Family Travel Unpacked: Make the Most of Travel With Kids

Portugal on Points: A Case Study

• Melissa Conn • Season 1 • Episode 30

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Award travel case study: how our family is booking Portugal flights and hotels for 4 people using points — and spending under $1,000 out of pocket.

Ever wonder what it actually looks like to build a trip from scratch using points and miles? In this episode, I walk you through exactly how I planned our family's upcoming spring break trip to Portugal — flights, hotels, layovers, and all the creative problem-solving in between. This one was inspired by coffee with a local friend who had done a great job earning points but couldn't figure out how to actually use them. Sound familiar?

We're covering Lisbon, Cascais, and Porto, with four nights in each of the first and last stops. I'll tell you which programs I used, how many points each piece cost, where I got creative (Southwest to DC, anyone?), and what I would do differently next time.

If you've been sitting on a stash of points and wondering how to turn them into a real trip, this episode will show you how.

In This Episode:

  • Why Portugal in March — and how a band concert blew up my original plan
  • Two different strategies to fly between the US and Portugal on points
  • Three different tricks for booking accommodations for free
  • How traveling as a couple is different than traveling as a family
  • The four lessons I'll carry into every future award booking

New to points and miles? Start with Episode 7 (fundamentals) and Episode 8 (credit card benefit hunting) before this one.


