Daily Getaways

I Won the $10,000 Daily Getaways Giveaway – Help Me with Trip Suggestions!

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Written by Charlie

I actually won the $10,000 Daily Getaways travel giveaway! This is for a custom trip in the US so please help us out with your favorite places and activities!

Chalk this one up to a total surprise! I mean, like everyone else that visited the Daily Getaways website this year, I had seen the banner about the $10,000 travel giveaway to celebrate 10 years of these getaways, but I did not think for a moment that I would win!

I Won the $10,000 Daily Getaways Giveaway

$10,000 travel giveaway

What was the Giveaway and How Did People Enter?

Everyone who purchased a package (or sent a postcard to the address they gave in the terms) received an entry for the $10,000 travel getaway package. Given the number of packages, that would mean there would be about 10,000 entries, maybe more? Of course, I did not buy any of the packages to gain an entry, in fact, I don’t even think I gave it much attention at all as that was not the focus of the Daily Getaways for me.

Apparently, the entry that won the package for me was the Alamo car rental discounts. That was actually funny how that happened – I tried to buy 3 at once (the limit) but it kept only processing it to the end as a single coupon. So, finally, I bought one and then bought two in the next one to still reach the limit. One of those was the entry that was selected.

The $10,000 Trip Prize

In fact, I had given the whole thing such little attention that when I was contacted about being the winner, I thought it was a cash prize at first! 🙂 But, it is actually a vacation package in the US that will be a “custom” package to go up to $10,000 in total. I can go over that amount but will need to pay the difference. To book it, I need to go through the US Travel Association travel department so we are supposed to be talking soon to start putting some things in order.

It will be for my family and I (6 people) and it has to be used within 1 year from last week. Also, I will be responsible for the taxes at the end of the year on the total actual retail value of the price, of course, so this isn’t exactly a “free” package for me – consider it a much cheaper version of what it could be!

Another thing that stood out was that I cannot earn frequent flyer miles (awww, come on!!!! 🙂). Also, I would imagine that since they will be using some travel portal that I will not be able to earn hotel points/nights either. That is a big bummer also!

Planning the $10,000 Travel Getaway

So, what will we be doing? The package covers things like airfare, car rentals, hotels, and activity packages (that can be purchased online – things like Disney, etc). Of course, we could go with miles and points to cover a lot of that on our own but we are hoping to utilize this prize for a destination and activities that would have really pushed the envelope of the redemption amount with miles and points.

No miles or points this trip!

One of the things that I am looking forward to is the hotels for this reason. When we travel together as a family of 6, we would normally have to get two rooms or book a room and upgrade to a large enough suite.

Booking such rooms with points or booking two rooms with points can be an expensive points proposition. But, they may not be that bad with cash (for some hotels, a large enough suite for 6 of us may cost $280 per night while a basic room could cost $200 that would be bookable with points – but the suite wouldn’t be bookable with points or would cost way too much).

Our Tentative Destination

For our destination, we are thinking of San Diego sometime next year, in either February or April. I have been through there quickly before but it was always something on our to-do list for a visit. Plus, there are a ton of activities out there to do with children.

Please Help with Trip Suggestions!

But, we are not set in stone on that yet! So, we would like to have some suggestions from you all on potential other destinations for those months with 4 children (ages 4 – 11). We are from western NY so the East Coast is not something that is high on our list. We have also spent some time in Arizona so that isn’t exactly on our repeat list this time.

  • What cities do you recommend as must-see places in either February or April (in the US)?
  • What activities do you recommend for kids in San Diego that you think we should not skip?
  • What hotels in the San Diego area would be places you would recommend to stay at for a longer period (at least 10 days)?
  • Just give us any suggestions for places you would think would be awesome to visit and why!

Of course, I will be covering some of this trip and the things we do in future blog posts. I didn’t really even want to write this post because I didn’t want it to come off that we were gloating about winning this. But, this is about travel and we will be doing posts about the travel we do with this so it would seem strange to not write about! Plus, we really would like to get your input on some potential destinations and activities! We want to really make this trip something special!

