At the end of the week, I’ll be on my way to Italy for 11 days. This is my first trip planned entirely with points and miles. I’m excited to share how I booked an 11 day/10 night trip to Italy for my boyfriend and me for $292. That’s less than $150 per person! This trip valued at over $6,500 includes economy airfare, 10 nights of hotels, 3 one-way train rides, and one tour in Rome. This trip to Italy has been almost a year in the making and we have credit card churning to thank for it! Here are the details on how I planned our trip to Italy using points and miles for under $300.

The Plan

My boyfriend and I are flying to Rome and leaving from Milan. Neither of us has been to Italy before so we wanted to hit all the major spots. We are spending 4 nights in Rome, 3 in Florence, 2 in Venice, and 1 in Milan. We’ll be taking trains to get between locations.

Note: It’s difficult to determine the actual value of some of our bookings, especially airfare which can change dramatically based on when you book a flight. I like to keep it conservative to account for the fact that I probably wouldn’t pay these prices out of pocket. As a result, it’s likely that my valuation is an underestimate.


BOS to FCO on Alitalia – 60,000 Delta SkyMiles and $11.20

Alitalia Delta Flight
This direct flight from Boston to Rome is pretty pricy!

For these flights, my boyfriend and I each opened the Delta Gold SkyMiles credit card from American Express with a sign-up bonus of 50,000 miles. Delta’s award availability is best if you can book early. We booked our two economy tickets a few days after flights for our departure date were released. We wanted the direct flight on Alitalia, so it was important that we started planning early! When it comes to planning trips, it doesn’t hurt that my boyfriend’s vacation time is determined a year in advance (oh, the life of a medical resident).

Since our miles were in two different Delta accounts, I had to book our tickets separately. I tweeted at Delta to link our reservations after they were ticketed.

The cost of this flight is well over $1,000 but for my purposes, I’m going to consider the value to be $800 per person.

LIN to BOS on Lufthansa – 60,000 United Miles and $165.32

We chose to fly out of Milan Linate AirportĀ since it’s easier to get to than Malpensa. United had a lot of availability for flights home so we weren’t in a huge rush to book these. I ended up earning 33,000 United miles mainly by taking surveys and using their shopping portal. You can read more about that here.

My crazy surveying was enough to cover more than one of our flights home. I transferred 27,000 Chase Ultimate Rewards points from the Chase Sapphire Reserve sign-up bonus to United to complete our booking.

I’m not counting the Chase Sapphire Reserve annual fee in this valuation because I got $600 in travel credit in the first year of having the card. This more than covers the $450 annual fee. Of course, I won’t be counting the travel credit as an actual travel redemption, merely as a means of offsetting the fee.

I’m valuing these flights at about $600 per person.

Total spent (airfare): $176.52
Total value (airfare): $2,800


It’s easy to stay in nice hotels when you’re only in a city for a few nights. Instead of saving points from one loyalty program for a whole vacation’s worth of hotels, we were able to earn points here and there through different hotel chains. Here’s how we booked our 10 nights in Italy.

Rome – 2 Hilton Free Night Certificates, a $95 Annual Fee, and 27,753 Chase Points

Nights 1 and 2: Waldorf Astoria Rome Cavalieri

Mad Men Waldorf Astoria
Staying at the Waldorf Astoria will be just like that episode of Mad Men.

We booked two nights at the Waldorf Astoria using 2 free weekend night certificates from the Citi Hilton HHonors Reserve card. You can only use these certificates if you find a room available at the standard award redemption rate.

We found one weekend night for a King Deluxe room and booked that immediately. A few weeks later, a twin room opened up so I booked that as well. By February, award availability had improved so I was able to switch the twin room to a king so we wouldn’t have to change rooms. After a small incident that involved a $920 charge to my credit card, our Hilton reservations were squared away.

We had to pay a $95 fee for the credit card but the two nights are valued at about $960.

Nights 3 and 4Hotel Diocleziano

For our last two nights in Rome, I used Chase Ultimate Rewards points to book through the travel portal. Points are worth 1.5x when booked from your Chase Sapphire Reserve account which presents a pretty great value. This hotel includes free breakfast which is always a plus!

I used 27,753 Chase points for a value of $416.

Florence – 36,086 Chase Points

Nights 5-7: Hotel Pendini

I also used Chase Ultimate Rewards points for our stay in Florence. I used 36,086 Chase points for a value of $541.