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Hey there and welcome back to Family Travel Unpacked. I'm your host, Melissa, and in case you're new here, you can always find tons of detailed destination guides, travel tips, hacks, and more on my website, thefamilyvoyage.com. And if you've been enjoying the show, be sure to hit follow wherever you're listening, so you never miss an episode. So yesterday I grabbed coffee with a friend of mine who lives here in Columbus. She's been doing a really solid job building up a points and miles strategy from scratch. She has some of the fundamentals down. She's earning points. She's got a couple of the right credit cards. But when it came to actually using those points and making all the various credits work together, she was kind of spinning her wheels. She couldn't quite figure out how to turn what she had into a real trip that her family would love. And honestly, that conversation is what inspired today's episode because I think a lot of people are in that exact position. You've heard the terms, you've maybe even gotten a card or two, but translating points into an actual itinerary for your family on your actual dates, that's where it can get complicated. So today I am gonna walk you through exactly what it looks like in practice, using our upcoming Portugal trip as a real life case study. We are leaving next week for spring break with our two kids, and I can't wait to report back on how everything went. But for now I'm excited to pull back the curtain on the decisions, the trade-offs, the specific programs, and the exact redemptions that I used to pull it all together. Even if you don't have Portugal in the works, the strategies I'm gonna talk about today will definitely give you ideas for other destinations because they're the same no matter where you're going. One quick note before we get started. If you're newer to the points in Miles world and some of what I covered today feels like it's coming outta left field, you might wanna hit pause on this episode and go back to listen to episode seven first. That's where I cover the fundamentals. And episode eight is all about credit card treasure hunting, which will come up today too. Links to both of those episodes are in the show notes down below. Now, let me start at the beginning: how we ended up with Portugal on our plans in the first place. Our spring break falls in mid-March, and we always do something warm and beachy over winter break with our extended family. So another visit to Europe felt like the right fit. The challenge with March is that the weather in a lot of Europe is genuinely unpredictable. You could get lucky or you could get rained on for a week straight. I'm super jealous of you guys who have your spring break in mid-April. That's a lot easier. Now Portugal tends to be milder and more manageable than a lot of other European destinations in March, and it's been on our list to visit for years. So the destination choice was pretty easy, but the logistics were a lot messier. I started planning last spring assuming we could leave the Thursday night before spring break begins. Our kids are in middle school and missing a Friday here and there isn't usually a big deal, especially if it's the last day of the term. The airfares I was seeing for that Thursday departure were pretty reasonable, open jaw flying into Lisbon and out of Porto to minimize our ground transportation. We were all excited about it and we checked out books from the library and started sketching out our plans. I really like to start working on these bigger trips a year out because it gives us the best chance of locking in flights and hotels at reasonable rates. And then the school sent home the band calendar for the following year. Concert Thursday night. Both kids non-negotiable. I mean, talk about a buzzkill, right? So all of a sudden my Thursday departure's gone, and I'm looking at Friday. And Friday is a whole different story. The prices were higher, the itineraries were worse, and I had to completely rethink my approach. Okay, so let's talk about those flights. I wanna walk you through both directions because they were completely different experiences in terms of booking. I'll begin with the flight home from Porto to Columbus because that was surprisingly the easier piece of the puzzle. There's really only one carrier that was offering an itinerary that made any sense, and that was united. It worked out to 40,000 united miles per person in economy. Is that a great redemption? Nope, but I'd call it acceptable. I've had alerts set on PointsYeah and Google flights since I booked it, hoping that something better would come up. And so far nothing has. I used United Miles that I'd accumulated from a few different United Credit Card welcome offers last year, and I'm at peace with it. I'll mention here that just the other week, United announced some big changes that have made it close to a requirement to hold one of their credit cards if you wanna book award, travel through them. So check out the show notes for an article that I wrote, breaking all of that down. Now for the outbound leg, booking our flight to Lisbon was a true saga. I spent a lot of time racking my brains, but I really couldn't figure out a great way to get there. When I finally booked our flights back in September, the best I could get was 40,000 miles per person from Cleveland, and that's a two hour drive from our house. Everything from Columbus was at least 60,000 points in economy, and when you multiply that by four people, you're looking at a huge chunk of points for flights that aren't even in a premium cabin. I was really frustrated, but I booked the Cleveland flight just to have something in place, and I promised the family that I'd keep looking. I was still cranky about that Cleveland flight for months. I mean, who wants to drive two hours then deal with two flights, including a layover in Newark and still pay 40,000 points per person? Literally, the only thing that I liked about that itinerary is that it got us to Portugal without totally bankrupting our points stash. Now the conventional advice in this situation is to book a separate repositioning ticket- that's a cheap flight from your home airport to a bigger gateway city like New York's JFK, where the award availability tends to be much better. Either you can find the same economy ticket for fewer points, or you can use the same number of points and step up to business class. Except when I looked at the repositioning tickets from Columbus to New York, the only options that had a reasonable schedule for us were gonna cost another 30,000 points or$300 per person on top of whatever we'd be spending for the international flight. Either that or we'd have to deal with a 12 to 14 hour layover, and that just felt like adding insult to injury. It was the same story for the other major East coast airports. So I sat on it. I kept the Cleveland flight as backup and kept looking and thinking about my options. And then in January I got an alert that made a light bulb finally go off. Tap air portugal was showing a nonstop flight from Washington Dulles that came out to under 40,000 points per person, thanks to their 25% discount on award flights for kids. Since my