SIGN UP NOW

Our latest reader success story comes from Kristi, who writes a travel blog called Fairy Tale Travel Guide all about traveling solo with two kids and tells us all about her trip to Portugal with another mom friend and three toddlers.  Kristi is a brave lady 💪! Here is her story:

 

Travel to Portugal

I’ve been casually using points and miles for a long time, but it wasn’t until I discovered the Travel Mom Squad podcast about a year and a half ago that I got serious about it. Their advice gave me the confidence to start making real travel dreams happen, and more frequently.

This spring, I planned a ten-day trip to Portugal with my friend Megan and our three toddlers, ages two, three, and four. It was just the two of us and our kids. No husbands, multiple cities, international travel, and nearly the entire thing booked with points. It felt ambitious, but with careful planning and a flexible mindset, we made it work. The result was one of the most memorable, joy-filled adventures of my life.

We chose Portugal for a few key reasons. It wasn’t too far, which meant shorter transatlantic flights and more time actually exploring. It also felt like a safe, welcoming destination for two solo moms traveling with young kids. And maybe best of all, our husbands didn’t mind sitting this one out. Portugal wasn’t high on their travel wish lists, so there was no FOMO involved.

 

Using Points and Miles to Make it Happen

We booked a ten-day, multi-city itinerary that took us through Cascais, Lisbon, Douro Valley, and Porto. Between the two of us, we used a mix of points and credits from American Airlines, Hilton, Hyatt, Marriott, and American Express Membership Rewards®, with a few paid stays and upgrades to round things out.

Our trip began with a stay at the Sheraton Cascais Resort, where we each used 76,000 Marriott Bonvoy points for two nights in a Premium Deluxe Room. We both placed a €100 bid to upgrade and were each awarded a spacious suite. To top it off, we both received a birthday dessert and wine in our rooms.

 

 

 

Next, we stayed two nights at the Hyatt Regency Lisbon. Megan used 54,000 Hyatt points for one suite (for me!) and paid $785.77 in cash for a standard twin river view room. Although she was offered a complimentary upgrade to a suite for the paid room, she declined since the hotel had already decorated her standard room for her birthday. Read the TMS review of this hotel here.

 

 

In the Douro Valley, we spent three nights at Quinta dos Padres Santos, a beautiful villa property that we paid for in cash since it wasn’t available on points.

We wrapped up our trip with two nights at the Hilton Porto Gaia, where we each used 100,000 Hilton Honors points for our rooms. Both of us received suite upgrades (thank you to Pam’s template!) and were given access to the executive lounge after asking for it at check-in. The hotel also surprised us with birthday desserts, and Megan was especially impressed that the staff took her daughter’s egg allergy into account by crafting a fruit-based treat just for her.

 

Transportation in Lisbon

We relied on trains, Ubers, and private transfers to navigate between cities. Portugal’s Uber policy (no car seats required) made things a bit easier for us as traveling moms. One of the most memorable moments was a spontaneous 50-minute boat tour on the Douro River in Régua that we booked on a whim from a souvenir shop. The kids were completely mesmerized. A few days later, we took a private charter bridge tour in Porto, arranged through the Hilton’s concierge. Watching our toddlers wide-eyed and thrilled on the water made all the travel logistics feel more than worth it.

 

 

 

When it came time to head home, we split up a bit. I originally had a long routing through Dublin and JFK, booked with JetBlue and Delta points. But after several hotel switches and some unexpected flooding back home, I changed plans and my crew flew standby as a pilot’s family—United from Porto to Newark—then rented a car to get the rest of the way. Points gave me the flexibility to adapt and cancel without major losses.

 

Credit Cards Used

• Citi® / AAdvantage Business™ World Elite Mastercard® (welcome offer used for AA flights)
• card_name (Hilton stay + $50 credit)
• The Ritz-Carlton™ Card (used at Sheraton and for Chase Sapphire Lounge in BOS)
• card_name (lounge access + Hilton credits)
• card_name (minimum spend for welcome offer)
• card_name (backup for vendors that didn’t take Amex)

All information about the Citi® / AAdvantage Business™ World Elite Mastercard® has been collected independently by Travel Mom Squad. The Citi® / AAdvantage Business™ World Elite Mastercard® is no longer available through Travel Mom Squad.

 

Flights

Kristi

• ROC–BOS: 60,000 American Airlines miles (20,000 per person)
• BOS–LIS: 66,000  Membership Rewards® (22,000 each) + €91.05 on Delta booked through Air France
• OPO–EWR: Standby on United (original plan was JetBlue and Delta with refunded points)

Megan

• ROC–BOS: $478.96 for two tickets booked with American Airlines (covered partially with a $250 AA gift certificate, which was purchased using a Platinum $200 airline credit)
• BOS–LIS: 44,000 Membership Rewards® (22,000 each)  + $66 on Delta booked through Air France
• OPO–EWR: 80,000 Membership Rewards® + $194.62 on United booked through Avianca
• EWR–ROC: $412.02 covered with a United flight credit (no out-of-pocket cost)

 

What I Learned

Points gave us freedom. I realized that you don’t need the absolute best redemptions to make a trip magical. Sometimes the destination itself matters more than the flight class or hotel category. If you’re a solo parent planning something similar, stay flexible and follow your kids’ natural rhythms. There were definitely some challenging moments, but the little joys made every bit of it worthwhile.

Thanks to points and miles and the inspiration from Travel Mom Squad, we turned a big birthday dream into a smooth and unforgettable adventure.

Well done, Kristi. 🙌  Your success story about going to Portugal on points with toddlers is inspiring to all of us who travel!

 

Related Posts

Review of Hyatt Regency Lisbon

Portugal on Points and Miles

Podcast 96. Lisbon & Azores Uncovered: A Family’s Journey on Points

Reader Success Story: Points and Miles Save a Trip to Japan