Cleared for Takeoff: Booking a milestone birthday trip to Rome and Florence

Cleared for Takeoff is a weekly series showing readers like you the best ways to book adventures using points and miles. If you’d like tips on booking your own trip using miles, please email us with your preferred itinerary and current mileage balance.

In this edition of Cleared for Takeoff, we're helping reader Kent Henderson plan a milestone trip for his wife's 60th birthday in Rome and Florence.

"I am looking to book a 10-12 day trip to Italy for my wife's 60th birthday next June-August. I will spend the bulk of the time in Rome but also plan to spend a couple of days in Florence. I can use my Southwest points and Companion Pass to do a repositioning trip from my home base in Phoenix if that is advantageous

I am also willing to pay cash for accommodations if that makes more sense.

Finally, in addition to the time to build up some point balances, I am open to applying for another Capital One, American or United credit card to boost any needed point balances below.

Thanks for any advice you can provide.

Kind regards,

Kent Henderson"

Thankfully, Kent has diversified his points portfolio to include numerous airlines, hotels and transferable points programs. This will be a massive help when it comes to booking both hotels and business class flights, as it gives Kent more options on when to plan his trip and whom to book it with.

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Points stash

Kent has a trove of points spread across numerous programs — here's a snapshot of his tallies:

• Southwest Rapid Rewards: 346,000 (with Companion Pass)
• American Airlines AAdvantage: 121,000
• Delta SkyMiles: 154,000
• United MileagePlus: 82,000
• Chase Ultimate Rewards: 105,000
• Capital One Rewards: 109,000
• Hilton Honors: 501,000 (Diamond Elite)
• Marriott Bonvoy: 361,000 (Lifetime Titanium Elite)

While the majority of his airline miles are with Southwest, he can't use them to fly to Europe. That said, they may come in handy when positioning from his home in Phoenix (PHX) to a larger hub airport with international connections like Philadelphia (PHL) or Chicago-O'Hare (ORD). Further, he has a solid number of American, Delta and United miles, which should — in theory — make booking award flights easier.

Related: No major airport near you? Here’s how expert travelers still get amazing flight deals

Airfare to Rome

Ideally, I'd like to use Kent's American miles to get him to Rome. Unfortunately, there is no business class saver award space for two passengers on American flights to Rome throughout the entirety of next summer when the couple plans to travel. Almost mystifyingly, I was having the same issue with United award space, so I knew I was going to have to get creative in how I searched for this itinerary.

Thankfully, Air France-KLM's joint Flying Blue loyalty program came to the rescue on the outbound journey. The program prices award tickets dynamically, but has some business class awards available for 55,000 miles and ~$235 per person one-way from Chicago-O'Hare (ORD) to Rome (FCO) with Air France or KLM, respectively, in mid-June. This is a solid deal for a business-class ticket from the U.S. to Rome during peak summer travel months.

Kent can book these tickets by transferring Chase Ultimate Rewards points or Capital One miles to Flying Blue at a 1:1 transfer ratio. I recommend he transfer Capital One miles for this particular redemption, as the Chase points will come in handy for booking hotels. Kent has 109,000 Capital One points, so he'll need to transfer these and 1,000 Ultimate Rewards points to book his two tickets.

On the way back, I was able to find sporadic Iberia award space from Rome to Chicago via Madrid (MAD) using American AAdvantage miles. Kent can book these tickets for 57,500 miles and $215.27 per person, which is a solid deal. This is marginally cheaper than booking the same flights with Iberia Plus, as dates are peak ones on the Iberia Plus calendar, and the itinerary requires a connection, which ups the required miles.

Of course, Kent will also need round-trip tickets from Phoenix to Chicago. Southwest Airlines recently expanded to Chicago-O'Hare (ORD) and has nonstop flights from Phoenix (PHX) to the airport. Unfortunately, we cannot search for Southwest awards yet as the booking calendar hasn't opened up that far in advance.

How to book this award with points

You can book all of these flights online. Just search for the outbound tickets on Air France's website by logging into your Flying Blue account and selecting "Book with Miles," then entering your cities and dates. For the return, use AA.com to search for award flights by checking the "Redeem Miles" box. If a mileage transfer is required, don't move your points until you've found award space online.