daughter's still 11 for a few more months, she qualifies. Ronnie and I both had Capital One miles from our Venture X Cards and with a quick phone call, we were able to pool our points and transfer them to tap to book those four tickets. So why did that work when all of my other repositioning options didn't? The answer is Southwest. We have a huge stash of Southwest points, and both of us hold the companion pass right now, which means we each get to bring a kid with us on every flight for just the mandatory$5.60 cents security fee. While Southwest doesn't fly from Columbus to Dulles, they do fly to nearby Washington National Airport, and the points cost was just 11,000 for each of us adults. Compare that to 120,000 points that it would've cost to reposition through New York, and suddenly the whole thing starts to feel a lot smarter. There's one more piece of this that I actually love. Our layover in DC is almost eight hours. That's a long time, but my family lives near DC so we're gonna use that time to have dinner with them. A logistical constraint turned into a much needed visit. That's the kind of creative problem solving that this crazy hobby rewards when you're willing to stick with it. So here's the total flight recap round trip: 160,000 United Miles for the flight's home, 157,000 capital one miles for the tap flights to Lisbon and another 22,000 Southwest points for the Columbus to DC hop. That's a lot of points, but we're getting four people to and from Portugal on exactly the dates that we needed with minimal out-of-pocket cost. I promised my coffee friend, and I'm promising you four takeaways from all of this flight complexity and here they are. One: start early. Award availability is best when it first opens, which is usually 10 to 12 months before departure. If I had locked in our dates earlier, I might have had more options and maybe spent fewer points. But that band concert definitely threw off my planning and then I spent more time than I should have analyzing the situation before I pulled the trigger. Two: flexibility is powerful. I thought being flexible by even a day would be enough. But when that flexibility disappeared, I had no other levers to pull. If you can be flexible on your destination or your dates even a little bit, you're in a much stronger position to follow the deals. Three: a diverse stash of points matters. For this trip I used United Miles Capital One Miles and Southwest Points. No single program could have gotten us there cleanly. Having multiple currencies available gave me options, and options are everything in this game. And four: creativity pays off. That repositioning through DC on Southwest Idea didn't come to me immediately. It took some time and a lot of thinking, but that solution saved us about a hundred thousand points compared to what I would've spent if I just accepted the first reasonable flights I saw from our home airport. A hundred thousand points is real money, and now I know that I can look at that option in the future, if we wanna go somewhere that's served by Dulles, we just need to build in enough time to travel between airports. Maybe for your family it's gonna look like flying into LaGuardia to catch a flight from JFK or hopping to Midway for a long haul from O'Hare. Just sit down and look at the route maps and see how you can get creative. Now let's talk about where we're staying because this is where it gets fun. Three cities, three totally different approaches. Thankfully, this process was a lot less stressful because there are basically always gonna be places that you can stay, even if they're a little less than ideal. First off, the Hyatt Regency Lisbon for four nights. Now, if you've ever tried booking a hotel room in Europe for a family of four, you've probably run into the wall that I ran into. Most of the nicer hotels only accommodate two people, or possibly two adults and one small child in a single room. A lot of families just default to Airbnb in Portugal, which makes sense. The cash rates are pretty reasonable. But this is gonna be a nine night trip, so I really wanted to minimize my out-of-pocket spending while keeping everyone comfortable. I started digging and I found something great. The Hyatt Regency Lisbon has 47 standard suites that can accommodate a family of four. And we're talking about a 700 square foot unit with a kitchen and laundry. It's basically an apartment and there's tons of availability. I did notice something interesting when I was booking. Our kids are 11 and 14 right now, and the configuration works fine. I also tested the Hyatt site to see what would happen when they're 12 and 15, and it still allows the booking. But once my daughter hits 13, the Hyatt website won't allow it. If that becomes an issue down the road, the best workaround is to book for three adults and then call the hotel directly to price out adding a fourth person. There's definitely enough space there. It's just a matter of those occupancy restrictions. Now, here's the part that makes this a really special redemption. The Hyatt Regency in Lisbon is currently a category four property. That means a standard suite runs 24,000 world of Hyatt points per night. Or if you've earned a sweet upgrade award from past stays, you can combine that with just 15,000 points per night. And that's what I'm doing now for context. A lot of those Chase credit cards that I talk about on the show, the Sapphire Preferred Sapphire Reserve, and the different ink cards, those offer welcome bonuses between 75,000 and 150,000 points. So a single welcome bonus could cover a huge chunk of that stay. Now, full disclosure, last week, Hyatt broke a lot of hearts, including mine when they announced changes to the award chart later this year. The Hyatt Regency Lisbon suite will cost 29,000 points per night as a standard amount, but with a range of 21,000 to 34,000 points, depending on the date. If you have one of those suite upgrade awards to use, the range will be 12,000 to 25,000 points per night. I still think it's an incredible value, but I don't want you to be caught off guard if you go to book this specific property. Unfortunately, you'll see that type of change across the board at Hyatts in May. So now's a great time to lock in places that you wanna visit in the next 13 months. Almost all award bookings with Hyatt are cancelable with no penalty, so there's no downside. Now moving on to a happier topic. After Lisbon, we're spending one night in Cascais, a small town just west of the city along the coast. I've heard it's super charming and I'm excited to experience a different kind of Portuguese town. There aren't any hotels right in the area we wanted to stay that participate in a points program, so we had to try a different approach. I went into the Capital One travel portal and I used part of Ronnie's annual$300 travel credit from his Venture X card to book us on nice big family room, right by the water. It was the same price we would've paid on Expedia, but our out-of-pocket cost was zero. And I wanna say something about that Venture X credit, because I think it's underused. The Capital One travel credit isn't flexible the way some credits are. You do have to book through their portal. But what I love about it is that it applies