Ana sent us this story about her couples’ trip to Rome and Tuscany. We love Italy, so we are happy to share it with you! Here’s her story:

Couples’ Trip to Rome and Tuscany with Points and Miles

I’ve been collecting points since the ’90s—back when you actually earned them by flying! While the landscape has evolved, I love that points and miles are now more accessible than ever. My story is a little different since I’m based in Canada, but thanks to tips from TMS, I was able to plan our first couples’ trip since our daughter was born.

We used ChatGPT to make suggestions on where to go: I input our age, interests, and asked it to suggest places within a ten-hour flight from Toronto. We chose Italy, specifically Rome and Tuscany, as I had never been! We had fixed travel dates, so there was no business class award space available. But with strategic redemptions, we still made it happen—mostly on points!

 

Flights/Land Transportation

• Toronto to Rome: 20,000 Flying Blue miles per person, transferred from American Express Membership Rewards®. My husband and I both have a stash of Membership Rewards®. We used the TMS tip of paying ~$150 each for extra-legroom seats via KLM. Unfortunately, there were no cash upgrades to business class available, so no KLM souvenir Delft houses, but we had a comfortable economy ride!
• Rome to Florence: Fast train with Italo. €55 each in business class.
• Florence and Tuscany to Milan: rental car with Europcar for $185 for two days. We had to get an International Driver’s license before leaving to be able to drive in Canada—that was $25 each.
• Milan to Dublin: €136 on Ryanair with carry-on and checked bags for two people
• Dublin to Toronto: I booked mine using 22,500 Alaska miles (now Atmos Rewards) and my husband’s for just 13,000 on an Aer Lingus direct flight. You can also find this deal to Boston; their chart is distance-based, so these low points prices work for Toronto and Boston. While I transferred those from points I had earned from Canadian cards, there are many more options in the U.S. to acquire these points. 

 

Lodging

• Rome: two nights at Hilton DoubleTree Rome Monti at 60,000 Hilton Honors points per night (a steal compared to the €550/night cash rate). We booked this over the more expensive Aleph we were also considering to conserve points. Thanks to our Gold status, which we achieved through our cards, we enjoyed a fantastic breakfast buffet daily, valued at €22 per person. We accumulated the points through the Hilton Honors American Express Surpass® Card and a no-fee Hilton card.
• Florence: two nights at a three-star hotel near the train station, booked using our $200 American Express Platinum Canada Travel Credit (one each).
• Chianti: one night at Castello di Gabbiano, a castle with an on-site winery and restaurant—booked in cash for about €200, totally worth it!
• Dublin: one night at the Radisson Blu Hotel, Dublin Airport, partially offset with a travel credit from one of my Canadian cards. Convenient for our early morning flight—and yes, we stocked up on Irish whiskey at duty free!

 

 

Other Perks

• Priority Pass lounges at Toronto and Amsterdam—breakfast at AMS was a game-changer. I screwed up and couldn’t find the lounge in Milan, and we didn’t have enough time in Dublin, but we could have used those as well.

 

Cards Used – Canadian Cards

• American Express Platinum – transferred points to Flying Blue, travel credits for Florence & Dublin hotels, lounge access.
• Hilton Cards – Hilton Gold status for free breakfast and award nights. I got free-night certificates with both of my cards in 2024, I am using the four certificates for an overwater bungalow at an SLH property in the Maldives for this year’s couples’ trip!
• Alaska Airlines miles & British Airways Avios – I acquired these points with Canadian cards, but there are multiple options to acquire these points in the U.S. Unfortunately, the Canadian Alaska card has since been discontinued!

 

Bottom Line

While not every stay was on points, this trip was a no-brainer, thanks to using miles to cover most of the significant costs. TMS helped us think more strategically—like upgrading to extra legroom on a transatlantic flight and using Avios for a cheap return from Europe.

By flying economy and booking mid-range hotels on sightseeing days, we stretched our points further—enough to help cover four major trips in 2025, including a stay in the Maldives using Hilton free-night certificates.

Tools like seats.aero and rooms.aero gave us the confidence to piece together a flexible, creative itinerary. Thanks to TMS for showing that even Canadian families can make points and miles go a long way!

 

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