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About the author


Charlie has been an avid traveler and runner for many years. He has run in marathons around the world for less than it would cost to travel to the next town - all as a result of collecting and using miles and points. Over the years, he has flown hundreds of thousands of miles and collected millions of miles and points.
Now he uses this experience and knowledge to help others through Running with Miles.


  • What a coincidence, a travel blogger within Boarding Area won this prize, this ensuring plenty of free additional promotion for this and future years… funny how that worked out.

    • This was another reason I didn’t want to write about it – because I knew there would be some comment like this made. Let me be clear – this giveaway was administered by one of the top agencies in the US for things like this (which I found out when I looked them up) and they would be in huge trouble if they ever played games with the giveaway.
      Also, my information for the packets I bought was not tied to the blog.
      Finally, if you looked back through the BoardingArea posts, I was probably the blogger that posted about them the least, saying up front that I would only write about the items that I thought were good deals since not all of them were (some blogs wrote about the Daily Getaways every single day).
      But, hey, thanks for trying to crush some of the excitement of winning something.

      • There’s always a troll to piss on anything good or fun… Congrats on winning! I’m happy for you! I won 80,000 Hawaiian miles a few years ago using the Miles Finder toolbar. I didn’t believe it at first–I didn’t even know I had entered a sweepstakes. What a fun surprise!
        Enjoy your trip!

        • Thanks, Erick! That kind of surprise has to be the best – when you weren’t even expecting it! The funny part with this is that I am wondering if I win a different thing that I had specifically entered for and got a call on this – that I hadn’t even thought about entering!

      • I’m actually glad that you won and we get to read about it! Congratulations!
        San Diego Zoo Safari Park is worth visiting. And elsewhere in US in April I’d say Washington D.C. for cherry blossom.

        • Thanks, Jason! We are waiting to hear if the GoCity pass is something that would be covered because it would open up a lot of activities. The Safari Zoo park is definitely something we had a list and good to hear a voice for it! Thanks!

  • Charlie, congrats! Couldn’t have happened to a nicer guy. San Diego is a great idea, but if you want to be really exotic, I suggest Anchorage, Alaska. Even in February, you could have a great time at Fur Rondy and the start of the Iditarod (although June is better). Would be a very memorable trip and $10,000 should take care of the fact that it is a more expensive destination. You know how to get a hold of me for specific suggestions for an Alaska trip.

    Your friend Glenn

    • Thanks so much, Glenn! I will definitely check that out as well. I know half of the family would love that by my wife is definitely not a big snow person. 🙂 So, I may need to push that out a bit more to get a bit warmer weather! I’ll definitely send you an e-mail if that is a direction we all agree to entertain! 🙂 Thanks!

  • I don’t have any suggestions, especially for travel with kids, but congratulations! I enter tons of sweeps/contests and it is always fun to get that winning email or call. Have a great time!

  • Congratulations, that is exciting! What about Hawaii? Lots of activities and February would be during whale season. Maui is our favorite island. Have fun! Can’t wait to see future posts about the trip.

    • Thanks! Will consider that a bit as well. We are trying to balance the trip time against the length of the whole trip itself so Hawaii is in the mix but we have to see which month we end up going with. Thanks!

  • You should give it away to someone who needs a vacation/trip….I’m not sure you need another, but maybe I’m wrong.

    I’m just looking at life, and thinking….you could do the same.

    • I appreciate that thought and, believe it or not, that was my first thought. But, it is something that only goes to the selected winner and, even if I could select it to go to someone else, I would still be on the hook for the taxes.
      It is not something that I talk about on the blog (since I feel it is more private) but I do give away points and miles for others for their trips as well.So, I do appreciate your thought.

