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Cleared for Takeoff: Business-class award trip to Italy for a family of 4

The Points Guy logo The Points Guy 9/28/2021 Benji Stawski
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Cleared for Takeoff is a weekly series showing readers like you the best ways to book post-pandemic 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.

Italy is one of the more popular European destinations, and luckily, there are many ways to get there with miles and stay using your points. Plus, Americans are welcome again so long as they can provide proof of vaccination or a recent negative COVID-19 test (always check the updated rules before planning your own trip).

This week, we’ll look into TPG reader Darren Greene’s request for help planning a family vacation to Rome and Venice:

Our trip dream. Four people out of RSW (ft myers) in June 2022.

Italy in business class or even first. Rome or Venice, returning from the opposite.


Darren Greene

Darren has a mix of American Express Membership Rewards points, Chase Ultimate Rewards points, United MileagePlus miles and Marriott Bonvoy points. Follow along as we take a look at how he could redeem these points to cover both flights and hotels.

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In This Post

Current points stash

Darren is off to a great start with the points and miles he already has and should be able to cover the entire family’s vacation. That said, ideally, he could get the rest of his family to start earning their own points to rack up rewards even faster. After all, booking award travel is easier when you approach it as a multiplayer game.

Related: A guide to earning transferable points and why they’re so valuable

Round-trip airfare to Italy

(Photo by Benji Stawski/The Points Guy) © The Points Guy (Photo by Benji Stawski/The Points Guy)

Route: RSW-EWR-LIS-FCO on United Airlines and TAP Air Portugal in business class; FCE-BRU-EWR-RSW on Brussels Airlines and United Airlines in business class.

Miles needed: 88,000 miles plus $184 per person.

There aren’t any nonstop flights to Italy from Fort Myers, Florida (RSW), so Darren and his family will need to connect through a gateway city like Newark (EWR).

In an ideal world, Darren and his family would fly RSW to EWR and then straight to Rome (FCO) or Venice (VCE). However, finding business-class availability on the nonstop flights between the U.S. and Italy is no easy task — especially when you’re booking for a family of four — so they’ll likely need to have two layovers if they really want business class.

I recommend Darren and his family book through ANA Mileage Club, a 1:1 transfer partner of Amex Membership Rewards.

The Star Alliance has a strong network in Europe and the program would allow them to redeem just 88,000 miles per round-trip business-class ticket. Plus, although the program requires round-trip bookings, it will allow Darren and his family to return from Venice if they fly into Rome first.

Darren can then use his Chase Ultimate Rewards points to book cheap flights from Rome to Venice through the Chase travel portal.

Related: Planning a trip to Italy? Here’s how to get there on points and miles

How to book this award with points

ANA allows you to book award tickets online, though availability may be more limited than with other Star Alliance programs. On the flip side, it can be almost 50% cheaper than booking through programs like United MileagePlus and Air Canada Aeroplan.

Step 1: Log in to your Mileage Club account

You must be logged in to your Mileage Club account in order to search for awards. If you don’t have one, you can sign up here. Then, just click on the “Award Booking” tab on the home page.

(Screenshot courtesy of © The Points Guy (Screenshot courtesy of

Step 2: Enter your trip information

Since this itinerary involves so many stops, on the award booking page, we’ll need to select the “Multiple cities/Mixed classes” tab. Then, enter all the dates and cities you want to include in your itinerary. In this case, we’ll search for Fort Myers to Rome via Newark and return from Venice. Since award availability changes quickly, we’ll search for random dates in December for the purpose of this example.

Given the complex itinerary, you might want to first search for award space segment by segment using your favorite website for searching Star Alliance award availability. This way, you don’t need to play around with the dates on ANA’s site too much.

(Screenshot courtesy of © The Points Guy (Screenshot courtesy of

Step 3: Choose your flight segments

On the next page, you’ll be able to select your flights by segment. Just click on the flights you want, hit “Next” and continue until you’ve chosen every segment in your itinerary.

(Screenshot courtesy of © The Points Guy (Screenshot courtesy of

When booking a complex itinerary like this one, certain segments, such as the flight from Fort Myers to Newark, might only have economy-class seats available. Just make sure you’re selecting business class for the longer flights.

(Screenshot courtesy of © The Points Guy (Screenshot courtesy of

Step 5: Confirm and pay

Once you have all of your flights picked out, you’ll be taken to a page that shows the total cost of your award, including taxes. Round-trip business-class awards will always come out to 88,000 miles, though the taxes and fees will depend on the airlines you’re flying and the countries you’re visiting. As a general rule of thumb, you’ll pay much higher surcharges on carriers like Austrian Airlines, Lufthansa and Swiss than Air Canada, United Airlines, TAP Air Portugal, LOT Polish Airlines, SAS and Turkish Airlines.

Be sure to pay for the taxes and fees using a card like The Platinum Card® from American Express or Chase Sapphire Reserve so that you may be covered by perks like trip delay reimbursement and trip cancellation and interruption protection when things go wrong.