to basically anything: hotels, Airbnb style, apartments, rental cars, tours, activities. So if you've been putting off booking something because it felt like a splurge, that credit's a great way to just do it. And if there's any expense beyond that$300 credit, you'll earn five to 10 points per dollar that you spend within the portal. Then you can turn around and apply those points directly to the charge on your statement to defray another part of the cost. This is one of the big strategies that I recommended to my friend over coffee because her family loves to ski and they're usually renting a car wherever they go and then staying in a condo. Instead of paying for the whole thing out of pocket with cash, they could book that condo or the rental car through the Capital One travel portal to use a$300 credit, earn more points on whatever they're doing, and then erase the cost with their points. Now, Porto was the trickiest piece of the accommodation puzzle. It has the same problem as Lisbon. The hotels where we'd wanna use our points only have rooms for two or maybe three people. And when you have to book two rooms for your family, those redemptions start to look a lot less attractive. I've been looking at Airbnbs and I was finding decent options in the$800 range for four nights. Not terrible, but still a chunk of cash that I'd rather keep in my pocket. Then I remembered the Citi Strata Elite card that Ronnie had opened in December. It's not cheap, it's close to$600 a year. But here's the benefit that made it work. The card comes with a$300 hotel credit every calendar year that can be used to book a stay of at least two nights through the Citi travel portal. So I logged in on December 31st, and I booked the first two nights. Then I logged back in on January 1st and book the next two nights. Same property, same room, two separate bookings, two separate$300 credits. I've already spoken with the property directly and they assured me that it'll be treated as one continuous stay. Our out-of-pocket for those four nights in Porto came out to around$350. Compared to the$800 Airbnbs I've been eyeing, i'll take it. And this card has already paid for itself in other ways before we even get on the plane. We've used additional credits like American Airlines and Black Lane Car Service. And when you add it all up, the math is clearly working in our favor for this first year, even with that$595 annual fee. by the way, what I ended up booking was a spacious two bedroom fully serviced apartment. Honestly, it's the best of both worlds. It has all the space and flexibility of a rental apartment, but without the uncertainty you can sometimes get with Airbnb and the out-of-pocket expense that goes with it. The second bedroom even has separate beds for each kid, which I'm sure they'll appreciate after a week on the road. Both Citi and Capital One do have lots of apartments available through their portals. So even if you're not a hotel person, you still have really good options. You don't have to default to Airbnb just because you want more space. Now I did wanna pause here for a second, because I know that not everyone listening is traveling with a family of four. If you're booking for just two adults, your hotel strategy in Portugal and other places with strict occupancy limits would look pretty different. And honestly, it's a lot more straightforward for you. Four or five nights in Lisbon or Porto would be a great fit for taking advantage of benefits with programs like IHG Hilton or Marriott, where booking five nights get you the fifth night free if you meet certain requirements. The family size constraint that pushed me toward apartments just doesn't exist for a party of two. For example, there are a few really lovely Hilton properties in Porto, including some of their boutiquey tapestry collection hotels. Those price out around 45,000 Hilton points per night. I have free Hilton Gold status through my Amex Platinum card, which means my fifth night is free and I get complimentary breakfast for two every morning, which is a nice perk. When you transfer Amex membership rewards points to Hilton it's at a one to two ratio, meaning one Amex point becomes two Hilton points. So five nights in Porto would cost just 90,000 Amex points total. And if that blew your mind, you should definitely go back and listen to episode 14. That one is all about hacking hotels, and it goes deep on exactly this kind of strategy. So let's talk about the dollars and cents. If I had paid cash for every flight and every hotel night on this trip, we'd be looking at roughly$6,000, and that's before a single meal, a single activity or a single took, took ride through the streets of Lisbon, just getting there and sleeping somewhere as a family of four. Instead, my all in cost for flights and accommodations is under a thousand dollars, and most of that is taxes and fees on the flights, which you really can't avoid when you're traveling internationally. The main cards that made this trip possible are the Citi Strata Elite at$595, the Capital One Venture X at$395, the Chase Sapphire preferred at$95 and the United Explorer Card- which is free the first year, and each adult can get their own. If you're doing the math, that's just over a thousand dollars in annual fees across those cards. We didn't open any of them explicitly for this trip, but we also didn't use every single point and credit that the cards come with for this one trip. We've still got plenty left over to use in the future. But here's the thing I want you to think about. If someone handed you a coupon for$5,000 worth of travel, and all it cost you was$1,000 in fees, you'd take that deal, right? I know I would, every single time. So that's the Portugal case study. I know this was a pretty detailed episode and you can always go back to listen again if you feel like you missed something. But I wanna bring it back to the conversation I had over coffee with my friend yesterday because I think there's something important in it. She'd been doing everything right in terms of earning points. She just couldn't see how to get from there to an actual trip. And what I told her is the same thing I wanna leave you with. The earning is just the first part, and in some ways it's the easiest. The magic is in the using, and it takes some practice, some patience, and honestly some creativity. But there really isn't a wrong way to use your points as long as they let you travel more, while you spend less. Start early, be flexible where you can build up diverse points, balances across a few programs to give yourself options, and don't just accept the first option You see. Sometimes the best answer is hiding in a combination of things that you wouldn't have thought to put together. If you want more details on any of the specific programs or cards I mentioned today, there are links down in the show notes to the articles I've written that go a lot deeper. And if you have questions about your own situation like my friend did over coffee, the best place to find me is at thefamilyvoyage.com/freetravel. You'll find tons of resources there and you can always leave a comment at the bottom with your question. Thanks so much for spending time with me today. Until next time, safe travels.