How to earn enough miles for this award

Kent may want to replenish his stash of transferable points after using the bulk of his Capital One miles to book outbound flights to Rome. He may consider starting to earn Citi ThankYou points, which also transfer to Flying Blue, by opening a Citi Premier® Card. This card currently earns 80,000 ThankYou points after you spend $4,000 in the first three months of account opening.

Citi ThankYou points can be transferred to Avianca LifeMiles, Air France-KLM Flying Blue and a slew of other great transfer partners.

Related: How to redeem Citi ThankYou Points for maximum value

Hotels in Rome and Florence

Kent noted that he has points and elite status with Hilton and Marriott. Further, he has a large stash of Chase Ultimate Rewards points that transfer to World of Hyatt, IHG Rewards and Marriott Bonvoy. This gives the couple a ton of different options for booking hotels in Rome and Florence.

The Westin Excelsior Rome

In Rome, I recommend that Kent use 240,000 Marriott Bonvoy points for a five-night stay at The Westin Excelsior Rome. This historic Category 7 property is outfitted with beautiful finishes and furnishings you'd expect from a high-end hotel in Italy, all in a palatial setting. Better yet, Kent only has to pay for four-nights on his five-night stay due to to Marriott's fifth-night free benefit.

Rome Cavalieri, A Waldorf Astoria Hotel

Since the couple wants to spend the bulk of their time in Rome, they can burn some Hilton Honors points for five nights at the Rome Cavalieri, A Waldorf Astoria Hotel. This is one of my favorite hotels in the world, with ultra-posh rooms, a huge outdoor space including a pool and gardens and incredible on-site dining.

You can book this property for as low as 80,000 points per night this June. Plus, Kent is a Hilton Diamond elite member, so he qualifies for a fifth night free on this stay.

Hilton calculates its fifth night free by totaling the points cost of a five-night stay and subtracting a fifth from the total points cost from that. If all nights are 80,000 points, the five-night stay would cost 320,000 Hilton points — not bad given this hotel costs $375 to $700 per night throughout the summer.

Hotel Lungarno Florence

The Hotel Lungarno is a Small Luxury Hotels (SLH) property that Kent can book by transferring Chase Ultimate Rewards points to World of Hyatt. It costs a hefty 40,000 points per night — but that's still a great deal considering paid reservations often hit $920 per night this summer. This means the couple would pay 80,000 Chase points for two nights in Florence.

The recently renovated property is located right in the center of Florence on the Arno River. You'll take in views of Florence's most iconic sights, like the Piazza del Signoria and the Ponte Vecchio. Better yet, rooms are modern with a classic Italian touch, and more than large enough for the couple's two night stay.

It might seem like overkill for the points price, but why not go all out for this milestone birthday?

Related: Take the family to Florence: A complete planning guide

How to book hotels with points

Like airfare, you can book these hotels online. Just head to each hotel chain's website, input your desired itinerary and make sure to select the pay with points option. Then, follow the on-screen prompts to book your hotel room.

How to earn hotel points

You can earn Chase Ultimate Rewards points with select Chase credit cards, and you can transfer them to three different hotel partners. Here's a look at current offers:

• Chase Sapphire Preferred Card: Earn 60,000 bonus points after you spend $4,000 on purchases in the first three months from account opening. Its earning rates include 3 Ultimate Rewards points per dollar on dining and 2 Ultimate Rewards points per dollar on travel purchases (though travel reservations made through the Chase Ultimate Rewards portal earn 5 points per dollar).
• Chase Sapphire Reserve: Earn 60,000 bonus points after you spend $4,000 on purchases in the first three months from account opening. Its earning rates include 3 Ultimate Rewards points per dollar on travel and dining purchases.
• Ink Business Preferred Credit Card: Earn 100,000 bonus points after you spend $15,000 in the first three months from account opening. Its earning rates include 3 Ultimate Rewards points per dollar on the first $150,000 spent per account anniversary year (then 1 point per dollar) on shipping, internet, cable, phone, advertising with social media sites and search engines and travel.

Related: How to redeem Chase Ultimate Rewards points for maximum value

Bottom line

Kent and his wife can easily maximize their points and miles stash to book a trip to Rome and Florence next summer. Better yet, they can fly in business class and stay exclusively in five-star hotels, making this birthday trip an extremely memorable one.

Have a destination in mind and need help figuring out your points strategy? Send us an email to be featured in the next installment of Cleared for Takeoff.

Feature photo by Catarina Belova /Shutterstock.com.