Related: Book This, Not That: Star Alliance award tickets

(Screenshot courtesy of © The Points Guy (Screenshot courtesy of

How to earn enough miles for this award

Darren has just enough Amex Membership Rewards to transfer to ANA to book the four tickets. However, if you’re looking to replicate this itinerary and need more points, you can do so fairly easily by picking up a card, such as one of the following:

  • The Platinum Card from American Express: Earn 100,000 points after you spend $6,000 in the first six months of card membership. Plus, earn 10x points on eligible purchases at restaurants worldwide and when you “Shop Small” in the U.S., on up to $25,000 in combined eligible purchases, during your first six months of card membership.
  • The Business Platinum Card® from American Express: Earn 100,000 bonus points after you spend $15,000 on eligible purchases within the first three months of card membership.
  • American Express® Business Gold Card: Earn 70,000 bonus points after you spend $10,000 on eligible purchases in the first three months of card membership.
  • American Express® Gold Card: Earn 60,000 points after you spend $4,000 on purchases in the first six months of card membership.

Hotels in Italy

Darren has 395,000 Marriott Bonvoy points to spend on accommodations, which should be enough to cover a roughly week-long vacation in Italy. That said, if he needs more points, he can transfer some from Amex Membership Rewards or Chase Ultimate Rewards. Amex is even offering a 30% bonus on transfers to Marriott through Oct. 31.

He’ll be able to stretch the value of his points by taking advantage of Marriott’s fifth-night-free perk. Plain and simple, whenever you book five or more consecutive nights on points, you’ll get the fifth night free.

Related: These are the best hotels in Italy for every type of traveler

Hotel in Rome

Marriott has 13 properties to choose from in the greater Rome area. The most luxurious options include the Category 8 St. Regis and W Rome (70,000 to 100,000 points per night) and the Category 7 Westin Excelsior and Rome Marriott Grand Hotel Flora (50,000 to 70,000 points per night).

That said, given Darren’s point balance, I recommend he books one of the more budget-friendly options like the Le Meridien Visconti Rome (Category 6), which costs 40,000 to 60,000 points per night, or the Courtyard Rome Central Park (Category 4), which costs 20,000 to 30,000 points per night. After all, the hotels will probably charge peak pricing many nights during the summer, when Darren wants to go to Italy.

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Hotel in Venice

In Venice, the best match for Darren will probably be the AC Hotel Venezia. It costs 40,000 to 60,000 points per night so it won’t break the bank, but it’s still a nice, family-friendly option with a central location. Other options include the St. Regis Venice and the JW Marriott Venice Resort & Spa, but they’re much more expensive at 70,000 to 100,000 and 50,000 to 70,000 points per night, respectively.

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How to book a Marriott hotel with points

To book Marriott award nights, go to Marriott’s website and enter your search details as you normally would for a paid booking. However, before clicking the “Find Hotels” button, you’ll need to check the “Use Points/Certificates” box.

(Screenshot courtesy of © The Points Guy (Screenshot courtesy of

Then, simply select your hotel and room and complete the checkout process as usual.

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Related: How to spend a million Marriott points for an epic post-pandemic trip

How to earn Marriott Bonvoy points

The quickest way to boost your Marriott Bonvoy balance is by transferring points from American Express Membership Rewards or Chase Ultimate Rewards. That said, although it could make sense to transfer Amex points right now with the 30% transfer bonus, transferring to Marriott Bonvoy normally isn’t the best use of these transferable points.

Instead, you might want to consider adding a new Marriott Bonvoy card to your wallet. In addition to generous welcome bonuses, the cards can help you fast-track Marriott Bovnoy elite status and perks like annual free-night certificates. Most of the cards are currently offering elevated welcome offers — here’s a look:

  • Marriott Bonvoy Brilliant™ American Express® Card: Earn 150,000 Marriott Bonvoy bonus points after using your new card to make $5,000 in purchases within the first three months of card membership. Additionally, earn a bonus free-night award worth up to 85,000 points.
  • Marriott Bonvoy Boundless Credit Card: Earn 125,000 bonus points plus one free night (valued at up to 50,000 points) after you spend $5,000 in the first three months from account opening (for a total of up to 175,000 bonus points).
  • Marriott Bonvoy Business™ American Express® Card: Earn 125,000 Marriott bonus points and two bonus free-night awards after you use your new card to make $5,000 in eligible purchases within the first three months of card membership. Each bonus free-night award has a redemption level up to $50,000 points. Certain hotels have resort fees. Offer ends Nov. 3, 2021.
  • Marriott Bonvoy Bold Credit Card: Earn 60,000 bonus points after you spend $2,000 on purchases in the first three months from account opening.

Related: 5 ways to maximize Marriott Bonvoy award-night redemptions

Bottom line

Booking international award travel for a family of four is no easy feat. Doing it in business class requires even more strategy (and points). However, it is possible and is certainly worth the effort. Although Darren’s dream trip isn’t until next summer, I recommend he book his flights soon as there’s been a jump in Europeans booking travel to the U.S. and availability will likely decrease quickly.

If you 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.

Featured photo by Nico De Pasquale Photography/Getty Images.

SPONSORED: With states reopening, enjoying a meal from a restaurant no longer just means curbside pickup.

And when you do spend on dining, you should use a credit card that will maximize your rewards and potentially even score special discounts. Thanks to temporary card bonuses and changes due to coronavirus, you may even be able to score a meal at your favorite restaurant for free. 

These are the best credit cards for dining out, taking out, and ordering in to maximize every meal purchase.


Editorial Disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airlines or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.


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