Venice – 80,000 Marriott Points and $20

Nights 8 and 9: JW Marriott Venice

JW Marriott Venice
Pretty excited to arrive at the JW Marriott Venice in style

The JW Marriott Venice seemed like an amazing redemption option since it’s located on its own private island away from the busy tourist areas. I’m sure we’ll spend more on water taxis, but I’m excited to check out this property.

The JW Marriott Venice is 40,000 points per night. I opened the American Express Starwood Preferred Guest credit card through an incognito offer to earn 30,000 points. I had 5,000 Marriott points already so I ended up needing to transfer 25,000 points to Marriott. At the 1:3 conversion rate, this gave me the extra 75,000 Marriott points needed to complete the booking.

There’s also a $20 fee associated with this booking. The total value of our stay is about $850.

Milan – 30,000 Hyatt Points

Night 10: Park Hyatt Milan

I recently wrote about how I’ve been earning lots of Chase points by using Plastiq. While 30,000 points is a lot for one night in a hotel, I really wanted to check out the Park Hyatt Milan. I transferred my points from Chase to complete this booking worth $740. You can read more about that here.

Total spent (hotels): $115
Total value (hotels): $3,507

Tours and Transportation

I wanted this vacation to cost as little as possible so I opened the Barclaycard Arrival Plus so I would have some points to spend flexibly.

Trains – 20,800 Barclaycard Arrival Plus miles

It’s easy to buy train tickets at the station, but in order to use Barclaycard Arrival Plus miles, I needed to make sure my booking totaled at least $100.

I booked one-way tickets for two from Rome to Florence, Florence to Venice, and Venice to Milan. This cost $208 which I was able to get back as a statement credit.

Barclaycard Arrival Plus redemption
Barclaycard Arrival Plus makes it easy to redeem points for non-loyalty program travel

Roman Catacombs Tour – 14,700 Barclaycard Arrival Plus miles

Since I had Arrival Plus miles left, I booked a tour of the Roman Catacombs. This cost $147 for two people which I also got back as a statement credit.

Total spent (tours and transportation): $0
Total value (tours and transportation): $355


I ended up spending a grand total of 329,339 points/miles (and two free night certificates) and $291.52 on my 11 day/10 night tour of Italy for two. That’s a total estimated value of $6,662! To earn all these points, my boyfriend and I opened six credit cards.

DescriptionPoints/Miles UsedFeesValueCredit Card Sign-Up Bonus?
BOS to FCO: 2 economy tickets on Alitalia 60,000 Delta miles$11.20$1,6002x American Express Gold Delta
LIN to BOS: 2 economy tickets on Lufthansa60,000 United miles (27,000 transferred from Chase)$165.32$1,200Chase Sapphire Reserve
2 nights Waldorf Astoria Rome Cavalieri2 Hilton free weekend night certificates$95$960Citi Hilton HHonors Reserve
2 nights Hotel Diocleziano (Rome)27,753 Chase points$0$416Chase Sapphire Reserve
2 nights Hotel Pendini (Florence)36,086 Chase points$0$541Chase Sapphire Reserve
2 nights JW Marriott Venice80,000 Marriott points (transferred from Starwood)$20$850American Express Starwood Preferred Guest
1 night Park Hyatt Milan30,000 Hyatt points$0$740n/a
2x train tickets from Rome to Florence, Florence to Venice, and Venice to Milan20,800 Arrival Plus miles$0$208Barclaycard Arrival Plus
2x Roman Catacombs tour14,700 Arrival Plus miles$0$147Barclaycard Arrival Plus
Total329,339$291.52$6,6626 credit cards

Final Thoughts

It’s exciting for me to share how I booked my first vacation almost entirely with points and miles. By spending less than $300 on all of our transportation, accommodations, and even one tour, we’ll feel less guilty indulging in some nice meals and maybe a little shopping! Next time, I’d like to see what business class is all about. I’ll be sharing reviews and travel guides from this trip so stay tuned!

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More from our Italy vacation:

Trip Reports:
Part 1:  Four Days in Rome
Part 2: Florence in 48 Hours
Part 3: The Best of Tuscany in One Day
Part 4: 48 Hours in Venice
Part 5: One Night in Milan
Hotel Review: Waldorf Astoria Rome Cavalieri
Hotel Review: JW Marriott Venice
Hotel Review: Park Hyatt Milan
Priority Pass Lounge Review: Air France Lounge at Boston Logan Airport 
Priority Pass Lounge Review: Club S.E.A. Sala Leonardo at Milan Linate Airport

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