  • Congrats! Since you won’t earn hotel points, maybe a cruise would be a good option. Cruises often aren’t a great value with points, so this might be a good time for one. Plus there will be lots for the kids to do

  • Yeah! love that you won. Good on you! I might agree with Alaska, or some out of the way spot. SAN is a great city for a family, lots to do. I’m in Alaska now, (temp in Juneau yesterday was 82 degrees). Maybe look into a cruise in Alaska – next year or maybe you’ll find a line that has lowered prices due to space, you’ve plenty of time to research the best bang for buck. I’m on a Crystal cruise, but there are tons of choices. Then no worries about meal costs, hotels, car rentals. It would be memorable for sure. And I’m not kidding when I say the glaciers are melting, and fast.

  • Congrats! With that amount and kids those ages, Disney is the first thing that pops in my head. It’s tougher to do with miles and points and your kids are the perfect ages for it. A cruise could also be a good option for you.

  • Charlie,
    I’m so glad you won!
    Please let us know where you will go!

  • One of my co-investors does the disney private tour every year. He says it’s awesome. Him and his wife (no kids) love the trip. I think a couple of days at Disney using the private tour will run you about 10k right there

  • Since you’re from Western NY and are looking at the months of February and April, I’m assuming you’re probably wanting to go somewhere relatively warm during those months, and the only kid-friendly places with enough stuff to do that I can think of during those months that are warm are San Diego, Maui, and Orlando, or perhaps a cruise (a Disney one maybe?). Any of these I think are going to be your best bet for the time of year, but if San Diego ends up being your destination, I’d recommend April over February for 2 reasons: 1) Less chance of winter weather affecting your travel leaving western NY and 2) It’s typically drier in SD in April vs February, as the winter in CA is the wet season due to the Mediterranean climate.

    Anyway, if San Diego is the winner, definitely take your kids to the San Diego Zoo, Balboa Park, Sunset Cliffs (for a sunset obviously!), and Coronado and La Jolla for beach days. If your kids want some fun things in a city not named Orlando, there’s also Legoland and Sea World, and if you were really feeling up for it, you could take them up to Anaheim for check out Disneyland (10 days is more than enough time to see all of San Diego). In addition, if you go in April, you’ll have the benefit of it also being baseball season, so you could also take your kids to a Padres game. Lastly, and most importantly, you definitely need to take your kids to Hodad’s for a burger and milkshake! There are a few in the area, and definitely have some of the best burgers I’ve ever had in my travels!

    As far as hotels, the best location to be in San Diego would be either the Bayfront or Gaslamp Quarters. The Hiltons and Marriotts in both areas are quite nice. If you want to be a little farther away from most of the sites you’ll want to see, you could put a dent in your $10k and stay at Hotel del Coronado on Coronado Island, and you’ll be right on the beach 🙂

  • So glad to find out you won. Anyone who knows how these work knows that the security around giveaways is gigantic. I’m sure you won fair-and-square, but oh boy, the USTA sure is getting some free publicity because you won. 🙂

    My brother used to live in San Diego. If that is your choice, the standard touristy areas mentioned above, like the zoo and Balboa Park, are where I go. (Those will chew up most of a day.) Heading up to the Mt Soledad Cross for the great view is a must, and that won’t take as long.

    As for hotels, I don’t travel for a week with 6 people, but those who do usually stay at places like Residence Inns. (Someday ask me about Brazilian families at Disneyworld.) 😉 Although staying someplace like Hotel del Coronado or the Pendry or even the Manchester Grand Hyatt sounds fun, it would seem like a hassle for 6 people for a week.

  • Have you ever done/thought about doing a cruise? you could even combine it with another trip. As for San Diego recommendations, if the gocity pass is available, get it, it was worth it. Aquatica, the seaworld water park is also great for kids, but be aware it is nowhere near Seaworld! Don’t make the mistake I did and show up at the Seaworld parking lot looking for a water park. The children’s museum in San Diego is great, and would probably keep all ages occupied. They have one room full of foam rubber tires and mattress walls. Everytime we have taken our grandkids there (4 and 7) they leave totally exhausted. A Kayak trip – very easy in La Jolla was also a highlight.

    • 4 of my family members get motion sickness so we would need to do a trial cruise of sort first. 🙂 We all love the idea but not sure how it would translate in real life practice once onboard.