.

    I’ve stayed at PointBreaks hotels in Panama City, Shanghai, Liverpool, Leeds, Quito, Baton Rouge, Indianapolis and Spartanburg, S.C. (those last one being lucky because I needed to be there anyway).

    After you’ve seen the big-name travel destinations, it’s fun (and economical) to just go wherever IHG puts a PointBreak hotel.

    • That is a great way! It is the hotel version of chase the fare, not the destination. Thanks for sharing!

  2. At the moment, we have the southwest companion pass, so we will be favoring destinations flown by southwest. We have to be back next Christmas break for the resumption of dance practice by December 26th, so we are fitting in a week within striking area of Cancun, using the pass and where there are numerous points option hotels. But Russia is high on my wish list, so heading there for two weeks the day school finishes on June 22 for two weeks, to be back before summer dance practice resumes. My advice,…Absolutely travel away during the summer while your girls are young and free from such all encompassing commitments!

  3. I like # 5 and 6 the best. Recently we had a great trip planned to the Maldives with our kids 90% on points. Then my wife hit me over the head and said how much fun is that going to be with the kids. So we are going to Japan instead where we will be doing all kinds of stuff including Disney and Universal Studios.
    Some vacations are fun where you can go on pennies on the dollars with points, but also dont get so wrapped up in the points game that you miss a destination you really want to go to.

  4. Well, it is easier said than done. I agree with all your points on this post but when it comes to planing a family vacation when you have time restrictions to match kids vacations with adult vacations that becomes a bit more difficult. I am in the middle of planing our summer vacation for this year (Yes, I know it is very late but I had no choice) to go to Europe (I will be spending work time there so it is easier to have family come there to go on vacation) and it is not an easy process. We always try to go to a beach destination in the summer and since it is very hard to find properties in Europe that allow 4 people in the same room it makes almost impossible to use points for hotels there. Also, flights tend to be very expensive since we don’t fly out of the East and West Coasts so no great deals available either for paid tickets or using miles. Thus, when it comes to summer vacation with my family the destination sometimes becomes more important than where the good deals are since we have several constraints. Since I usually have lots of miles and points I don’t spend much time doing all the calculations if I am getting the most for my redemptions but sometimes using points and miles (lots of them) becomes the only way to make our vacation plans feasible.

  5. Homes/cottages/apartments are sometimes the most economical & pleasant mode of family lodging. For sites like VRBO, etc., I try to find open dates mid-week & off-season, then contact the owner for sizable discounts. They know they probably weren’t going to rent the property out then anyways, so they are willing to negotiate.

    As children get older and a family requires more room/kitchen facilities while on vacay, I have found timeshares and home rentals can provide a better experience over hotel stays. Wyndham Rewards is a “points” method for transisting into larger spaces at 15k points/night/bedroom. Marriott Rewards, too, can often be used towards their multi-room timeshare properties, though there is a point “upcharge.” Fewer rewards are usually required for Sun-Thurs travel with them as well. Both methods do not require buying a timeshare, though purchasing with Starwood offers SPG Gold elite status as long as you own the timeshare!

    Just saying hotel stays can be a grind after awhile for larger families, & it’s nice to spread out into a larger space. I personally like to keep an arsenal of airline miles, hotel points, and timeshare points always at my disposal for whatever size of group travel.

  6. Given our travel dates, we pick the most awesome sounding destination that we can book for four people using miles that:
    1. only requires one NONSTOP flight to get to the primary destination
    2. we can get the hotels for free using hotel points or nearly free using credit card points
    3. where what the adults want to see & do also appeals to the kids.

    We are only able to go after low hanging fruit when accumulating points & miles right now, but we still managed to get to Australia last year and are headed to Maui this summer.

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